Zalcitabine

Modify Date: 2024-01-01 20:36:24

Zalcitabine Structure
Zalcitabine structure
 Common Name Zalcitabine
CAS Number 7481-89-2 Molecular Weight 211.218
Density 1.6±0.1 g/cm3 Boiling Point 415.0±55.0 °C at 760 mmHg
Molecular Formula C9H13N3O3 Melting Point 217-218 °C(lit.)
MSDS Chinese USA Flash Point 204.8±31.5 °C
Symbol GHS08
GHS08		 Signal Word Warning

 Use of Zalcitabine


Zalcitabine is a potent nucleoside analogue reverse transcriptase inhibitor used in the treatment of HIV infection.

 Names

Name zalcitabine
Synonym More Synonyms

 Zalcitabine Biological Activity

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.

 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

 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
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

 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%

 Articles62

More 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...

 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
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Related Compounds: More...
Zalcitabine Monophosphate Sodium Salt
104086-76-2
Chemsrc provides Zalcitabine(CAS#:7481-89-2) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of Zalcitabine are included as well.>> amp version: Zalcitabine

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