Seqens Seqens

X

Find Decitabine manufacturers, exporters & distributors on PharmaCompass

PharmaCompass
API SUPPLIERS
API Suppliers

API Suppliers

US DMFs Filed

US DMFs Filed

CEP/COS Certifications

CEP/COS Certifications

0

JDMFs Filed

JDMFs Filed

0

Other Certificates

Other Certificates

Other Suppliers

Other Suppliers

API REF. PRICE (USD / KG)
INTERMEDIATES
DOSSIERS // FDF
USA (Orange Book)

USA (Orange Book)

Europe

Europe

Canada

Canada

Australia

Australia

0

South Africa

South Africa

Uploaded Dossiers

Uploaded Dossiers

GLOBAL SALES (USD Million)

U.S. Medicaid

Annual Reports

0

EXCIPIENTS
PATENTS & EXCLUSIVITIES

USFDA Orange Book Patents

USFDA Exclusivities

DIGITAL CONTENT

Blog #PharmaFlow

0

News

REF STANDARD

EDQM

0

USP

0

JP

0

Other Listed Suppliers

SERVICES

0

Decitabine
Also known as: 5-aza-2'-deoxycytidine, 2353-33-5, Dacogen, 2'-deoxy-5-azacytidine, 5-azadeoxycytidine, Azadc
Molecular Formula
C8H12N4O4
Molecular Weight
228.21  g/mol
InChI Key
XAUDJQYHKZQPEU-KVQBGUIXSA-N
FDA UNII
776B62CQ27

An azacitidine derivative and antineoplastic antimetabolite. It inhibits DNA methyltransferase to re-activate silent genes, limiting METASTASIS and NEOPLASM DRUG RESISTANCE. Decitabine is used in the treatment of MYELODISPLASTIC SYNDROMES, and ACUTE MYELOID LEUKEMIA.
Decitabine is a Nucleoside Metabolic Inhibitor. The mechanism of action of decitabine is as a Nucleic Acid Synthesis Inhibitor.
1 2D Structure

Decitabine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one
2.1.2 InChI
InChI=1S/C8H12N4O4/c9-7-10-3-12(8(15)11-7)6-1-4(14)5(2-13)16-6/h3-6,13-14H,1-2H2,(H2,9,11,15)/t4-,5+,6+/m0/s1
2.1.3 InChI Key
XAUDJQYHKZQPEU-KVQBGUIXSA-N
2.1.4 Canonical SMILES
C1C(C(OC1N2C=NC(=NC2=O)N)CO)O
2.1.5 Isomeric SMILES
C1[C@@H]([C@H](O[C@H]1N2C=NC(=NC2=O)N)CO)O
2.2 Other Identifiers
2.2.1 UNII
776B62CQ27
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2' Deoxy 5 Azacytidine

2. 2'-deoxy-5-azacytidine

3. 5 Aza 2' Deoxycytidine

4. 5 Azadeoxycytidine

5. 5 Deoxyazacytidine

6. 5-aza-2'-deoxycytidine

7. 5-azadc

8. 5-azadeoxycytidine

9. 5-deoxyazacytidine

10. 5azadc

11. Azadc Compound

12. Compound, Azadc

13. Dacogen

14. Decitabine Mesylate

15. Mesylate, Decitabine

16. Nsc 127716

17. Nsc-127716

18. Nsc127716

2.3.2 Depositor-Supplied Synonyms

1. 5-aza-2'-deoxycytidine

2. 2353-33-5

3. Dacogen

4. 2'-deoxy-5-azacytidine

5. 5-azadeoxycytidine

6. Azadc

7. 5-aza-cdr

8. 5-aza-dc

9. Dezocitidine

10. Nsc 127716

11. Dac

12. 5-aza-deoxycytidine

13. Alpha-decitibine

14. 4-amino-1-((2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,3,5-triazin-2(1h)-one

