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Chemistry

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Also known as: 147-94-4, Ara-c, Cytosine arabinoside, Arabinocytidine, Aracytin, Depocyt
Molecular Formula
C9H13N3O5
Molecular Weight
243.22  g/mol
InChI Key
UHDGCWIWMRVCDJ-CCXZUQQUSA-N
FDA UNII
04079A1RDZ

Cytarabine
A pyrimidine nucleoside analog that is used mainly in the treatment of leukemia, especially acute non-lymphoblastic leukemia. Cytarabine is an antimetabolite antineoplastic agent that inhibits the synthesis of DNA. Its actions are specific for the S phase of the cell cycle. It also has antiviral and immunosuppressant properties. (From Martindale, The Extra Pharmacopoeia, 30th ed, p472)
Cytarabine is a Nucleoside Metabolic Inhibitor. The mechanism of action of cytarabine is as a Nucleic Acid Synthesis Inhibitor.
1 2D Structure

Cytarabine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
2.1.2 InChI
InChI=1S/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6-,7+,8-/m1/s1
2.1.3 InChI Key
UHDGCWIWMRVCDJ-CCXZUQQUSA-N
2.1.4 Canonical SMILES
C1=CN(C(=O)N=C1N)C2C(C(C(O2)CO)O)O
2.1.5 Isomeric SMILES
C1=CN(C(=O)N=C1N)[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)O
2.2 Other Identifiers
2.2.1 UNII
04079A1RDZ
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Ara C

2. Ara-c

3. Arabinofuranosylcytosine

4. Arabinoside, Cytosine

5. Arabinosylcytosine

6. Aracytidine

7. Aracytine

8. Beta Ara C

9. Beta-ara C

10. Cytarabine Hydrochloride

11. Cytonal

12. Cytosar

13. Cytosar U

14. Cytosar-u

15. Cytosine Arabinoside

2.3.2 Depositor-Supplied Synonyms

1. 147-94-4

2. Ara-c

3. Cytosine Arabinoside

4. Arabinocytidine

5. Aracytin

6. Depocyt

7. Cytosar-u

8. Aracytine

9. Tarabine

10. Udicil

11. 1-beta-d-arabinofuranosylcytosine

12. Arabinofuranosylcytosine

13. Aracytidine

14. Depocyte

15. Cytarabinoside

16. Cytarabin

17. Cytosar

18. Arabinocytosine

19. Cytarabinum

20. Arabinosylcytosine

21. Cytosine Beta-d-arabinofuranoside

22. Spongocytidine

23. Cytosinearabinoside

24. Citarabina

25. Alexan

26. Beta-d-arabinosylcytosine

27. Cytarabinum [inn-latin]

28. 4-amino-1-((2r,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1h)-one

29. Citarabina [inn-spanish]

30. Arac

31. Cytosine Beta-d-arabinoside

32. Arabitin

33. Cytarabina

34. Arafcyt

35. Erpalfa

36. Iretin

37. Cytosine-1-beta-d-arabinofuranoside

38. 1beta-d-arabinosylcytosine

39. 4-amino-1-beta-d-arabinofuranosyl-2(1h)-pyrimidinone

40. Cytosine Arabinose

41. 1beta-arabinofuranasylcytosine

42. Cytosine 1-beta-d-arabinofuranoside

43. Cytarabine Liposome

44. 1beta-d-arabinofuranosylcytosine

45. 1-beta-d-arabinofaranosylcytosine

46. U 19920a

47. Cytosine-beta-d-arabinofuranoside

48. Cytosine Arabinofuranoside

49. Depocyt (liposomal)

50. 1-arabinofuranosylcytosine

51. 4-amino-1-beta-d-arabinofuranosylpyrimidin-2(1h)-one

52. U-19,920

53. 1-beta-d-arabinosylcytosine

54. Arabinoside C

55. 1-beta-d-arabinofuranosyl-4-amino-2(1h)pyrimidinone

56. Chembl803

57. U-19920

58. 4-amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidin

59. 4-amino-1-[(2r,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one

60. 2(1h)-pyrimidinone, 4-amino-1-.beta.-d-arabinofuranosyl-

61. Ar3

62. Cytonal

63. Chebi:28680

64. Chx 3311

65. 04079a1rdz

66. 1-beta-d-arabinofuranosyl-cytosine

67. Ccris 913

68. Beta-ara C

69. 4-amino-1-[(2r,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one

70. Nsc-287459

71. Cytosine, 1-beta-d-arabinosyl-

72. Hsdb 3049

73. (beta-d-arabinofuranosyl)cytosine

74. Ncgc00093356-03

75. 2(1h)-pyrimidinone, 4-amino-1-y-d-arabinofuranosyl- [cas]

