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    Chemistry

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    Also known as: 5-azacytidine, 320-67-2, Azacytidine, Ladakamycin, Vidaza, Mylosar
    Molecular Formula
    C8H12N4O5
    Molecular Weight
    244.20  g/mol
    InChI Key
    NMUSYJAQQFHJEW-KVTDHHQDSA-N
    FDA UNII
    M801H13NRU
    Azacitidine
    A pyrimidine analogue that inhibits DNA methyltransferase, impairing DNA methylation. It is also an antimetabolite of cytidine, incorporated primarily into RNA. Azacytidine has been used as an antineoplastic agent.
    Azacitidine is a Nucleoside Metabolic Inhibitor. The mechanism of action of azacitidine is as a Nucleic Acid Synthesis Inhibitor.
    1 2D Structure

    Azacitidine

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one
    2.1.2 InChI
    InChI=1S/C8H12N4O5/c9-7-10-2-12(8(16)11-7)6-5(15)4(14)3(1-13)17-6/h2-6,13-15H,1H2,(H2,9,11,16)/t3-,4-,5-,6-/m1/s1
    2.1.3 InChI Key
    NMUSYJAQQFHJEW-KVTDHHQDSA-N
    2.1.4 Canonical SMILES
    C1=NC(=NC(=O)N1C2C(C(C(O2)CO)O)O)N
    2.1.5 Isomeric SMILES
    C1=NC(=NC(=O)N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)N
    2.2 Other Identifiers
    2.2.1 UNII
    M801H13NRU
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 5 Azacytidine

    2. 5-azacytidine

    3. Azacytidine

    4. Nsc 102816

    5. Nsc-102816

    6. Nsc102816

    7. Vidaza

    2.3.2 Depositor-Supplied Synonyms

    1. 5-azacytidine

    2. 320-67-2

    3. Azacytidine

    4. Ladakamycin

    5. Vidaza

    6. Mylosar

    7. 5-azacitidine

    8. Azacitidinum

    9. Azacitidina

    10. Azacitidinum [inn-latin]

    11. 5-azac

    12. Azacitidina [inn-spanish]

    13. Nsc-102816

    14. U-18496

    15. Onureg

    16. Nsc 102816

    17. 4-amino-1-beta-d-ribofuranosyl-1,3,5-triazin-2(1h)-one

    18. 4-amino-1-beta-d-ribofuranosyl-s-triazin-2(1h)-one

    19. Nsc102816

    20. 5azac

    21. Antibiotic U 18496

    22. 4-amino-1-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,3,5-triazin-2(1h)-one

    23. Chebi:2038

    24. M801h13nru

    25. 4-amino-1-(beta-d-ribofuranosyl)-1,3,5-triazin-2(1h)-one

    26. U-18,496

    27. 4-amino-1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one

    28. 4-amino-1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydro-1,3,5-triazin-2-one

    29. Wr-183027

    30. Ncgc00090851-04

    31. Dsstox_cid_116

    32. U 18496

    33. Dsstox_rid_75378

    34. Dsstox_gsid_20116

    35. C8h12n4o5

    36. 1,3,5-triazin-2(1h)-one, 4-amino-1-.beta.-d-ribofuranosyl-

    37. Mfcd00006539

    38. Ccris 60

    39. Smr000857239

    40. Vidaza (tn)

    41. Hsdb 6879

    42. 5-aza-cr

    43. Sr-01000075662

    44. Einecs 206-280-2

    45. Brn 0620461

    46. Unii-m801h13nru

    47. Azacitidine (jan/usan/inn)

    48. Azacitidine [usan:inn:ban]

    49. 4-amino-1-beta-d-ribofuranosyl-1,3,5-traizin-2(1h)-one

    50. Ns-17

    51. 4-amino-1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1,3,5-triazin-2-one

