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STAVUDINE
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Name

STAVUDINE

 EINECS 641-374-0
CAS No. 3056-17-5 Density 1.374 g/cm3
PSA 84.32000 LogP -0.70910
Solubility Water solubility: 5-10 g/100 mL at 21 °C Melting Point 159-160 °C
Formula C10H12N2O4 Boiling Point N/A
Molecular Weight 224.216 Flash Point N/A
Transport Information N/A Appearance white powder
Safety 26-S36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 3056-17-5 (Stavudine) Hazard Symbols IrritantXi
Synonyms

Thymidine,2',3'-didehydro-3'-deoxy-;Thymine,1-(2,3-dideoxy-b-D-glycero-pent-2-enofuranosyl)- (7CI,8CI);2'-Thymidinene, 3'-deoxy- (8CI);2',3'-Didehydro-3'-deoxythymidine;3'-Deoxy-2',3'-didehydrothymidine;Avostav;BMY 27857;D 4T (nucleoside);NSC163661;Stag;Stavir;Virostav;Zerit;d4T;

Article Data 76

STAVUDINE Synthetic route

125440-17-7

1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pento-2-enofuranosyl>thymine

3056-17-5

stavudin

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 1.5h; Ambient temperature;100%
With tetrabutyl ammonium fluoride In tetrahydrofuran at 25℃;90%
With tetrabutyl ammonium fluoride In tetrahydrofuran Ambient temperature;78%
With tetrabutyl ammonium fluoride In tetrahydrofuran Yield given;
131933-47-6

1-<2',3'-dideoxy-3'(R)-phenylseleno-β-D-glycero-pentofuranosyl>thymine

3056-17-5

stavudin

Conditions
ConditionsYield
With dihydrogen peroxide; acetic acid In tetrahydrofuran 1) 0 deg C, 0.25 h, 2) warm to RT, 1 h;99%
126209-27-6

1-(5-0-Pivaloyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)thymine

3056-17-5

stavudin

Conditions
ConditionsYield
With sodium methylate In methanol at 23℃; for 4h;95%
With buffer In ethanol at 40℃; Rate constant; hydrolysis, also enzymatic hydrolysis; various pH-values;
15981-92-7

2,3'-anhydrothymidine

3056-17-5

stavudin

Conditions
ConditionsYield
With 1-(2-methoxyethyl)-3-methylimidazolium trifluoroacetate; sodium hydride In mineral oil at 100℃; for 0.0833333h;93%
With sodium hydride In N,N-dimethyl acetamide at 100℃; for 0.5h;81%
122567-97-9

5'-O-benzoyl-2',3'-didehydro-3'-deoxythymidine

3056-17-5

stavudin

Conditions
ConditionsYield
With sodium methylate In methanol Ambient temperature;92%
With N-butylamine at 70℃; for 6h;90%
With N-butylamine90%
149666-71-7

1-{5-[bis(4-methoxyphenyl)phenyl-methoxymethyl]-2,5-dihydrofuran-2-yl}-5-methyl-1H-pyrimidine-2,4-dione

3056-17-5

stavudin

Conditions
ConditionsYield
In methanol; tetrachloromethane at 25 - 40℃; for 3h; ultrasonic;92%
With methanol; Dowex 50W H(1+) form for 0.166667h;90%

stavudine N,N-dimethylacetamide solvate

3056-17-5

stavudin

Conditions
ConditionsYield
In water; isopropyl alcohol at 0 - 70℃; for 1.33333h; Purification / work up;91.4%
In water; acetone at 0℃; for 2.16667h; Purification / work up;76%
In water at 0 - 65℃; for 2.33333h; Purification / work up;73.7%
938050-90-9

2',3'-didehydro-3'-deoxythymidine N,N-dimethyl propylene urea solvate

3056-17-5

stavudin

Conditions
ConditionsYield
Stage #1: 2',3'-didehydro-3'-deoxythymidine N,N-dimethyl propylene urea solvate In water; isopropyl alcohol at 82℃;
Stage #2: In isopropyl alcohol at 0 - 5℃; for 1.5h; Purification / work up;		87.2%
In isopropyl alcohol at 0 - 82℃; for 1.5h; Product distribution / selectivity;87.2%
Stage #1: 2',3'-didehydro-3'-deoxythymidine N,N-dimethyl propylene urea solvate In water; acetone at 55℃;
Stage #2: In acetone at 0 - 40℃; for 1h; Purification / work up;		84%
77421-68-2