76. 4-amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidine

77. Mfcd00066487

78. Dsstox_cid_2877

79. Cytosine, 1-beta-d-arabinofuranosyl-

80. Nsc 287459

81. Ac-1075

82. Dsstox_rid_76771

83. Dsstox_gsid_22877

84. Ai3-52329

85. Cytosine Arabinoside (van)

86. 2(1h)-pyrimidinone, 4-amino-1-beta-d-arabinofuranosyl-

87. Beta-arabinosylcytosine

88. Beta-cytosine Arabinoside

89. Cytosine-beta-arabinoside

90. Ara-cytidine

91. Cytarabine Liposome Injection

92. Arabinosyl Cytosine

93. Cytosine, Beta-d-arabinoside

94. Cas-147-94-4

95. Smr000449317

96. Depocyt (tn)

97. 69-74-9

98. Cytosine B-d-arabinofuranoside

99. Einecs 205-705-9

100. 1-(arabinofuranosyl)cytosine

101. Cytartbine

102. Unii-04079a1rdz

103. 1-beta-arabinofuranosylcytosine

104. 1-.beta.-d-arabinofuranosylcytosine

105. Sr-01000075773

106. Nsc287459

107. 4-amino-1-beta-d-arabinofuranosyl-2(1h)-pyrimidinon [czech]

108. 4-amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidin [czech]

