Tìm theo
Amprenavir
Các tên gọi khác (5 ) :
  • (3S)-Tetrahydro-3-furanyl ((1S,2R)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)carbamate
  • Agenerase
  • Amprenavir
  • Amprénavir
  • Amprenavirum
anti hiv agents, antibiotics antitubercular, hiv protease inhibitors
Thuốc Gốc
Small Molecule
CAS: 161814-49-9
ATC: J05AE05, J05AE07
ĐG : Catalent Pharma Solutions , http://www.catalent.com
CTHH: C25H35N3O6S
PTK: 505.627
Amprenavir is a protease inhibitor used to treat HIV infection.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C25H35N3O6S
Phân tử khối
505.627
Monoisotopic mass
505.224656557
InChI
InChI=1S/C25H35N3O6S/c1-18(2)15-28(35(31,32)22-10-8-20(26)9-11-22)16-24(29)23(14-19-6-4-3-5-7-19)27-25(30)34-21-12-13-33-17-21/h3-11,18,21,23-24,29H,12-17,26H2,1-2H3,(H,27,30)/t21-,23-,24+/m0/s1
InChI Key
InChIKey=YMARZQAQMVYCKC-OEMFJLHTSA-N
IUPAC Name
(3S)-oxolan-3-yl N-[(2S,3R)-3-hydroxy-4-[N-(2-methylpropyl)(4-aminobenzene)sulfonamido]-1-phenylbutan-2-yl]carbamate
Traditional IUPAC Name
amprenavir
SMILES
CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N)C=C1
Độ hòa tan
4.91e-02 g/l
logP
2.43
logS
-4
pKa (strongest acidic)
13.61
pKa (Strongest Basic)
2.39
PSA
131.19 Å2
Refractivity
134.08 m3·mol-1
Polarizability
53.6 Å3
Rotatable Bond Count
11
H Bond Acceptor Count
6
H Bond Donor Count
3
Physiological Charge
0
Number of Rings
3
Bioavailability
0
MDDR-Like Rule
true
Dược Lực Học : Amprenavir is a protease inhibitor with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Protease inhibitors block the part of HIV called protease. HIV-1 protease is an enzyme required for the proteolytic cleavage of the viral polyprotein precursors into the individual functional proteins found in infectious HIV-1. Amprenavir binds to the protease active site and inhibits the activity of the enzyme. This inhibition prevents cleavage of the viral polyproteins resulting in the formation of immature non-infectious viral particles. Protease inhibitors are almost always used in combination with at least two other anti-HIV drugs.
Cơ Chế Tác Dụng : Amprenavir is a protease inhibitor used to treat HIV infection. Amprenavir inhibits the HIV viral proteinase enzyme which prevents cleavage of the gag-pol polyprotein, resulting in noninfectious, immature viral particles.
Dược Động Học :
▧ Absorption :
Rapidly absorbed after oral administration in HIV-1-infected patients with a time to peak concentration (Tmax) typically between 1 and 2 hours after a single oral dose. The absolute oral bioavailability of amprenavir in humans has not been established.
▧ Protein binding :
Very high (90%). Amprenavir has the highest affinity for alpha(1)-acid glycoprotein.
▧ Metabolism :
Hepatic. Amprenavir is metabolized in the liver by the cytochrome P450 3A4 (CYP3A4) enzyme system. The 2 major metabolites result from oxidation of the tetrahydrofuran and aniline moieties. Glucuronide conjugates of oxidized metabolites have been identified as minor metabolites in urine and feces.
▧ Half Life :
7.1-10.6 hours
Chỉ Định : For the treatment of HIV-1 infection in combination with other antiretroviral agents.
Tương Tác Thuốc :
  • Abacavir The serum concentration of Abacavir may be decreased by protease inhibitors such as Amprenavir. The antiviral response should be closely monitored.
  • Acenocoumarol Amprenavir may increase the anticoagulant effect of acenocoumarol by increasing its serum concentration.
  • Alprazolam Amprenavir may increase the effect and toxicity of the benzodiazepine, alprazolam.
  • Aluminium The antiacid decreases the absorption of amprenavir
  • Amiodarone The protease inhibitor, amprenavir, may increase the effect and toxicity of amiodarone.
  • Anisindione Amprenavir may increase the anticoagulant effect of anisindione by increasing its serum concentration.
