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药品详细

Stavudine(司他夫定)

化学结构式图
中文名
司他夫定
英文名
Stavudine
分子式
C10H12N2O4
化学名
1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
分子量
Average: 224.2133
Monoisotopic: 224.079706882
CAS号
3056-17-5
ATC分类
J05A Direct acting antivirals
药物类型
small molecule
阶段
approved
商品名
Zerit;Zerit XR;Zerut XR;
同义名
2',3'-Didehydro-3'-deoxythimidine;3'-Deoxy-2'-thymidinene;Estavudina [INN-Spanish];Sanilvudine;stavudine;Stavudine [Usan:Ban:Inn];Stavudinum [INN-Latin];STV;
基本介绍

A dideoxynucleoside analog that inhibits reverse transcriptase and has in vitro activity against HIV. [PubChem]

生产厂家
  • Aurobindo pharma ltd
  • Bristol myers squibb co
  • Bristol myers squibb co pharmaceutical research institute
  • Cipla ltd
  • Hetero drugs ltd
  • Matrix laboratories ltd
  • Mylan pharmaceuticals inc
封装厂家
参考
Synthesis Reference Not Available
General Reference Not Available
剂型
规格
化合物类型
Type small molecule
Classes
  • Pyrimidines and Derivatives
Substructures
  • Hydroxy Compounds
  • Alkanes and Alkenes
  • Ethers
  • Alcohols and Polyols
  • Pyrimidines and Derivatives
  • Heterocyclic compounds
  • Aromatic compounds
  • Cyanamides
适应症
ANTIVIRALS 抗病毒;
药理
Indication For the treatment of human immunovirus (HIV) infections.
Pharmacodynamics Stavudine is a nucleoside reverse transcriptase inhibitor (NRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Stavudine is phosphorylated to active metabolites that compete for incorporation into viral DNA. They inhibit the HIV reverse transcriptase enzyme competitively and act as a chain terminator of DNA synthesis. The lack of a 3'-OH group in the incorporated nucleoside analogue prevents the formation of the 5' to 3' phosphodiester linkage essential for DNA chain elongation, and therefore, the viral DNA growth is terminated.
Mechanism of action Stavudine inhibits the activity of HIV-1 reverse transcriptase (RT) both by competing with the natural substrate dGTP and by its incorporation into viral DNA.
Absorption Following oral administration, stavudine is rapidly absorbed (bioavailability is 68-104%).
Volume of distribution
  • 46 ± 21 L
Protein binding Negligible
Metabolism
Phosphorylated intracellularly to stavudine triphosphate, the active substrate for HIV-reverse transcriptase.
Route of elimination Not Available
Half life 0.8-1.5 hours (in adults)
Clearance
  • Renal cl=272 mL/min [Healthy subjects receiving 80 mg PO]
  • 594 +/- 164 mL/min [HIV-infected adult and pediatric patients following 1-hour IV infusion]
  • 9.75 +/- 3.76 mL/min/kg [HIV- Exposed or -Infected Pediatric Patients(Age 5 weeks – 15 years) following 1-hour IV infusion]
Toxicity Side effects include peripheral neuropathy tingling, burning, numbness, or pain in the hands or feet), fatal lactic acidosis has been reported in patients treated with stavudine (ZERIT) in combination with other antiretroviral agents, severe liver enlargement, inflammation (pain and swelling) of the liver, and liver failure.
Affected organisms
  • Human Immunodeficiency Virus
Pathways Not Available
理化性质
Properties
State solid
Experimental Properties
Property Value Source
melting point 159-160 °C Not Available
water solubility 5-10 g/100 mL at 21 °C Not Available
logP -0.72 SANGSTER (1993)
Predicted Properties
Property Value Source
water solubility 4.05e+01 g/l ALOGPS
logP -0.73 ALOGPS
logP -0.23 ChemAxon
logS -0.74 ALOGPS
pKa (strongest acidic) 9.95 ChemAxon
pKa (strongest basic) -3 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 4 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 78.87 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 55.32 ChemAxon
polarizability 21.33 ChemAxon
药物相互作用
Drug Interaction
Zidovudine Zidovudine may decrease the efficacy of stavudine. Concomitant therapy should be avoided.
食物相互作用
Not Available

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