109. 1-.beta.-d-arabinofuranosyl-cytosine

110. 4-amino-1-b-d-arabinofuranosyl-2-(1h)-pyrimidinone

111. 4-amino-1-beta-d-arabinofuranosyl-2(1h)-pyrimidinon

112. 1-beta-d-arabinofuranosylcytosine, Cytosine Arabinoside

113. Cytarabine [usan:usp:inn:ban:jan]

114. Mk 8242

115. Beta -arabinosylcytosine

116. Cytarabine [mi]

117. Cytarabine [inn]

118. Cytarabine [jan]

119. Cytarabine [hsdb]

120. Cytarabine [usan]

121. Beta -cytosine Arabinoside

122. Beta -d-arabinosylcytosine

123. Cytosine-beta -arabinoside

124. Cytarabine [vandf]

125. Cytarabine [mart.]

126. Schembl3140

127. 1beta -d-arabinosylcytosine

128. Cytarabine [usp-rs]

129. Cytarabine [who-dd]

130. Cytarabine [who-ip]

131. Bidd:pxr0139

132. Lopac0_000316

133. Mls000758310

134. Mls001066340

135. Mls001424023

136. 1-beta-d-arabinosyl-cytosine

137. Bidd:gt0371

138. Cytarabine [ema Epar]

139. Cytosine, Beta -d-arabinoside

140. 1beta -arabinofuranasylcytosine

141. Cytarabine (jp17/usp/inn)

142. Gtpl4827

143. 1-ss-d-arabinofuranosylcytosine

144. Cytarabine [orange Book]

145. Dtxsid3022877

146. Schembl22591193

147. Schembl23152019

148. 1beta -d-arabinofuranosylcytosine

149. Cytarabine [ep Monograph]

150. Cytarabine [usp Impurity]

151. Cytosine, 1-beta -d-arabinosyl-

152. Vyxeos Component Cytarabine

153. 1-beta -d-arabinofuranosylcytosine

154. 1-beta-d-arabinofuranosyl Cytosine

155. Cytarabine [usp Monograph]

156. Cytosine-beta -d-arabinofuranoside

157. Hms2051k19

158. Hms2090a18

159. Hms2230m16

160. Hms3713n12

161. 1-beta -d-arabinofaranosylcytosine

162. Cytarabine Liposome [vandf]

163. Cytarabinum [who-ip Latin]

164. Bcp02876

165. Zinc3795098

166. Tox21_111203

167. Tox21_301971

168. Bdbm50087289

169. Ccg-51297

170. S1648

171. (non-labelled)cytarabine-13c-15n2

172. Akos007930145

173. Akos015896896

174. Am84428

175. Cytosine, 1-beta -d-arabinofuranosyl-

176. Db00987

177. Ks-5063

178. Nc00070

179. Sdccgsbi-0050304.p002

180. Ncgc00093356-04

181. Ncgc00093356-05

182. Ncgc00093356-06

183. Ncgc00093356-19

184. Ncgc00142483-02

185. Ncgc00255381-01

186. Ba164339

187. Hy-13605

188. Sri-10828-19

189. Sri-10828-20

190. Sri-10828_24

191. Sl-000002

192. Sw197450-5

193. C02961

194. D00168

195. 1-beta-d-arabinofuranosylcytosine; Ara-c

196. 147c944

197. A808710

198. Q180983

199. Sr-01000721860

200. J-520199

201. J-700005

202. J-700166

203. Sr-01000075773-3

204. Sr-01000075773-5

205. Sr-01000721860-6

206. 1-beta -d-arabinofuranosyl-4-amino-2(1h)pyrimidinone

207. 2(1h)-pyrimidinone, 4-amino-1- -d-arabinofuranosyl

208. Brd-k33106058-001-07-7

209. Brd-k33106058-003-20-6

210. 2(1h)-pyrimidinone, 4-amino-1beta -d-arabinofuranosyl-

211. Z1522566619

212. 2(1h)-pyrimidinone, 4-amino-1-beta -d-arabinofuranosyl-

213. Cytarabine, European Pharmacopoeia (ep) Reference Standard

214. Cytarabine, United States Pharmacopeia (usp) Reference Standard

215. Cytosine Beta-d-arabinofuranoside, Crystalline, >=90% (hplc)

216. Cytosine Beta-d-arabinofuranoside, Vetec(tm) Reagent Grade, 90%

217. Cytarabine, Pharmaceutical Secondary Standard; Certified Reference Material

218. 4-amino-1-[(2r,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 243.22 g/mol
Molecular Formula C9H13N3O5
XLogP3-2.1
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count5
Rotatable Bond Count2
Exact Mass243.08552052 g/mol
Monoisotopic Mass243.08552052 g/mol
Topological Polar Surface Area129 Ų
Heavy Atom Count17
Formal Charge0
Complexity383
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 6  
Drug NameCytarabine
PubMed HealthCytarabine
Drug ClassesAntimetabolite, Antineoplastic Agent
Drug LabelCytarabine Injection, an antineoplastic agent, is a sterile preserved solution for intravenous or subcutaneous administration, and is available in a 500 mg (20 mg/mL) multidose vial. Each mL contains: 20 mg Cytarabine, USP and the following inactive...
Active IngredientCytarabine
Dosage FormInjectable
RouteInjection
Strength20mg/ml; 500mg/vial; 100mg/vial; 100mg/ml; 2gm/vial; 1gm/vial
Market StatusPrescription
CompanyFresenius Kabi Usa; Hospira; Onco Therapies; Eurohlth Intl

2 of 6  
Drug NameCytosar-u
PubMed HealthCytarabine, Liposome (Injection)
Drug ClassesAntineoplastic Agent
Drug LabelDepoCyt (cytarabine liposome injection) is a sterile, injectable suspension of the antimetabolite cytarabine, encapsulated into multivesicular lipid-based particles using proprietary DepoFoam formulation technology. Chemically, cytarabine is 4-am...
Active IngredientCytarabine
Dosage FormInjectable
RouteInjection
Strength500mg/vial; 100mg/vial; 1gm/vial; 2gm/vial
Market StatusPrescription
CompanyTeva Pharms Usa

3 of 6  
Drug NameDepocyt
Active IngredientCytarabine
Dosage FormInjectable, liposomal
RouteInjection
Strength10mg/ml
Market StatusPrescription
CompanyPacira Pharms

4 of 6  
Drug NameCytarabine
PubMed HealthCytarabine
Drug ClassesAntimetabolite, Antineoplastic Agent
Drug LabelCytarabine Injection, an antineoplastic agent, is a sterile preserved solution for intravenous or subcutaneous administration, and is available in a 500 mg (20 mg/mL) multidose vial. Each mL contains: 20 mg Cytarabine, USP and the following inactive...
Active IngredientCytarabine
Dosage FormInjectable
RouteInjection
Strength20mg/ml; 500mg/vial; 100mg/vial; 100mg/ml; 2gm/vial; 1gm/vial
Market StatusPrescription
CompanyFresenius Kabi Usa; Hospira; Onco Therapies; Eurohlth Intl

5 of 6  
Drug NameCytosar-u
PubMed HealthCytarabine, Liposome (Injection)
Drug ClassesAntineoplastic Agent
Drug LabelDepoCyt (cytarabine liposome injection) is a sterile, injectable suspension of the antimetabolite cytarabine, encapsulated into multivesicular lipid-based particles using proprietary DepoFoam formulation technology. Chemically, cytarabine is 4-am...
Active IngredientCytarabine
Dosage FormInjectable
RouteInjection
Strength500mg/vial; 100mg/vial; 1gm/vial; 2gm/vial
Market StatusPrescription
CompanyTeva Pharms Usa

6 of 6  
Drug NameDepocyt
Active IngredientCytarabine
Dosage FormInjectable, liposomal
RouteInjection
Strength10mg/ml
Market StatusPrescription
CompanyPacira Pharms

4.2 Therapeutic Uses

Antimetabolites, Antineoplastic; Antiviral Agents; Immunosuppressive Agents; Teratogens