  • Astemizole Increased risk of cardiotoxicity and arrhythmias
  • Atorvastatin Amprenavir may increase the serum concentration of atorvastatin by decreasing its metabolism. Concomitant therapy is contraindicated.
  • Bepridil Amprenavir may increase the effect and toxicity of bepridil.
  • Bismuth Subsalicylate The antiacid decreases the absorption of amprenavir
  • Calcium The antiacid decreases the absorption of amprenavir
  • Cisapride Amprenavir may increase the effect and toxicity of cisapride.
  • Clorazepate Amprenavir may increase the effect and toxicity of the benzodiazepine, clorazepate.
  • Cyclosporine The protease inhibitor, amprenavir, may increase the effect of cyclosporine.
  • Delavirdine Decreased levels of delavirdine with increased levels of amprenavir
  • Diazepam Amprenavir may increase the effect and toxicity of the benzodiazepine, diazepam.
  • Dicoumarol Amprenavir may increase the anticoagulant effect of dicumarol by increasing its serum concentration.
  • Dihydroergotamine Amprenavir may increase the serum concentration of dihydroergotamine. Concomitant therapy is contraindicated.
  • Dihydroxyaluminium The antiacid decreases the absorption of amprenavir
  • Disulfiram Increased irsk of side effects (oral solution)
  • Ergotamine Amprenavir may increase the effect and toxicity of ergotamine.
  • Ethinyl Estradiol Ritonavir could decrease the contraceptive efficacy
  • Fentanyl The protease inhibitor, amprenavir, may increase the effect and toxicity of fentanyl.
  • Flurazepam Amprenavir may increase the effect and toxicity of the benzodiazepine, flurazepam.
  • Fusidic Acid The protease inhibitor, amprenavir, may increase the effect and toxicity of fusidic acid.
  • Lovastatin Amprenavir may increase the serum concentration of the lovastatin. Concomitant therapy is contraindicated.
  • Magnesium The antiacid decreases the absorption of amprenavir
  • Magnesium oxide The antiacid decreases the absorption of amprenavir
  • Mestranol Ritonavir could decrease the contraceptive efficacy
  • Methadone The protease inhibitor, amprenavir, may decrease the effect of methadone.
  • Metronidazole Increased risk of side effects (oral solution)
  • Midazolam Amprenavir may increase the effect and toxicity of the benzodiazepine, midazolam.
  • Pimozide Amprenavir may increase the effect and toxicity of pimozide.
  • Ranolazine Amprenavir, a strong CYP3A4 inhibitor, may increase the serum concentratin of ranolazine by inhibiting its metabolism. Concomitant therapy is contraindicated.
  • Rifabutin Amprenavir may increase the effect and toxicity of rifabutin.
  • Rifampicin In presence of rifampin anticipate decrease of amprenavir efficiency
  • Sildenafil The protease inhibitor, amprenavir, may increase the effect and toxicity of sildenafil.
  • Simvastatin Amprenavir may increase the effect and toxicity of simvastatin. Concomitant therapy is contraindicated.
  • St. John's Wort St. John's Wort decreases the effect of indinavir
  • Tacrolimus The protease inhibitor, Amprenavir, may increase the blood concentration of Tacrolimus. Monitor for changes in the therapeutic/toxic effects of Tacrolimus if Amprenavir therapy is initiated, discontinued or altered.
  • Tadalafil Amprenavir may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
  • Tamoxifen Amprenavir may increase the serum concentration of Tamoxifen by decreasing its metabolism. Monitor for increased adverse/toxic effects of Tamoxifen.
  • Tamsulosin Amprenavir, a CYP3A4 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Amprenavir is initiated, discontinued, or dose changed.
  • Telithromycin Co-administration may result in altered plasma concentrations of Amprenavir and/or Telithromycin. Consider alternate therapy or monitor the therapeutic/adverse effects of both agents.
  • Temsirolimus Amprenavir may inhibit the metabolism and clearance of Temsirolimus. Concomitant therapy should be avoided.
  • Teniposide The strong CYP3A4 inhibitor, Amprenavir, may decrease the metabolism and clearance of Teniposide, a CYP3A4 substrate. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Teniposide if Amprenavir is initiated, discontinued or dose changed.
