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    Chemistry

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    Also known as: 738-70-5, Proloprim, Trimpex, Trimetoprim, Bactramin, Monotrim
    Molecular Formula
    C14H18N4O3
    Molecular Weight
    290.32  g/mol
    InChI Key
    IEDVJHCEMCRBQM-UHFFFAOYSA-N
    FDA UNII
    AN164J8Y0X
    Trimethoprim
    A pyrimidine inhibitor of dihydrofolate reductase, it is an antibacterial related to PYRIMETHAMINE. It is potentiated by SULFONAMIDES and the TRIMETHOPRIM, SULFAMETHOXAZOLE DRUG COMBINATION is the form most often used. It is sometimes used alone as an antimalarial. TRIMETHOPRIM RESISTANCE has been reported.
    Trimethoprim is a Dihydrofolate Reductase Inhibitor Antibacterial. The mechanism of action of trimethoprim is as a Dihydrofolate Reductase Inhibitor, and Cytochrome P450 2C8 Inhibitor, and Organic Cation Transporter 2 Inhibitor.
    1 2D Structure

    Trimethoprim

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine
    2.1.2 InChI
    InChI=1S/C14H18N4O3/c1-19-10-5-8(6-11(20-2)12(10)21-3)4-9-7-17-14(16)18-13(9)15/h5-7H,4H2,1-3H3,(H4,15,16,17,18)
    2.1.3 InChI Key
    IEDVJHCEMCRBQM-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    COC1=CC(=CC(=C1OC)OC)CC2=CN=C(N=C2N)N
    2.2 Other Identifiers
    2.2.1 UNII
    AN164J8Y0X
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Proloprim