    52. Cas-320-67-2

    53. Azacitidine (vidaza)

    54. 2-(beta-d-ribofuranosyl)-4-amino-1,3,5-triazin-2-one

    55. Antibiotic U18496

    56. U18496

    57. Spectrum_001262

    58. 4-amino-1-beta-d-ribofuranosyl-1,3,5-triazine-2(1h)-one

    59. Azacitidine [mi]

    60. Spectrum2_000786

    61. Spectrum3_001509

    62. Spectrum4_000922

    63. Spectrum5_001166

    64. Azacitidine [inn]

    65. Azacitidine [jan]

    66. Azacitidine [hsdb]

    67. Azacitidine [iarc]

    68. Azacitidine [usan]

    69. Molmap_000062

    70. 4-amino-1-.beta.-d-ribofuranosyl-s-triazin-2(1h)-one

    71. A 2385

    72. Azacitidine [vandf]

    73. Schembl3741

    74. Azacitidine [mart.]

    75. Chembl1489

    76. Azacitidine (5-azacytidine)

    77. Lopac0_000035

    78. Azacitidine [usp-rs]

    79. Azacitidine [who-dd]

    80. Bspbio_003157

    81. Kbiogr_001444

    82. Kbiogr_002556

    83. Kbioss_001742

    84. Kbioss_002565

    85. Mls001333121

    86. Mls001333122

    87. Mls002153249

    88. Mls002548894

    89. Divk1c_000125

    90. Spectrum1502111

    91. Spbio_000892

    92. Azacitidine [ema Epar]

    93. Gtpl6796

    94. Dtxsid9020116

    95. S-triazin-2(1h)-one, 4-amino-1-beta-d-ribofuranosyl-

    96. Bcbcmap01_000083

    97. Hms500g07

    98. Kbio1_000125

    99. Kbio2_001742

    100. Kbio2_002556

    101. Kbio2_004310

    102. Kbio2_005124

    103. Kbio2_006878

    104. Kbio2_007692

    105. Kbio3_002657

    106. Kbio3_003034

    107. Nmusyjaqqfhjew-kvtdhhqdsa-

    108. Azacitidine [orange Book]

    109. Pyrimidine Antimetabolite: Inhibits Nucleic Acid Replication

    110. Cmap_000082

    111. Ninds_000125

    112. Hms1921j22

    113. Hms2092d08

    114. Hms2231f15

    115. Hms3259d19

    116. Hms3260g11

    117. Pharmakon1600-01502111

    118. Zinc3861768

    119. 5-azacytidine, >=98% (hplc)

    120. Tox21_111032

    121. Tox21_302985

    122. Tox21_500035

    123. Bdbm50424715

    124. Ccg-39046

    125. Nsc758186

    126. S1782

    127. Onureg (cc-486; Oral Azacitidine)

    128. Akos015896938

    129. Tox21_111032_1

    130. Am83944

    131. Cs-1287

    132. Db00928

    133. Lp00035

    134. Nc00672

    135. Nsc-758186

    136. Nsc103-627

    137. 4-amino-1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triaz

    138. Idi1_000125

    139. Ncgc00090851-01

    140. Ncgc00090851-02

    141. Ncgc00090851-03

    142. Ncgc00090851-05

    143. Ncgc00090851-06

    144. Ncgc00090851-07

    145. Ncgc00090851-08

    146. Ncgc00090851-10

    147. Ncgc00090851-14

    148. Ncgc00090851-22

    149. Ncgc00178234-01

    150. Ncgc00256541-01

    151. Ncgc00260720-01

    152. As-13697

    153. Hy-10586

    154. Sri-10756_10

    155. Sri-10756_12

    156. Wr183027

    157. Db-006955

    158. Sl-000003

    159. Eu-0100035

    160. D03021

    161. F10504

    162. 320a672

    163. A821115

    164. Q416451

    165. J-700085

    166. Sr-01000075662-1

    167. Sr-01000075662-3

    168. Sr-01000075662-7

    169. Brd-k03406345-001-02-1

    170. Brd-k03406345-001-27-8

    171. 4-amino-1-?-d-ribofuranosyl-1,3,5-triazin-2(1h)-one

    172. Z1522566611

    173. 4-amino-1-(bet.-d-ribofuranosyl)-1,3,5-triazin-2(1h)-one

    174. 4-amino-1-beta-d-ribofuranosyl-1,3,5-tr Iazin-2(1h)-one

    175. Azacitidine, United States Pharmacopeia (usp) Reference Standard

    176. 4-amino-1-(beta-d-ribofuranosyl)-1,3,5-triazin-2(1h)-one; Ladakamycin

    177. Azacitidine, Pharmaceutical Secondary Standard; Certified Reference Material

    178. 1401238-97-8

    179. 5-azacytidine, Hybri-max(tm), Gamma-irradiated, Lyophilized Powder, Bioxtra, Suitable For Hybridoma

    180. 5ae

    181. 6-amino-3-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1h-1,3,5-triazin-3-ium-2-one

    2.4 Create Date
    2004-09-16
    3 Chemical and Physical Properties
    Molecular Weight 244.20 g/mol
    Molecular Formula C8H12N4O5
    XLogP3-2.2
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count2
    Exact Mass244.08076950 g/mol
    Monoisotopic Mass244.08076950 g/mol
    Topological Polar Surface Area141 Ų
    Heavy Atom Count17
    Formal Charge0
    Complexity384
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    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 NameAzacitidine
    PubMed HealthAzacitidine (Injection)
    Drug ClassesAntineoplastic Agent
    Drug LabelVidaza (azacitidine for injectable suspension) contains azacitidine, which is a pyrimidine nucleoside analog of cytidine. Azacitidine is 4-amino-1--D-ribofuranosyl-s-triazin-2(1H)-one. The structural formula is as follows:The empirical formula i...
    Active IngredientAzacitidine
    Dosage FormInjectable
    RouteIntravenous, subcutaneous
    Strength100mg/vial
    Market StatusPrescription
    CompanyDr Reddys Labs

