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    Chemistry

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    Also known as: 59-05-2, Amethopterin, Rheumatrex, Methylaminopterin, Abitrexate, Trexall
    Molecular Formula
    C20H22N8O5
    Molecular Weight
    454.4  g/mol
    InChI Key
    FBOZXECLQNJBKD-ZDUSSCGKSA-N
    FDA UNII
    YL5FZ2Y5U1
    Methotrexate
    An antineoplastic antimetabolite with immunosuppressant properties. It is an inhibitor of TETRAHYDROFOLATE DEHYDROGENASE and prevents the formation of tetrahydrofolate, necessary for synthesis of thymidylate, an essential component of DNA.
    Methotrexate is a Folate Analog Metabolic Inhibitor. The mechanism of action of methotrexate is as a Folic Acid Metabolism Inhibitor.
    1 2D Structure

    Methotrexate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]pentanedioic acid
    2.1.2 InChI
    InChI=1S/C20H22N8O5/c1-28(9-11-8-23-17-15(24-11)16(21)26-20(22)27-17)12-4-2-10(3-5-12)18(31)25-13(19(32)33)6-7-14(29)30/h2-5,8,13H,6-7,9H2,1H3,(H,25,31)(H,29,30)(H,32,33)(H4,21,22,23,26,27)/t13-/m0/s1
    2.1.3 InChI Key
    FBOZXECLQNJBKD-ZDUSSCGKSA-N
    2.1.4 Canonical SMILES
    CN(CC1=CN=C2C(=N1)C(=NC(=N2)N)N)C3=CC=C(C=C3)C(=O)NC(CCC(=O)O)C(=O)O
    2.1.5 Isomeric SMILES
    CN(CC1=CN=C2C(=N1)C(=NC(=N2)N)N)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)O)C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    YL5FZ2Y5U1
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Amethopterin

    2. Dicesium Salt Methotrexate

    3. Hydrate, Methotrexate

    4. Methotrexate Hydrate

    5. Methotrexate Sodium

    6. Methotrexate, (d)-isomer

    7. Methotrexate, (dl)-isomer

    8. Methotrexate, Dicesium Salt

    9. Methotrexate, Disodium Salt

    10. Methotrexate, Sodium Salt

    11. Mexate

    12. Sodium, Methotrexate

    2.3.2 Depositor-Supplied Synonyms

    1. 59-05-2

    2. Amethopterin

    3. Rheumatrex

    4. Methylaminopterin

    5. Abitrexate

    6. Trexall

    7. Mexate

    8. Metatrexan

    9. Hdmtx

    10. Methylaminopterinum

    11. Mtx

    12. (s)-2-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)pentanedioic Acid

    13. Methotrexatum

    14. Rasuvo

    15. 4-amino-10-methylfolic Acid

    16. Metotrexato

    17. Maxtrex

    18. Nsc-740

    19. Mexate-aq

    20. N-bismethylpteroylglutamic Acid

    21. Folex

    22. Nci-c04671

    23. Cl-14377

    24. Antifolan

    25. Methotrexate Lpf

    26. Xatmep

    27. 133073-73-1

    28. Amethopterine

    29. Farmitrexat

    30. Emt 25,299

    31. L-amethopterin

    32. Cl 14377

    33. Methotrexat-ebewe

    34. Tcmdc-125858

    35. (2s)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]pentanedioic Acid

    36. Abitrexate (methotrexate)

    37. R 9985

    38. Yl5fz2y5u1

    39. Methotextrate

    40. Methotrexat

    41. Chembl34259

    42. Nsc740

    43. Chebi:44185

    44. Adx-2191

    45. N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-l-glutamic Acid

    46. N-[(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}phenyl)carbonyl]-l-glutamic Acid

    47. Cl14377

    48. Ncgc00025060-04

    49. Nsc 740

    50. 4-amino-n(10)-methylpteroylglutamic Acid

    51. A-methopterin

    52. Dsstox_cid_822

    53. A-methpterin

    54. Amethopterin L-

    55. Folex-pfs

    56. R-9985

    57. (2s)-2-[(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}phenyl)formamido]pentanedioic Acid

    58. Dsstox_rid_75810

    59. Methotrexate, L-

    60. Dsstox_gsid_20822

    61. X 133

    62. Metotressato [dcit]

    63. Methotrexate, D-

    64. Fauldexato

    65. Medsatrexate

    66. Methoblastin

    67. Metotressato

    68. Brimexate

    69. Emthexat

    70. Emthexate

    71. Lantarel

    72. Lumexon

    73. Metrotex

    74. Novatrex

    75. Otrexup

    76. Tremetex

    77. Trexeron

    78. Trixilem

    79. Metex

    80. Texate

    81. Mls001401431

    82. Methotrexatum [inn-latin]

    83. Metotrexato [inn-spanish]

    84. [3h]methotrexate

    85. Smr000112001

    86. [3h]-methotrexate

    87. Folic Acid Antagonist

    88. Ccris 1109

    89. 4-aminomethylpteroylglutamic Acid

    90. Hsdb 3123

    91. L-(+)-n-(p-(((2,4-diamino-6-pteridinyl)methyl)methylamino)benzoyl)glutamic Acid

    92. N-(p-(((2,4-diamino-6-pteridinyl)methyl)methylamino)benzoyl)-l-(+)-glutamic Acid

    93. Sr-01000075682

    94. Smr000449324

    95. Einecs 200-413-8

    96. Unii-yl5fz2y5u1

    97. Metolate

    98. Nordimet

    99. Ai3-25299

    100. Intradose-mtx

    101. 4-amino-n(sup 10)-methylpteroylglutamic Acid

    102. 1dhi

    103. 1dhj

    104. 2drc

    105. 4ocx

    106. (2s)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methyl-amino]benzoyl]amino]pentanedioic Acid

