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药品详细

Nevirapine(奈韦拉平)

化学结构式图
中文名
奈韦拉平
英文名
Nevirapine
分子式
C15H14N4O
化学名
2-cyclopropyl-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-10-one
分子量
Average: 266.2979
Monoisotopic: 266.11676109
CAS号
129618-40-2
ATC分类
J05A Direct acting antivirals
药物类型
small molecule
阶段
approved
商品名
Viramune;
同义名
NEV;NVP;
基本介绍

A potent, non-nucleoside reverse transcriptase inhibitor used in combination with nucleoside analogues for treatment of HIV infection and AIDS. [PubChem]

生产厂家
  • Boehringer ingelheim 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
  • Benzodiazepines
  • Lactams
Substructures
  • Benzodiazepines
  • Amino Ketones
  • Aliphatic and Aryl Amines
  • Pyridines and Derivatives
  • Cyclopropane and Derivatives
  • Carboxylic Acids and Derivatives
  • Aminopyridines and Derivatives
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Lactams
适应症
ANTIVIRALS 抗病毒;
药理
Indication For use in combination with other antiretroviral drugs in the ongoing treatment of HIV-1 infection.
Pharmacodynamics Nevirapine is a non-nucleoside reverse transcriptase inhibitor (nNRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). HIV-2 RT and eukaryotic DNA polymerases (such as human DNA polymerases alpha, beta, or sigma) are not inhibited by nevirapine. Nevirapine is, in general, only prescribed after the immune system has declined and infections have become evident. It is always taken with at least one other HIV medication such as Retrovir or Videx. The virus can develop resistance to nevirapine if the drug is taken alone, although even if used properly, nevirapine is effective for only a limited time.
Mechanism of action Nevirapine binds directly to reverse transcriptase (RT) and blocks the RNA-dependent and DNA-dependent DNA polymerase activities by causing a disruption of the enzyme's catalytic site. The activity of nevirapine does not compete with template or nucleoside triphosphates.
Absorption 90% (absolute bioavailability 93 ± 9%)
Volume of distribution
  • 1.21 ± 0.09 L/kg
Protein binding 60%
Metabolism
Hepatic. In vivo studies in humans and in vitro studies with human liver microsomes have shown that nevirapine is extensively biotransformed via cytochrome P450 3A4 metabolism to several hydroxylated metabolites.

Important The metabolism module of DrugBank is currently in beta. Questions or suggestions? Please contact us.