    2 of 4  
    Drug NameVidaza
    PubMed HealthAzacitidine (Injection)
    Drug ClassesAntineoplastic Agent
    Drug LabelVidaza (azacitidine for injectable suspension) contains azacitidine, which is a pyrimidine nucleoside analog of cytidine. Azacitidine is 4-amino-1--D-ribofuranosyl-s-triazin-2(1H)-one. The structural formula is as follows:The empirical formula i...
    Active IngredientAzacitidine
    Dosage FormInjectable
    RouteIntravenous, subcutaneous
    Strength100mg/vial
    Market StatusPrescription
    CompanyCelgene

    3 of 4  
    Drug NameAzacitidine
    PubMed HealthAzacitidine (Injection)
    Drug ClassesAntineoplastic Agent
    Drug LabelVidaza (azacitidine for injectable suspension) contains azacitidine, which is a pyrimidine nucleoside analog of cytidine. Azacitidine is 4-amino-1--D-ribofuranosyl-s-triazin-2(1H)-one. The structural formula is as follows:The empirical formula i...
    Active IngredientAzacitidine
    Dosage FormInjectable
    RouteIntravenous, subcutaneous
    Strength100mg/vial
    Market StatusPrescription
    CompanyDr Reddys Labs

    4 of 4  
    Drug NameVidaza
    PubMed HealthAzacitidine (Injection)
    Drug ClassesAntineoplastic Agent
    Drug LabelVidaza (azacitidine for injectable suspension) contains azacitidine, which is a pyrimidine nucleoside analog of cytidine. Azacitidine is 4-amino-1--D-ribofuranosyl-s-triazin-2(1H)-one. The structural formula is as follows:The empirical formula i...
    Active IngredientAzacitidine
    Dosage FormInjectable
    RouteIntravenous, subcutaneous
    Strength100mg/vial
    Market StatusPrescription
    CompanyCelgene

    4.2 Therapeutic Uses

    Anticancer agent used to treat acute myclogenous leukemia

    Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. V5 (1993) 872

    Expl Ther: The ability of phenylacetate to prevent carcinogenesis by the chemotherapeutic hypomethylating drug 5-aza-2'-deoxycytidine (5AzadC) was tested in vitro and in mice. Transient exposure of immortalized, but poorly tumorigenic ras-transformed 4C8 fibroblasts to 5AzadC resulted in neoplastic transformation manifested by loss of contact inhibition of growth, acquired invasiveness, and increased tumorigenicity in athymic mice.

    Prasanna P et al; Clin Cancer Res 1 (8): 865-71

    5-Azacytidine, an inhibitor of DNA methylation as well as a cytidine antimetabolite, becomes incorporated predominantly into RNA and has antileukemic and differentiating action. A newer analog, 2',2'-difluorodeoxycytidine (gemcitabine), becomes incorporated into DNA and inhibits the elongation of nascent DNA strands. It has promising activity in various human solid tumors, including lung cancer and ovarian cancer ... .

    Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 1249

    4.3 Drug Indication

    For treatment of patients with the following French-American-British myelodysplastic syndrome subtypes: refractory anemia or refractory anemia with ringed sideroblasts (if accompanied by neutropenia or thrombocytopenia or requiring transfusions), refractory anemia with excess blasts, refractory anemia with excess blasts in transformation (now classified as acute myelogenous leukemia with multilineage dysplasia), and chronic myelomonocytic leukemia.

    FDA Label

    Azacitidine Mylan is indicated for the treatment of adult patients who are not eligible for haematopoietic stem cell transplantation (HSCT) with:

    - intermediate 2 and high risk myelodysplastic syndromes (MDS) according to the International Prognostic Scoring System (IPSS),

    - chronic myelomonocytic leukaemia (CMML) with 10 29% marrow blasts without myeloproliferative disorder,

    - acute myeloid leukaemia (AML) with 20 30% blasts and multi lineage dysplasia, according to World Health Organisation (WHO) classification,

    - AML with > 30% marrow blasts according to the WHO classification.