    107. Cas-59-05-2

    108. Glutamic Acid, N-(p-(((2,4-diamino-6-pteridinyl)methyl)methylamino)benzoyl)-, L-

    109. Kyselina N-(p-((2,4-diamino-6-pteridinylmethyl)methylamino)benzoyl)-l-glutamova

    110. Mpi-2505

    111. Prestwick_322

    112. Otrexup (tn)

    113. Xatmep (tn)

    114. Reditrex

    115. Kyselina 4-amino-n(sup 10)-methylpteroylglutamova [czech]

    116. Methylaminopterin; Mtx

    117. Methotrexate [usan:usp:inn:ban:jan]

    118. Spectrum_001836

    119. Tocris-1230

    120. 4kn0

    121. Wr-19039

    122. Prestwick0_000135

    123. Prestwick1_000135

    124. Prestwick2_000135

    125. Spectrum2_001077

    126. Spectrum3_000497

    127. Spectrum4_000616

    128. Spectrum5_000958

    129. Methotrexate - Abitrexate

    130. Methotrexate [mi]

    131. N-(p-(((2,4-diamino-6-pteridyl)methyl)methylamino)benzoyl)glutamic Acid

    132. Methotrexate [inn]

    133. Methotrexate [jan]

    134. L(+)-amethopterin Hydrate

    135. Methotrexate [hsdb]

    136. Methotrexate [iarc]

    137. Methotrexate [inci]

    138. Methotrexate [usan]

    139. N-(4-(((2,4-diamino-6-pteridinyl)methyl)methylamino)benzoyl)-l-glutamicacid

    140. Ncimech_000767

    141. Schembl3711

    142. Kyselina N-(p-((2,4-diamino-6-pteridinylmethyl)methylamino)benzoyl)-l-glutamova [czech]

    143. Methotrexate [vandf]

    144. Bidd:pxr0175

    145. Lopac0_000020

    146. Kbiogr_001172

    147. Kbioss_002341

    148. Methotrexate [mart.]

    149. Kyselina 4-amino-n(sup 10)-methylpteroylglutamova

    150. Mls000049968

    151. Mls002154208

    152. Divk1c_000114

    153. Methotrexate [usp-rs]

    154. Methotrexate [who-dd]

    155. Methotrexate [who-ip]

    156. Spbio_001094

    157. Spbio_002149

    158. Amy235

    159. Cid_126941

    160. Cid_165528

    161. Gtpl4674

    162. Gtpl4815

    163. Dtxsid4020822

    164. Schembl12421860

    165. Schembl23111732

    166. Bdbm18050

    167. Bdbm66082

    168. Hms500f16

    169. Kbio1_000114

    170. Kbio2_002338

    171. Kbio2_004906

    172. Kbio2_007474

    173. Kbio3_001493

    174. Methotrexate (jp17/usp/inn)

    175. G301

    176. Ninds_000114

    177. Bio1_000486

    178. Bio1_000975

    179. Bio1_001464

    180. Hms1568k12

    181. Hms2095k12

    182. Hms2233o18

    183. Hms3260c21

    184. Hms3414l09

    185. Hms3678l07

    186. Hms3712k12

    187. Methotrexate [orange Book]

    188. Methotrexate [ep Monograph]

    189. Methotrexate [usp Impurity]

    190. Act03341

    191. Apc-2002

    192. Bcp13701

    193. Mpi-5004

    194. Zinc1529323

    195. Methotrexate [usp Monograph]

    196. Tox21_110944

    197. Tox21_300269

    198. Tox21_500020

    199. Ccg-35800

    200. Emt-25299

    201. Methotrexatum [who-ip Latin]

    202. Mfcd00064370

    203. S1210

    204. Stl535338

    205. (4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzoyl)-l-glutamic Acid

    206. Akos016340329

    207. Tox21_110944_1

    208. Cs-1732

    209. Db00563

    210. Ks-5093

    211. Lp00020

    212. Sdccgsbi-0050009.p003

    213. Wr19039

    214. Idi1_000114

    215. N-(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}benzoyl)-l-glutamic Acid

    216. Smp2_000020

    217. (methyl)amino)benzamido)pentanedioic Acid

    218. Ncgc00025060-01

    219. Ncgc00025060-02

    220. Ncgc00025060-03

    221. Ncgc00025060-05

    222. Ncgc00025060-06

    223. Ncgc00025060-07

    224. Ncgc00025060-08

    225. Ncgc00025060-09

    226. Ncgc00025060-10

    227. Ncgc00025060-11

    228. Ncgc00025060-12

    229. Ncgc00025060-13

    230. Ncgc00025060-15

    231. Ncgc00025060-16

    232. Ncgc00254216-01

    233. Ncgc00260705-01

    234. Hy-14519

    235. Eu-0100020

    236. G-301

    237. Sw198601-3

    238. Methotrexate 1.0 Mg/ml In Dimethyl Sulfoxide

    239. 73m731

    240. A10021

    241. C01937

    242. D00142

    243. Q422232

    244. Sr-01000597411

    245. W-60383

    246. (s)-2-(4-(((2,4-diaminopteridin-6-yl)methyl)

    247. Q-201366

    248. Sr-01000075682-1

    249. Sr-01000075682-2

    250. Sr-01000075682-6

    251. Sr-01000597411-1

    252. W-105347

    253. Brd-k59456551-001-09-3

    254. Brd-k59456551-001-11-9

    255. Wln: T66 Bn Dn Gn Jnj Cz Ez H1n1&r Dvmyvq2vq

    256. Z1541638527

    257. N,n,n,n-ethylenediaminetetra(methylenephosphonicacid)

    258. Methotrexate, European Pharmacopoeia (ep) Reference Standard

    259. Methotrexate, United States Pharmacopeia (usp) Reference Standard

    260. Glutamic Acid,4-diamino-6-pteridinyl)methyl] Methylamino]benzoyl]-, L-(+)-

    261. L-glutamic Acid,4-diamino-6-pteridinyl)methyl]- Methylamino]benzoyl]-

    262. (s)-2-(4-(((2,4-diaminopteridin-6-yl)methyl)-(methyl)amino)benzamido)pentanedioic Acid

