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Stavudine

Stavudine Struktur
3056-17-5
CAS-Nr.
3056-17-5
Englisch Name:
Stavudine
Synonyma:
D4T;ZERIT;Stavir;Avostav;Virostav;STAVUDINE;BMY-27857;NSC 163661;Stauvidine;sanilvudine
CBNumber:
CB4450928
Summenformel:
C10H12N2O4
Molgewicht:
224.21
MOL-Datei:
3056-17-5.mol

Stavudine Eigenschaften

Schmelzpunkt:
159-160°C
alpha 
D25 -39.4° (c = 0.701 in water); D20 -46.1° (c = 0.7 in water)
Dichte
1.374±0.06 g/cm3(Predicted)
Brechungsindex
-46 ° (C=0.69, H2O)
storage temp. 
-20°C
L?slichkeit
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±0.10(Predicted)
Farbe
White
Wasserl?slichkeit
5-10 g/100 mL at 21 ºC
BCS Class
1,3
Stabilit?t:
Stable. Combustible. Incompatible with strong oxidizing agents.
InChIKey
XNKLLVCARDGLGL-JGVFFNPUSA-N
CAS Datenbank
3056-17-5(CAS DataBase Reference)
EPA chemische Informationen
Thymidine, 2',3'-didehydro-3'-deoxy- (3056-17-5)
Sicherheit
  • Risiko- und Sicherheitserkl?rung
  • Gefahreninformationscode (GHS)
Kennzeichnung gef?hrlicher Xi
R-S?tze: 36/37/38
S-S?tze: 26-36
WGK Germany  2
RTECS-Nr. XP2075000
HS Code  29349990
Giftige Stoffe Daten 3056-17-5(Hazardous Substances Data)
Toxizit?t LD50 oral in rat: 4gm/kg
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H341 Kann vermutlich genetische Defekte verursachen. Keimzellmutagenit?t Kategorie 2 Warnung P201,P202, P281, P308+P313, P405,P501
Sicherheit
P201 Vor Gebrauch besondere Anweisungen einholen.
P202 Vor Gebrauch alle Sicherheitshinweise lesen und verstehen.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P308+P313 BEI Exposition oder falls betroffen: ?rztlichen Rat einholen/?rztliche Hilfe hinzuziehen.
P405 Unter Verschluss aufbewahren.
P501 Inhalt/Beh?lter ... (Entsorgungsvorschriften vom Hersteller anzugeben) zuführen.

Stavudine Chemische Eigenschaften,Einsatz,Produktion Methoden

R-S?tze Betriebsanweisung:

R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.

S-S?tze Betriebsanweisung:

S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.

Beschreibung

Stavudine, 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%.

Chemische Eigenschaften

Colourless solid

Verwenden

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

Indications

Stavudine (d4T, Zerit) is a thymidine nucleoside analogue that is active against HIV-1 and HIV-2. It is approved for the therapy of HIV infection as part of a multidrug regimen and is also used for postexposure prophylaxis.

Definition

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

Antimicrobial activity

Stavudine is active against HIV-1, HIV-2 and HTLV-1.

Acquired resistance

Resistance to stavudine is identical to that seen for zidovudine. Mutations at positions 41, 67 and 70, and positions 210, 215 and 219 (the ‘thymidine analog mutations’) of the reverse transcriptase genes are associated with diminished antiretroviral efficacy.

Allgemeine Beschreibung

Stavudine, 2'3'-didehydro-2'-deoxythymidine (D4T, Zerit), isan unsaturated pyrimidine nucleoside that is related to thymidine.The drug inhibits the replication of HIV by a mechanismsimilar to that of its close congener, AZT.Stavudine is bioactivatedby cellular enzymes to a triphosphate.
Stavudine is available as capsules for oral administration.The drug is acid stable and well absorbed (about 90%) followingoral administration. Stavudine has a short half-life(1–2 hours) in plasma and is excreted largely unchanged(85%–90%) in the urine.As with ddC, the primary doselimitingeffect is peripheral neuropathy.
Stavudine isrecommended for the treatment of adults with advancedHIV infection who are intolerant of other approved therapiesor who have experienced clinical or immunological deteriorationwhile receiving these therapies.

Air & Water Reaktionen

Water soluble.

Reaktivit?t anzeigen

Stavudine is sensitive to heat. Incompatible with strong oxidizing agents .

Hazard

Moderately toxic by ingestion.

Brandgefahr

Literature sources indicate that Stavudine is combustible.

Pharmazeutische Anwendungen

An analog of thymidine formulated for oral administration.

Pharmakokinetik

Oral absorption: 86%
Cmax 40 mg twice daily: 0.54 mg/L
Plasma half-life: 1.4 h
Volume of distribution: 0.66 L/kg
Plasma protein binding: <5%
Absorption and distribution
It is rapidly absorbed with or without food. CNS penetration is moderate. The estimated semen:plasma ratio is >1. It is secreted into breast milk.
Metabolism and excretion
The metabolic fate in humans has not been elucidated. Renal elimination accounts for approximately 40% of overall clearance at a rate almost twice that of endogenous creatinine, indicating glomerular filtration and active tubular secretion. Clearance decreases as creatinine clearance decreases and the dosage should be adjusted in patients with reduced renal function. Pharmacokinetics are not significantly altered in patients with hepatic impairment.

Clinical Use

Treatment of HIV infection in adults and children

Nebenwirkungen

The adverse effects with which stavudine is most frequently associated are headache, diarrhea, skin rash, nausea, vomiting, insomnia, anorexia, myalgia, and weakness. Peripheral neuropathy consisting of numbness, tingling, or pain in the hands or feet is also common with higher doses of the drug. Significant elevation of hepatic enzymes may be seen in approximately 10 to 15% of patients. Lactic acidosis occurs more frequently with stavudine than with other NRTIs. Viral resistance to stavudine may develop, and cross-resistance to zidovudine and didanosine may occur.