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


DepoCyt (cytarabine liposome injection) is indicated for the intrathecal treatment of lymphomatous meningitis. This indication is based on demonstration of increased complete response rate compared to unencapsulated cytarabine. There are no controlled trials that demonstrate a clinical benefit resulting from this treatment, such as improvement in disease-related symptoms, or increased time to disease progression, or increased survival. /Cytarabine liposome injection/

Physicians Desk Reference 61st ed, Thomson PDR, Montvale, NJ 2007., p. 1143


Cytarabine is indicated, in combination with other antineoplastic agents, for treatment of acute nonlymphocytic leukemia in adults and children. /Included US product label/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 933


Cytarabine is indicated for treatment of acute lymphocytic leukemia and chronic myelocytic leukemia (blast phase). /Included in US product label/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 933


For more Therapeutic Uses (Complete) data for CYTARABINE (10 total), please visit the HSDB record page.


4.3 Drug Warning

The patient's hematologic status must be carefully monitored. Leukocyte and platelet counts should be performed frequently during cytarabine therapy. The manufacturers state that leukocyte and platelet counts should be determined daily during remission induction therapy of acute leukemia. The manufacturers also recommend frequent bone marrow examinations after blast cells have disappeared from the peripheral blood.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 992


Patients who receive myelosuppressive drugs experience an increased frequency of infections (e.g., viral, bacterial, fungal) as well as possible hemorrhagic complications. Because these complications are potentially fatal, the patient should be instructed to notify the clinician if fever, sore throat, or unusual bleeding or bruising occurs. ...Treatment with cytarabine should be initiated only with extreme caution in patients with preexisting drug-induced bone marrow suppression.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 992


The manufacturers recommend that periodic determinations of renal function be performed in patients receiving cytarabine. Periodic determinations of hepatic function should also be performed in patients receiving cytarabine, and the manufacturers state that the drug should be used with caution and in reduced dosage in patients with poor hepatic function.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 992


Cytarabine is contraindicated in patients with known hypersensitivity to the drug.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 992


For more Drug Warnings (Complete) data for CYTARABINE (30 total), please visit the HSDB record page.


4.4 Drug Indication

For the treatment of acute non-lymphocytic leukemia, acute lymphocytic leukemia and blast phase of chronic myelocytic leukemia. Cytarabine is indicated in combination with [daunorubicin] for the treatment of newly-diagnosed therapy-related acute myeloid leukemia (t-AML) or AML with myelodysplasia-related changes (AML-MRC) in adults and pediatric patients 1 year and older.


FDA Label


Intrathecal treatment of lymphomatous meningitis. In the majority of patients such treatment will be part of symptomatic palliation of the disease.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Cytarabine is an antineoplastic anti-metabolite used in the treatment of several forms of leukemia including acute myelogenous leukemia and meningeal leukemia. Anti-metabolites masquerade as purine or pyrimidine - which become the building blocks of DNA. They prevent these substances becoming incorporated in to DNA during the "S" phase (of the cell cycle), stopping normal development and division. Cytarabine is metabolized intracellularly into its active triphosphate form (cytosine arabinoside triphosphate). This metabolite then damages DNA by multiple mechanisms, including the inhibition of alpha-DNA polymerase, inhibition of DNA repair through an effect on beta-DNA polymerase, and incorporation into DNA. The latter mechanism is probably the most important. Cytotoxicity is highly specific for the S phase of the cell cycle.


5.2 MeSH Pharmacological Classification

Antiviral Agents

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)


Antimetabolites, Antineoplastic

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


Immunosuppressive Agents

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


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
CYTARABINE
5.3.2 FDA UNII
04079A1RDZ
5.3.3 Pharmacological Classes
Nucleoside Metabolic Inhibitor [EPC]; Nucleic Acid Synthesis Inhibitors [MoA]
5.4 ATC Code

L01BC01


L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01B - Antimetabolites

L01BC - Pyrimidine analogues

L01BC01 - Cytarabine


5.5 Absorption, Distribution and Excretion

Absorption

Less than 20% of the orally administered dose is absorbed from the gastrointestinal tract.


Route of Elimination

The primary route of elimination of cytarabine is metabolism to the inactive compound ara-U, followed by urinary excretion of ara-U.


