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7481-89-2

7481-89-2 structure
7481-89-2 structure
Name zalcitabine
Synonyms 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
Description Zalcitabine is a potent nucleoside analogue reverse transcriptase inhibitor used in the treatment of HIV infection.
Related Catalog
Target

Target: HIV

In Vitro Zalcitabine is a dideoxynucleoside antiretroviral agent that is phosphorylated to the active metabolite 2',3'-dideoxycytidine 5'-triphosphate (ddCTP) within both uninfected and HIV-infected cells. At therapeutic concentrations, ddCTP inhibits HIV replication by inhibiting the enzyme reverse transcriptase and terminating elongation of the proviral DNA chain[1]. Zalcitabine exhibits the inhibition effect on the cellular uptake of [3H]-PAH in CHO/hOAT1 cells with an IC50 value of 1.23 mM. Furthermore, the cellular uptake of zalcitabine increased threefold with the enhancement of hOATI activity in CHO/hOAT1 cells[2].
References

[1]. Adkins JC, et al. Zalcitabine. An update of its pharmacodynamic and pharmacokinetic properties and clinical efficacy in the management of HIV infection.Drugs. 1997 Jun;53(6):1054-80

[2]. Jin MJ, et al. Interaction of zalcitabine with human organic anion transporter 1. Pharmazie. 2006 May;61(5):491-2.
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

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
Symbol GHS08
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
HS Code 2934999090
Summary 2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%
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