    Azacitidine betapharm is indicated for the treatment of adult patients who are not eligible for haematopoietic stem cell transplantation (HSCT) with:

    - intermediate-2 and high-risk myelodysplastic syndromes (MDS) according to the International Prognostic Scoring System (IPSS),

    - chronic myelomonocytic leukaemia (CMML) with 10 % to 29 % marrow blasts without myeloproliferative disorder,

    - acute myeloid leukaemia (AML) with 20 % to 30 % blasts and multi-lineage dysplasia, according to World Health Organization (WHO) classification,

    - AML with > 30 % marrow blasts according to the WHO classification.

    Azacitidine Accord is indicated for the treatment of adult patients who are not eligible for haematopoietic stem cell transplantation (HSCT) with:

    - intermediate-2 and high-risk myelodysplastic syndromes (MDS) according to the International Prognostic Scoring System (IPSS),

    - chronic myelomonocytic leukaemia (CMML) with 10-29 % marrow blasts without myeloproliferative disorder,

    - acute myeloid leukaemia (AML) with 20-30 % blasts and multi-lineage dysplasia, according to World Health Organisation (WHO) classification,

    - AML with > 30% marrow blasts according to the WHO classification.

    Azacitidine Celgene is indicated for the treatment of adult patients who are not eligible for haematopoietic stem cell transplantation (HSCT) with:

    - intermediate 2 and high-risk myelodysplastic syndromes (MDS) according to the International Prognostic Scoring System (IPSS),

    - chronic myelomonocytic leukaemia (CMML) with 10 29 % marrow blasts without myeloproliferative disorder,

    - acute myeloid leukaemia (AML) with 20 30 % blasts and multi-lineage dysplasia, according to World Health Organisation (WHO) classification,

    - AML with > 30% marrow blasts according to the WHO classification.

    Vidaza is indicated for the treatment of adult patients who are not eligible for haematopoietic stem cell transplantation (HSCT) with:

    - intermediate 2 and high-risk myelodysplastic syndromes (MDS) according to the International Prognostic Scoring System (IPSS),

    - chronic myelomonocytic leukaemia (CMML) with 10 29 % marrow blasts without myeloproliferative disorder,

    - acute myeloid leukaemia (AML) with 20 30 % blasts and multi-lineage dysplasia, according to World Health Organisation (WHO) classification.

    Vidaza is indicated for the treatment of adult patients aged 65 years or older who are not eligible for HSCT with AML with > 30% marrow blasts according to the WHO classification.

    Treatment of myelodysplastic syndrome (including juvenile myelomonocytic leukaemia), Treatment of acute myeloid leukaemia

    Onureg is indicated as maintenance therapy in adult patients with acute myeloid leukaemia (AML) who achieved complete remission (CR) or complete remission with incomplete blood count recovery (CRi) following induction therapy with or without consolidation treatment and who are not candidates for, including those who choose not to proceed to, hematopoietic stem cell transplantation (HSCT).

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Azacitidine is believed to exert its antineoplastic effects by causing hypomethylation of DNA and direct cytotoxicity on abnormal hematopoietic cells in the bone marrow. The concentration of azacitidine required for maximum inhibition of DNA methylation in vitro does not cause major suppression of DNA synthesis. Hypomethylation may restore normal function to genes that are critical for differentiation and proliferation. The cytotoxic effects of azacitidine cause the death of rapidly dividing cells, including cancer cells that are no longer responsive to normal growth control mechanisms. Non-proliferating cells are relatively insensitive to azacitidine. Upon uptake into cells, azacitidine is phosphorylated to 5-azacytidine monophosphate by uridine-cytidine kinase, then to diphosphate by pyrimidine monophosphate kinases and triphosphate by diphosphate kinases. 5-Azacitidine triphosphate is incorporated into RNA, leading to the disruption of nuclear and cytoplasmic RNA metabolism and inhibition of protein synthesis. 5-Azacytidine diphosphate is reduced to 5-aza-deoxycytidine diphosphate by ribonucleotide reductase. The resultant metabolite is phosphorylated to 5-azadeoxycitidine triphosphate by nucleoside diphosphate kinases. 5-azadeoxycitidine triphosphate is then incoporated into DNA, leading to inhibition of DNA synthesis. Azacitidine is most toxic during the S-phase of the cell cycle.

    5.2 MeSH Pharmacological Classification

    Antimetabolites, Antineoplastic

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

    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.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    AZACITIDINE
    5.3.2 FDA UNII
    M801H13NRU
    5.3.3 Pharmacological Classes
    Nucleoside Metabolic Inhibitor [EPC]; Nucleic Acid Synthesis Inhibitors [MoA]
    5.4 ATC Code

    L01BC07

    L01BC07

    L01BC07

    L01BC07

    L01BC07

    L01BC07

    L01BC07

    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

    L01BC - Pyrimidine analogues

    L01BC07 - Azacitidine

    5.5 Absorption, Distribution and Excretion

    Absorption

    Azacitidine is rapidly absorbed after subcutaneous administration. The bioavailability of subcutaneous azacitidine relative to IV azacitidine is approximately 89%, based on area under the curve.