Less than 20% of a dose of conventional cytarabine is absorbed from the GI tract, and the drug is not effective when administered orally. Following subcutaneously or im injection of conventional cytarabine H 3, peak plasma concentrations of radioactivity occur within 20-60 min and are considerably lower than those attained after iv administration. Continuous iv infusions of conventional cytarabine produce relatively constant plasma concn of the drug in 8-24 hr.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 993


Cytarabine is rapidly and widely distributed into tissues and fluids, including liver, plasma, and peripheral granulocytes. Following rapid IV injection of cytarabine in one study, approximately 13% of the drug was bound to plasma proteins.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 993


Cytarabine crosses the blood-brain barrier to a limited extent. During a continuous IV or subcutaneous infusion, cytarabine concentrations in the CSF are higher than those attained after rapid IV injection and are about 40-60% of plasma concentrations. Most of an intrathecal dose of cytarabine diffuses into the systemic circulation but is rapidly metabolized and usually only low plasma concentrations of unchanged drug occur.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 993


The drug apparently crosses the placenta. It is not known if cytarabine or ara-U is distributed into milk.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 993


For more Absorption, Distribution and Excretion (Complete) data for CYTARABINE (7 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Hepatic.


Cytarabine is rapidly and extensively metabolized mainly in the liver but also in kidneys, GI mucosa, granulocytes, and to a lesser extent in other tissues by the enzyme cytidine deaminase, producing the inactive metabolite 1--d-arabinofuranosyluracil (ara-U, uracil arabinoside). After the initial distribution phase, more than 80% of the drug in plasma is present as ara-U. In the CSF, only minimal amounts of cytarabine are converted to ara-U because of low CSF concentrations of cytidine deaminase. Intracellularly, cytarabine is metabolized by deoxycytidine kinase and other nucleotide kinases to cytarabine triphosphate, the active metabolite of the drug. Cytarabine triphosphate is inactivated by a pyrimidine nucleoside deaminase, which produces the uracil derivative.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 994


The primary route of elimination of cytarabine is metabolism to the inactive compound ara-U (1-(beta)-D-arabinofuranosyluracil or uracilarabinoside), followed by urinary excretion of ara-U. In contrast to systemically administered cytarabine, which is rapidly metabolized to ara-U, conversion to ara-U in the CSF is negligible after intrathecal administration because of the significantly lower cytidine deaminase activity in the CNS tissues and CSF. The CSF clearance rate of cytarabine is similar to the CSF bulk flow rate of 0.24 mL/min. /Cytarabine liposome injection/

Physicians Desk Reference 61st ed, Thomson PDR, Montvale, NJ 2007., p. 1143


Cytarabine must be converted to the 5'-monophosphate nucleotide by deoxycytidine kinase to be active. Ara-cytidine diphosphate &/or ara-cytidine triphosphate are presumably the form that inhibit DNA polymerase & block ribonucleoside diphosphate reductase.

Booth, N.H., L.E. McDonald (eds.). Veterinary Pharmacology and Therapeutics. 5th ed. Ames, Iowa: Iowa State University Press, 1982., p. 792


5.7 Biological Half-Life

10 minutes


After rapid IV injection of cytarabine, plasma drug concentrations appear to decline in a biphasic manner with a half-life of about 10 minutes in the initial phase and about 1-3 hours in the terminal phase. Cytarabine reportedly undergoes triphasic elimination in some patients. After intrathecal injection, cytarabine concentrations in the CSF reportedly decline with a half-life of about 2 hours.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 994


Peak levels were followed by a biphasic elimination profile with a terminal phase half-life of 100 to 263 hours over a dose range of 12.5 mg to 75 mg. In contrast, intrathecal administration of 30 mg of free cytarabine showed a biphasic CSF concentration profile with a terminal phase half-life of 3.4 hours. /Cytarabine liposome injection/

Physicians Desk Reference 61st ed, Thomson PDR, Montvale, NJ 2007., p. 1143


After iv admin, there is a rapid phase of disappearance of AraC (half-life = 10 min), followed by a slower phase of elimination with a half-time of about 2.5 hr ... After intrathecal admin of the drug at a dose of 50 mg/sq m ... peak concn of 1 to 2 mM are achieved, which decline slowly with a terminal half-life of approx 3.4 hr.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1410


5.8 Mechanism of Action

Cytarabine acts through direct DNA damage and incorporation into DNA. Cytarabine is cytotoxic to a wide variety of proliferating mammalian cells in culture. It exhibits cell phase specificity, primarily killing cells undergoing DNA synthesis (S-phase) and under certain conditions blocking the progression of cells from the G1 phase to the S-phase. Although the mechanism of action is not completely understood, it appears that cytarabine acts through the inhibition of DNA polymerase. A limited, but significant, incorporation of cytarabine into both DNA and RNA has also been reported.