    2. Trimpex

    2.3.2 Depositor-Supplied Synonyms

    1. 738-70-5

    2. Proloprim

    3. Trimpex

    4. Trimetoprim

    5. Bactramin

    6. Monotrim

    7. Monotrimin

    8. Trimopan

    9. Wellcoprim

    10. 2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine

    11. Monoprim

    12. Syraprim

    13. Trimanyl

    14. Triprim

    15. Uretrim

    16. 5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine

    17. Trimethoprimum

    18. Trimethoprime

    19. 5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine

    20. Nsc-106568

    21. Nih 204

    22. Primsol

    23. Component Of Bactrim

    24. Bw 56-72

    25. 2,4-pyrimidinediamine, 5-[(3,4,5-trimethoxyphenyl)methyl]-

    26. Infectotrimet

    27. Polytrim

    28. Tcmdc-125538

    29. 5-(3,4,5-trimethoxybenzyl)-2,4-pyrimidinediamine

    30. Trimethoprim-d9

    31. 5-[(3,4,5-trimethoxyphenyl)methyl]-2,4-pyrimidinediamine

    32. Nsc 106568

    33. 5-(3,4,5-trimethoxybenzyl)-2,4-diaminopyrimidine

    34. Bw-56-72

    35. Chebi:45924

    36. Chembl22

    37. Trimpex (tn)

    38. 2,4-pyrimidinediamine, 5-((3,4,5-trimethoxyphenyl)methyl)-

    39. Abaprim

    40. Mfcd00036761

    41. Apo-sulfatrim

    42. Bw 5672

    43. Pyrimidine, 2,4-diamino-5-(3,4,5-trimethoxybenzyl)-

    44. Mls000079023

    45. An164j8y0x

    46. Briscotrim

    47. Novotrimel

    48. Streptoplus

    49. Sulfoxaprim

    50. Trimethioprim

    51. Urobactrim

    52. Wellcoprin

    53. Anitrim

    54. Antrima

    55. Antrimox

    56. Bacidal

    57. Bacticel

    58. Bactoprim

    59. Bencole

    60. Bethaprim

    61. Biosulten

    62. Chemotrin

    63. Colizole

    64. Conprim

    65. Cotrimel

    66. Duocide

    67. Esbesul

    68. Espectrin

    69. Euctrim

    70. Exbesul

    71. Fermagex

    72. Fortrim

    73. Ikaprim

    74. Kombinax

    75. Lagatrim

    76. Lastrim

    77. Metoprim

    78. Pancidim

    79. Protrin

    80. Resprim

    81. Salvatrim

    82. Setprin

    83. Sinotrim

    84. Sugaprim

    85. Sulfamar

    86. Sulthrim

    87. Sultrex

    88. Trimexol

    89. Trimezol

    90. Trimono

    91. Trisulcom

    92. Trisulfam

    93. Trisural

    94. Utetrin

    95. Velaten

    96. Xeroprim

    97. Zamboprim

    98. 2,4-pyrimidinediamine, 5-((3,4,5-trimethoxyphenyl)-methyl)-

    99. Bacdan

    100. Bacide

    101. Deprim

    102. Omstat

    103. Purbal

    104. Roubac

    105. Roubal

    106. Stopan

    107. Toprim

    108. Trisul

    109. Bacin

    110. Bacta

    111. Futin

    112. Nih-204

    113. Trimpex 200

    114. Co-trimoxizole

    115. Lagatrim Forte

    116. Septrin Forte

    117. Alcorim-f

    118. Colizole Ds

    119. Septrin S

    120. Septrin Ds

    121. Smz-tmp

    122. Nsc106568

    123. Trimez-ifsa

    124. U-prin

    125. Component Of Septra

    126. Ncgc00016055-05

    127. Trimethopriom

    128. 5-((3,4,5-trimethoxyphenyl)methyl)-2,4-pyrimidinediamine

    129. Bactifor

    130. Cas-738-70-5

    131. Dosulfin

    132. Instalac

    133. Smr000035999

    134. Trimetoprim [dcit]

    135. Trimogal

    136. Lescot

    137. Tiempe

    138. Trimetoprim [polish]

    139. Resprim Forte

    140. Trimethoprim 100 Microg/ml In Acetonitrile

    141. Uro-d S

    142. Dsstox_cid_3712

    143. Tmp Smx

    144. Dsstox_rid_77158

    145. Dsstox_gsid_23712

    146. 5-(3,4,5-trimethoxy-benzyl)-pyrimidine-2,4-diamine

    147. Trimethoprime [inn-french]

    148. Trimethoprimum [inn-latin]

    149. Trimetoprima [inn-spanish]

    150. 2,4-diamino-5-(3',4',5'-trimethoxybenzyl)pyrimidine

    151. Bacterial [antibiotic]

    152. Nih 204 (van)

    153. Trimethoprim D3 (4-methoxy D3)

    154. Proloprim (tn)

    155. Wr 5949

    156. Ccris 2410

    157. Hsdb 6781

    158. Sr-01000075652

    159. Einecs 212-006-2

    160. 5-(3, 4, 5-trimethoxybenzyl)-2, 4-pyrimidinediamine

    161. Brn 0625127

    162. Unii-an164j8y0x

    163. Trimethoprim (jan/usp/inn)

    164. 5-{[3,4,5-tris(methyloxy)phenyl]methyl}pyrimidine-2,4-diamine

    165. Ai3-52594

    166. Trimethoprim D3 (4-methoxy D3) 100 Microg/ml In Acetonitrile

    167. B-lock

    168. Kuc103659n

    169. Trimethoprim,(s)

    170. Prestwick_485

    171. Ksc-4-158

    172. Trimethoprim (tmp)

    173. Bactrim (salt/mix)

    174. Azt + Tmp/smx (mixture) Combination

    175. Spectrum_000167

    176. Tocris-0650

    177. Trimethoprim [usan:usp:inn:ban:jan]

    178. 2w9h

    179. 3fl9

    180. 3n0h

    181. 3s3v

    182. 4km2

    183. Opera_id_1760

    184. Prestwick0_000208

    185. Prestwick1_000208

    186. Prestwick2_000208

    187. Prestwick3_000208

    188. Spectrum2_000937

    189. Spectrum3_000643

    190. Spectrum4_000372

    191. Spectrum5_001559

    192. Lopac-t-7883

    193. Trimethoprim [mi]

    194. Trimethoprim [inn]

    195. Trimethoprim [jan]

    196. Epitope Id:119684

    197. Upcmld-dp132

    198. T 7883

    199. Trimethoprim [hsdb]

    200. Trimethoprim [usan]

    201. Trimethoprim [vandf]

    202. Lopac0_001271

    203. Oprea1_495058

    204. Schembl24506

    205. Bspbio_000195

    206. Bspbio_002245

    207. Kbiogr_000863

    208. Kbioss_000647

    209. Trimethoprim [mart.]

    210. 5-25-13-00429 (beilstein Handbook Reference)