    Route of Elimination

    Following IV administration of radioactive azacitidine to 5 cancer patients, the cumulative urinary excretion was 85% of the radioactive dose. Fecal excretion accounted for <1% of administered radioactivity over three days. Mean excretion of radioactivity in urine following SC administration of 14C-azacitidine was 50%.

    Volume of Distribution

    76 26 L

    Clearance

    167 +/- 49 L/h

    5.6 Metabolism/Metabolites

    An in vitro study of azacitidine incubation in human liver fractions indicated that azacitidine may be metabolized by the liver. The potential of azacitidine to inhibit cytochrome P450 (CYP) enzymes is not known.

    5.7 Biological Half-Life

    Mean elimination half-life is approximately 4 hours.

    5.8 Mechanism of Action

    Azacitidine (5-azacytidine) is a chemical analogue of the cytosine nucleoside used in DNA and RNA. Azacitidine may induce antineoplastic activity by inhibition of DNA methyltransferase at low doses and cytotoxicity through incorporation into RNA and DNA at high doses. Covalent binding to DNA methyltransferase results in hypomethylation of DNA and prevents DNA synthesis. As azacitidine is a ribonucleoside, it incoporates into RNA to a larger extent than into DNA. The incorporation into RNA leads to the dissembly of polyribosomes, defective methylation and acceptor function of transfer RNA, and inhibition of the production of protein, resulting in cell death.

    Telomerase activation is thought to be a critical step in cellular immortality and oncogenesis. Several reagents including differentiation-inducing and antineoplastic agents are known to inhibit telomerase activity, although the molecular mechanisms through which they inhibit telomerase activity remain unclear. Demethylating reagents have recently been used as potential antineoplastic drugs for some types of cancers including those of the prostate. In the present study, we examined the effect of the demethylating reagent 5-azacytidine (5-aza-CR) on telomerase activity using cells of two prostate cancer cell lines, DU-145 and TSU-PR1. 5-aza-CR treatment significantly reduced telomerase activity in TSU-PR1 cells, but not in DU-145 cells, although growth inhibition was observed to a similar extent in both cell lines. Reverse transcription-PCR analyses revealed that inhibition of telomerase activity was accompanied by down-regulation of telomerase catalytic subunit (hTERT) mRNA expression. Transient expression assays showed that 5-aza-CR repressed the transcriptional activity of the hTERT promoter and that the E-box within the core promoter was responsible for this down-regulation. Western blot analyses revealed that 5-aza-CR reactivated p16 expression and repressed c-Myc expression in TSU-PR1 cells but not in DU-145 cells. Overexpression of p16 in TSU-PR1 cells led to significant repression of c-Myc transcription. These findings suggest that 5-aza-CR inhibits telomerase activity via transcriptional repression of hTERT, in which p16 and c-Myc may play a key role.

    PMID:10914736 Kitagawa Y et al; Clin cancer Res 6 (7): 2868-75 (2000)

    Cellular differentiation is controlled by a variety of factors including gene methylation, which represses particular genes as cell fate is determined. The incorporation of 5-azacytidine (5azaC) into DNA in vitro prevents methylation and thus can alter cellular differentiation pathways. Human bone marrow fibroblasts and MG63 cells treated with 5azaC were used as models of osteogenic progenitors and of a more mature osteoblast phenotype, respectively. The capacity for differentiation of these cells following treatment with glucocorticoids was investigated. 5azaC treatment led to significant expression of the osteoblastic marker alkaline phosphatase in MG63 osteosarcoma cells, which was further augmented by glucocorticoids; however, in human marrow fibroblasts alkaline phosphatase activity was only observed in glucocorticoid-treated cultures. MG63 cells represent a phenotype late in the osteogenic lineage in which demethylation is sufficient to induce alkaline phosphatase activity. Marrow fibroblasts are at an earlier stage of differentiation and require stimulation with glucocorticoids. In contrast, the expression of osteocalcin, an osteoblastic marker, was unaffected by 5azaC treatment, suggesting that regulation of expression of the osteocalcin gene does not involve methylation. These models provide novel approaches to the study of the control of differentiation in the marrow fibroblastic system.

    Locklin RM et al; Cell Biol Int 22 (3): 207-15

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    GDUFA

    DMF Review : Complete

    Rev. Date : 2023-01-26

    Pay. Date : 2022-12-16

    DMF Number : 23416

    Submission : 2009-12-22

    Status : Active

    Type : II

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    02

    Dr Reddys Laboratories Ltd

    India
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    Virtual BoothDRL offers a portfolio of products & services, including APIs, CMO services, generics, biosimilars & differentiated formulations.