15. Nsc-127716

16. 4-amino-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one

17. 5a2dc

18. 5-aza-2-deoxycytidine

19. 4-amino-1-(2-deoxy-beta-d-erythro-pentofuranosyl)-s-triazin-2(1h)-one

20. 4-amino-1-(2-deoxy-beta-d-erythro-pentofuranosyl)-1,3,5-triazin-2(1h)-one

21. Mls001332587

22. Chebi:50131

23. 776b62cq27

24. Smr000857076

25. 4-amino-1-[(2s,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one

26. Dsstox_cid_10432

27. Dsstox_rid_78849

28. Dsstox_gsid_30432

29. 4-amino-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydro-1,3,5-triazin-2-one

30. 5-azadc

31. Nsc127716

32. 2-deoxyazacytidine

33. 4-amino-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1,3,5-triazin-2-one

34. Dacogen (tn)

35. Cas-2353-33-5

36. 2-desoxy-5-azacytidine

37. Ncgc_5adoc

38. Decitabine (usan/inn)

39. Decitabine [usan:inn:ban]

40. Ccris 8227

41. Unii-776b62cq27

42. Ncgc00166088-01

43. 22432-95-7

44. Decitabine- Bio-x

45. Deoxy-5-azacytidine

46. Einecs 219-089-4

47. Mfcd00043011

48. Brn 0617982

49. Decitabine, Free Base

50. Jnj 30979754

51. Jnj-30979754

52. Decitabine [mi]

53. Decitabine [inn]

54. Decitabine [usan]

55. 4-amino-1-(2-deoxy-beta-d-ribofuranosyl)-1,3,5-triazin-2(1h)-one

56. Decitabine [vandf]

57. Molmap_000063

58. E-7373

59. Decitabine [mart.]

60. Schembl4006

61. Decitabine [who-dd]

62. Mls001332588

63. Mls006010136

64. Astx-727

65. Cid_451668

66. Gtpl6805

67. Chembl1201129

68. Decitabine [orange Book]

69. Dtxsid7030432

70. Bdbm96274

71. Ex-a961

72. Inqovi Component Decitabine

73. Hms2235o03

74. Hms3413l07

75. Hms3677l07

76. 105597-46-4

77. 4-amino-1-((2s,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,3,5-triazin-2(1h)-one

78. Act00147

79. Amy33354

80. Bcp02870

81. Hy-a0004

82. 5-aza-2'-deoxycytidine, >=97%

83. Tox21_112311

84. Astx727 Component Decitabine

85. S1200

86. Zinc16929327

87. Decitabine Component Of Inqovi

88. 4-amino-1-(2-deoxy-?-d-erythro-pentofuranosyl)-1,3,5-triazin-2(1h)-one

89. Akos015895047

90. Astx-727 Component Decitabine

91. Inqovi (decitabine + Cedazuridine)

92. Tox21_112311_1

93. Ac-1135

94. Bcp9000593

95. Ccg-208143

96. Cs-0372

97. Db01262

98. 1,3,5-triazin-2(1h)-one, 4-amino-1-(2-deoxy-.beta.-d-erythro-pentofuranosyl)-