    211. Mls001201740

    212. Mls002303068

    213. Mls002548881

    214. Bidd:gt0190

    215. Divk1c_000589

    216. Spectrum1500595

    217. Trimethoprim [usp-rs]

    218. Trimethoprim [who-dd]

    219. Spbio_000874

    220. Spbio_002116

    221. Bpbio1_000215

    222. Dtxsid3023712

    223. Upcmld-dp132:001

    224. Bdbm18069

    225. Gtpl10931

    226. Hms501n11

    227. Kbio1_000589

    228. Kbio2_000647

    229. Kbio2_003215

    230. Kbio2_005783

    231. Kbio3_001465

    232. Trimethoprim [green Book]

    233. Trimethoprim, >=98% (hplc)

    234. Ninds_000589

    235. 2,4,5-trimethoxybenzyl)pyrimidine

    236. Hms1568j17

    237. Hms1921i03

    238. Hms2090d14

    239. Hms2092a10

    240. Hms2095j17

    241. Hms2230l06

    242. Hms3259i11

    243. Hms3263p04

    244. Hms3371o18

    245. Hms3652e03

    246. Hms3712j17

    247. Pharmakon1600-01500595

    248. Trimethoprim [ep Impurity]

    249. Trimethoprim [orange Book]

    250. Trimethoprim For System Suitability

    251. Trimethoprim [ep Monograph]

    252. 2,4,5-trimethoxyphenzyl)pyrimidine

    253. Albb-028968

    254. Bcp12148

    255. Cotrim Component Trimethoprim

    256. Hy-b0510

    257. Septra Component Trimethoprim

    258. Zinc6627681

    259. Co-trimoxazole Component Trimethoprim

    260. Tox21_110291

    261. Tox21_200157

    262. Tox21_501271

    263. Trimethoprim [usp Monograph]

    264. Bactrim Component Trimethoprim

    265. Bbl005584

    266. Ccg-40335

    267. Nsc752719

    268. Nsc757370

    269. S3129

    270. Stk177322

    271. Stl455117

    272. Uroplus Component Trimethoprim

    273. Trimethoprimum [who-ip Latin]

    274. Akos001650069

    275. Sulfatrim Component Trimethoprim

    276. Sulmeprim Component Trimethoprim

    277. Tox21_110291_1

    278. Ac-8427

    279. Bw-5672

    280. Db00440

    281. Ks-1145

    282. Lp01271

    283. Nc00483

    284. Nsc-752719

    285. Nsc-757370

    286. Sdccgsbi-0051237.p004

    287. Trimethoprim Component Of Cotrim

    288. Trimethoprim Component Of Septra

    289. Bactrim Ds Component Trimethoprim

    290. Idi1_000589

    291. Smp2_000262

    292. Trimethoprim 100 Microg/ml In Methanol

    293. Trimethoprim Component Of Bactrim

    294. Trimethoprim Component Of Uroplus

    295. Ncgc00016055-01

    296. Ncgc00016055-02

    297. Ncgc00016055-03

    298. Ncgc00016055-04

    299. Ncgc00016055-06

    300. Ncgc00016055-07

    301. Ncgc00016055-08

    302. Ncgc00016055-09

    303. Ncgc00016055-10

    304. Ncgc00016055-11

    305. Ncgc00016055-12

    306. Ncgc00016055-13

    307. Ncgc00016055-14

    308. Ncgc00016055-16

    309. Ncgc00016055-17

    310. Ncgc00016055-27

    311. Ncgc00024707-01

    312. Ncgc00024707-03

    313. Ncgc00024707-04

    314. Ncgc00024707-05

    315. Ncgc00024707-06

    316. Ncgc00024707-07

    317. Ncgc00024707-08

    318. Ncgc00257711-01

    319. Ncgc00261956-01

    320. Cotrim D.s. Component Trimethoprim

    321. Sy031734

    322. Trimethoprim Component Of Sulfatrim

    323. Trimethoprim Component Of Sulmeprim

    324. Trimethoprim/sulfamethoxazole (commercial)

    325. Sbi-0051237.p003

    326. Db-055812

    327. Sulfamethoprim Component Trimethoprim

    328. Trimethoprim Component Of Bactrim Ds

    329. 2, 5-[(3,4,5-trimethoxyphenyl)methyl]-

    330. Ab00052118

    331. Bb 0258034

    332. Eu-0101271

    333. Ft-0601630

    334. Ft-0675578

    335. Ft-0675579

    336. Ft-0675580

    337. Sw196690-3

    338. T2286

    339. Trimethoprim 1000 Microg/ml In Acetonitrile

    340. Trimethoprim Component Of Cotrim D.s.

    341. Bactrim Pediatric Component Trimethoprim

    342. C01965

    343. D00145

    344. Trimethoprim Component Of Sulfamethoprim

    345. Trimethoprim, Crystallized, >=99.0% (hplc)

    346. Wln: T6n Cnj Bz Dz E1r Co1 Do1 Eo1

    347. 5-(3,5-trimethoxybenzyl)-2,4-diaminopyrimidine

    348. Ab00052118-30

    349. Ab00052118-32

    350. Ab00052118_33

    351. Ab00052118_34

    352. Trimethoprim, Vetranal(tm), Analytical Standard

    353. 738t705

    354. Formulated Trimethoprim (nsc 106568) In Ethanol

    355. Q422665

    356. Trimethoprim Component Of Bactrim Pediatric

    357. 2,4-diamino-5-(3,4,5-trimethoxybenzyl) Pyrimidine

    358. 2,4-diamino-5-(3,4,5-trimethoxybenzyl)-pyrimidine

    359. Pyrimidine,4-diamino-5-(3,4,5-trimethoxybenzyl)-

    360. Sr-01000075652-1

    361. Sr-01000075652-3

    362. Sr-01000075652-6

    363. W-104441

    364. 5-(3,4,5-trimethoxybenzyl)-2,4-pyrimidinediamine #

    365. Brd-k07208025-001-06-5