1-(5-O-acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-thymine

3056-17-5

stavudin

Conditions
ConditionsYield
With sodium methylate In methanol for 2h; Ambient temperature;87%
With sodium hydroxide In acetonitrile for 0.5h; Yield given;
With buffer In ethanol at 40℃; Rate constant; hydrolysis, also enzymatic hydrolysis; various pH-values;
131933-44-3

1-(2,3-dideoxy-3-C-selenophenyl-β-D-erythro-pentofuranosyl)thymine

3056-17-5

stavudin

Conditions
ConditionsYield
With dihydrogen peroxide; acetic acid In tetrahydrofuran 1) 0 deg C, 0.25 h, 2) warm to RT, 1 h;86%

STAVUDINE Chemical Properties

IUPAC Name:1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4-dione
Molecular Formula:C10H12N2O4
Molecular Weight:224.213280：
Melting Point:159-160°C
refractive index:-46 ° (C=0.69, H2O)
storage temp.:20°C
Water Solubility:5-10 g/100 mL at 21°C
CAS DataBase Reference:3056-17-5(CAS DataBase Reference)
EPA Substance Registry System:3056-17-5(EPA Substance)
Synonyms of STAVUDINE(3056-17-5):
STAVUDINE;ZERIT;3'-deoxythymidin-2'-ene;3'-DEOXY-2',3'-DIDEHYDROTHYMIDINE;1-((2R,5S)-5-HYDROXYMETHYL-2,5-DIHYDRO-FURAN-2-YL)-5-METHYL-1H-PYRIMIDINE-2,4-DIONE;1-[2,3-DIDEOXY-BETA-D-GLYCERO-PENT-2-ENOFURANOSYL]THYMINE;2',3'-DIDEHYDRO-3'-DEOXYTHYMIDINE;2',3'-DIHYDRO-2',3'-DEOXYTHYMIDINE
Categories of STAVUDINE(3056-17-5):
Active Pharmaceutical Ingredients;chiral;Antivirals for Research and Experimental Use;Biochemistry;Chemical Reagents for Pharmacology Research;Nucleosides and their analogs;Nucleosides, Nucleotides & Related Reagents;Bases & Related Reagents;Nucleotides;Pharmaceuticals;API's

STAVUDINE History

STAVUDINE(3056-17-5) was the fourth antiretroviral drug on the market, its patent expired in the United States on 2008-06-25.
STAVUDINE(3056-17-5) was first synthetized in the sixties by Jerome Horwitz,subsequently reconsidered as an anti-HIV agent by the Rega Institute for Medical Research in Belgium.
STAVUDINE(3056-17-5) was approved by the U.S.FDA in Jun 24, 1994 for adults and in Sep 6, 1996 for pediatric use.
STAVUDINE(3056-17-5) was approved by the U.S.FDA  for once-a-day dosing in 2001.

STAVUDINE Uses

STAVUDINE(3056-17-5) is used as a antiviral drug.

STAVUDINE Toxicity Data With Reference

1.   

dni-hmn-lym 20 µmol/L

   MOPMA3    Molecular Pharmacology. 39 (1991),625.
2.   

cyt-orl-mus 600 mg/kg/3D-C

   EMMUEG    Environmental and Molecular Mutagenesis. 18 (1991),168.
3.   

orl-rat LD50:4 g/kg

   YAKUD5    Gekkan Yakuji. Pharmaceuticals Monthly. 40 (1998),1944.
4.   

ivn-rat LD50:>1200 mg/kg

   YAKUD5    Gekkan Yakuji. Pharmaceuticals Monthly. 40 (1998),1944.
5.   

orl-mus LD50:1 g/kg

   YAKUD5    Gekkan Yakuji. Pharmaceuticals Monthly. 40 (1998),1944.
6.   

ivn-mus LD50:1 g/kg

   YAKUD5    Gekkan Yakuji. Pharmaceuticals Monthly. 40 (1998),1944.
7.   

orl-dog LD :>2 g/kg

   YAKUD5    Gekkan Yakuji. Pharmaceuticals Monthly. 40 (1998),1944.
8.   

ivn-dog LD :>1680 mg/kg

   YAKUD5    Gekkan Yakuji. Pharmaceuticals Monthly. 40 (1998),1944.

STAVUDINE Safety Profile

Safety Information of STAVUDINE(3056-17-5):
Hazard Codes:Xi 
Risk Statements:36/37/38
36/37/38:Irritating to eyes, respiratory system and skin 
Safety Statements:26-36
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:Wear suitable protective clothing   
WGK Germany:2
RTECS:XP2075000
Hazardous Substances Data:3056-17-5(Hazardous Substances Data)
Moderately toxic by ingestion and intravenous routes. Mutation data reported. When heated to decomposition it emits toxic vapors of NOx.

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