Stavudine

Modify Date: 2024-01-02 17:45:57

Stavudine Structure
Stavudine structure
 Common Name Stavudine
CAS Number 3056-17-5 Molecular Weight 224.213
Density 1.5±0.1 g/cm3 Boiling Point 440.6±55.0 °C at 760 mmHg
Molecular Formula C10H12N2O4 Melting Point 159-160°C
MSDS Chinese USA Flash Point 220.3±31.5 °C

 Use of Stavudine


Stavudine is a nucleoside analog that inhibits reverse transcriptase and has in vitro activity against HIV.Target: HIV RT; NRTIsStavudine is a dideoxynucleoside analog that inhibits reverse transcriptase and has in vitro activity against HIV. Stavudine is an analog of thymidine. It is phosphorylated by cellular kinases into active triphosphate. Stavudine triphosphate inhibits the HIV reverse transcriptase by competing with natural substrate, thymidine triphosphate. It also causes termination of DNA synthesis by incorporating into it [1]. Mice were treated for 2 weeks with stavudine d4T (500 mg/kg/day), L-carnitine (200 mg/kg/day) or both drugs concomitantly. Body fatness was assessed by dual energy X-ray absorptiometry, and investigations were performed in plasma, liver, muscle and WAT. D4T reduced the gain of body adiposity, WAT leptin, whole body FAO and plasma ketone bodies, and increased liver triglycerides and plasma aminotransferases with mild ultrastructural abnormalities in hepatocytes [2].Clinical indications: HIV-1 infection FDA Approved Date: June 24, 1994 Toxicity: peripheral neuropathy; lipodystrophy

 Names

Name stavudine
Synonym More Synonyms

 Stavudine Biological Activity

Description Stavudine is a nucleoside analog that inhibits reverse transcriptase and has in vitro activity against HIV.Target: HIV RT; NRTIsStavudine is a dideoxynucleoside analog that inhibits reverse transcriptase and has in vitro activity against HIV. Stavudine is an analog of thymidine. It is phosphorylated by cellular kinases into active triphosphate. Stavudine triphosphate inhibits the HIV reverse transcriptase by competing with natural substrate, thymidine triphosphate. It also causes termination of DNA synthesis by incorporating into it [1]. Mice were treated for 2 weeks with stavudine d4T (500 mg/kg/day), L-carnitine (200 mg/kg/day) or both drugs concomitantly. Body fatness was assessed by dual energy X-ray absorptiometry, and investigations were performed in plasma, liver, muscle and WAT. D4T reduced the gain of body adiposity, WAT leptin, whole body FAO and plasma ketone bodies, and increased liver triglycerides and plasma aminotransferases with mild ultrastructural abnormalities in hepatocytes [2].Clinical indications: HIV-1 infection FDA Approved Date: June 24, 1994 Toxicity: peripheral neuropathy; lipodystrophy
Related Catalog
References

[1]. Lea AP, et al. Stavudine: a review of its pharmacodynamic and pharmacokinetic properties and clinical potential in HIV infection. Drugs. 1996 May;51(5):846-64.

[2]. Igoudjil A, et al. High doses of stavudine induce fat wasting and mild liver damage without impairing mitochondrial respiration in mice. Antivir Ther. 2007;12(3):389-400.

 Chemical & Physical Properties

Density 1.5±0.1 g/cm3
Boiling Point 440.6±55.0 °C at 760 mmHg
Melting Point 159-160°C
Molecular Formula C10H12N2O4
Molecular Weight 224.213
Flash Point 220.3±31.5 °C
Exact Mass 224.079712
PSA 84.32000
LogP -1.25
Vapour Pressure 0.0±2.4 mmHg at 25°C
Index of Refraction 1.646
Storage condition −20°C
Stability Stable. Combustible. Incompatible with strong oxidizing agents.
Water Solubility 5-10 g/100 mL at 21 ºC

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
XP2075000
CHEMICAL NAME :
Thymidine, 2',3'-didehydro-3'-deoxy-
CAS REGISTRY NUMBER :
3056-17-5
LAST UPDATED :
199612
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C10-H12-N2-O4
MOLECULAR WEIGHT :
224.24

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xi
Risk Phrases R36/37/38
Safety Phrases S26-S36
RIDADR NONH for all modes of transport
WGK Germany 2
RTECS XP2075000
HS Code 2938901000

 Synthetic Route

 Customs

HS Code 2938901000
Summary HS: 2938901000. 4-amino-1-((2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1h)-one. VAT:17.0%. tax rebate rate:13.0%. supervision conditions:None. MFN tarrif:6.5%. general tariff:20.0%

 Articles62

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2',3'-Dideoxythymidine (ddThd) and its 2',3'-unsaturated derivative 2',3'-dideoxythymidinene (ddeThd) are potent and selective inhibitors of human immunodeficiency virus (HIV) in vitro. When evaluated...
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Viral protein R (Vpr) of HIV-1 plays an important role in viral replication in macrophages. Various lines of evidence suggest that expression of Vpr in macrophages causes immunopathogenesis; however, ...

 Synonyms

1-(2,3-Dideoxy-Beta-D-Glycero-2-Pentenofuranosyl)Thymine
Sanilvudine
Virostav
2,4(1H,3H)-Pyrimidinedione, 1-[(2R,5S)-2,5-dihydro-5-(hydroxymethyl)-2-furanyl]-5-methyl-
1-[(2R,5S)-5-(Hydroxymethyl)-2,5-dihydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione
4-Hydroxy-1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydro-2-furanyl]-5-methyl-2(1H)-pyrimidinone
Stavudine
Stauvidine
3'-Deoxy-2'-thymidinene
1-(2,3-Dideoxy-β-D-glycero-2-pentenofuranosyl)thymine
Zerit
1-[(2R,5S)-5-(Hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidin-2,4(1H,3H)-dion
2(1H)-Pyrimidinone, 1-[(2R,5S)-2,5-dihydro-5-(hydroxymethyl)-2-furanyl]-4-hydroxy-5-methyl-
2',3'-dideoxy-2',3'-didehydrothymidine
1-[(2R,5S)-5-(hydroxyméthyl)-2,5-dihydrofuran-2-yl]-5-méthylpyrimidine-2,4(1H,3H)-dione
Thymidine, 2',3'-didehydro-3'-deoxy-
2',3'-didehydro-3'-deoxythimidine
1-(2,3-Dideoxy-b-glycero-pent-2-enofuranosyl)thymine
D 4T
D4T
estavudina
MFCD00132921
2',3'-Anhydrothymidine
Stavir
Avostav
Sanilvudine (JAN)
1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione
2',3'-Didehydro-3'-deoxythyMidine
Thymine, 1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)- (7CI,8CI)
2',3'-dideoxy-2',3'-didehydrothymine
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Related Compounds: More...
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880256-72-4
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Stavudine Triphosphate TEA Salt
1795791-25-1
Lamivudine/Nevirapine/Stavudine
811471-91-7
stavudine 4-methoxyphenylalanyl phosphoramidate
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stavudine-5'-β-naphthyl O-methoxy-L-alanyl phosphate
905601-32-3
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