    366. Sr-01000075652-10

    367. 2-amino-5-(3,4,5-trimethoxybenzyl)-4-pyrimidinylamine

    368. F0914-5266

    369. Trimethoprim, Certified Reference Material, Tracecert(r)

    370. Z1522566629

    371. 5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4(1h,3h)-diimine

    372. Trimethoprim, British Pharmacopoeia (bp) Reference Standard

    373. Trimethoprim, European Pharmacopoeia (ep) Reference Standard

    374. Trimethoprim, United States Pharmacopeia (usp) Reference Standard

    375. Trimethoprim For System Suitability, European Pharmacopoeia (ep) Reference Standard

    376. Trimethoprim, Pharmaceutical Secondary Standard; Certified Reference Material

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 290.32 g/mol
    Molecular Formula C14H18N4O3
    XLogP30.9
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count5
    Exact Mass290.13789045 g/mol
    Monoisotopic Mass290.13789045 g/mol
    Topological Polar Surface Area106 Ų
    Heavy Atom Count21
    Formal Charge0
    Complexity307
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    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 6  
    Drug NamePolytrim
    PubMed HealthTrimethoprim (By mouth)
    Drug ClassesAntibiotic, Antiseptic
    Active Ingredienttrimethoprim sulfate; Polymyxin b sulfate
    Dosage FormSolution/drops
    RouteOphthalmic
    Strength10,000 units/ml; eq 1mg base/ml
    Market StatusPrescription
    CompanyAllergan

    2 of 6  
    Drug NamePrimsol
    PubMed HealthTrimethoprim (By mouth)
    Drug ClassesAntibiotic, Antiseptic
    Active IngredientTrimethoprim hydrochloride
    Dosage FormSolution
    RouteOral
    Strengtheq 50mg base/5ml
    Market StatusPrescription
    CompanyFsc

    3 of 6  
    Drug NameTrimethoprim
    Drug LabelTrimethoprim is a synthetic antibacterial available as 100 mg tablets for oral administration.Trimethoprim is 2,4-Diamino-5-(3,4,5-trimethoxybenzyl) pyrimidine. It is a white to cream colored, odorless, bitter compound. The structural formula is repr...
    Active IngredientTrimethoprim
    Dosage FormTablet
    RouteOral
    Strength100mg
    Market StatusPrescription
    CompanyTeva; Novel Labs; Watson Labs

    4 of 6  
    Drug NamePolytrim
    PubMed HealthTrimethoprim (By mouth)
    Drug ClassesAntibiotic, Antiseptic
    Active Ingredienttrimethoprim sulfate; Polymyxin b sulfate
    Dosage FormSolution/drops
    RouteOphthalmic
    Strength10,000 units/ml; eq 1mg base/ml
    Market StatusPrescription
    CompanyAllergan

    5 of 6  
    Drug NamePrimsol
    PubMed HealthTrimethoprim (By mouth)
    Drug ClassesAntibiotic, Antiseptic
    Active IngredientTrimethoprim hydrochloride
    Dosage FormSolution
    RouteOral
    Strengtheq 50mg base/5ml
    Market StatusPrescription
    CompanyFsc

    6 of 6  
    Drug NameTrimethoprim
    Drug LabelTrimethoprim is a synthetic antibacterial available as 100 mg tablets for oral administration.Trimethoprim is 2,4-Diamino-5-(3,4,5-trimethoxybenzyl) pyrimidine. It is a white to cream colored, odorless, bitter compound. The structural formula is repr...
    Active IngredientTrimethoprim
    Dosage FormTablet
    RouteOral
    Strength100mg
    Market StatusPrescription
    CompanyTeva; Novel Labs; Watson Labs

    4.2 Therapeutic Uses

    Anti-Infective Agents, Urinary; Antimalarials; Antimetabolites; Folic Acid Antagonists

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

    Trimethoprim given alone has also been effective for urinary tract infections, but the development of resistant organisms limits the usefulness of this treatment.

    Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1056

    Trimethoprim is indicated in the treatment of initial, uncomplicated urinary tract infections caused by susceptible strains of Escherichia coli, Proteus mirabilis, Klebsiella pneumoniae, Enterobacter species, & coagulase-negative Staphylococcus species, including Staphylococcus saprophyticus. /Included in US product labeling/

    MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 22nd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2002. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 2848

    trimethoprim is used in the prophylaxis of bacterial urinary tract infections. /NOT included in US product labeling/

    MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 22nd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2002. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 2848

    For more Therapeutic Uses (Complete) data for TRIMETHOPRIM (8 total), please visit the HSDB record page.