    263. L-glutamic Acid,n-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-,hydrate(9ci)

    264. Methotrexate For Peak Identification, European Pharmacopoeia (ep) Reference Standard

    265. Methotrexate For System Suitability, European Pharmacopoeia (ep) Reference Standard

    266. Methotrexate, Pharmaceutical Secondary Standard; Certified Reference Material

    267. N-[4-[[(2,4-diamino-6-pteridinyl)methyl] Methylamino]benzoyl]-l-glutamic Acid

    268. (2s)-2-((4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzoyl)amino)pentanedioic Acid

    269. (2s)-2-[[[4-[(2,4-diamino-6-pteridinyl)methyl-methylamino]phenyl]-oxomethyl]amino]pentanedioic Acid;hydrate

    270. (2s)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methyl-amino]benzoyl]amino]glutaric Acid;hydrate

    271. (2s)-2-[[4-[[2,4-bis(azanyl)pteridin-6-yl]methyl-methyl-amino]phenyl]carbonylamino]pentanedioic Acid;hydrate

    272. 102613-64-9

    273. L-glutamic Acid,n-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-, Hydrate (9ci)

    274. Methotrexate, Pharmagrade, Manufactured Under Appropriate Controls For Use As A Raw Material In Pharma Or Biopharmaceutical Production, Meets Ep, Usp Testing Specifications

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 454.4 g/mol
    Molecular Formula C20H22N8O5
    XLogP3-1.8
    Hydrogen Bond Donor Count5
    Hydrogen Bond Acceptor Count12
    Rotatable Bond Count9
    Exact Mass454.17131583 g/mol
    Monoisotopic Mass454.17131583 g/mol
    Topological Polar Surface Area211 Ų
    Heavy Atom Count33
    Formal Charge0
    Complexity704
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameMethotrexate sodium
    Drug LabelMethotrexate (formerly Amethopterin) is an antimetabolite used in the treatment of certain neoplastic diseases, severe psoriasis, and adult rheumatoid arthritis. Chemically methotrexate is N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-...
    Active IngredientMethotrexate sodium
    Dosage FormTablet; Injectable
    RouteInjection; Oral
    Strengtheq 200mg base/8ml (eq 25mg base/ml); eq 250mg base/10ml (eq 25mg base/ml); eq 50mg base/2ml (eq 25mg base/ml); eq 2.5mg base; eq 100mg base/4ml (eq 25mg base/ml)
    Market StatusPrescription
    CompanyHospira; Roxane; Dava Pharms; Fresenius Kabi Usa; Eurohlth Intl; Mylan; Barr

    2 of 4  
    Drug NameTrexall
    PubMed HealthMethotrexate
    Drug ClassesAntineoplastic Agent, Antipsoriatic, Antirheumatic, Antirheumatic, Cytotoxic
    Drug LabelTrexall (methotrexate tablets USP) (formerly Amethopterin) is an antimetabolite used in the treatment of certain neoplastic diseases, severe psoriasis, and adult rheumatoid arthritis. Chemically methotrexate, USP is N-[4[[(2,4-diamino-6-pteridiny...
    Active IngredientMethotrexate sodium
    Dosage FormTablet
    RouteOral
    Strengtheq 5mg base; eq 7.5mg base; eq 15mg base; eq 10mg base
    Market StatusPrescription
    CompanyBarr

    3 of 4  
    Drug NameMethotrexate sodium
    Drug LabelMethotrexate (formerly Amethopterin) is an antimetabolite used in the treatment of certain neoplastic diseases, severe psoriasis, and adult rheumatoid arthritis. Chemically methotrexate is N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-...
    Active IngredientMethotrexate sodium
    Dosage FormTablet; Injectable
    RouteInjection; Oral
    Strengtheq 200mg base/8ml (eq 25mg base/ml); eq 250mg base/10ml (eq 25mg base/ml); eq 50mg base/2ml (eq 25mg base/ml); eq 2.5mg base; eq 100mg base/4ml (eq 25mg base/ml)
    Market StatusPrescription
    CompanyHospira; Roxane; Dava Pharms; Fresenius Kabi Usa; Eurohlth Intl; Mylan; Barr

    4 of 4  
    Drug NameTrexall
    PubMed HealthMethotrexate
    Drug ClassesAntineoplastic Agent, Antipsoriatic, Antirheumatic, Antirheumatic, Cytotoxic
    Drug LabelTrexall (methotrexate tablets USP) (formerly Amethopterin) is an antimetabolite used in the treatment of certain neoplastic diseases, severe psoriasis, and adult rheumatoid arthritis. Chemically methotrexate, USP is N-[4[[(2,4-diamino-6-pteridiny...
    Active IngredientMethotrexate sodium
    Dosage FormTablet
    RouteOral
    Strengtheq 5mg base; eq 7.5mg base; eq 15mg base; eq 10mg base
    Market StatusPrescription
    CompanyBarr

    4.2 Therapeutic Uses

    Abortifacient Agents, Nonsteroidal; Antimetabolites, Antineoplastic; Antirheumatic Agents; Dermatologic Agents; Enzyme Inhibitors; Folic Acid Antagonists; Immunosuppressive Agents; Nucleic Acid Synthesis Inhibitors

    National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

    Methotrexate is indicated for treatment of breast carcinoma, head and neck cancers (epidermoid), non-small cell lung carcinoma (especially squamous cell types), small cell lung carcinoma, and gestational trophoblastic tumors (gestational choriocarcinoma, chorioadenoma destruens, hydatidiform mole). /Included in US product labeling/

    Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 1911

    Methotrexate is indicated for treatment of cervical carcinoma, ovarian carcinoma, bladder carcinoma, colorectal carcinoma, esophageal carcinoma, gastric carcinoma, pancreatic carcinoma, and penile carcinoma. /NOT included in US product labeling/

    Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 1911

    Methotrexate is indicated for treatment of acute lymphocytic leukemia and prophylaxis and treatment of meningeal leukemia. /Included in US product labeling/

    Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 1911

    For more Therapeutic Uses (Complete) data for METHOTREXATE (17 total), please visit the HSDB record page.