Substrate Enzymes Product
Nevirapine
12-Hydroxynevirapine Details
Nevirapine
2-Hydroxynevirapine Details
Nevirapine
8-Hydroxynevirapine Details
Nevirapine
3-Hydroxynevirapine Details
Nevirapine
    		12-hydroxynevirapine glucuronide Details
    Nevirapine
      		2-hydroxynevirapine glucuronide Details
      Nevirapine
        		3-hydroxynevirapine glucuronide Details
        Nevirapine
          		4-carboxynevirapine Details
          Nevirapine
            		8-hydroxynevirapine glucuronide Details
            Route of elimination Thus cytochrome P450 metabolism, glucuronide conjugation, and urinary excretion of glucuronidated metabolites represent the primary route of nevirapine biotransformation and elimination in humans. Only a small fraction (<5%) of the radioactivity in urine (representing <3% of the total dose) was made up of parent compound; therefore, renal excretion plays a minor role in elimination of the parent compound.
            Half life 45 hours
            Clearance Not Available
            Toxicity Symptoms of overdose include edema, erythema nodosum, fatigue, fever, headache, insomnia, nausea, pulmonaryinfiltrates, rash, vertigo, vomiting, and weight decrease.
            Affected organisms
            • Human Immunodeficiency Virus
            Pathways Not Available
            理化性质
            Properties
            State solid
            Experimental Properties
            Property Value Source
            melting point 196.06 Not Available
            water solubility 0.7046 mg/L Not Available
            logP 2.5 Not Available
            Caco2 permeability -4.52 ADME Research, USCD
            Predicted Properties
            Property Value Source
            water solubility 1.05e-01 g/l ALOGPS
            logP 1.75 ALOGPS
            logP 2.49 ChemAxon
            logS -3.4 ALOGPS
            pKa (strongest acidic) 10.37 ChemAxon
            pKa (strongest basic) 5.06 ChemAxon
            physiological charge 0 ChemAxon
            hydrogen acceptor count 4 ChemAxon
            hydrogen donor count 1 ChemAxon
            polar surface area 58.12 ChemAxon
            rotatable bond count 1 ChemAxon
            refractivity 77.48 ChemAxon
            polarizability 27.8 ChemAxon
            药物相互作用
            Drug Interaction
            Acenocoumarol Nevirapine may decrease the anticoagulant effect of acenocoumarol.
            Anisindione Nevirapine may decrease the anticoagulant effect of anisindione.
            Atazanavir Nevirapine, a strong CYP3A4 inducer, may decrease the serum concentration of atazanavir by increasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of atazanavir if nevirapine is initiated, discontinued or dose changed.
            Atorvastatin Nevirapine, a strong CYP3A4 inducer, may decrease the serum concentration of atorvastatin by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of atorvastatin if nevirapine is initiated, discontinued or dose changed.
            Dicumarol Nevirapine may decrease the anticoagulant effect of dicumarol.
            Estradiol valerate/Dienogest Affects CYP3A4 metabolism, decreases or effects levels of Estradiol valerate/Dienogest.
            Etravirine Nevirapine may cause a significant decrease in plasma levels of etravirine and a loss of efficacy. Combination of two NNRTIs has not been demonstrated to be of benefit to HIV therapy.
            Ketoconazole Nevirapine, a strong CYP3A4 inducer, may decrease the serum concentration of ketoconazole by increasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of ketoconazole if nevirapine is initiated, discontinued or dose changed.
            Lovastatin The strong CYP3A4 inducer, nevirapine, may decrase the effect of lovastatin by increasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of lovastatin if nevirapine is initiated, discontinued or dose changed.
            Methadone The antiretroviral agent decreases the effect of methadone
            Nelfinavir Nevirapine may decrease the effect of nelfinavir.
            Quinupristin This combination presents an increased risk of toxicity
            Roflumilast Affects CYP3A4 metabolism, decreases level or effect of roflumilast.
            Saquinavir Decreases the effect of saquinavir
            Simvastatin The strong CYP3A4 inducer, nevirapine, may decrase the effect of simvastatin by increasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of simvastatin if nevirapine is initiated, discontinued or dose changed.
            St. John's Wort St. John's Wort decreases nevirapine effect
            Telithromycin Nevirapine may decrease the plasma concentration of Telithromycin. Consider alternate therapy.
            Temsirolimus Nevirapine may increase the metabolism of Temsirolimus decreasing its efficacy. Concomitant therapy should be avoided.
            Tipranavir Nevirapine, a CYP3A4 inducer, may decrease the serum concentration of Tipranavir, a CYP3A4 substrate. Monitor for changesin Tipranavir effect if Nevirapine is initiated, discontinued or dose changed.
            Tramadol Nevirapine may decrease the effect of Tramadol by increasing Tramadol metabolism and clearance.
            Trazodone The CYP3A4 inducer, Nevirapine, may decrease Trazodone efficacy by increasing Trazodone metabolism and clearance. Monitor for changes in Trazodone efficacy/toxicity if Nevirapine is initiated, discontinued or dose changed.
            Vandetanib Decreases levels of vandetanib by affecting CYP3A4 metabolism. Contraindicated.
            Warfarin Nevirapine may decrease the anticoagulant effect of warfarin by increasing metabolism of R-warfarin via CYP3A4.
            食物相互作用
            • Avoid alcohol.
            • Take without regard to meals.

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