    4.3 Drug Warning

    Because trimethoprim may interfere with folic acid metabolism, the drug should be used with caution in nursing women.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 842

    Adverse GI reactions occur in approximately 6% of patients receiving trimethoprim and may include epigastric discomfort, nausea, vomiting, glossitis, and abnormal taste sensation. Elevations in serum aminotransferase (transaminase) and bilirubin concentrations have been reported in patients receiving the drug, but the clinical importance of these findings is not known. Cholestatic jaundice has been reported rarely.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 842

    The most frequent adverse effects of trimethoprim are rash and pruritus. Mild to moderate rashes appearing 7-14 days after initiation of trimethoprim therapy reportedly occur in 2.9-6.7% of patients receiving 200 mg of the drug daily. Rashes are generally maculopapular, morbilliform, and pruritic. Rashes have been reported to occur in up to 24% of patients receiving 400 mg or more trimethoprim for 14 days. Photosensitivity (e.g., erythematous phototoxic eruptions with subsequent hyperpigmentation of sun-exposed skin) also has occurred. Exfoliative dermatitis, toxic epidermal necrolysis (Lyell's syndrome), erythema multiforme, and Stevens-Johnson syndrome have been reported rarely in patients receiving the drug. Anaphylaxis also has occurred rarely.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 842

    Safety and efficacy of trimethoprim in infants younger than 2 months of age and efficacy of the drug when used as single agent in children younger than 12 years of age have not been established. Trimethoprim should be used with caution in children who have the fragile X chromosome associated with mental retardation, because folate depletion may worsen the psychomotor regression associated with the disorder.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 842

    For more Drug Warnings (Complete) data for TRIMETHOPRIM (28 total), please visit the HSDB record page.

    4.4 Drug Indication

    As a monotherapy, trimethoprim is indicated for the treatment of acute episodes of uncomplicated urinary tract infections caused by susceptible bacteria, including _E. coli._, _K. pneumoniae_, _Enterobacter spp._, _P. mirabilis_, and coagulase-negative _Staphylococcus_ species. In various formulations in combination with [sulfamethoxazole], trimethoprim is indicated for the following infections caused by bacteria with documented susceptibility: urinary tract infections, acute otitis media in pediatric patients (when clinically indicated), acute exacerbations of chronic bronchitis in adults, enteritis caused by susceptible _Shigella_, prophylaxis and treatment of _Pneumocystis jiroveci_ pneumonia, and travelers' diarrhea caused by enterotoxigenic _E. coli_. Trimethoprim is available as an ophthalmic solution in combination with [polymyxin B] for the treatment of acute bacterial conjunctivitis, blepharitis, and blepharoconjunctivitis caused by susceptible bacteria.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Trimethoprim exerts its antimicrobial effects by inhibiting an essential step in the synthesis of bacterial nucleic acids and proteins. It has shown activity against several species of gram-negative bacteria, as well as coagulase-negative _Staphylococcus_ species. Resistance to trimethoprim may arise via a variety of mechanisms, including alterations to the bacterial cell wall, overproduction of dihydrofolate reductase, or production of resistant dihydrofolate reductase. Rarely, trimethoprim can precipitate the development of blood disorders (e.g. thrombocytopenia, leukopenia, etc.) which may be preceded by symptoms such as sore throat, fever, pallor, and or purpura - patients should be monitored closely for the development of these symptoms throught the course of therapy. As antimicrobial susceptibility patterns are geographically distinct, local antibiograms should be consulted to ensure adequate coverage of relevant pathogens prior to use.

    5.2 MeSH Pharmacological Classification

    Cytochrome P-450 CYP2C8 Inhibitors

    Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 CYP2C8. (See all compounds classified as Cytochrome P-450 CYP2C8 Inhibitors.)

    Anti-Infective Agents, Urinary

    Substances capable of killing agents causing urinary tract infections or of preventing them from spreading. (See all compounds classified as Anti-Infective Agents, Urinary.)

    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.)

    Antimalarials

    Agents used in the treatment of malaria. They are usually classified on the basis of their action against plasmodia at different stages in their life cycle in the human. (From AMA, Drug Evaluations Annual, 1992, p1585) (See all compounds classified as Antimalarials.)

