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Substance Name: Cytarabine [USAN:USP:INN:BAN:JAN]
RN: 147-94-4
UNII: 04079A1RDZ
InChIKey: UHDGCWIWMRVCDJ-CCXZUQQUSA-N

Note

  • 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).

Molecular Formula

  • C9-H13-N3-O5

Molecular Weight

  • 243.218
 

Classification Codes

  • Anti-Infective Agents
  • Antimetabolites
  • Antimetabolites, Antineoplastic
  • Antineoplastic
  • Antineoplastic Agents
  • Antiviral
  • Antiviral (COVID-19)
  • Antiviral Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Immunologic Factors
  • Immunosuppressive Agents
  • Mutation Data
  • Noxae
  • Reproductive Effect
  • Skin / Eye Irritant
  • Tumor Data

Names and Synonyms

Name of Substance

  • Cytarabine
  • Cytarabine [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Cytarabine

Synonyms

  • 1-Arabinofuranosylcytosine
  • 1-beta-D-Arabinofaranosylcytosine
  • 1-beta-D-Arabinofuranosyl-4-amino-2(1H)pyrimidinone
  • 1-beta-D-Arabinofuranosylcytosine
  • 1-beta-D-Arabinosylcytosine
  • 1beta-Arabinofuranasylcytosine
  • 1beta-D-Arabinofuranosylcytosine
  • 1beta-D-Arabinosylcytosine
  • 2(1H)-Pyrimidinone, 4-amino-1-beta-D-arabinofuranosyl-
  • 4-Amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidin
  • 4-Amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidin [Czech]
  • 4-Amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidine
  • 4-Amino-1-beta-D-arabinofuranosyl-2(1H)-pyrimidinon
  • 4-Amino-1-beta-D-arabinofuranosyl-2(1H)-pyrimidinon [Czech]
  • 4-Amino-1-beta-D-arabinofuranosyl-2(1H)-pyrimidinone
  • AC-1075
  • AI3-52329
  • Alexan
  • Ara-C
  • Arabinocytidine
  • Arabinofuranosylcytosine
  • Arabinosylcytosine
  • Arabitin
  • Aracytidine
  • Aracytin
  • Arafcyt
  • beta-D-Arabinosylcytosine
  • CCRIS 913
  • CHX 3311
  • Citarabina
  • Citarabina [INN-Spanish]
  • Cytarabin
  • Cytarabina
  • Cytarabine
  • Cytarabinoside
  • Cytarabinum
  • Cytarabinum [INN-Latin]
  • Cytosar
  • Cytosar-U
  • Cytosine 1-beta-D-arabinofuranoside
  • Cytosine arabinofuranoside
  • Cytosine arabinose
  • Cytosine arabinoside
  • Cytosine arabinoside (VAN)
  • Cytosine beta-D-arabinoside
  • Cytosine, 1-beta-D-arabinofuranosyl-
  • Cytosine, 1-beta-D-arabinosyl-
  • Cytosine-beta-D-arabinofuranoside
  • Cytosinearabinoside
  • Depocyt
  • Depocyt (liposomal)
  • DepoCyte
  • EINECS 205-705-9
  • Erpalfa
  • HSDB 3049
  • Iretin
  • MK 8242
  • NCI-C04728
  • NSC 287459
  • Spongocytidine
  • Tarabine
  • U 19920A
  • U-19,920
  • Udicil
  • UNII-04079A1RDZ

Systematic Names

  • 2(1H)-Pyrimidinone, 4-amino-1-beta-D-arabinofuranosyl-
  • Cytarabine
  • Cytosine arabinoside
  • Cytosine, 1-beta-D-arabinofuranosyl-

Superlist Name

  • Cytarabine

Registry Numbers

CAS Registry Number

  • 147-94-4

FDA UNII

  • 04079A1RDZ

Related Registry Number

  • 69-74-9 (hydrochloride)

System Generated Number

  • 0000147944

Structure Descriptors

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

InChIKey

UHDGCWIWMRVCDJ-CCXZUQQUSA-N

Smiles

NC1=NC(=O)N(C=C1)[C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo intravenous 33200ug/kg/24 (33.2mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 Cancer Vol. 42, Pg. 53, 1978.
human TDLo intravenous 17241mg/kg/6D (17241mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE" Annals of Internal Medicine. Vol. 102, Pg. 556, 1985.
man LDLo intravenous 1536mg/kg/43W (1536mg/kg) PERIPHERAL NERVE AND SENSATION: FASCICULATIONS

BEHAVIORAL: ATAXIA		 Drug Intelligence and Clinical Pharmacy. Vol. 21, Pg. 177, 1987.
man TDLo intraspinal 11429ug/kg (11.429mg/kg) PERIPHERAL NERVE AND SENSATION: PARESTHESIS Journal of Toxicology, Clinical Toxicology. Vol. 38, Pg. 246, 2000.
man TDLo intravenous 23500ug/kg/7D (23.5mg/kg) SENSE ORGANS AND SPECIAL SENSES: CONJUNCTIVE IRRITATION: EYE

SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE		 American Journal of Ophthalmology. Vol. 113, Pg. 587, 1992.
man TDLo intravenous 649mg/kg/4D-I (649mg/kg) PERIPHERAL NERVE AND SENSATION: FASCICULATIONS Drug Intelligence and Clinical Pharmacy. Vol. 21, Pg. 177, 1987.
man TDLo subcutaneous 60mg/kg/90W-I (60mg/kg) BLOOD: CHANGES IN SPLEEN

SENSE ORGANS AND SPECIAL SENSES: CHANGE IN ACUITY: EAR

BEHAVIORAL: ATAXIA		 Drug Intelligence and Clinical Pharmacy. Vol. 21, Pg. 798, 1987.
mouse LD50 intraperitoneal 3779mg/kg (3779mg/kg)   Cancer Research. Vol. 39, Pg. 2204, 1979.
mouse LD50 intravenous > 7gm/kg (7000mg/kg)   Drugs in Japan Vol. 6, Pg. 321, 1982.
mouse LD50 oral 3150mg/kg (3150mg/kg)   Drugs in Japan Vol. 6, Pg. 321, 1982.
mouse LD50 subcutaneous > 10gm/kg (10000mg/kg)   Drugs in Japan Vol. 6, Pg. 321, 1982.
rat LD50 intraperitoneal > 5gm/kg (5000mg/kg)   Drugs in Japan Vol. 6, Pg. 321, 1982.
rat LD50 intravenous > 5gm/kg (5000mg/kg)   Drugs in Japan Vol. 6, Pg. 321, 1982.
rat LD50 oral > 5gm/kg (5000mg/kg)   Drugs in Japan Vol. 6, Pg. 321, 1982.
rat LD50 subcutaneous > 5gm/kg (5000mg/kg)   Drugs in Japan Vol. 6, Pg. 321, 1982.
women TDLo intravenous 720mg/kg/3D-I (720mg/kg) BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES Neurology. Vol. 35, Pg. 1475, 1985.
women TDLo subcutaneous 6480ug/kg/12D (6.48mg/kg) BLOOD: OTHER CHANGES New England Journal of Medicine. Vol. 310, Pg. 1328, 1984.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 212.5 deg C   EXP
log P (octanol-water) -2.460 (none)   EST
Atmospheric OH Rate Constant 1.23E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.