Tìm theo
Nevirapine
Các tên gọi khác (5 ) :
  • 11-Cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido(3,2-b:2',3'-e)(1,4)diazepin-6-one
  • NEV
  • Nevirapine
  • NVP
  • Viramune
Thuốc trị ký sinh trùng, chống nhiễm khuẩn
Thuốc Gốc
Small Molecule
CAS: 129618-40-2
ATC: J05AG01
ĐG : Boehringer Ingelheim Ltd. , http://www.boehringer-ingelheim.com
CTHH: C15H14N4O
PTK: 266.2979
A potent, non-nucleoside reverse transcriptase inhibitor (NNRTI) used in combination with nucleoside analogues for treatment of Human Immunodeficiency Virus Type 1 (HIV-1) infection and AIDS. [PubChem] Structurally, nevirapine belongs to the dipyridodiazepinone chemical class.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C15H14N4O
Phân tử khối
266.2979
Monoisotopic mass
266.11676109
InChI
InChI=1S/C15H14N4O/c1-9-6-8-17-14-12(9)18-15(20)11-3-2-7-16-13(11)19(14)10-4-5-10/h2-3,6-8,10H,4-5H2,1H3,(H,18,20)
InChI Key
InChIKey=NQDJXKOVJZTUJA-UHFFFAOYSA-N
IUPAC Name
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
Traditional IUPAC Name
nevirapine
SMILES
CC1=C2NC(=O)C3=C(N=CC=C3)N(C3CC3)C2=NC=C1
Độ tan chảy
196.06
Độ hòa tan
0.7046 mg/L
logP
2.5
logS
-3.4
pKa (strongest acidic)
10.37
pKa (Strongest Basic)
5.06
PSA
58.12 Å2
Refractivity
77.48 m3·mol-1
Polarizability
27.8 Å3
Rotatable Bond Count
1
H Bond Acceptor Count
4
H Bond Donor Count
1
Physiological Charge
0
Number of Rings
4
Bioavailability
1
Rule of Five
true
Ghose Filter
true
caco2 Permeability
-4.52
Dược Lực Học : 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.
Cơ Chế Tác Dụng : A potent, non-nucleoside reverse transcriptase inhibitor (NNRTI) used in combination with nucleoside analogues for treatment of Human Immunodeficiency Virus Type 1 (HIV-1) infection and AIDS. [PubChem] Structurally, nevirapine belongs to the dipyridodiazepinone chemical class. 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.
Dược Động Học :
▧ Absorption :
Nevirapine is readily absorbed (greater than 90%) after oral administration in healthy subjects and adults with HIV-1 infection. The absolute bioavailability in healthy adults following a single dose administration is 93 ± 9% (mean ± SD) for a 50 mg tablet and 91 ± 8% for an oral solution. Peak plasma nevirapine concentrations of 2 ± 0.4 mcg/mL (7.5 micromolar) were attained by 4 hours following a single 200 mg dose. Nevirapine tablets and suspension have been shown to be comparably bioavailable and interchangeable at doses up to 200 mg. When the oral tablet is given with a high-fat meal, the extent of absorption is compared to that of the fasted-state.
▧ Volume of Distribution :
* 1.21 ± 0.09 L/kg [apparent volume of distribution, healthy adults, IV] Nevirapine is capable of crossing the placenta and is found in breast milk.
▧ Protein binding :
60% bound to plasma protein.
▧ 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.
▧ 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
Độc Tính : Symptoms of overdose include edema, erythema nodosum, fatigue, fever, headache, insomnia, nausea, pulmonaryinfiltrates, rash, vertigo, vomiting, and weight decrease. The most common adverse reaction is rash.
Chỉ Định : For use in combination with other antiretroviral drugs in the ongoing treatment of HIV-1 infection.
Tương Tác Thuốc :
  • 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.
  • Dicoumarol 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.
Liều Lượng & Cách Dùng : Suspension - Oral - 50 mg/5 mL
Tablet - Oral - 200 mg
Tablet, extended release - Oral - 100 mg, 400 mg
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Viramune
  • Công ty :
    Sản phẩm biệt dược : Viramune XR
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00238
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=4463
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46506789
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07263
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00435
ChemSpider
http://www.chemspider.com/Chemical-Structure.4308.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=1434
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0597-0046-60
PharmGKB
http://www.pharmgkb.org/drug/PA450616
Wikipedia
http://en.wikipedia.org/wiki/Nevirapine
RxList
http://www.rxlist.com/cgi/generic2/nevira.htm
Drugs.com
http://www.drugs.com/cdi/nevirapine.html
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