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    DMF Review : Complete

    Rev. Date : 2020-11-20

    Pay. Date : 2020-11-17

    DMF Number : 23564

    Submission : 2010-02-23

    Status : Active

    Type : II

    Dr Reddy Company Banner

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    03

    Teva Pharmaceutical Industries Ltd

    Israel
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    CPhI WW Frankfurt
    Booth #6.1A32
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    Virtual BoothTAPI offers customized CDMO Solutions for API development and manufacturing services.

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    GDUFA

    DMF Review : Complete

    Rev. Date : 2013-10-24

    Pay. Date : 2012-11-13

    DMF Number : 26126

    Submission : 2012-06-04

    Status : Active

    Type : II

    TAPI Company Banner

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    04

    Euticals Spa

    Italy

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    04

    Euticals Spa

    Italy
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    Not Confirmed

    GDUFA

    DMF Review : N/A

    Rev. Date :

    Pay. Date :

    DMF Number : 25265

    Submission : 2011-09-07

    Status : Inactive

    Type : II

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    05

    Ash Stevens Inc

    U.S.A

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    05

    Ash Stevens Inc

    U.S.A
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    GDUFA

    DMF Review : N/A

    Rev. Date :

    Pay. Date :

    DMF Number : 3562

    Submission : 1979-07-09

    Status : Inactive

    Type : II

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    06

    Laurus Labs Ltd

    India

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    06

    Laurus Labs Ltd

    India
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    GDUFA

    DMF Review : Complete

    Rev. Date : 2013-06-03

    Pay. Date : 2013-02-07

    DMF Number : 26846

    Submission : 2013-02-07

    Status : Active

    Type : II

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    07

    Scinopharm Taiwan Ltd

    Taiwan

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    Not Confirmed

    07

    Scinopharm Taiwan Ltd

    Taiwan
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    GDUFA

    DMF Review : Complete

    Rev. Date : 2013-04-04

    Pay. Date : 2012-11-29

    DMF Number : 22360

    Submission : 2008-12-31

    Status : Active

    Type : II

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    08

    Antibody Engineering
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    08

    Shilpa Pharma Lifesciences Ltd

    India
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    GDUFA

    DMF Review : Complete

    Rev. Date : 2014-03-15

    Pay. Date : 2013-09-23

    DMF Number : 27487

    Submission : 2013-09-23

    Status : Active

    Type : II

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    09

    Antibody Engineering
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    09

    Mylan Laboratories Ltd

    U.S.A
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    GDUFA

    DMF Review : N/A

    Rev. Date :

    Pay. Date :

    DMF Number : 22801

    Submission : 2009-05-26

    Status : Inactive

    Type : II

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    10

    Heinrich Mack Nachf

    Country

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    Not Confirmed

    10

    Heinrich Mack Nachf

    Country
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    Antibody Engineering
    Not Confirmed

    GDUFA

    DMF Review : N/A

    Rev. Date :

    Pay. Date :

    DMF Number : 5129

    Submission : 1983-10-21

    Status : Inactive

    Type : II

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    Listed Suppliers

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    01

    ChemWerth Inc

    U.S.A
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    CPhI WW Frankfurt
    Booth #12.1F43
    • fda
    • EDQM
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    Virtual BoothChemWerth works in generic API development & supply, non-infringement patent strategy development and regulatory support.

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    Azacitidine

    About the Company : Established in 1982, ChemWerth is a US-headquartered full-service generic active pharmaceutical ingredient (API) development and supply company. ChemWerth offers cGMP-quality APIs ...

    Established in 1982, ChemWerth is a US-headquartered full-service generic active pharmaceutical ingredient (API) development and supply company. ChemWerth offers cGMP-quality APIs to regulated markets worldwide and has exclusive partnerships for new product development, compliance support and secure supply chain logistics. ChemWerth has access to over 500 APIs and more than 30 manufacturing facilities in the US, Europe, India and China. ChemWerth acts as a regulatory agent for over 25 FDA-approved facilities and sells more than 100 products. It has established its presence in 38 countries. In 2020, ChemWerth filed its 500th DMF with the FDA.
    Chemwerth Compnay Banner

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    02

    LGM Pharma

    U.S.A
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    Virtual BoothLGM Pharma accelerates & optimizes the new product pathway from early development through commercialization.

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    Azacitidine

    About the Company : LGM Pharma is a global leader in sourcing hard-to-find APIs and intermediates for the pharmaceutical and biotech industries. LGM is also a full service CDMO providing formulation, ...