    Anti-Dyskinesia Agents

    Drugs used in the treatment of movement disorders. Most of these act centrally on dopaminergic or cholinergic systems. Among the most important clinically are those used for the treatment of Parkinson disease (ANTIPARKINSON AGENTS) and those for the tardive dyskinesias. (See all compounds classified as Anti-Dyskinesia Agents.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    TRIMETHOPRIM
    5.3.2 FDA UNII
    AN164J8Y0X
    5.3.3 Pharmacological Classes
    Dihydrofolate Reductase Inhibitor Antibacterial [EPC]; Dihydrofolate Reductase Inhibitors [MoA]; Organic Cation Transporter 2 Inhibitors [MoA]; Cytochrome P450 2C8 Inhibitors [MoA]
    5.4 ATC Code

    J01EE01

    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

    J - Antiinfectives for systemic use

    J01 - Antibacterials for systemic use

    J01E - Sulfonamides and trimethoprim

    J01EA - Trimethoprim and derivatives

    J01EA01 - Trimethoprim

    5.5 Absorption, Distribution and Excretion

    Absorption

    Steady-state concentrations are achieved after approximately 3 days of repeat administration. Average peak serum concentrations of approximately 1 g/mL (Cmax) are achieved within 1 to 4 hours (Tmax) following the administration of a single 100mg dose. Trimethoprim appears to follow first-order pharmacokinetics, as a single 200mg dose results in serum concentrations approximately double that of a 100mg dose. The steady-state AUC of orally administered trimethoprim is approximately 30 mg/Lh.

    Route of Elimination

    Approximately 10-20% of an ingested trimethoprim dose is metabolized, primarily in the liver, while a large portion of the remainder is excreted unchanged in the urine. Following oral administration, 50% to 60% of trimethoprim is excreted in the urine within 24 hours, approximately 80% of which is unchanged parent drug.

    Volume of Distribution

    Trimethoprim is extensively distributed into various tissues following oral administration. It distributes well into sputum, middle ear fluid, and bronchial secretions. Trimethoprim distributes efficiently into vaginal fluids, with observed concentrations approximately 1.6-fold higher than those seen in the serum. It may pass the placental barrier and into breast milk. Trimethoprim is also sufficiently excreted in the feces to markedly reduce and/or eliminate trimethoprim-susceptible fecal flora.

    Clearance

    Following oral administration, the renal clearance of trimethoprim has been variably reported between 51.7 - 91.3 mL/min.

    Trimethoprim is widely distributed into body tissues & fluids including the aqueous humor, middle ear fluid, saliva, lung tissue, sputum, seminal fluid, prostatic tissue & fluid, vaginal secretions, bile, bone, & /cerebrospinal fluid/. The apparent volume of distribution of trimethoprim in adults with normal renal function ranges from 100-120 l. ... Trimethoprim is 42-46% bound to plasma proteins. Trimethoprim readily crosses the placenta, & amniotic fluid concns are reported to be 80% of concurrent maternal serum concns.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 843

    Only small amounts of trimethoprim are excreted in feces via biliary elimination. Trimethoprim may be moderately removed by hemodialysis.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 844

    Trimethoprim is readily & almost completely absorbed from the GI tract. Peak serum concns of approx 1, 1.6, & 2 ug/ml are reached in 1-4 hr after single 100-, 160-, & 200 mg oral doses of trimethoprim. Following multiple-dose oral admin, steady-state peak serum concns of trimethoprim usually are 50% greater than those obtained after single-dose admin of the drug. Steady-state serum concns range from 1.2-3.2 ug/ml following oral admin of 160 mg of trimethoprim every 12 hr in adults with renal function.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 843

    Rapidly and widely distributed to various tissues and fluids, including kidneys, liver, spleen, bronchial secretions, saliva, and seminal fluid. Trimethoprim has also been demonstrated in bile; aqueous humor; bone marrow and spongy, but not compact, bone.

    MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 22nd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2002. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 2849

    For more Absorption, Distribution and Excretion (Complete) data for TRIMETHOPRIM (12 total), please visit the HSDB record page.

    5.6 Metabolism/Metabolites

    Trimethoprim undergoes oxidative metabolism to a number of metabolites, the most abundant of which are the demethylated 3'- and 4'- metabolites, accounting for approximately 65% and 25% of the total metabolite formation, respectively. Minor products include N-oxide metabolites (<5%) and benzylic metabolites in even smaller quantities. The parent drug is considered to be the therapeutically active form. The majority of trimethoprim biotransformation appears to involve CYP2C9 and CYP3A4 enzymes, with CYP1A2 contributing to a lesser extent.

    Trimethoprim is metabolized in the liver to oxide and hydroxylated metabolites ... .

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 844

    The pharmacokinetics were studied of sulfadimethoxine (SDM) or sulfamethoxazole (SMX) in combination with trimethoprim (TMP) administered as a single oral dose (25 mg + 5 mg/kg bw) to 2 groups of 6 healthy pigs. The elimination half-lives of SMX & TMP were quite similar (2-3 hr); SDM had a relatively long half-life of 13 hr. Both sulfonamides (S) were exclusively metabolized to N4-acetyl derivatives but to different extents. The main metabolic pathway for TMP was O-demethylation & subsequent conjugation. In addition, the plasma concns of these drugs & their main metabolites after medication with different in-feed concns were determined. The drug (S:TMP) concns in the feed were 250:50, 500:100, & 1000:200 mg/kg. Steady-state concns were achieved within 48 hr of feed medication, twice daily (SDM+TMP) or 3 times/day (SMX+TMP). Protein binding of SDM & its metabolite was high (>93%), whereas SMX, TMP & their metabolites showed moderate binding (48-75%). Feed medication with 500 ppm sulfonamide combined with 100 ppm TMP provided minimum steady-state plasma concns (C(ss,min)) higher than the concn required for inhibition of the growth of 90% of Actinobacillus pleuropneumoniae strains (n=20).