    4.3 Drug Warning

    Methotrexate is a highly toxic drug with a very low therapeutic index and a therapeutic response is not likely to occur without some evidence of toxicity. ... When methotrexate is used in combination with other antineoplastic agents and/or radiation therapy, toxic reactions may be more severe than would occur with methotrexate therapy alone. Although doses of methotrexate used in the management of psoriasis and rheumatoid arthritis are usually lower than those used in antineoplastic chemotherapy, severe toxicity may occur in any patient receiving the drug and deaths have been reported with the use of methotrexate in the management of psoriasis and rheumatoid arthritis.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 1111

    Methotrexate should be used with extreme caution in patients with infection, peptic ulcer, ulcerative colitis, or debility, and in very young or geriatric patients. Methotrexate should be used with extreme caution, if at all, in patients with malignant disease who have preexisting liver damage or impaired hepatic function, preexisting bone marrow depression, aplasia, leukopenia, thrombocytopenia, or anemia; the drug is usually contraindicated in patients with impaired renal function. In the management of psoriasis, methotrexate is contraindicated in patients with poor nutritional status or severe renal or hepatic disorders, those with overt or laboratory evidence of an immunodeficiency syndrome, and in those with preexisting blood dyscrasias such as bone marrow hypoplasia, leukopenia, thrombocytopenia, or clinically important anemia; relative contraindications also include cirrhosis, active or recent hepatitis, or excessive alcohol consumption. In the management of rheumatoid arthritis, methotrexate is contraindicated in patients with preexisting blood dyscrasias such as bone marrow hypoplasia, leukopenia, thrombocytopenia, or clinically important anemia; those with overt or laboratory evidence of immunodeficiency syndromes; and those with excessive alcohol consumption, alcoholic liver disease, or chronic liver disease.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 1112

    Elevations in serum uric acid concentrations may occur in patients receiving methotrexate as a result of cell destruction and hepatic and renal damage. In some patients, uric acid nephropathy and acute renal failure may result. Tumor lysis syndrome associated with other cytotoxic drugs (e.g., fludarabine, cladribine), also has been reported in patients with rapidly growing tumors who were receiving methotrexate. Pharmacologic and appropriate supportive treatment may prevent or alleviate this complication. Methotrexate also was reported to precipitate acute gouty arthritis in two patients being treated for psoriasis. Administration of large volumes of fluids, alkalinization of the urine, and/or administration of allopurinol may be useful in preventing acute attacks of hyperuricemia and uric acid nephropathy.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 1111

    Severe nephropathy manifested by azotemia, hematuria, and renal failure may occur in patients receiving methotrexate; fatalities have been reported. In one study, postmortem examination revealed extensive necrosis of the epithelium of the convoluted tubules. In patients with renal impairment, methotrexate accumulation and increased toxicity or additional renal damage may occur.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 1111

    For more Drug Warnings (Complete) data for METHOTREXATE (22 total), please visit the HSDB record page.

    4.4 Drug Indication

    Methotrexate oral solution is indicated for pediatric acute lymphoblastic leukemia and pediatric polyarticular juvenile idiopathic arthritis. Methotrexate injections for subcutaneous use are indicated for severe active rheumatoid arthritis, polyarticular juvenile idiopathic arthritis and severe, recalcitrant, disabling psoriasis. Other formulations are indicated to treat gestational choriocarcinoma, chorioadenoma destruens, hydatiform mole, breast cancer, epidermoid cancer of the head and neck, advanced mycosis fungoides, lung cancer, and advanced non-Hodgkin's lymphoma. It is also used in the maintenance of acute lymphocytic leukemia. Methotrexate is also given before treatment with leucovorin to prolong relapse-free survival following surgical removal of a tumour in non-metastatic osteosarcoma.

    FDA Label

    Nordimet is indicated for the treatment of:

    - active rheumatoid arthritis in adult patients,

    - polyarthritic forms of severe, active juvenile idiopathic arthritis (JIA), when the response to nonsteroidal anti-inflammatory drugs (NSAIDs) has been inadequate,

    - severe recalcitrant disabling psoriasis, which is not adequately responsive to other forms of therapy such as phototherapy, psoralens and ultraviolet A (PUVA), and retinoids, and severe psoriatic arthritis in adult patients,

    - induction of remission in moderate steroid-dependent Crohn's disease in adult patients, in combination with corticosteroids and for maintenance of remission, as monotherapy, in patients who have responded to methotrexate.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Methotrexate inhibits enzymes responsible for nucleotide synthesis which prevents cell division and leads to anti-inflammatory actions. It has a long duration of action and is generally given to patients once weekly. Methotrexate has a narrow therapeutic index. Do not take methotrexate daily.

    5.2 MeSH Pharmacological Classification

    Abortifacient Agents, Nonsteroidal

    Non-steroidal chemical compounds with abortifacient activity. (See all compounds classified as Abortifacient Agents, Nonsteroidal.)

    Enzyme Inhibitors

    Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

    Antimetabolites, Antineoplastic

    Antimetabolites that are useful in cancer chemotherapy. (See all compounds classified as Antimetabolites, Antineoplastic.)

    Immunosuppressive Agents

    Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging. (See all compounds classified as Immunosuppressive Agents.)

    Antirheumatic Agents

    Drugs that are used to treat RHEUMATOID ARTHRITIS. (See all compounds classified as Antirheumatic Agents.)

    Dermatologic Agents

    Drugs used to treat or prevent skin disorders or for the routine care of skin. (See all compounds classified as Dermatologic Agents.)

    Folic Acid Antagonists

    Inhibitors of the enzyme, dihydrofolate reductase (TETRAHYDROFOLATE DEHYDROGENASE), which converts dihydrofolate (FH2) to tetrahydrofolate (FH4). They are frequently used in cancer chemotherapy. (From AMA, Drug Evaluations Annual, 1994, p2033) (See all compounds classified as Folic Acid Antagonists.)