99. Astx727 (decitabine + Cedazuridine)

100. Decitabine (nsc127716, 5aza-cdr)

101. Decitabine (nsc127716; 5aza-cdr)

102. Ncgc00166088-02

103. Ncgc00166088-05

104. As-17558

105. Ba164359

106. Bcp0726000271

107. Db-029060

108. Sw218076-2

109. D03665

110. Ab00918337-07

111. Ab00918337_08

112. 353a335

113. Sr-01000838879

114. J-700084

115. Q1181878

116. Sr-01000838879-4

117. Decitabine (2 Inverted Exclamation Marka-deoxy-5-azacytidine).cd

118. S-triazin-2(1h)-one, 4-amino-1-(2-deoxy-beta-d-erythro-pentofuranosyl)-

119. 1,3, 5-triazin-2(1h)-one, 4-amino-1-(2-deoxy--d-erythro-pentofuranosyl)-

120. 4-amino-1-(2-deoxy-.beta.-d-erythro-pentofuranosyl)-s-triazin-2(1h)-one

2.4 Create Date
2005-08-01
3 Chemical and Physical Properties
Molecular Weight 228.21 g/mol
Molecular Formula C8H12N4O4
XLogP3-1.2
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Exact Mass228.08585488 g/mol
Monoisotopic Mass228.08585488 g/mol
Topological Polar Surface Area121 Ų
Heavy Atom Count16
Formal Charge0
Complexity356
Isotope Atom Count0
Defined Atom Stereocenter Count3
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 NameDacogen
PubMed HealthDecitabine (Injection)
Drug ClassesAntineoplastic Agent
Drug LabelDacogen (decitabine) for Injection contains decitabine (5-aza-2-deoxycitidine), an analogue of the natural nucleoside 2-deoxycytidine. Decitabine is a fine, white to almost white powder with the molecular formula of C8H12N4O4 and a mo...
Active IngredientDecitabine
Dosage FormInjectable
RouteIntravenous
Strength50mg/vial
Market StatusPrescription
CompanyEisai

2 of 4  
Drug NameDecitabine
PubMed HealthDecitabine (Injection)
Drug ClassesAntineoplastic Agent
Drug LabelDecitabine for Injection contains decitabine (5-aza-2deoxycitidine), an analogue of the natural nucleoside 2-deoxycytidine. Decitabine is a fine, white to almost white powder with the molecular formula of C8H12N4O4 and a molecular weight of 228...
Active IngredientDecitabine
Dosage FormInjectable; Powder
RouteIntravenous
Strength50mg/vial
Market StatusPrescription
CompanyDr Reddys Labs; Sandoz; Sun Pharma Global

3 of 4  
Drug NameDacogen
PubMed HealthDecitabine (Injection)
Drug ClassesAntineoplastic Agent
Drug LabelDacogen (decitabine) for Injection contains decitabine (5-aza-2-deoxycitidine), an analogue of the natural nucleoside 2-deoxycytidine. Decitabine is a fine, white to almost white powder with the molecular formula of C8H12N4O4 and a mo...
Active IngredientDecitabine
Dosage FormInjectable
RouteIntravenous
Strength50mg/vial
Market StatusPrescription
CompanyEisai

4 of 4  
Drug NameDecitabine
PubMed HealthDecitabine (Injection)
Drug ClassesAntineoplastic Agent
Drug LabelDecitabine for Injection contains decitabine (5-aza-2deoxycitidine), an analogue of the natural nucleoside 2-deoxycytidine. Decitabine is a fine, white to almost white powder with the molecular formula of C8H12N4O4 and a molecular weight of 228...
Active IngredientDecitabine
Dosage FormInjectable; Powder
RouteIntravenous
Strength50mg/vial
Market StatusPrescription
CompanyDr Reddys Labs; Sandoz; Sun Pharma Global

4.2 Drug Indication

Decitabine is indicated for the treatment of patients with myelodysplastic syndromes (MDS) including all French-American-British subtypes (refractory anemia, refractory anemia with ringed sideroblasts, refractory anemia with excess blasts, refractory anemia with excess blasts in transformation, and chronic myelomonocytic leukemia), as well as for MDS scored as belonging to the intermediate-1, intermediate-2, or high-risk group in the International Prognostic Scoring System.


FDA Label


Treatment of adult patients with newly diagnosed de novo or secondary acute myeloid leukaemia (AML), according to the World Health Organization (WHO) classification, who are not candidates for standard induction chemotherapy.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Decitabine is a prodrug analogue of the natural nucleotide 2-deoxycytidine, which, upon being phosphorylated intracellularly, is incorporated into DNA and exerts numerous effects on gene expression. The use of decitabine is associated with neutropenia and thrombocytopenia. In addition, decitabine can cause fetal harm in pregnant women; effective contraception and avoidance of pregnancy are recommended during treatment with decitabine.