Vorsichtsma?nahmen

Stavudine possesses several clinically significant interactionswith other drugs. Although hydroxyurea enhancesthe antiviral activity of stavudine and didanosine,combination therapy that includes stavudine anddidanosine, with or without hydroxyurea, increases therisk of pancreatitis. Combinations of stavudine and didanosineshould not be given to pregnant women becauseof the increased risk of metabolic acidosis.Zidovudine inhibits the phosphorylation of stavudine;thus, this combination should be avoided.

Stavudine Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Stavudine Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

Global( 518)Lieferanten
Firmenname Telefon E-Mail Land Produktkatalog Edge Rate
Hebei Weibang Biotechnology Co., Ltd
+8615531157085
abby@weibangbio.com China 8810 58
Hebei Mojin Biotechnology Co., Ltd
+86 13288715578 +8613288715578
sales@hbmojin.com China 12835 58
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512
info@tianfuchem.com China 21634 55
career henan chemical co
+86-0371-86658258 +8613203830695
sales@coreychem.com China 29880 58
SHANDONG ZHI SHANG CHEMICAL CO.LTD
+86 18953170293
sales@sdzschem.com China 2930 58
Hubei Jusheng Technology Co.,Ltd.
18871490254
linda@hubeijusheng.com CHINA 28172 58
Xiamen AmoyChem Co., Ltd
+86-86-5926051114 +8618959220845
sales@amoychem.com China 6383 58
Hubei xin bonus chemical co. LTD
86-13657291602
linda@hubeijusheng.com CHINA 22963 58
Standardpharm Co. Ltd.
86-714-3992388
overseasales1@yongstandards.com United States 14332 58
BOC Sciences
+1-631-485-4226
inquiry@bocsci.com United States 19553 58

3056-17-5()Verwandte Suche:


  • STAVUDINE
  • 3'-deoxythymidin-2'-ene
  • 3'-DEOXY-2',3'-DIDEHYDROTHYMIDINE
  • ZERIT
  • STAVUDINE[2'',3''-DIDEHYDRO-3''-DEOXYTHYMIDINE]
  • NSC 163661
  • Stavir
  • Thymidine, 2'', 3''-didehydro-3''-deoxy-
  • 1-(5-(HYDROXYMETHYL)-2,5-DIHYDROFURAN-2-YL)-5-METHYLDIHYDROPYRIMIDINE-2,4(1H,3H)-DIONE
  • 1-(2,3-dideoxy-β-d-glycero-pent-2-enofuranosyl)thymine
  • STAVUDINE(PATENTEDNO-SUPPLY)
  • 2',3'-Didehydro-3'-deoxy-D-thymidine
  • 2'-Thymidinene, 3'-deoxy- (8CI)
  • D 4T (nucleoside)
  • sanilvudine
  • Thymidine, 2',3'-didehydro-3'-deoxy- (9CI)
  • Thymine, 1-(2,3-dideoxy-b-D-glycero-pent-2-enofuranosyl)- (7CI, 8CI)
  • Stavudine (250 mg)
  • Stauvidine Hydrochloride
  • 1-[(2R,3R,4R,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide and 1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione
  • 1-(2,3-Dideoxy-β-D-glycero-2-pentenofuranosyl)thymine
  • 2',3'-Dideoxythymidiene
  • 2μ,3μ-Anhydrothymidine, d4T, Stavudine, 1-(2,3-Dideoxy-β-D-glycero-pent-2-enofuranosyl)thymine
  • Stavudine SysteM Suitability Mixture
  • 2'', 3''-DIDEHYDRO-3''-DEOXYTHMIDINE (D4T: STAVUDINE)
  • Stauvidine
  • 1-(2,3-Dideoxy-beta-D-glycero-2-pentenofuranosyl)thymine
  • 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
  • 2',3'-ANHYDROTHYMIDINE
  • 1-(2,3-dideoxy-beta-d-glycero-pent-2-enofuranosyl)-thymin
  • 2’,3’-didehydro-3’-deoxy-thymidin
  • 2’,3’-dideoxy-2’,3’-didehydrothymidine
  • Stavudine(DT4)
  • Stavudine(D4T)
  • BMY-27857
  • D4T
  • 2',3'-Didehydro-2',3'-dideoxythymidine
  • 2',3'-Didehydro-3'-deoxythyMidine, 3'-Deoxy-2'-thyMidinene
  • Avostav
  • D4t, BMY-27857, Zerit
  • Virostav
  • d4T 2',3'-Anhydrothymidine 1-(2,3-Dideoxy-beta-D-glycero-2-pentenofuranosyl)thymine Stavudine Sanilvudine
  • Zidovudine EP IMpurity A
  • 2',3'-Didehydro-3'-deoxythymidine, D4t, BMY-27857, Zerit
  • 1-(5-(hydroxymethyl)-2,5-dihydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
  • 2',3'-Didehydro-3'-deoxythmidine, 98%, a nucleoside analog that inhibits reverse transcriptase
  • 1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
  • Zidovudine ImpuritⅡ:Stavudine
  • Stavudine Impurit Ⅱ: 2',3'-Didehydro-3'-deoxythymidine, 3'-Deoxy-2'-thymidinene( Stavudine)
  • Zidovudine EP Impurity A (Stavudine)
  • 1-[(2R,5S)-2,5-Dihydro-5-(hydroxymethyl)-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione
  • 2',3'-Didehydro-3'-deoxythymidine>
  • Stavudine CRS
  • Stavudine for system suitability CRS
  • 2’,3’-Dideoxy-2’,3’-didehydrothymidine, Stavudine
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