    Mengelers MF, et al; Vet Res Commun 25 (6): 461-481. 2001.

    5.7 Biological Half-Life

    Trimethoprim half-life ranges from 8-10 hours, but may be prolonged in patients with renal dysfunction.

    Trimethoprim has a serum half-life of approx 8-11 hr in adults with normal renal function. In adults with creatinine clearances of 10-30 or 0-10 ml/min, serum half-life of the drug may incr to 15 hr or >26 hr, respectively. Trimethoprim serum half-lives of about 7.7 & 5.5 hr have been reported in children <1 yr of age & between 1 & 10 yr of age, respectively.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 843

    5.8 Mechanism of Action

    Trimethoprim is a reversible inhibitor of dihydrofolate reductase, one of the principal enzymes catalyzing the formation of tetrahydrofolic acid (THF) from dihydrofolic acid (DHF). Tetrahydrofolic acid is necessary for the biosynthesis of bacterial nucleic acids and proteins and ultimately for continued bacterial survival - inhibiting its synthesis, then, results in bactericidal activity. Trimethoprim binds with a much stronger affinity to bacterial dihydrofolate reductase as compared to its mammalian counterpart, allowing trimethoprim to selectively interfere with bacterial biosynthetic processes. Trimethoprim is often given in combination with sulfamethoxazole, which inhibits the preceding step in bacterial protein synthesis - given together, sulfamethoxazole and trimethoprim inhibit two consecutive steps in the biosynthesis of bacterial nucleic acids and proteins. As a monotherapy trimethoprim is considered bacteriostatic, but in combination with sulfamethoxazole is thought to exert bactericidal activity.

    Trimethoprim is a bacteriostatic lipophilic weak base structurally related to pyrimethamine. It binds to and reversibly inhibits the bacterial enzyme dihydrofolate reductase, selectively blocking conversion of dihydrofolic acid to its functional form, tetrahydrofolic acid. This depletes folate, an essential cofactor in the biosynthesis of nucleic acids, resulting in interference with bacterial nucleic acid and protein production. Bacterial dihydrofolate reductase is approximately 50,000 to 60,000 times more tightly bound by trimethoprim than is the corresponding mammalian enzyme.

    US Pharmacopeial Convention; US Pharmacopeia Dispensing Information (USP DI); Drug Information for the Health Care Professional 12th ed, V.IB p.2531 (1992)

    To determine the incidence & severity of hyperkalemia during trimethoprim therapy, 30 consecutive patients with acquired immunodeficiency syndrome receiving high-dose (20 mg/kg/day) trimethoprim were studied; in addition, the mechanism of trimethoprim-induced hyperkalemia was investigated in rats. Trimethoprim increased serum potassium concn by 0.6 mmol/l despite normal adrenocortical function & glomerular filtration rate. Serum potassium levels >5 mmol/l were observed during trimethoprim treatment in 15 of 30 patients. In rats, iv trimethoprim inhibited renal potassium excretion by 40% & increased sodium excretion by 46%. It was concluded that trimethoprim blocks apical membrane sodium channels in the mammalian distal nephron. As a consequence, the transepithelial voltage is reduced & potassium secretion is inhibited. Decreased renal potassium excretion secondary to these direct effects on kidney tubules leads to hyperkalemia in a substantial number of patients being treated with trimethoprim-containing drugs.

    PMID:8328738 Velazquez H, et al; Ann. Intern. Med. 119 (Aug 15): 296-301 (1993)

