Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C25H36N3O9PS |
Molecular Weight | 585.607 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)CN(C[C@@H](OP(O)(O)=O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]2CCOC2)S(=O)(=O)C3=CC=C(N)C=C3
InChI
InChIKey=MLBVMOWEQCZNCC-OEMFJLHTSA-N
InChI=1S/C25H36N3O9PS/c1-18(2)15-28(39(33,34)22-10-8-20(26)9-11-22)16-24(37-38(30,31)32)23(14-19-6-4-3-5-7-19)27-25(29)36-21-12-13-35-17-21/h3-11,18,21,23-24H,12-17,26H2,1-2H3,(H,27,29)(H2,30,31,32)/t21-,23-,24+/m0/s1
Molecular Formula | C25H36N3O9PS |
Molecular Weight | 585.607 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/23519392 | https://www.ncbi.nlm.nih.gov/pubmed/11152018 | https://www.ncbi.nlm.nih.gov/pubmed/15341507
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/23519392 | https://www.ncbi.nlm.nih.gov/pubmed/11152018 | https://www.ncbi.nlm.nih.gov/pubmed/15341507
Amprenavir is an inhibitor of HIV-1 protease. Amprenavir binds to the active site of HIV-1 protease and thereby prevents the processing of viral gag and gag-pol polyprotein precursors, resulting in the formation of immature non-infectious viral particles. Amprenavir-containing combination regimens have shown virological efficacy, and have generally been well tolerated, in patients with HIV infection (primarily treatment-naive or protease inhibitor-naive). Fosamprenavir (GW433908, Lexiva, Telzir) is an oral prodrug of amprenavir, with a reduced daily pill burden. The use of protease inhibitors has also been associated with dyslipidemia and an increased risk of cardiovascular disease. Amprenavir activates Pregnane X receptor to mediate dyslipidemia.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3401 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23519392 |
8.6 µM [EC50] | ||
Target ID: CHEMBL2364675 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10952482 |
2.5 µM [IC50] | ||
Target ID: CHEMBL243 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | AGENERASE Approved UseAGENERASE (amprenavir) is indicated in combination with other antiretroviral agents for the treatment of HIV-1 infection. Launch Date9.2404803E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5.36 μg/mL |
1200 mg 2 times / day multiple, oral dose: 1200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
AMPRENAVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
6.18 μg/mL |
1200 mg single, oral dose: 1200 mg route of administration: Oral experiment type: SINGLE co-administered: |
AMPRENAVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: HIGH-FAT |
|
9.72 μg/mL |
1200 mg single, oral dose: 1200 mg route of administration: Oral experiment type: SINGLE co-administered: |
AMPRENAVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
6.77 μg/mL |
20 mg/kg bw 2 times / day multiple, oral dose: 20 mg/kg bw route of administration: Oral experiment type: MULTIPLE co-administered: |
AMPRENAVIR plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN |
|
3.99 μg/mL |
15 mg/kg bw 3 times / day multiple, oral dose: 15 mg/kg bw route of administration: Oral experiment type: MULTIPLE co-administered: |
AMPRENAVIR plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
18.5 μg × h/mL |
1200 mg 2 times / day multiple, oral dose: 1200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
AMPRENAVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
22.06 μg × h/mL |
1200 mg single, oral dose: 1200 mg route of administration: Oral experiment type: SINGLE co-administered: |
AMPRENAVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: HIGH-FAT |
|
28.05 μg × h/mL |
1200 mg single, oral dose: 1200 mg route of administration: Oral experiment type: SINGLE co-administered: |
AMPRENAVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
15.46 μg × h/mL |
20 mg/kg bw 2 times / day multiple, oral dose: 20 mg/kg bw route of administration: Oral experiment type: MULTIPLE co-administered: |
AMPRENAVIR plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN |
|
8.73 μg × h/mL |
15 mg/kg bw 3 times / day multiple, oral dose: 15 mg/kg bw route of administration: Oral experiment type: MULTIPLE co-administered: |
AMPRENAVIR plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
8.85 h |
1200 mg 2 times / day multiple, oral dose: 1200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
AMPRENAVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10% |