    Nucleic Acid Synthesis Inhibitors

    Compounds that inhibit cell production of DNA or RNA. (See all compounds classified as Nucleic Acid Synthesis Inhibitors.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    METHOTREXATE
    5.3.2 FDA UNII
    YL5FZ2Y5U1
    5.3.3 Pharmacological Classes
    Copper-containing Intrauterine Device [EPC]; Decreased Embryonic Implantation [PE]; Decreased Sperm Motility [PE]; Inhibit Ovum Fertilization [PE]; Copper [CS]
    5.4 ATC Code

    L04AX03

    L04AX03

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    L - Antineoplastic and immunomodulating agents

    L01 - Antineoplastic agents

    L01B - Antimetabolites

    L01BA - Folic acid analogues

    L01BA01 - Methotrexate

    L - Antineoplastic and immunomodulating agents

    L04 - Immunosuppressants

    L04A - Immunosuppressants

    L04AX - Other immunosuppressants

    L04AX03 - Methotrexate

    5.5 Absorption, Distribution and Excretion

    Absorption

    Methotrexate has a bioavailability of 64-90%, though this decreases at oral doses above 25mg due to saturation of the carrier mediated transport of methotrexate.. Methotrexate has a Tmax of 1 to 2 hours. oral doses of 10-15g reach serum levels of 0.01-0.1M.

    Route of Elimination

    Methotrexate is >80% excreted as the unchanged drug and approximately 3% as the 7-hydroxylated metabolite. Methotrexate is primarily excreted in the urine with 8.7-26% of an intravenous dose appearing in the bile.

    Volume of Distribution

    The volume of distribution of methotrexate at steady state is approximately 1L/kg.

    Clearance

    Methotrexate clearance varies widely between patients and decreases with increasing doses. Currently, predicting clearance of methotrexate is difficult and exceedingly high serum levels of methotrexate can still occur when all precautions are taken.

    In adults, oral absorption of methotrexate appears to be dose dependent. Peak serum levels are reached within one to two hours. At doses of 30 mg/sq m or less, methotrexate is generally well absorbed with a mean bioavailability of about 60%. The absorption of doses greater than 80 mg/sq m is significantly less, possibly due to a saturation effect.

    Physicians Desk Reference. 58th ed. Thomson PDR. Montvale, NJ 2004., p. 806

    After intravenous administration, the initial volume of distribution is approximately 0.18 L/kg (18% of body weight) and steady-state volume of distribution is approximately 0.4 to 0.8 L/kg (40% to 80% of body weight).

    Physicians Desk Reference. 58th ed. Thomson PDR. Montvale, NJ 2004., p. 806

    Protein binding: Moderate (approximately 50%), primarily to albumin.

    Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 1912

    At serum methotrexate concentrations exceeding 0.1 umol/mL passive diffusion becomes a major means of intracellular transport of the drug. The drug is widely distributed into body tissues with highest concn in the kidneys, gallbladder, spleen, liver, and skin.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 1113

    For more Absorption, Distribution and Excretion (Complete) data for METHOTREXATE (10 total), please visit the HSDB record page.

    5.6 Metabolism/Metabolites

    Methotrexate is metabolized by folylpolyglutamate synthase to methotrexate polyglutamate in the liver as well as in tissues. Gamma-glutamyl hydrolase hydrolyzes the glutamyl chains of methotrexate polyglutamates converting them back to methotrexate. A small amount of methotrexate is also converted to 7-hydroxymethotrexate.

    After absorption, methotrexate undergoes hepatic and intracellular metabolism to form methotrexate polyglutamate, metabolites which by hydrolysis may be converted back to methotrexate. Methotrexate polyglutamates inhibit dihydrofolate reductase and thymidylate synthetase. Small amounts of these polyglutamate metabolites may remain in tissues for extended periods; the retention and prolonged action of these active metabolites vary among different cells, tissues, and tumors. In addition, small amounts of methotrexate polyglutamate may be converted to 7-hydroxymethotrexate; accumulation of this metabolite may become substantial following administration of high doses of methotrexate, since the aqueous solubility of 7-hydroxymethotrexate is threefold to fivefold lower than that of the parent compound. Following oral administration of methotrexate, the drug also is partially metabolized by the intestinal flora.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 1113

    5.7 Biological Half-Life

    The half life of low dose methotrexate is 3 to 10 hours in adults. The half life for high dose methotrexate is 8 to 15 hours. Pediatric patients taking methotrexate for acute lymphoblastic anemia experience a terminal half life of 0.7 to 5.8 hours. Pediatric patients taking methotrexate for juvenile idiopathic arthritis experience a half life of 0.9 to 2.3 hours.

    Terminal: Low doses: 3 to 10 hours. High doses: 8 to 15 hours. Note: There is wide interindividual variation in clearance rates. Small amounts of methotrexate and its metabolites are protein-bound and may remain in tissues (kidneys, liver) for weeks to months; the presence of fluid loads, such as ascites or pleural effusion, and renal function impairment will also delay clearance.

    Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 1912

    5.8 Mechanism of Action

    Methotrexate enters tissues and is converted to a methotrexate polyglutamate by folylpolyglutamate. Methotrexate's mechanism of action is due to its inhibition of enzymes responsible for nucleotide synthesis including dihydrofolate reductase, thymidylate synthase, aminoimidazole caboxamide ribonucleotide transformylase (AICART), and amido phosphoribosyltransferase. Inhibtion of nucleotide synthesis prevents cell division. In rheumatoid arthritis, methotrexate polyglutamates inhibit AICART more than methotrexate. This inhibition leads to accumulation of AICART ribonucleotide, which inhibits adenosine deaminase, leading to an accumulation of adenosine triphosphate and adenosine in the extracellular space, stimulating adenosine receptors, leading to anti-inflammatory action.