Cytarabine is converted intracellularly to the nucleotide, cytarabine triphosphate (ara-CTP, cytosine arabinoside triphosphate). Although the exact mechanism(s) of action of cytarabine has not been fully elucidated, cytarabine triphosphate appears to inhibit DNA polymerase by competing with the physiologic substrate, deoxycytidine triphosphate, resulting in the inhibition of DNA synthesis. Although limited, incorporation of cytarabine triphosphate into DNA and RNA may also contribute to the cytotoxic effects of the drug.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 993


Cytarabine is a potent immunosuppressant which can suppress humoral and/or cellular immune responses; however, the drug does not decrease preexisting antibody titers and has no effect on established delayed hypersensitivity reactions.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 993


Cytarabine liposome injection is a sustained-release formulation of the active ingredient cytarabine designed for direct administration into the cerebrospinal fluid (CSF). Cytarabine is a cell cycle phase-specific antineoplastic agent, affecting cells only during the S-phase of cell division. Intracellularly, cytarabine is converted into cytarabine-5'-triphosphate (ara-CTP), which is the active metabolite. The mechanism of action is not completely understood, but it appears that ara-CTP acts primarily through inhibition of DNA polymerase. Incorporation into DNA and RNA may also contribute to cytarabine cytotoxicity. Cytarabine is cytotoxic to a wide variety of proliferating mammalian cells in culture. /Cytarabine liposome injection/

Physicians Desk Reference 61st ed, Thomson PDR, Montvale, NJ 2007., p. 1143


Listed Suppliers

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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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Cytarabine

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.
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02

Archimica

Italy
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Archimica

Italy
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Cytarabine

About the Company : We provide quality products and services, consistently, reliably responsibly and continuously applying some of the world’s most difficult to handle chemical technologies. Synth...

We provide quality products and services, consistently, reliably responsibly and continuously applying some of the world’s most difficult to handle chemical technologies. Synthesis: Manufacturing services and products for all user industries, using Archimica´s highly differentiated setup and technologies APIs, Building blocks, GMP intermediates, Regulatory Starting Materials. For all global markets including the United States of America, in total Archimica products reach 25 countries.
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03

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Cytarabine

About the Company : Beijing Mesochem Technology Co. Ltd., which is located in the national economic and technological development area of Yizhuang, China, manufactures pharmaceutical chemicals, fine c...

Beijing Mesochem Technology Co. Ltd., which is located in the national economic and technological development area of Yizhuang, China, manufactures pharmaceutical chemicals, fine chemicals and fundamental chemical materials. It has an efficient research and development team. Beijing Mesochem provides its customers customized development, craft optimization, contract customization and outsourcing services. The company has a well-established industrial base in Weinan, Shanxi Province. The production base features a 20,000 ㎡ plant with a production capacity of over 8,000 MT per year.
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04

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About the Company : Biesterfeld Spezialchemie GmbH is a part of the Biesterfeld Group. Biesterfeld Spezialchemie GmbH is a pan-European, rapidly growing distributor of products requiring special perfo...

Biesterfeld Spezialchemie GmbH is a part of the Biesterfeld Group. Biesterfeld Spezialchemie GmbH is a pan-European, rapidly growing distributor of products requiring special performance in the fields of LifeScience, Nutrition, CASE (Coatings, Adhesives, Sealants, Elastomers) & Performance Products. In cooperation with leading companies in the chemical industry, our sales team - with its focus on technical applications - is constantly working on innovative products for the international market.
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05

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Cytarabine

About the Company : Fujian South Pharmaceutical Co., Ltd. (Southern Pharmaceutical) was established in September 2001 and is located in Mingxi County, Fujian Province. After 16 years of development, ...

Fujian South Pharmaceutical Co., Ltd. (Southern Pharmaceutical) was established in September 2001 and is located in Mingxi County, Fujian Province. After 16 years of development, Nanfang Pharmaceutical has grown into a major domestic manufacturer of anti-tumor raw materials and intermediates, and has expanded to non-anti-tumor drugs. Using the company's accumulated rich experience and first-class technology in plant extraction, the company's product line has been expanded to the field of plant-derived products.
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06

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Cytarabine

About the Company : Founded in 1986, Kekule has developed from a manufacturer of few molecules to a preferred vendor for many complex molecules requiring multistage synthesis. Working with customers a...

Founded in 1986, Kekule has developed from a manufacturer of few molecules to a preferred vendor for many complex molecules requiring multistage synthesis. Working with customers across the world, Kekule has always leveraged its strengths in basic chemistry as well as chemical engineering to deliver high quality APIs and Intermediates in time and at competitive prices. Our value based approach to business has been a foundation for a mutually beneficial long term relationship with our customers. Our employees, technology and infrastructure match the highest international standards.
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Cytarabine

About the Company : Established in 2010, Mac-Chem is a NMM Group company. Mac-Chem is focused on oncology and other niche specialty APIs. It supplies quality APIs to the top 15 oncology players in Ind...