1200 mg 2 times / day multiple, oral dose: 1200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
AMPRENAVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
1200 mg 2 times / day multiple, oral Recommended Dose: 1200 mg, 2 times / day Route: oral Route: multiple Dose: 1200 mg, 2 times / day Co-administed with:: lamivudine, po(150 mg, BID) Sources: Page: p.1387zidovudine, po(300 mg, BID) |
unhealthy, 21-62 n = 113 Health Status: unhealthy Condition: HIV-1 infection Age Group: 21-62 Sex: M+F Population Size: 113 Sources: Page: p.1387 |
Disc. AE: Nausea, Vomiting... AEs leading to discontinuation/dose reduction: Nausea (12%) Sources: Page: p.1387Vomiting (6%) Loose stools (3%) Abdominal pain (2%) Abdominal discomfort (2%) Rash (3%) |
1200 mg single, oral Recommended Dose: 1200 mg Route: oral Route: single Dose: 1200 mg Sources: Page: p.1688 |
unhealthy, 33+/-6.7 n = 12 Health Status: unhealthy Condition: HIV-1 infection Age Group: 33+/-6.7 Sex: M+F Population Size: 12 Sources: Page: p.1688 |
|
1200 mg 2 times / day multiple, oral Recommended Dose: 1200 mg, 2 times / day Route: oral Route: multiple Dose: 1200 mg, 2 times / day Sources: Page: p.11 |
unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: Page: p.11 |
Disc. AE: Reaction skin, Stevens-Johnson syndrome... AEs leading to discontinuation/dose reduction: Reaction skin (grade 3-4) Sources: Page: p.11Stevens-Johnson syndrome (grade 3-4) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Nausea | 12% Disc. AE |
1200 mg 2 times / day multiple, oral Recommended Dose: 1200 mg, 2 times / day Route: oral Route: multiple Dose: 1200 mg, 2 times / day Co-administed with:: lamivudine, po(150 mg, BID) Sources: Page: p.1387zidovudine, po(300 mg, BID) |
unhealthy, 21-62 n = 113 Health Status: unhealthy Condition: HIV-1 infection Age Group: 21-62 Sex: M+F Population Size: 113 Sources: Page: p.1387 |
Abdominal discomfort | 2% Disc. AE |
1200 mg 2 times / day multiple, oral Recommended Dose: 1200 mg, 2 times / day Route: oral Route: multiple Dose: 1200 mg, 2 times / day Co-administed with:: lamivudine, po(150 mg, BID) Sources: Page: p.1387zidovudine, po(300 mg, BID) |
unhealthy, 21-62 n = 113 Health Status: unhealthy Condition: HIV-1 infection Age Group: 21-62 Sex: M+F Population Size: 113 Sources: Page: p.1387 |
Abdominal pain | 2% Disc. AE |
1200 mg 2 times / day multiple, oral Recommended Dose: 1200 mg, 2 times / day Route: oral Route: multiple Dose: 1200 mg, 2 times / day Co-administed with:: lamivudine, po(150 mg, BID) Sources: Page: p.1387zidovudine, po(300 mg, BID) |
unhealthy, 21-62 n = 113 Health Status: unhealthy Condition: HIV-1 infection Age Group: 21-62 Sex: M+F Population Size: 113 Sources: Page: p.1387 |
Loose stools | 3% Disc. AE |
1200 mg 2 times / day multiple, oral Recommended Dose: 1200 mg, 2 times / day Route: oral Route: multiple Dose: 1200 mg, 2 times / day Co-administed with:: lamivudine, po(150 mg, BID) Sources: Page: p.1387zidovudine, po(300 mg, BID) |
unhealthy, 21-62 n = 113 Health Status: unhealthy Condition: HIV-1 infection Age Group: 21-62 Sex: M+F Population Size: 113 Sources: Page: p.1387 |
Rash | 3% Disc. AE |
1200 mg 2 times / day multiple, oral Recommended Dose: 1200 mg, 2 times / day Route: oral Route: multiple Dose: 1200 mg, 2 times / day Co-administed with:: lamivudine, po(150 mg, BID) Sources: Page: p.1387zidovudine, po(300 mg, BID) |
unhealthy, 21-62 n = 113 Health Status: unhealthy Condition: HIV-1 infection Age Group: 21-62 Sex: M+F Population Size: 113 Sources: Page: p.1387 |
Vomiting | 6% Disc. AE |
1200 mg 2 times / day multiple, oral Recommended Dose: 1200 mg, 2 times / day Route: oral Route: multiple Dose: 1200 mg, 2 times / day Co-administed with:: lamivudine, po(150 mg, BID) Sources: Page: p.1387zidovudine, po(300 mg, BID) |
unhealthy, 21-62 n = 113 Health Status: unhealthy Condition: HIV-1 infection Age Group: 21-62 Sex: M+F Population Size: 113 Sources: Page: p.1387 |
Reaction skin | grade 3-4 Disc. AE |
1200 mg 2 times / day multiple, oral Recommended Dose: 1200 mg, 2 times / day Route: oral Route: multiple Dose: 1200 mg, 2 times / day Sources: Page: p.11 |
unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: Page: p.11 |
Stevens-Johnson syndrome | grade 3-4 Disc. AE |
1200 mg 2 times / day multiple, oral Recommended Dose: 1200 mg, 2 times / day Route: oral Route: multiple Dose: 1200 mg, 2 times / day Sources: Page: p.11 |
unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: Page: p.11 |