5.2 MeSH Pharmacological Classification

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.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
DECITABINE
5.3.2 FDA UNII
776B62CQ27
5.3.3 Pharmacological Classes
Nucleoside Metabolic Inhibitor [EPC]; Nucleic Acid Synthesis Inhibitors [MoA]
5.4 ATC Code

L01BC08


L01BC08

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

L01BC08 - Decitabine


5.5 Absorption, Distribution and Excretion

Absorption

Decitabine administered intravenously at 15 mg/m2 for three hours every eight hours over three days resulted in a Cmax of 73.8 ng/mL (66% coefficient of variation, CV), an AUC0- of 163 ng\*h/mL (62% CV), and a cumulative AUC of 1332 ng\*h/mL (95% CI of 1010-1730). Similarly, decitabine at 20 mg/m2 for one hour once daily over five days resulted in a Cmax of 147 ng/mL (49% CV), an AUC0- of 115 ng\*h/mL (43% CV), and a cumulative AUC of 570 ng\*h/mL (95% CI of 470-700).


Route of Elimination

Less than 1% of administered decitabine is excreted in the urine.


Volume of Distribution

Decitabine as an apparent volume of distribution of 4.59 1.42 L/kg.


Clearance

Decitabine has a clearance of 125 L/hr/m2 (53% CV) when administered intravenously at 15 mg/m2 for three hours every eight hours over three days, and a clearance of 210 L/hr/m2 (47% CV) at 20 mg/m2 for one hour once daily over five days.


5.6 Metabolism/Metabolites

Decitabine is phosphorylated inside cells by the sequential action of deoxycytidine kinase, nucleotide monophosphate kinase, and nucleotide diphosphate kinase, prior to being incorporated into newly synthesized DNA by DNA polymerase. Decitabine not incorporated into cellular DNA undergoes deamination by cytidine deaminase followed by additional degradation prior to excretion.


5.7 Biological Half-Life

Decitabine has a half-life of 0.62 hours (49% CV) when administered intravenously at 15 mg/m2 for three hours every eight hours over three days, and a half-life of 0.54 hours (43% CV) at 20 mg/m2 for one hour once daily over five days.


5.8 Mechanism of Action

Myelodysplastic syndromes (MDS) are a group of hematopoietic neoplasms that manifest in peripheral cytopenias and may eventually progress to secondary acute myeloid leukemia (sAML). Included in the over 45 genes commonly mutated in MDS patients are those involved in DNA methylation and histone modification, and it is well-established that alteration of the epigenetic landscape is a feature of myeloid leukemias. Decitabine is considered a prodrug, as it requires transport into cells and subsequent phosphorylation by distinct kinases to generate the active molecule 5-aza-2'-deoxycytidine-triphosphate, which is incorporated by DNA polymerase during DNA replication. Once incorporated into DNA, decitabine is recognized as a substrate by DNA methyltransferase enzymes (DNMTs), specifically DNMT1, but due to the presence of an N5 rather than C5 atom, traps the DNMT through the irreversible formation of a covalent bond. At low concentrations, this mode of action depletes DNMTs and results in global DNA hypomethylation while at high concentrations, it additionally results in double-strand breaks and cell death. The general hypothesis regarding decitabine's therapeutic efficacy is that the global hypomethylation it induces results in the expression of previously silent tumour suppressor genes. However, there are other putative mechanisms also related to this change in DNA methylation, including indirect alteration of transcription through effects on transcription factors, indirectly altering histone modifications and chromatin structure, and activating pathways involved in DNA damage response. The overall effect of decitabine is a decrease in neoplastic cell proliferation and an increase in the expression of tumour suppressor genes.


Ask Us for Pharmaceutical Supplier and Partner
Ask Us, Find A Supplier / Partner
No Commissions, No Strings Attached, Get Connected for FREE

What are you looking for?

How can we help you?

The request can't be empty

Please read our Privacy Policy carefully

You must agree to the privacy policy

The name can't be empty
The company can't be empty.
The email can't be empty Please enter a valid email.
The mobile can't be empty
Post Enquiry
POST ENQUIRY