    Methotrexate and its polyglutanate metabolites reversibly inhibits dihydrofolate reductase, the enzyme that reduces folic acid to tetrahydrofolic acid. Inhibition of tetrahydrofolate formation limits the availability of one-carbon fragments necessary for synthesis of purines and the conversion of deoxyuridylate to thymidylate in the synthesis of DNA and cell reproduction. The affinity of dihydrofolate reductase for methotrexate is far greater than its affinity for folic acid or dihydrofolic acid. and, therefore, even very large doses of folic acid given simultaneously will not reverse the effects of methotrexate. Leucovorin calcium, a derivative of tetrahydrofolic acid, may block the effects of methotrexate if given shortly after the antineoplastic agent. Results of one study indicate that methotrexate also causes an increase in intracellular deoxyadenosine triphosphate, which is thought to inhibit ribonucleotide reduction, and polynucleotide ligase, an enzyme concerned in DNA synthesis and repair. Tissues with high rates of cellular proliferation such as neoplasms, psoriatic epidermis, bone marrow, the lining of the GI tract, hair matrix, and fetal cells are most sensitive to the effects of methotrexate.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 1113

    Methotrexate ... has immunosuppressive activity, in part possibly as a result of inhibition of lymphocyte multiplication. The mechanism(s) of action in the management of rheumatoid arthritis of the drug is not known, although suggested mechanisms have included immunosuppressive and/or antiinflammatory effects.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 1113

    API Reference Price

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METHOTREXATE DISODIUM (T\/L # SW\/ND\/CT-17\/2024\/000002821)","address":"48, KANDIVLI INDUSTRIAL ESTATE,","city":"MUMBAI, MAHARASHTRA.","supplier":"FERMION OY","supplierCountry":"FINLAND","foreign_port":"HELSINKI","customer":"IPCA LABORATORIES","customerCountry":"INDIA","quantity":"2.87","actualQuantity":"2.87","unit":"KGS","unitRateFc":"4600","totalValueFC":"14640.6","currency":"EUR","unitRateINR":"426420","date":"29-Jul-2024","totalValueINR":"1223825.4","totalValueInUsd":"14640.6","indian_port":"Bombay Air","hs_no":"29419090","bill_no":"4768290","productDescription":"API","marketType":"REGULATED MARKET","country":"FINLAND","selfForZScoreResived":"Pharma Grade","supplierPort":"HELSINKI","supplierAddress":"KOIVU-MANKKAAN TIE 6 A, P.O.BOX 28FI-02101 ESPOO ., , FinlandSDNF Finland","customerAddress":"48, KANDIVLI INDUSTRIAL ESTATE,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1724610600,"product":"METHOTREXATE SODIUM ( METHOTREXATE DISODIUM SALT MILLED)","address":"ALEMBIC ROAD","city":"GUJARAT","supplier":"FLAVINE","supplierCountry":"GERMANY","foreign_port":"FRANKFURT\/MAIN INT\\'L","customer":"ALEMBIC PHARMACEUTICALS LIMITED","customerCountry":"INDIA","quantity":"149.78","actualQuantity":"149.78","unit":"KGS","unitRateFc":"3600","totalValueFC":"545452.9","currency":"USD","unitRateINR":"305460","date":"26-Aug-2024","totalValueINR":"45751798.8","totalValueInUsd":"545452.9","indian_port":"Bombay Air","hs_no":"29335990","bill_no":"5257156","productDescription":"API","marketType":"REGULATED MARKET","country":"GERMANY","selfForZScoreResived":"Pharma Grade","supplierPort":"FRANKFURT\/MAIN INT\\'L","supplierAddress":"61 SOUTH PARAMUS ROAD,SUITE 565 PARMUS,NEW JERSEY 07652SDNF U.S.A.","customerAddress":"ALEMBIC ROAD"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1725906600,"product":"METHOTREXATE (LIST 3 SR NO.29; IGST LIST NO.1 SR NO.29)","address":"MUMBAI CENTRAL,","city":"MUMBAI, MAHARASHTRA.","supplier":"HUZHOU ZHANWANG PHARMACEUTICAL","supplierCountry":"CHINA","foreign_port":"HONG KONG","customer":"CIPLA","customerCountry":"INDIA","quantity":"0.35","actualQuantity":"0.35","unit":"KGS","unitRateFc":"3700","totalValueFC":"1312","currency":"USD","unitRateINR":"314130","date":"10-Sep-2024","totalValueINR":"109945.5","totalValueInUsd":"1312","indian_port":"Bombay Air","hs_no":"29335990","bill_no":"5520785","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"HONG KONG","supplierAddress":"CO., LTD WEST DEVELOPMENT AREA RD, LINGHU TOWN, HUZHOU, ZHEJIANG CHINA CHINA","customerAddress":"MUMBAI CENTRAL,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1726857000,"product":"METHOTREXATE USP","address":"S.C.O.857, CABIN NO. 10, 2ND FLOOR,","city":"CHANDIGARH.","supplier":"HANGZHOU ZHONGBAO IMP.&EXP.CORP. ","supplierCountry":"CHINA","foreign_port":"BEIJING","customer":"VENUS REMEDIES","customerCountry":"INDIA","quantity":"10.00","actualQuantity":"10","unit":"KGS","unitRateFc":"2700","totalValueFC":"27257.4","currency":"USD","unitRateINR":"228420","date":"21-Sep-2024","totalValueINR":"2284200","totalValueInUsd":"27257.4","indian_port":"Delhi Air","hs_no":"29419090","bill_no":"5720820","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"BEIJING","supplierAddress":"13F\/E -8 BUILDING WESTPORT NEW TERR ITORIES NO.206 ZHENHUA RD,HANGZHOU 310030 Hangzhou, , CHINA CHINA","customerAddress":"S.C.O.857, CABIN NO. 10, 2ND FLOOR,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q4","strtotime":1731436200,"product":"METHOTREXATE","address":"NAIR BAUG, AKURLI ROAD","city":"MUMBAI ,MAHARASHTRA","supplier":"FERMION OY","supplierCountry":"FINLAND","foreign_port":"HELSINKI","customer":"BDH INDUSTRIES LIMITED","customerCountry":"INDIA","quantity":"73.40","actualQuantity":"73.4","unit":"KGS","unitRateFc":"3200","totalValueFC":"256762","currency":"EUR","unitRateINR":"295200","date":"13-Nov-2024","totalValueINR":"21667680","totalValueInUsd":"256762","indian_port":"Bombay Air","hs_no":"29335990","bill_no":"6648039","productDescription":"API","marketType":"REGULATED MARKET","country":"FINLAND","selfForZScoreResived":"Pharma Grade","supplierPort":"HELSINKI","supplierAddress":"KOIVU-MANKKAAN TIE 6 A P.O.BOX 28,F1-02101 ESPOO , FINLAND","customerAddress":"NAIR BAUG, AKURLI ROAD"}]
    19-Jan-2021
    13-Nov-2024
    KGS
    overview
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    Average Price (USD/KGS)