PubMed
Title | Date | PubMed |
---|---|---|
Four new antiretroviral medications will soon offer more options to HIV patients. | 1998 Jul-Aug |
|
Structural and kinetic analyses of the protease from an amprenavir-resistant human immunodeficiency virus type 1 mutant rendered resistant to saquinavir and resensitized to amprenavir. | 2000 Aug |
|
Early detection of mixed mutations selected by antiretroviral agents in HIV-infected primary human lymphocytes. | 2001 |
|
Development of HIV protease inhibitors: a survey. | 2001 |
|
Open-label phase II trial of amprenavir, abacavir, and fixed-dose zidovudine/lamivudine in newly and chronically HIV-1--infected patients. | 2001 Apr 1 |
|
A phase II trial of dual protease inhibitor therapy: amprenavir in combination with indinavir, nelfinavir, or saquinavir. | 2001 Apr 15 |
|
A pilot study of the use of mycophenolate mofetil as a component of therapy for multidrug-resistant HIV-1 infection. | 2001 Apr 15 |
|
[Determining resistance in HIV therapy. Careful interpretation only]. | 2001 Apr 2 |
|
HIV and drug allergy. | 2001 Aug |
|
Antiviral drugs: current state of the art. | 2001 Aug |
|
Human immunodeficiency virus type 1 hypersusceptibility to amprenavir in vitro can be associated with virus load response to treatment in vivo. | 2001 Dec 15 |
|
Ritonavir, efavirenz, and nelfinavir inhibit CYP2B6 activity in vitro: potential drug interactions with bupropion. | 2001 Feb |
|
Possible linkage of amprenavir with intracranial bleeding in an HIV-infected hemophiliac. | 2001 Jul |
|
Capillary electrophoretic separation of protease inhibitors used in human immunodeficiency virus therapy. | 2001 Jul 13 |
|
Amprenavir: new preparation. Another HIV protease inhibitor: no proven advance. | 2001 Jun |
|
A dose-ranging study to evaluate the antiretroviral activity and safety of amprenavir alone and in combination with abacavir in HIV-infected adults with limited antiretroviral experience. | 2001 Jun |
|
Antiretroviral activity and safety of abacavir in combination with selected HIV-1 protease inhibitors in therapy-naive HIV-1-infected adults. | 2001 Jun |
|
Effect of reduced-dose amprenavir in combination with lopinavir on plasma levels of amprenavir in patients infected with HIV. | 2001 Mar |
|
Assessment of active transport of HIV protease inhibitors in various cell lines and the in vitro blood--brain barrier. | 2001 Mar 9 |
|
Resistant to everything. | 2001 May |
|
Drifting agenda for federal treatment research. | 2001 May |
|
Pharmacokinetics and safety of amprenavir and ritonavir following multiple-dose, co-administration to healthy volunteers. | 2001 May 25 |
|
Simultaneous determination of the HIV protease inhibitors indinavir, amprenavir, saquinavir, ritonavir and nelfinavir in human plasma by high-performance liquid chromatography. | 2001 May 5 |
|
From amprenavir to GW433908. | 2001 Nov |
|
New developments in anti-HIV chemotherapy. | 2001 Nov |
|
Pharmacokinetics of amprenavir and lopinavir in combination with nevirapine in highly pretreated HIV-infected patients. | 2001 Nov 23 |
|
Methadone blood concentrations are decreased by the administration of abacavir plus amprenavir. | 2001 Oct |
|
Mismatched double-stranded RNA (polyI-polyC(12)U) is synergistic with multiple anti-HIV drugs and is active against drug-sensitive and drug-resistant HIV-1 in vitro. | 2001 Sep |
|
Effectors of HIV-1 protease peptidolytic activity. | 2001 Sep 18 |
|
Amping amprenavir with ritonavir. | 2001 Spring |
|
Retroviral proteases. | 2002 |
|
Interaction potential of lercanidipine, a new vasoselective dihydropyridine calcium antagonist. | 2002 |
|
In-vitro and in-vivo pharmacokinetic interactions of amprenavir, an HIV protease inhibitor, with other current HIV protease inhibitors in rats. | 2002 Feb |
|
A potent human immunodeficiency virus type 1 protease inhibitor, UIC-94003 (TMC-126), and selection of a novel (A28S) mutation in the protease active site. | 2002 Feb |
|
HIV-1 genotype and phenotype correlate with virological response to abacavir, amprenavir and efavirenz in treatment-experienced patients. | 2002 Feb 15 |
|
Clinical pharmacology and pharmacokinetics of amprenavir. | 2002 Jan |
|
[Advances in the domain of HIV]. | 2002 Jan 19 |
|
Unfavourable interaction of amprenavir and lopinavir in combination with ritonavir? | 2002 Jan 25 |
|
