Zalcitabine

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Names

[ CAS No. ]:
7481-89-2

[ Name ]:
Zalcitabine

[Synonym ]:
ddCyd
[3H]-Zalcitabine
2',3'-DIDEOXYCYTIDINE
4-Amino-1-[(2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2(1H)-one
DDC
DDC (VAN)
Zalcitabine
1-[(2R,5S)-5-(Hydroxymethyl)tetrahydro-2-furanyl]-4-imino-1,4-dihydro-2-pyrimidinol
4-amino-1-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
HIVID
MFCD00012188
2-Pyrimidinol, 1,4-dihydro-4-imino-1-[(2R,5S)-tetrahydro-5-(hydroxymethyl)-2-furanyl]-
4-Amino-1-[(2R,5S)-5-(hydroxymethyl)tetrahydro-2-furanyl]-2(1H)-pyrimidinone
Cytidine,2',3'-dideoxy
Dideoxycytidine
3'-Azido-3'-deoxythymidine
4-Amino-1-[(2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2(1H)-on
Zalcitibine
2',3'-Dideoxycytidinene
CYTIDINE, 2',3'-DIDEOXY-
ddC (Antiviral)
2(1H)-Pyrimidinone, 4-amino-1-[(2R,5S)-tetrahydro-5-(hydroxymethyl)-2-furanyl]-
4-amino-1-[(2R,5S)-5-(hydroxyméthyl)tétrahydrofuran-2-yl]pyrimidin-2(1H)-one

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
415.0±55.0 °C at 760 mmHg

[ Melting Point ]:
217-218 °C(lit.)

[ Molecular Formula ]:
C9H13N3O3

[ Molecular Weight ]:
211.218

[ Flash Point ]:
204.8±31.5 °C

[ Exact Mass ]:
211.095688

[ PSA ]:
90.37000

[ LogP ]:
-1.30

[ Vapour Pressure ]:
0.0±2.2 mmHg at 25°C

[ Index of Refraction ]:
1.686

[ Storage condition ]:
2-8°C

[ Stability ]:
Stable. Combustible. Incompatible with strong oxidizing agents.

[ Water Solubility ]:
5-10 g/100 mL at 19 ºC

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
HA3870000
CHEMICAL NAME :
Cytidine, 2',3'-dideoxy-
CAS REGISTRY NUMBER :
7481-89-2
BEILSTEIN REFERENCE NO. :
0654956
LAST UPDATED :
199712
DATA ITEMS CITED :
9
MOLECULAR FORMULA :
C9-H13-N3-O3
MOLECULAR WEIGHT :
211.25

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
188 gm/kg/94D-I
TOXIC EFFECTS :
Blood - changes in bone marrow (not otherwise specified) Blood - changes in erythrocyte (RBC) count Blood - changes in leukocyte (WBC) count
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
94 gm/kg/94D-I
TOXIC EFFECTS :
Blood - other changes Blood - changes in other cell count (unspecified) Blood - changes in erythrocyte (RBC) count
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
14500 mg/kg/29D-I
TOXIC EFFECTS :
Blood - other changes Blood - changes in other cell count (unspecified) Blood - changes in erythrocyte (RBC) count
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
91 mg/kg/13W-I
TOXIC EFFECTS :
Tumorigenic - neoplastic by RTECS criteria Endocrine - tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
10 gm/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
20 gm/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetal death

MUTATION DATA

TEST SYSTEM :
Rodent - mouse
DOSE/DURATION :
600 mg/kg/3D (Continuous)
REFERENCE :
EMMUEG Environmental and Molecular Mutagenesis. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.10- 1987- Volume(issue)/page/year: 18,168,1991

Safety Information

[ Symbol ]:

GHS08

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H351

[ Precautionary Statements ]:
P280

[ Personal Protective Equipment ]:
Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
Xn:Harmful

[ Risk Phrases ]:
R40

[ Safety Phrases ]:
S22-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
HA3870000

[ HS Code ]:
2934999090

Synthetic Route

Precursor & DownStream

Precursor

  • Dideoxycytidinene
  • N4-acetyl-1-(2,3-dideoxy-β-D-glycero-pentofuranosyl)cytosine
  • N4-acetyl-5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-2',3'-dideoxycytidine
  • N-Acetylcytidine
  • 1-[2,3-dideoxy-5-O-(4-phenybenzoyl)-β-D-glycero-pentofuranosyl]-4-(isobutyrylamino)-2(1H)-pyrimidinone*0.25H2O
  • N4,O5'-diacetyl-2',3'-dideoxycytidine
  • N-[1-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide

DownStream

  • 2',3'-Dideoxyuridine

Customs

[ HS Code ]: 2934999090

[ Summary ]:
2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Absence of a universal mechanism of mitochondrial toxicity by nucleoside analogs.

Antimicrob. Agents Chemother. 51 , 2531-9, (2007)

Nucleoside analogs are associated with various mitochondrial toxicities, and it is becoming increasingly difficult to accommodate these differences solely in the context of DNA polymerase gamma inhibi...

Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.

Chem. Res. Toxicol. 23 , 171-83, (2010)

Drug-induced liver injury is one of the main causes of drug attrition. The ability to predict the liver effects of drug candidates from their chemical structures is critical to help guide experimental...

Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).

J. Sci. Ind. Res. 65(10) , 808, (2006)

Drug-induced liver injury (DILI) is a significant concern in drug development due to the poor concordance between preclinical and clinical findings of liver toxicity. We hypothesized that the DILI typ...


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Related Compounds

  • Zalcitabine Monophosphate Sodium Salt
  • 2-(tert-Butoxycarbonyl)-2-azaspiro[4.5]decane-3-carboxylic acid
  • 2-Bromo-4-(difluoromethyl)-6-methoxynicotinic acid
  • 6-Bromo-3-(difluoromethyl)-5-methoxypyridin-2-ol
  • 2-(2-Bromo-3-(difluoromethyl)-5-iodopyridin-4-yl)acetonitrile
  • 2-Bromo-5-(bromomethyl)-4-(difluoromethyl)-3-(trifluoromethyl)pyridine
  • 2-Bromo-5-phenyl-1H-pyrrolo[2,3-b]pyridine
  • 2,5-Dibromo-3,6-difluorophenol
  • 2-Bromo-4-(difluoromethyl)-5-fluoropyridine-3-sulfonamide
  • 2-(6-Chloro-2-(difluoromethyl)-5-nitropyridin-3-yl)acetic acid
  • 2-Cyano-5-(difluoromethyl)-4-methoxypyridine-3-sulfonamide
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