Established in 2010, Mac-Chem is a NMM Group company. Mac-Chem is focused on oncology and other niche specialty APIs. It supplies quality APIs to the top 15 oncology players in India. It is also the sole manufacturer of some of the molecules in the oncology segment and general segment. The company’s investments are mostly geared toward exports, especially to regulated markets. Mac-Chem has a cGMP-compliant manufacturing facility near Mumbai in India. The company’s facility is USFDA, EDQM, COFEPRIS, ANVISA, MFDS-Korea, WHO-GMP-approved and ISO-certified. Mac-Chem enjoys a global reach, serving more than 40 countries.
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Cytarabine

About the Company : Established in the year 2004, Sakar is engaged in manufacturing of Pharmaceutical products providing Liquid Orals, Cephalosporin Tablet, Capsule, Dry Powder Syrup, Dry Powder Injec...

Established in the year 2004, Sakar is engaged in manufacturing of Pharmaceutical products providing Liquid Orals, Cephalosporin Tablet, Capsule, Dry Powder Syrup, Dry Powder Injections, Liquid Injectables (SVP) in Ampoules and Vials & Lyophilized Injections. Sakar is managed by a team of professionals with an endeavour to offer Quality Pharmaceutical & Health Care Products in various countries. The company operates as contract development and manufacturing organisation (CDMO), being the EU GMP approved CMO for leading multinational pharmaceutical companies.
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Cytarabine

About the Company : Haorui, established in 1997, is a manufacturer and supplier of APIs, intermediates, veterinary and food additives. Meanwhile, it is assisting global pharmaceutical companies to get...

Haorui, established in 1997, is a manufacturer and supplier of APIs, intermediates, veterinary and food additives. Meanwhile, it is assisting global pharmaceutical companies to get the domestic registration of their finished dosage for their international expansion. Our USFDA approved products Flumazenil, Granisetron HCl, Granisetron Base, Docetaxel Anhydrous, Irinotecan HCl, Dasatinib Monohydrate, Oxaliplatin and Temozolomide have been recognized by our customers globally. In addition, our Amisulpride API acquired CEP, UK GMP & USDMF.
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Cytarabine

About the Company : Shouyuan chemical (one of the leading chemicals supplier in China) specializes in manufacturing, supplying, and custom synsthesis latest chemicals. Our products cover all kinds of ...

Shouyuan chemical (one of the leading chemicals supplier in China) specializes in manufacturing, supplying, and custom synsthesis latest chemicals. Our products cover all kinds of range like pharmaceuticals, agrochemicals, electronic chemicals, surfactants and other specialty chemicals.
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23-Jan-2021
29-Jul-2024
KGS
overview
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Average Price (USD/KGS)

Number of Transactions

Total Quantity (KGS)

Total Value (USD)

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

API Imports and Exports

Importing Country Total Quantity
(KGS)
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(USD/KGS)
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Europe

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ACCORD HEALTHCARE LIMITED

United Kingdom
26th North American ISSX
Not Confirmed
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ACCORD HEALTHCARE LIMITED

United Kingdom
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26th North American ISSX
Not Confirmed

Cytarabine

Brand Name : Cytarabine

Dosage Form : Cytarabine 2.000Mg 20Ml 1 Units Parenteral Use

Dosage Strength : 1 vial EV SC 20 ml 100 mg/ml

Packaging :

Approval Date :

Application Number :

Regulatory Info :

Registration Country : Italy

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02

26th North American ISSX
Not Confirmed
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26th North American ISSX
Not Confirmed

Cytarabine

Brand Name : Cytarabine

Dosage Form : Cytarabine 1.000Mg 10Ml 1 Units Parenteral Use

Dosage Strength : 1 vial EV 10 ml 100 mg/ml

Packaging :

Approval Date :

Application Number :

Regulatory Info :

Registration Country : Italy

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03

26th North American ISSX
Not Confirmed
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26th North American ISSX
Not Confirmed

Cytarabine

Brand Name : Cytarabine

Dosage Form : Cytarabine 100Mg 1Ml 1 Units Parenteral Use

Dosage Strength : 1 vial EV 1 ml 100 mg/ml

Packaging :

Approval Date :

Application Number :

Regulatory Info :

Registration Country : Italy

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04

26th North American ISSX
Not Confirmed
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26th North American ISSX
Not Confirmed

Cytarabine

Brand Name : Cytarabin Fresenius Kabi

Dosage Form : Injection/infusion fluid, resolution

Dosage Strength : 100 mg/ml

Packaging : Hood glass

Approval Date :

Application Number :

Regulatory Info :

Registration Country : Norway

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05

26th North American ISSX
Not Confirmed
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26th North American ISSX
Not Confirmed