Longitudinal use of phenotypic resistance testing to HIV-1 protease inhibitors in patients developing HAART failure. | 2002 Jul |
|
In vitro antiviral interaction of lopinavir with other protease inhibitors. | 2002 Jul |
|
New developments in anti-HIV chemotherapy. | 2002 Jul 18 |
|
Fosamprenavir. Vertex Pharmaceuticals/GlaxoSmithKline. | 2002 Mar |
|
The utility of inhibitory quotients in determining the relative potency of protease inhibitors. | 2002 Mar 29 |
|
Delavirdine increases drug exposure of ritonavir-boosted protease inhibitors. | 2002 Mar 29 |
|
Drug interaction between amprenavir and lopinavir/ritonavir in salvage therapy. | 2002 Mar 29 |
|
Parallel decline of CD8+/CD38++ T cells and viraemia in response to quadruple highly active antiretroviral therapy in primary HIV infection. | 2002 Mar 8 |
|
Amprenavir-resistant HIV-1 exhibits lopinavir cross-resistance and reduced replication capacity. | 2002 May 3 |
|
Select HIV protease inhibitors alter bone and fat metabolism ex vivo. | 2002 May 31 |
Sample Use Guides
Adults: The recommended oral dose of AGENERASE Capsules for adults is 1200 mg (eight 150-mg capsules) twice daily in combination with other antiretroviral agents. Concomitant Therapy: If AGENERASE and ritonavir are used in combination, the recommended dosage regimens are: AGENERASE 1200 mg with ritonavir 200 mg once daily or AGENERASE
600 mg with ritonavir 100 mg twice daily.
Pediatric Patients: For adolescents (13 to 16 years), the recommended oral dose of AGENERASE Capsules is 1200 mg (eight 150-mg capsules) twice daily in combination with other antiretroviral agents. For patients between 4 and 12 years of age or for patients 13 to 16 years of age with weight of
<50 kg, the recommended oral dose of AGENERASE Capsules is 20 mg/kg twice daily or 15 mg/kg 3 times daily (to a maximum daily dose of 2400 mg) in combination with other antiretroviral agents.
Route of Administration:
Oral
The in vitro antiviral activity of amprenavir was evaluated against HIV-1 IIIB in both acutely and chronically infected lymphoblastic cell lines (MT-4, CEM-CCRF, 43 H9) and in peripheral blood lymphocytes. The 50% inhibitory concentration (IC50) of amprenavir ranged from 0.012 to 0.08 µM in acutely infected cells and was 0.41 µM in chronically infected cells (1 µM = 0.50 mcg/mL).
Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 23:02:27 UTC 2023
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on
Thu Jul 06 23:02:27 UTC 2023
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Record UNII |
WOU1621EEG
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C97366
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WHO-ATC |
J05AE07
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NDF-RT |
N0000000246
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LIVERTOX |
NBK548011
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WHO-VATC |
QJ05AE07
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NDF-RT |
N0000175889
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DTXSID2048296
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1240
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Fosamprenavir
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C83720
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82941
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CHEMBL1664
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WOU1621EEG
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M5546
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SUB25386
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358262
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226700-79-4
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100000089382
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DB01319
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131536
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7340
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8011
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Fosamprenavir
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C426859
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SALT/SOLVATE -> PARENT |
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METABOLITE ACTIVE -> PRODRUG |
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ACTIVE MOIETY |
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Biological Half-life | PHARMACOKINETIC |
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