  • Terfenadine Increased risk of cardiotoxicity and arrhythmias
  • Tiagabine The strong CYP3A4 inhibitor, Amprenavir, may decrease the metabolism and clearance of Tiagabine, a CYP3A4 substrate. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Tiagabine if Amprenavir is initiated, discontinued or dose changed.
  • Tolterodine Amprenavir may decrease the metabolism and clearance of Tolterodine. Adjust the Tolterodine dose and monitor for efficacy and toxicity.
  • Tramadol Amprenavir may increase Tramadol toxicity by decreasing Tramadol metabolism and clearance.
  • Trazodone The protease inhibitor, Amprenavir, may increase the efficacy/toxicity of Trazodone by inhibiting Trazodone metabolism and clearance. Monitor for changes in Trazodone efficacy/toxicity if Amprenavir is initiated, discontinued or dose changed.
  • Triazolam Amprenavir may increase the effect and toxicity of the benzodiazepine, triazolam.
  • Trimipramine The strong CYP3A4 inhibitor, Amprenavir, may decrease the metabolism and clearance of Trimipramine, a CYP3A4 substrate. Consider alternate therapy or monitor for changes in therapeutic and adverse effects of Trimipramine if Amprenavir is initiated, discontinued or dose changed.
  • Vardenafil Amprenavir, a strong CYP3A4 inhibitor, may reduce the metabolism and clearance of Vardenafil. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Vardenafil.
  • Venlafaxine Amprenavir, a CYP3A4 inhibitor, may decrease the metabolism and clearance of Venlafaxine, a CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Venlafaxine if Amprenavir is initiated, discontinued, or dose changed.
  • Verapamil Amprenavir, a strong CYP3A4 inhibitor, may increase the serum concentration of Veramapil, a CYP3A4 substrate, by decreasing its metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Verapamil if Amprenavir is initiated, discontinued or dose changed.
  • Vinblastine Amprenavir, a strong CYP3A4 inhibitor, may decrease the metabolism of Vinblastine. Consider alternate therapy to avoid Vinblastine toxicity. Monitor for changes in the therapeutic/adverse effects of Vinblastine if Amprenavir is initiated, discontinued or dose changed.
  • Vincristine Amprenavir, a strong CYP3A4 inhibitor, may increase the serum concentration of Vincristine by decreasing its metabolism. Consider alternate therapy to avoid Vincristine toxicity. Monitor for changes in the therapeutic and adverse effects of Vincristine if Amprenavir is initiated, discontinued or dose changed.
  • Vinorelbine Amprenavir, a strong CYP3A4 inhibitor, may increase the serum concentration of Vinorelbine by decreasing its metabolism. Consider alternate therapy to avoid Vinorelbine toxicity. Monitor for changes in the therapeutic and adverse effects of Vinorelbine if Amprenavir is initiated, discontinued or dose changed.
  • Vitamin E Increased serum levels of vitamin E
  • Voriconazole Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of amprenavir by decreasing its metabolism. The serum concentration of voriconazole may be increased by amprenavir. Monitor for changes in the therapeutic and adverse effects of both agents if concomitant therapy is initiated, discontinued or if doses are changed.
  • Warfarin Amprenavir may increase the anticoagulant effect of warfarin by increasing its serum concentration.
  • Zolpidem Amprenavir, a strong CYP3A4 inhibitor, may increase the serum concentration of zolpidem by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zolpidem if amprenavir is initiated, discontinued or dose changed.
  • Zonisamide Amprenavir, a strong CYP3A4 inhibitor, may increase the serum concentration of zonisamide by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zonisamide if amprenavir is initiated, discontinued or dose changed.
  • Zopiclone Amprenavir, a strong CYP3A4 inhibitor, may increase the serum concentration of zopiclone by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zopiclone if amprenavir is initiated, discontinued or dose changed.
Liều Lượng & Cách Dùng : Capsule - Oral
Liquid - Oral
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Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00701
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=65016
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46507537
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C08086
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00894
ChemSpider
http://www.chemspider.com/Chemical-Structure.58532.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=577
PharmGKB
http://www.pharmgkb.org/drug/PA448422
Wikipedia
http://en.wikipedia.org/wiki/Amprenavir
RxList
http://www.rxlist.com/cgi/generic/ampren.htm
PDRhealth
http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/age1526.shtml
Drugs.com
http://www.drugs.com/cdi/amprenavir.html
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