Zalcitabine

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

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	Signal Word	Warning

Use of Zalcitabine

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

Name	zalcitabine
Synonym	More Synonyms

Description	Zalcitabine is a potent nucleoside analogue reverse transcriptase inhibitor used in the treatment of HIV infection.
Related Catalog	Signaling Pathways >> Anti-infection >> HIV Signaling Pathways >> Anti-infection >> Reverse Transcriptase Research Areas >> Infection
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

Zalcitabine MSDS(Chinese)

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
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

Precursor 7
CAS#:7481-88-1 Dideoxycytidinene CAS#:119818-52-9 N4-acetyl-1-(2,... CAS#:119794-42-2 N4-acetyl-5'-O-... CAS#:3768-18-1 N-Acetylcytidine
CAS#:125612-00-2 1-[2,3-dideoxy-... CAS#:120885-66-7 N4,O5'-diacetyl... CAS#:120885-60-1 N-[1-[(2R,5S)-5...
DownStream 1
CAS#:5983-09-5 2',3'-Dideoxyuridine

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

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...

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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China
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