    LGM Pharma is a global leader in sourcing hard-to-find APIs and intermediates for the pharmaceutical and biotech industries. LGM is also a full service CDMO providing formulation, analytical method development and testing, and commercial manufacturing. LGM Pharma offers custom API synthesis, analytical development, and regulatory services. With a network of over 300 accredited CGMP manufacturing partners, LGM provides unparalleled supply chain security. And, with over 100,000 square feet of FDA-inspected cGMP manufacturing and warehouse capacity, LGM Pharma provides a one-stop solution for solid dose, powder, semi-solid and liquid drugs.
    LGM Pharma CB

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    03

    DKSH

    Switzerland
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    • fda
    • EDQM
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    Virtual BoothDKSH is your trusted partner for companies looking to grow their business in Asia & beyond.

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    Azacitidine

    About the Company : DKSH, founded with the goal of improving people's lives, assists businesses with market expansion and business growth in both existing and emerging markets. It has been fostering g...

    DKSH, founded with the goal of improving people's lives, assists businesses with market expansion and business growth in both existing and emerging markets. It has been fostering growth for businesses in Asia and beyond for over 155 years. DKSH operates in 36 markets, is listed on the SIX Swiss Exchange, employs 33,100 specialists, and generated net sales of CHF 11.1 billion in 2021. It is the leading global distributor of innovative pharma ingredients for pharmaceutical synthesis and formulation. It offers a range of products, ranging from animal care products to packaging materials, intermediates to nutraceuticals, and APIs to excipients.
    DKSH Company Banner

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    04

    Dr. Reddy's Laboratories

    India
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    DDL Conference
    Not Confirmed
    • fda
    • EDQM
    • WHO-GMP

    Virtual BoothDRL offers a portfolio of products & services, including APIs, CMO services, generics, biosimilars & differentiated formulations.

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    Flag India
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    Azacitidine

    About the Company : Founded in 1984, DRL is well-known for its generic APIs and its track record in drug product development. It is one of the earliest pharma API manufacturers with a diverse portfoli...

    Founded in 1984, DRL is well-known for its generic APIs and its track record in drug product development. It is one of the earliest pharma API manufacturers with a diverse portfolio that provides high-quality, low-cost APIs to leading pharma companies in 80+ countries. It has 8 USFDA-inspected facilities – 6 in India & 1 each in Mexico & the UK & are inspected by international regulatory authorities on a regular basis. Its facilities are supplemented by formulation facilities that provide a wide range of dosage forms. Product(s) under patent(s) are offered only for R&D purposes U/S 107A of the Patent Act and not for commercial sale
    Dr Reddy Company Banner

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    05

    Chongqing Sintaho Pharmaceutical

    China
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    Not Confirmed
    • fda
    • EDQM
    • WHO-GMP

    Virtual BoothChongqing Sintaho Pharma: A trusted partner globally for chemosynthetic APIs.

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    Azacitidine

    About the Company : Sintaho Pharmaceutical Co., Ltd., located in Chongqing, China, contributes to being the most dependable partner for global pharmaceutical companies. Sintaho specializes in chemosyn...

    Sintaho Pharmaceutical Co., Ltd., located in Chongqing, China, contributes to being the most dependable partner for global pharmaceutical companies. Sintaho specializes in chemosynthetic APIs (application contains oncology, nervous system, and metabolic diseases and etc.,) with a product portfolio ranging from small molecule APIs, ADC compounds (linkers and payloads) to polypeptides, also provides CDMO services of cytotoxic and OEB4/5 grade APIs.
    Chongqing Sintaho Pharmaceutical

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    06

    HRV Global Life Sciences

    India
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    DDL Conference
    Not Confirmed
    • fda
    • EDQM
    • WHO-GMP

    Virtual BoothHRV Global Life Sciences - Market Expansion Leader in Pharmaceuticals.

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    Flag India
    Virtual Booth Virtual Booth
    Digital Content Digital Content

    Azacitidine

    About the Company : HRV Global is a leading global manufacturer, seller & exporter of a wide range of APIs, advanced intermediates, pellets, food grade chemicals, food additives & food ingredients. It...

    HRV Global is a leading global manufacturer, seller & exporter of a wide range of APIs, advanced intermediates, pellets, food grade chemicals, food additives & food ingredients. It offers services such as sourcing, manufacturing & supply, helping partners enter new markets worldwide. Its strong partnerships with major players in the pharma and food additive industries help HRV Global effectively promote projects and products. HRV Global represents over 30 large Indian drugmakers, primarily targeting Europe, the US & the Middle East markets. Headquartered in India, HRV Global has offices in the US, Switzerland, Dubai, Lithuania & Turkey.
    HRV Global Life Sciences

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    07

    TAPI Technology & API Services

    Israel
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    CPhI WW Frankfurt
    Booth #6.1A32
    • fda
    • EDQM
    • WHO-GMP

    Virtual BoothTAPI offers customized CDMO Solutions for API development and manufacturing services.

