Stavudine

HCID 18283CAS 3056-17-5

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Grundinformationen

Standard-SMILES: Cc1cn([C@H]2C=C[C@@H](CO)O2)c(=O)[nH]c1=O
InChIKey: XNKLLVCARDGLGL-JGVFFNPUSA-N
Summenformel: C10H12N2O4
Durchschnittliche Molmasse: 224,216 g/mol
Monoisotopische Masse: 224,07970686

Namen und Bezeichner

Bevorzugter Name: Stavudine
IUPAC: 1-[(2R,5S)-5-(Hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione
Englischer Name: Stavudine
Summenformel: C10H12N2O4
Molmasse: 224.21

Namen und Synonyme

sanilvudine1-(2,3-Dideoxy-beta-D-glycero-2-pentenofuranosyl)thymineD4TZERITStavirAvostavVirostavSTAVUDINEBMY-27857NSC 163661

Datenbank-Bezeichner

CAS: 3056-17-5
PubChem CID: 18283
DTXSID: DTXSID1023819
ChEMBL: CHEMBL991
ChEBI: CHEBI:63581
UNII: BO9LE4QFZF
EC Number: 641-374-0
Nikkaji: J83.276F

Eigenschaften

Physikochemische Eigenschaften

Schmelzpunkt: 159 · 159-160°C
Dichte: 1.374 · 1.374±0.06 g/cm3(Predicted)
Brechungsindex: -46 ° · -46 ° (C=0.69, H2O)
storage temp.: -20 °C · -20°C
Löslichkeit: Soluble in water, sparingly soluble in ethanol (96 per cent), slightly soluble in methylene chloride. It shows polymorphism (5.9).
Aggregatzustand: Solid
pka: 9.47 · 9.47±0.10(Predicted)
Farbe: White
Wasserlöslichkeit: 5 · 5-10 g/100 mL at 21 ºC
Henry's Law Constant: 4.3 · 4.3×109 mol/(m3Pa) at 25℃, HSDB (2015)
BCS Class: 1 · 1,3
Stabilität: Stable. Combustible. Incompatible with strong oxidizing agents.
InChI: 1S/C10H12N2O4/c1-6-4-12(10(15)11-9(6)14)8-3-2-7(5-13)16-8/h2-4,7-8,13H,5H2,1H3,(H,11,14,15)/t7-,8+/m0/s1
InChIKey: XNKLLVCARDGLGL-JGVFFNPUSA-N
SMILES: CC1=CN([C@@H]2O[C@H](CO)C=C2)C(=O)NC1=O
CAS Datenbank: 3056 · 3056-17-5(CAS DataBase Reference)
EPA chemische Informationen: 2 · Thymidine, 2',3'-didehydro-3'-deoxy- (3056-17-5)

Sicherheit und Regulatorisches

Sicherheitsdaten

wgk: 2
hs_code: 29349990
RTECS-Nr.: XP2075000
risk_code: 36/37/38
Toxizität: LD50 oral in rat: 4gm/kg
hazard_code: Xi
safety_code: 26-36
Speicherklasse: 11 - Combustible Solids
Giftige Stoffe Daten: 3056-17-5(Hazardous Substances Data)

Chemie und Industrie

Anwendungen · 2 Einträge

BeschreibungStavudine, a dideoxynucleoside analog of thymidine, has been introduced in the U.S.A. for the treatment of late-stage AIDS patients who are refractory to other AIDS treatments. Similar as other currently available agents for AIDS treatment such as zidovudine (AZT), didanosine, and zalcitabine, the anti-HIV activity of these 2'3'- dideoxynucleosides is ascribed to the inhibitory effect of their corresponding 5'- triphosphates against the HlVsncoded RNAdependent DNA polymerase (reverse transcriptase). While some of these drugs have rapid development of drug resistance, stavudine is active against AZT-resistant HIV strains. It has a favorable pharmacokinetic profile with more complete and less variable oral absorption than AZT and didanosine and has a bioavailability of 80-90%.

VerwendenStavudine (Zidovudine EP Impurity A) is used as an antiviral. A reverse transcriptase inhibitor.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Epoxy Kalium-tert-butanolat Thymidine Methansulfonylchlorid Ethylacetat Anhydrous pyridine Uridine, 5-methyl-, 2',3',5'-triacetate Uridine, 2',3'-dideoxy-2'-iodo-5-methyl-, 5'-(2,2-dimethylpropanoate)Thymidine, 2',3'-didehydro-3'-deoxy-5'-O-[(1,1-dimethylethyl)diphenylsilyl]- (9CI)((2S,5R)-5-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl acetate (R)-5-(tert-Butyldiphenylsiloxymethyl)dihydro-2(3H)furanone 5-Methyluridin

Anbieter50 Anbieter

国药集团化学试剂有限公司86-21-63210123 · [email protected]

北京华美互利生物化工010-56205725 · [email protected]

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

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T&W GROUP021-61551611 13296011611 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: A nucleoside analogue obtained by formal dehydration across positions 2 and 3 of thymidine. An inhibitor of HIV-1 reverse transcriptase