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 |
8.6 µM [EC50] | ||
Target ID: CHEMBL2364675 |
2.5 µM [IC50] | ||
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 |
|
| Inhibition of HIV-1 protease by a boron-modified polypeptide. | 2000 Oct 1 |
|
| In vitro resistance profile of the human immunodeficiency virus type 1 protease inhibitor BMS-232632. | 2000 Sep |
|
| Synthesis, stability, antiviral activity, and protease-bound structures of substrate-mimicking constrained macrocyclic inhibitors of HIV-1 protease. | 2000 Sep 21 |
|
| Development of HIV protease inhibitors: a survey. | 2001 |
|
| Metabolic disposition and pharmacokinetics of [14C]-amprenavir, a human immunodeficiency virus type 1 (HIV-1) protease inhibitor, administered as a single oral dose to healthy male subjects. | 2001 Apr |
|
| [Determining resistance in HIV therapy. Careful interpretation only]. | 2001 Apr 2 |
|
| Liquid chromatographic-tandem mass spectrometric determination of amprenavir (agenerase) in serum/plasma of human immunodeficiency virus type-1 infected patients receiving combination antiretroviral therapy. | 2001 Apr 20 |
|
| Antiretrovirals: simultaneous determination of five protease inhibitors and three nonnucleoside transcriptase inhibitors in human plasma by a rapid high-performance liquid chromatography--mass spectrometry assay. | 2001 Aug |
|
| Safety profile and tolerability of amprenavir in patients enrolled in an early access program. | 2001 Feb |
|
| 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 |
|
| High-performance liquid chromatographic assay to determine the plasma levels of HIV-protease inhibitors (amprenavir, indinavir, nelfinavir, ritonavir and saquinavir) and the non-nucleoside reverse transcriptase inhibitor (nevirapine) after liquid-liquid extraction. | 2001 Jul 15 |
|
| Synthesis of a chiral aziridine derivative as a versatile intermediate for HIV protease inhibitors. | 2001 Jul 26 |
|
| 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 |
|
| Phase III trials for new PI. | 2001 Mar |
|
| 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 |
|
| [Drug interactions with antiretroviral agents]. | 2001 May-Jun |
|
| In vitro activity of amprenavir against Pneumocystis carinii. | 2001 Sep |
|
| Retroviral proteases. | 2002 |
|
| New dosing regimen approved. | 2002 Apr |
|
| Simultaneous determination of the six HIV protease inhibitors (amprenavir, indinavir, lopinavir, nelfinavir, ritonavir, and saquinavir) plus M8 nelfinavir metabolite and the nonnucleoside reverse transcription inhibitor efavirenz in human plasma by solid-phase extraction and column liquid chromatography. | 2002 Apr |
|
| HIV-1 genotype and phenotype correlate with virological response to abacavir, amprenavir and efavirenz in treatment-experienced patients. | 2002 Feb 15 |
|
| Amino acid substitutions in Gag protein at non-cleavage sites are indispensable for the development of a high multitude of HIV-1 resistance against protease inhibitors. | 2002 Feb 22 |
|
| Determination of amprenavir, a HIV-1 protease inhibitor, in human seminal plasma using high-performance liquid chromatography-tandem mass spectrometry. | 2002 Jan 25 |
|
| In vitro antiviral interaction of lopinavir with other protease inhibitors. | 2002 Jul |
|
| The pharmacokinetics of amprenavir, zidovudine, and lamivudine in the genital tracts of men infected with human immunodeficiency virus type 1 (AIDS clinical trials group study 850). | 2002 Jul 15 |
|
| High-performance liquid chromatographic method for the simultaneous determination of the six HIV-protease inhibitors and two non-nucleoside reverse transcriptase inhibitors in human plasma. | 2002 Jun |
|
| Fosamprenavir. Vertex Pharmaceuticals/GlaxoSmithKline. | 2002 Mar |
|
| Drug interactions between HIV protease inhibitors based on physiologically-based pharmacokinetic model. | 2002 Mar |
|
| Efavirenz-induced skin eruption and successful desensitization. | 2002 Mar |
|
| FDA approves new dosing for amprenavir and ritonavir combination. | 2002 Mar 8 |
|
| Salvage therapy with amprenavir and ritonavir: prospective study in 17 heavily pretreated patients. | 2002 Mar-Apr |
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
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on
Edited
Sun Dec 18 20:42:32 UTC 2022
by
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Sun Dec 18 20:42:32 UTC 2022
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| Record UNII |
WOU1621EEG
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| Record Status |
Validated (UNII)
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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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PRIMARY | Merck Index | ||
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SUB25386
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358262
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226700-79-4
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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 |
| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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| Biological Half-life | PHARMACOKINETIC |
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