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CAS No.: | 3056-17-5 |
---|---|
Name: | Stavudine |
Article Data: | 76 |
Molecular Structure: | |
Formula: | C10H12N2O4 |
Molecular Weight: | 224.216 |
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; |
EINECS: | 641-374-0 |
Density: | 1.374 g/cm3 |
Melting Point: | 159-160 °C |
Solubility: | Water solubility: 5-10 g/100 mL at 21 °C |
Appearance: | white powder |
Hazard Symbols: | Xi |
Risk Codes: | 36/37/38 |
Safety: | 26-S36 |
PSA: | 84.32000 |
LogP: | -0.70910 |
1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pento-2-enofuranosyl>thymine
stavudin
Conditions | Yield |
---|---|
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; |
1-<2',3'-dideoxy-3'(R)-phenylseleno-β-D-glycero-pentofuranosyl>thymine
stavudin
Conditions | Yield |
---|---|
With dihydrogen peroxide; acetic acid In tetrahydrofuran 1) 0 deg C, 0.25 h, 2) warm to RT, 1 h; | 99% |
1-(5-0-Pivaloyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)thymine
stavudin
Conditions | Yield |
---|---|
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; |
2,3'-anhydrothymidine
stavudin
Conditions | Yield |
---|---|
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% |
5'-O-benzoyl-2',3'-didehydro-3'-deoxythymidine
stavudin
Conditions | Yield |
---|---|
With sodium methylate In methanol Ambient temperature; | 92% |
With N-butylamine at 70℃; for 6h; | 90% |
With N-butylamine | 90% |
1-{5-[bis(4-methoxyphenyl)phenyl-methoxymethyl]-2,5-dihydrofuran-2-yl}-5-methyl-1H-pyrimidine-2,4-dione
stavudin
Conditions | Yield |
---|---|
In methanol; tetrachloromethane at 25 - 40℃; for 3h; ultrasonic; | 92% |
With methanol; Dowex 50W H(1+) form for 0.166667h; | 90% |
stavudin
Conditions | Yield |
---|---|
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% |
2',3'-didehydro-3'-deoxythymidine N,N-dimethyl propylene urea solvate
stavudin
Conditions | Yield |
---|---|
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% |
1-(5-O-acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-thymine
stavudin
Conditions | Yield |
---|---|
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; |
1-(2,3-dideoxy-3-C-selenophenyl-β-D-erythro-pentofuranosyl)thymine
stavudin
Conditions | Yield |
---|---|
With dihydrogen peroxide; acetic acid In tetrahydrofuran 1) 0 deg C, 0.25 h, 2) warm to RT, 1 h; | 86% |
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(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.
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. |
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.