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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
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
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
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Links to Resources
NLM Resources (File Locators)
Regulatory Agencies (Superlist Locators)
Other Resources (Internet Locators)
Search for this InChIKey on the Web
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/s1InChIKey
UHDGCWIWMRVCDJ-CCXZUQQUSA-NSmiles
NC1=NC(=O)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.