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D6 D8, SY.NO. 234\/2,234\/3,","city":"TURKAPALLY(V),SHAMEERPET, HYDERABAD","supplier":"USP","supplierCountry":"INDIA","foreign_port":"WASHINGTON, DULLES I","customer":"UNITED STATES PHARMACOPEIA - INDIA PRIVATE LIMITED","customerCountry":"INDIA","quantity":"0.00","actualQuantity":"0.00005","unit":"KGS","unitRateFc":"36120000","totalValueFC":"1977.1","currency":"USD","unitRateINR":"3280919000","date":"08-Feb-2024","totalValueINR":"164045.95","totalValueInUsd":"1977.1","indian_port":"Hyderabad Air","hs_no":"29335990","bill_no":"2041880","productDescription":"Re-Import","marketType":"REGULATED MARKET","country":"INDIA","selfForZScoreResived":"Pharma Grade","supplierPort":"WASHINGTON, DULLES I","supplierAddress":"7135 ENGLISH MUFFIN WAY FREDERICK,MD 21704 USA Frederick, , United States United States","customerAddress":"P.NO. D6 D8, SY.NO. 234\/2,234\/3,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q1","strtotime":1707935400,"product":"TRIMETHOPRIM PH EUR","address":"564\/A\/22, ROAD NO.92","city":"HYDERABAD,ANDHRA PRADESH","supplier":"SHOUGUANG FUKANG PHARMACEUTICAL CO., LTD","supplierCountry":"CHINA","foreign_port":"SHANGHAI","customer":"VIATRIS","customerCountry":"INDIA","quantity":"320.00","actualQuantity":"320","unit":"KGS","unitRateFc":"34.9","totalValueFC":"11331.8","currency":"USD","unitRateINR":"2938.3","date":"15-Feb-2024","totalValueINR":"940240","totalValueInUsd":"11331.8","indian_port":"Indore-EPZ\/SEZ","hs_no":"29335920","bill_no":"1001056","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"SHANGHAI","supplierAddress":"NORTH-EAST OF DONGWAIHUAN ROAD,DONG CHENG INDUSTRIAL AREA,SHOUGUANG CIT Y, SHANDONG PROVINCE CHINA","customerAddress":"564\/A\/22, ROAD NO.92"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1713465000,"product":"(FOC) - TRIMETHOPRIM USP-NF - A-50112403050","address":"REGD. OFFICE: NO. 16\/2,","city":"BANGALORE, KARNATAKA","supplier":"SINOBRIGHT PHARMACEUTICAL COMPANY LTD","supplierCountry":"CHINA","foreign_port":"SHANGHAI","customer":"SOMERSET THERAPEUTICS LIMITED","customerCountry":"INDIA","quantity":"150.00","actualQuantity":"150","unit":"KGS","unitRateFc":"65","totalValueFC":"9854.2","currency":"USD","unitRateINR":"5486","date":"19-Apr-2024","totalValueINR":"822900","totalValueInUsd":"9854.2","indian_port":"Bangalore Air","hs_no":"29335920","bill_no":"3097502","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"SHANGHAI","supplierAddress":"OFFICE F 32\/F PLAZA 88 NO 88 YEUNGUK ROAD TSUEN WAN NT HONGHONG CHINAShanghai, , China China","customerAddress":"REGD. OFFICE: NO. 16\/2,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1715970600,"product":"TRIMETHOPRIM-IUPAC NAME:5-(3,4,5-TRIMETHOXYBENZYL) PYRIMIDINE-2,4-DIAMINE CAS NUMBER:738-70-5","address":"7\/1,CORPORATE PARK,SION-TROMBAY","city":"MUMBAI","supplier":"ASTARPHARM LIMITED.","supplierCountry":"CHINA","foreign_port":"BEIJING","customer":"FLAMINGO PHARMACEUTICALS LIMITED","customerCountry":"INDIA","quantity":"300.00","actualQuantity":"300","unit":"KGS","unitRateFc":"32.5","totalValueFC":"9866.5","currency":"USD","unitRateINR":"2741.4","date":"18-May-2024","totalValueINR":"822412.5","totalValueInUsd":"9866.5","indian_port":"Bombay Air","hs_no":"29335920","bill_no":"3551955","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"BEIJING","supplierAddress":"NO.2-1701 GANGHUI CENTRAL NINGWEI STREET,XIAOSHAN HANGZHOU ZHEJIANG,SDNF CHINA","customerAddress":"7\/1,CORPORATE PARK,SION-TROMBAY"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1717180200,"product":"TRIMETHOPRIM NON-MICRO USP","address":"PIRAMAL ANANTA, PIRAMAL AGASTYA PARK","city":"KURLA, MUMBAI","supplier":"FLAVINE","supplierCountry":"CHINA","foreign_port":"SHANGHAI - PU DONG","customer":"PIRAMAL PHARMA SOLUTIONS","customerCountry":"INDIA","quantity":"425.00","actualQuantity":"425","unit":"KGS","unitRateFc":"44","totalValueFC":"18895","currency":"USD","unitRateINR":"3711.4","date":"01-Jun-2024","totalValueINR":"1577345","totalValueInUsd":"18895","indian_port":"Bombay Air","hs_no":"29335920","bill_no":"3783000","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"SHANGHAI - PU DONG","supplierAddress":"61 SOUTH PARAMUS ROAD, SUITE 565 PARAMUS , NEW JERSEY 07652 Closter\/New Jersey, , United States United States","customerAddress":"PIRAMAL ANANTA, PIRAMAL AGASTYA PARK"}]
    04-Jan-2021
    28-Aug-2024
    KGS
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    Average Price (USD/KGS)

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    (USD/KGS)    		 Number of Transactions

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