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    Azacitidine

    About the Company : Founded in 1935, TAPI Technology & API Services has a long-standing tradition of advancing health through innovation and dedication. Today, we proudly build upon this legacy, drivi...

    Founded in 1935, TAPI Technology & API Services has a long-standing tradition of advancing health through innovation and dedication. Today, we proudly build upon this legacy, driving progress in the pharmaceutical industry. Leveraging our extensive experience and world-class expertise, we deliver one of the most comprehensive API portfolios in the industry. Additionally, we provide tailored CDMO services, harnessing our proficiency in diverse technologies to meet our partners' unique needs, ensuring flexibility and excellence in every project.
    TAPI Company Banner

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    08

    DEAFARMA

    Italy
    DDL Conference
    Not Confirmed
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    DEAFARMA

    Italy
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    DDL Conference
    Not Confirmed
    • fda
    • EDQM
    • WHO-GMP
    Virtual Booth Boost your online visibility by uploading your products, APIs, FDFs, intermediates, excipients, and services for free on PharmaCompass. Rank higher among suppliers and expand your reach across the internet efficiently and cost-effectively.
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    Virtual Booth Virtual Booth
    Digital Content Digital Content

    Azacitidine

    About the Company : In the dinamic pharmaceutical field, DEAFARMA is the reference point for primaries Pharmaceutical Laboratories for over twenty years, even in the national and international territo...

    In the dinamic pharmaceutical field, DEAFARMA is the reference point for primaries Pharmaceutical Laboratories for over twenty years, even in the national and international territory. DEAFARMA works with success in the pharmaceutical raw materials field through Agencies and professional relations with the most important European and Asiatic factories. Our partners are well known, reliable producers and all of them are operating in accordance with the latest GMP Rules. The APIs mentioned in the DEAFARMA catalogue are always supported by DMF and/or CEP.
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    09

    MSN Laboratories

    India
    DDL Conference
    Not Confirmed
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    MSN Laboratories

    India
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    DDL Conference
    Not Confirmed
    • fda
    • EDQM
    • WHO-GMP
    Virtual Booth Boost your online visibility by uploading your products, APIs, FDFs, intermediates, excipients, and services for free on PharmaCompass. Rank higher among suppliers and expand your reach across the internet efficiently and cost-effectively.
    Post an Enquiry Post an Enquiry
    Flag India
    Virtual Booth Virtual Booth
    Digital Content Digital Content

    Azacitidine

    About the Company : Founded in 2003, Hyderabad-based MSN Labs is one of the fastest-growing research-based pharmaceutical company in India. Boasting a diverse product portfolio, with multiple products...

    Founded in 2003, Hyderabad-based MSN Labs is one of the fastest-growing research-based pharmaceutical company in India. Boasting a diverse product portfolio, with multiple products in the market and in the pipeline, MSN has 6 API (including Oncology) and one finished dosage facilities (one more for Oncology is being built) and an integrated R&D Center for Contract Research And Manufacturing Services (CRAMS) located in Hyderabad. MSN has won the trust of more than 250 customers across 65 countries around the globe covering the US, Europe, Latin America, Middle-East, Asia Pacific, Africa and CIS markets. Our product basket offers 100 APIs
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    10

    Shilpa Medicare

    India
    DDL Conference
    Not Confirmed
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    Shilpa Medicare

    India
    arrow
    DDL Conference
    Not Confirmed
    • fda
    • EDQM
    • WHO-GMP
    Virtual Booth Boost your online visibility by uploading your products, APIs, FDFs, intermediates, excipients, and services for free on PharmaCompass. Rank higher among suppliers and expand your reach across the internet efficiently and cost-effectively.
    Post an Enquiry Post an Enquiry
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    Virtual Booth Virtual Booth
    Digital Content Digital Content

    Azacitidine

    About the Company : Shilpa Medicare Limited (SML) started its operations as API manufacturer way back in 1987 at Raichur, Karnataka- India. The commercial production in the SML was started in November...

    Shilpa Medicare Limited (SML) started its operations as API manufacturer way back in 1987 at Raichur, Karnataka- India. The commercial production in the SML was started in November 1989. Today Shilpa Medicare Limited is a global brand in manufacturing and supplying of affordable API and Formulation globally in different regulated markets.
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    API Reference Price

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    27-Jan-2021
    18-Oct-2024
    KGS
    overview
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    Average Price (USD/KGS)

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

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    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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