    Number of Transactions

    Total Quantity (KGS)

    Total Value (USD)

    Quantity (KGS) & Unit rate (USD/KGS) over time

    API Imports and Exports

    Importing Country Total Quantity
    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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    FDA Orange Book

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    01

    STRIDES PHARMA

    India
    arrow
    Antibody Engineering
    Not Confirmed
    • fda
    • EDQM
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    Virtual BoothStrides Pharma Science: Pioneering IP-driven formulations for niche finished dosage forms.

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    RLD : Yes

    TE Code :

    METHOTREXATE SODIUM

    Brand Name : METHOTREXATE SODIUM

    Dosage Form : TABLET;ORAL

    Dosage Strength : EQ 2.5MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    Approval Date : 1982-01-01

    Application Number : 8085

    RX/OTC/DISCN : DISCN

    RLD : Yes

    TE Code :

    Strides Pharma Science

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    02

    ABIC

    Israel
    Antibody Engineering
    Not Confirmed
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    ABIC

    Israel
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    Antibody Engineering
    Not Confirmed
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    RLD : No

    TE Code :

    METHOTREXATE SODIUM

    Brand Name : ABITREXATE

    Dosage Form : INJECTABLE;INJECTION

    Dosage Strength : EQ 100MG BASE/VIAL

    Approval Date : 1987-07-17

    Application Number : 89355

    RX/OTC/DISCN : DISCN

    RLD : No

    TE Code :

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    03

    ABRAXIS PHARM

    U.S.A
    Antibody Engineering
    Not Confirmed
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    ABRAXIS PHARM

    U.S.A
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    Antibody Engineering
    Not Confirmed
    • fda
    • EDQM
    • WHO-GMP
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    RLD : No

    TE Code :

    METHOTREXATE SODIUM

    Brand Name : METHOTREXATE SODIUM

    Dosage Form : INJECTABLE;INJECTION

    Dosage Strength : EQ 100MG BASE/VIAL

    Approval Date : 1985-10-11

    Application Number : 88937

    RX/OTC/DISCN : DISCN

    RLD : No

    TE Code :

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    04

    ALEMBIC

    India
    Antibody Engineering
    Not Confirmed
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    ALEMBIC

    India
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    Antibody Engineering
    Not Confirmed
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    RLD : No

    TE Code : AB

    METHOTREXATE SODIUM

    Brand Name : METHOTREXATE SODIUM

    Dosage Form : TABLET;ORAL

    Dosage Strength : EQ 2.5MG BASE

    Approval Date : 2024-06-03

    Application Number : 217552

    RX/OTC/DISCN : RX

    RLD : No

    TE Code : AB

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    05

    HIKMA

    United Kingdom
    Antibody Engineering
    Not Confirmed
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    HIKMA

    United Kingdom
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    Antibody Engineering
    Not Confirmed
    • fda
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    Digital Content Digital Content

    RLD : No

    TE Code :

    METHOTREXATE SODIUM

    Brand Name : METHOTREXATE SODIUM

    Dosage Form : INJECTABLE;INJECTION

    Dosage Strength : EQ 200MG BASE/8ML (EQ 25MG BASE/ML)

    Approval Date : 1986-09-16

    Application Number : 89342

    RX/OTC/DISCN : RX

    RLD : No

    TE Code :

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    06

    HOSPIRA

    U.S.A
    Antibody Engineering
    Not Confirmed
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    HOSPIRA

    U.S.A
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    Antibody Engineering
    Not Confirmed
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    RLD : Yes

    TE Code :

    METHOTREXATE SODIUM

    Brand Name : METHOTREXATE PRESERVATIVE FREE

    Dosage Form : INJECTABLE;INJECTION

    Dosage Strength : EQ 2.5GM BASE/100ML (EQ 25MG BASE/ML)

    Approval Date : 2005-04-13

    Application Number : 11719

    RX/OTC/DISCN : DISCN

    RLD : Yes

    TE Code :

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    07

    MEDEXUS

    Canada
    Antibody Engineering
    Not Confirmed
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    MEDEXUS

    Canada
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    Antibody Engineering
    Not Confirmed
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    RLD : Yes

    TE Code :

    METHOTREXATE

    Brand Name : RASUVO

    Dosage Form : SOLUTION;SUBCUTANEOUS

    Dosage Strength : 20MG/0.4ML (20MG/0.4ML)

    Approval Date : 2014-07-10

    Application Number : 205776

    RX/OTC/DISCN : RX

    RLD : Yes

    TE Code :

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    08

    NORBROOK

    United Kingdom
    Antibody Engineering
    Not Confirmed
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    NORBROOK

    United Kingdom
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    Antibody Engineering
    Not Confirmed
    • fda
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    RLD : No

    TE Code :

    METHOTREXATE SODIUM

    Brand Name : METHOTREXATE SODIUM

    Dosage Form : INJECTABLE;INJECTION

    Dosage Strength : EQ 25MG BASE/ML

    Approval Date : 1986-05-09

    Application Number : 88648

    RX/OTC/DISCN : DISCN

    RLD : No

    TE Code :

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    09

    NORDIC GRP

    France
    Antibody Engineering
    Not Confirmed
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    NORDIC GRP

    France
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    Antibody Engineering
    Not Confirmed
    • fda
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    RLD : Yes

    TE Code :

    METHOTREXATE

    Brand Name : REDITREX

    Dosage Form : SOLUTION;SUBCUTANEOUS

    Dosage Strength : 7.5MG/0.3ML (7.5MG/0.3ML)