Cytarabine

Brand Name : Cytarabine

Dosage Form : Cytarabine 2.000Mg 20Ml 1 Units Parenteral Use

Dosage Strength : 1 ampoule EV 2 g 20 ml

Packaging :

Approval Date :

Application Number :

Regulatory Info :

Registration Country : Italy

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06

26th North American ISSX
Not Confirmed
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26th North American ISSX
Not Confirmed

Cytarabine

Brand Name : Aracytin

Dosage Form : Cytarabine 100Mg 5Ml 1 Units Parenteral Use

Dosage Strength : 1 bottle SC EV 100 mg + 1 ampoule solv 5 ml

Packaging :

Approval Date :

Application Number :

Regulatory Info :

Registration Country : Italy

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07

Pfizer AS

U.S.A
26th North American ISSX
Not Confirmed
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Pfizer AS

U.S.A
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26th North American ISSX
Not Confirmed

Cytarabine

Brand Name : Cytarabine Pfizer

Dosage Form : Injection/infusion fluid, resolution

Dosage Strength : 100 mg/ml

Packaging : Bottle of plastic

Approval Date :

Application Number :

Regulatory Info :

Registration Country : Norway

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08

Pfizer AG

U.S.A
26th North American ISSX
Not Confirmed
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Pfizer AG

U.S.A
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26th North American ISSX
Not Confirmed

Cytarabinum

Brand Name : Cytosar Solution

Dosage Form : Inj L?s

Dosage Strength : 2g/20ml

Packaging :

Approval Date :

Application Number :

Regulatory Info :

Registration Country : Switzerland

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09

26th North American ISSX
Not Confirmed
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26th North American ISSX
Not Confirmed

cytarabine

Brand Name : Cytarabine Mylan

Dosage Form : INJECTION / INFUSION

Dosage Strength : 100 MG / ML

Packaging :

Approval Date :

Application Number :

Regulatory Info :

Registration Country : Sweden

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10

26th North American ISSX
Not Confirmed
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26th North American ISSX
Not Confirmed

cytarabine

Brand Name : Cytarabine Mylan

Dosage Form : INJECTION / INFUSION

Dosage Strength : 20 MG / ML

Packaging :

Approval Date :

Application Number :

Regulatory Info :

Registration Country : Sweden

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Canada

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01

26th North American ISSX
Not Confirmed
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26th North American ISSX
Not Confirmed

CYTARABINE

Brand Name : VYXEOS

Dosage Form : POWDER

Dosage Strength : 100MG

Packaging :

Approval Date :

Application Number : 2515490

Regulatory Info : Prescription

Registration Country : Canada

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02

26th North American ISSX
Not Confirmed
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26th North American ISSX
Not Confirmed

CYTARABINE

Brand Name : CYTARABINE INJECTION

Dosage Form : SOLUTION

Dosage Strength : 100MG/ML

Packaging : 1/10/20ML

Approval Date :

Application Number : 2126656

Regulatory Info : Prescription

Registration Country : Canada

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03

26th North American ISSX
Not Confirmed
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26th North American ISSX
Not Confirmed

CYTARABINE

Brand Name : PMS-CYTARABINE

Dosage Form : SOLUTION

Dosage Strength : 20MG/ML

Packaging : 5ML/VIAL

Approval Date :

Application Number : 2406764

Regulatory Info : Prescription

Registration Country : Canada

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04

26th North American ISSX
Not Confirmed
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26th North American ISSX
Not Confirmed

CYTARABINE

Brand Name : PMS-CYTARABINE

Dosage Form : SOLUTION

Dosage Strength : 100MG/ML

Packaging : 10ML/VIAL, 20ML/VIAL

Approval Date :

Application Number : 2406772

Regulatory Info : Prescription

Registration Country : Canada

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05

STERIMAX INC

Canada
26th North American ISSX
Not Confirmed
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STERIMAX INC

Canada
arrow
26th North American ISSX
Not Confirmed

CYTARABINE

Brand Name : CYTARABINE INJECTION

Dosage Form : SOLUTION

Dosage Strength : 100MG/ML

Packaging :

Approval Date :

Application Number : 2515296

Regulatory Info : Prescription

Registration Country : Canada

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Australia

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01

26th North American ISSX
Not Confirmed
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26th North American ISSX
Not Confirmed

cytarabine

Brand Name : Pfizer Australia Pty Ltd

Dosage Form :

Dosage Strength :

Packaging : 5

Approval Date :

Application Number :

Regulatory Info :

Registration Country : Australia

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02

26th North American ISSX
Not Confirmed
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26th North American ISSX
Not Confirmed

cytarabine

Brand Name : Pfizer Australia Pty Ltd

Dosage Form :

Dosage Strength :

Packaging : 5

Approval Date :

Application Number :

Regulatory Info :

Registration Country : Australia

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