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Substance Name: Zidovudine [USAN:USP:INN:BAN:JAN]
RN: 30516-87-1
UNII: 4B9XT59T7S
InChIKey: HBOMLICNUCNMMY-XLPZGREQSA-N
Note
- A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.
Molecular Formula
- C10-H13-N5-O4
Molecular Weight
- 267.2437
- All
- Classifications
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- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
Classification Codes
Classification Codes
- Anti-HIV Agents
- Anti-Infective Agents
- Anti-Retroviral Agents
- Antimetabolites
- Antiretroviral
- Antiviral
- Antiviral (COVID-19)
- Antiviral Agents
- Drug / Therapeutic Agent
- Enzyme Inhibitors
- Human Data
- Mutation Data
- Noxae
- Nucleic Acid Synthesis Inhibitors
- Reproductive Effect
- Reverse Transcriptase Inhibitors
- Tumor Data
Superlist Classification Code
- Overall Carcinogenic Evaluation: 2B
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Names and Synonyms
Name of Substance
- Zidovudine
- Zidovudine [USAN:USP:INN:BAN:JAN]
MeSH Heading
- Zidovudine
Synonyms
- 1-(3-Azido-2,3-dideoxy-beta-D-ribofuranosyl)-5-methylpyrimidine-2,4-(1H,3H)-dione
- 3'-Azido-3'-deoxythymidine
- Azidothymidine
- AZT
- BW A509U
- BW-A 509U
- CCRIS 105
- Compound S
- DRG-0004
- HSDB 6515
- NSC 602670
- Retrovir
- UNII-4B9XT59T7S
- ZDV
- Zidovudina
- Zidovudina [Spanish]
- Zidovudine
- Zidovudinum
- Zidovudinum [Latin]
Systematic Names
- Azidothymidine
- Thymidine, 3'-azido-3'-deoxy-
Superlist Names
- 3'-Azido-3'-deoxythymidine
- Zidovudine
Mixture Names
- Combivir
- Trizivir
Registry Numbers
CAS Registry Number
- 30516-87-1
FDA UNII
- 4B9XT59T7S
Other Registry Number
- 399024-19-2
System Generated Number
- 0030516871
Structure Descriptors
InChI
InChI=1S/C10H13N5O4/c1-5-3-15(10(18)12-9(5)17)8-2-6(13-14-11)7(4-16)19-8/h3,6-8,16H,2,4H2,1H3,(H,12,17,18)/t6-,7+,8+/m0/s1InChIKey
HBOMLICNUCNMMY-XLPZGREQSA-NSmiles
CC1=CN([C@H]2C[C@H](N=[N+]=[N-])Toxicity
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
man | LDLo | oral | 86mg/kg/1W-I (86mg/kg) | BEHAVIORAL: HEADACHE BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Lancet. Vol. 2, Pg. 1392, 1986. |
man | TDLo | oral | 434mg/kg/38D- (434mg/kg) | BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE BLOOD: APLASTIC ANEMIA BLOOD: CHANGES IN CELL COUNT (UNSPECIFIED) | Annals of Internal Medicine. Vol. 107, Pg. 502, 1987. |
man | TDLo | unreported | 69mg/kg (69mg/kg) | SENSE ORGANS AND SPECIAL SENSES: "RETINAL CHANGES (PIGMENTARY DEPOSITIONS, RETINITIS, OTHER): EYE" | Annals of Internal Medicine. Vol. 114, Pg. 297, 1991. |
mouse | LD50 | intravenous | > 70mg/kg (70mg/kg) | United States Patent Document. Vol. #4804651, | |
mouse | LD50 | oral | 3062mg/kg (3062mg/kg) | SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Fundamental and Applied Toxicology. Vol. 32, Pg. 129, 1996. |
mouse | LD50 | unreported | > 750mg/kg (750mg/kg) | United States Patent Document. Vol. #4857511, | |
rat | LD50 | intravenous | > 70mg/kg (70mg/kg) | United States Patent Document. Vol. #4804651, | |
rat | LD50 | oral | 3084mg/kg (3084mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE | Fundamental and Applied Toxicology. Vol. 32, Pg. 129, 1996. |
rat | LD50 | unreported | > 750mg/kg (750mg/kg) | United States Patent Document. Vol. #4857511, | |
women | TDLo | oral | 1gm/kg/6W-I (1000mg/kg) | SKIN AND APPENDAGES (SKIN): NAILS: OTHER | Annals of Internal Medicine. Vol. 107, Pg. 350, 1987. |
Physical Properties
Physical Property | Value | Units | Temp (deg C) | Source |
---|---|---|---|---|
Melting Point | 113-115 | deg C | EXP | |
log P (octanol-water) | 0.05 | (none) | EXP | |
Water Solubility | 852 | mg/L | 25 | EST |
Vapor Pressure | 5.23E-20 | mm Hg | 25 | EST |
Henry's Law Constant | 2.01E-22 | atm-m3/mole | 25 | EST |
Atmospheric OH Rate Constant | 7.70E-11 | cm3/molecule-sec | 25 | EST |
Physical property data is provided to ChemIDplus by SRC, Inc.