    Approval Date : 2019-11-27

    Application Number : 210737

    RX/OTC/DISCN : DISCN

    RLD : Yes

    TE Code :

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    10

    PHARMACHEMIE BV

    Netherlands
    Antibody Engineering
    Not Confirmed
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    PHARMACHEMIE BV

    Netherlands
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    Antibody Engineering
    Not Confirmed
    • fda
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    Flag Netherlands
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    Digital Content Digital Content

    RLD : No

    TE Code : AP

    METHOTREXATE SODIUM

    Brand Name : METHOTREXATE SODIUM PRESERVATIVE FREE

    Dosage Form : INJECTABLE;INJECTION

    Dosage Strength : EQ 50MG BASE/2ML (EQ 25MG BASE/ML)

    Approval Date : 2010-01-11

    Application Number : 40843

    RX/OTC/DISCN : RX

    RLD : No

    TE Code : AP

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    Only 10 entries up to this point, click to access all click full view read-more
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    DRUG PRODUCT COMPOSITIONS

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    DOSAGE - INJECTABLE;INJECTION - EQ 100MG BASE...DOSAGE - INJECTABLE;INJECTION - EQ 100MG BASE/VIAL

    USFDA APPLICATION NUMBER - 11719

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    DOSAGE - INJECTABLE;INJECTION - EQ 1GM BASE/V...DOSAGE - INJECTABLE;INJECTION - EQ 1GM BASE/VIAL

    USFDA APPLICATION NUMBER - 11719

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    DOSAGE - INJECTABLE;INJECTION - EQ 1GM BASE/4...DOSAGE - INJECTABLE;INJECTION - EQ 1GM BASE/40ML (EQ 25MG BASE/ML)

    USFDA APPLICATION NUMBER - 11719

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    DOSAGE - INJECTABLE;INJECTION - EQ 2.5GM BASE...DOSAGE - INJECTABLE;INJECTION - EQ 2.5GM BASE/100ML (EQ 25MG BASE/ML)

    USFDA APPLICATION NUMBER - 11719

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    DOSAGE - INJECTABLE;INJECTION - EQ 2.5MG BASE...DOSAGE - INJECTABLE;INJECTION - EQ 2.5MG BASE/ML

    USFDA APPLICATION NUMBER - 11719

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    DOSAGE - INJECTABLE;INJECTION - EQ 20MG BASE/...DOSAGE - INJECTABLE;INJECTION - EQ 20MG BASE/VIAL

    USFDA APPLICATION NUMBER - 11719

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    DOSAGE - INJECTABLE;INJECTION - EQ 20MG BASE/...DOSAGE - INJECTABLE;INJECTION - EQ 20MG BASE/2ML (EQ 10MG BASE/ML)

    USFDA APPLICATION NUMBER - 11719

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    DOSAGE - INJECTABLE;INJECTION - EQ 25MG BASE/...DOSAGE - INJECTABLE;INJECTION - EQ 25MG BASE/ML

    USFDA APPLICATION NUMBER - 11719

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    DOSAGE - INJECTABLE;INJECTION - EQ 500MG BASE...DOSAGE - INJECTABLE;INJECTION - EQ 500MG BASE/20ML (EQ 25MG BASE/ML) **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 11719

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    DOSAGE - INJECTABLE;INJECTION - EQ 50MG BASE/...DOSAGE - INJECTABLE;INJECTION - EQ 50MG BASE/VIAL

    USFDA APPLICATION NUMBER - 11719

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    DOSAGE - INJECTABLE;INJECTION - EQ 50MG BASE/...DOSAGE - INJECTABLE;INJECTION - EQ 50MG BASE/2ML (EQ 25MG BASE/ML)

    USFDA APPLICATION NUMBER - 11719

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    DOSAGE - SOLUTION;SUBCUTANEOUS - 10MG/0.4ML (...DOSAGE - SOLUTION;SUBCUTANEOUS - 10MG/0.4ML (10MG/0.4ML)

    USFDA APPLICATION NUMBER - 210737

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    DOSAGE - SOLUTION;SUBCUTANEOUS - 12.5MG/0.5ML...DOSAGE - SOLUTION;SUBCUTANEOUS - 12.5MG/0.5ML (12.5MG/0.5ML)

    USFDA APPLICATION NUMBER - 210737

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    DOSAGE - SOLUTION;SUBCUTANEOUS - 15MG/0.6ML (...DOSAGE - SOLUTION;SUBCUTANEOUS - 15MG/0.6ML (15MG/0.6ML)

    USFDA APPLICATION NUMBER - 210737

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    DOSAGE - SOLUTION;SUBCUTANEOUS - 17.5MG/0.7ML...DOSAGE - SOLUTION;SUBCUTANEOUS - 17.5MG/0.7ML (17.5MG/0.7ML)

    USFDA APPLICATION NUMBER - 210737

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    DOSAGE - SOLUTION;SUBCUTANEOUS - 20MG/0.8ML (...DOSAGE - SOLUTION;SUBCUTANEOUS - 20MG/0.8ML (20MG/0.8ML)

    USFDA APPLICATION NUMBER - 210737

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    DOSAGE - SOLUTION;SUBCUTANEOUS - 22.5MG/ML (2...DOSAGE - SOLUTION;SUBCUTANEOUS - 22.5MG/ML (22.5MG/ML)

    USFDA APPLICATION NUMBER - 210737

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    DOSAGE - SOLUTION;SUBCUTANEOUS - 25MG/1ML (25...DOSAGE - SOLUTION;SUBCUTANEOUS - 25MG/1ML (25MG/1ML)

    USFDA APPLICATION NUMBER - 210737

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    DOSAGE - SOLUTION;SUBCUTANEOUS - 7.5MG/0.3ML ...DOSAGE - SOLUTION;SUBCUTANEOUS - 7.5MG/0.3ML (7.5MG/0.3ML)

    USFDA APPLICATION NUMBER - 210737

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    DOSAGE - TABLET;ORAL - EQ 2.5MG BASE **Federa...DOSAGE - TABLET;ORAL - EQ 2.5MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 8085

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