Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C36H47N5O4.H2O |
Molecular Weight | 631.8048 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.CC(C)(C)NC(=O)[C@@H]1CN(CC2=CN=CC=C2)CCN1C[C@@H](O)C[C@@H](CC3=CC=CC=C3)C(=O)N[C@@H]4[C@H](O)CC5=CC=CC=C45
InChI
InChIKey=XTYSXGHMTNTKFH-BDEHJDMKSA-N
InChI=1S/C36H47N5O4.H2O/c1-36(2,3)39-35(45)31-24-40(22-26-12-9-15-37-21-26)16-17-41(31)23-29(42)19-28(18-25-10-5-4-6-11-25)34(44)38-33-30-14-8-7-13-27(30)20-32(33)43;/h4-15,21,28-29,31-33,42-43H,16-20,22-24H2,1-3H3,(H,38,44)(H,39,45);1H2/t28-,29+,31+,32-,33+;/m1./s1
Molecular Formula | H2O |
Molecular Weight | 18.0153 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C36H47N5O4 |
Molecular Weight | 613.7895 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.drugbank.ca/drugs/DB00224Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/dosage/indinavir.html
Sources: http://www.drugbank.ca/drugs/DB00224
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/dosage/indinavir.html
Indinavir is an antiretroviral drug for the treatment of HIV infection. Indinavir 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. Indinavir 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.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22514580
Curator's Comment: Median concentration of Indinavir in CSF was 210 nmol/l, which is the threshold for IC95 in vitro. Indinavir is essentially the only PI that reaches CSF concentrations above IC95. From a clinical point of view, the presence of Indinavir in CSF was associated with significant improvement of neurocognitive performances
Originator
Sources: http://adisinsight.springer.com/drugs/800002849
Curator's Comment: # Merck & Co
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1287617 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16118329 |
47.9 µM [Ki] | ||
Target ID: CHEMBL243 Sources: http://www.drugbank.ca/drugs/DB00224 |
0.37 nM [Ki] | ||
Target ID: CHEMBL612877 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22579524 |
100.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | CRIXIVAN® Approved UseCRIXIVAN in combination with antiretroviral agents is indicated for the treatment of HIV infection. Launch Date1996 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
12617 nM |
800 mg 3 times / day steady-state, oral dose: 800 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
INDINAVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
17181 nM |
500 mg/m² 3 times / day multiple, oral dose: 500 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered: |
INDINAVIR plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
30691 nM × h |
800 mg 3 times / day steady-state, oral dose: 800 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
INDINAVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
38742 nM × h |
500 mg/m² 3 times / day multiple, oral dose: 500 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered: |
INDINAVIR plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN |
|
9231 nM × h |
800 mg 3 times / day multiple, oral dose: 800 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
INDINAVIR unknown | Homo sapiens population: PREGNANT age: ADULT sex: FEMALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
40% |
800 mg 3 times / day steady-state, oral dose: 800 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
INDINAVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
2400 mg single, oral Overdose Dose: 2400 mg Route: oral Route: single Dose: 2400 mg Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Disc. AE: Renal disorders NEC, Gastrointestinal disorders NEC... AEs leading to discontinuation/dose reduction: Renal disorders NEC (23 patients) Sources: Gastrointestinal disorders NEC (23 patients) |
1200 mg 2 times / day steady, oral Higher than recommended Dose: 1200 mg, 2 times / day Route: oral Route: steady Dose: 1200 mg, 2 times / day Sources: |
unhealthy, mean 42 years Health Status: unhealthy Age Group: mean 42 years Sex: M+F Sources: |
Other AEs: Renal disorders NEC... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Gastrointestinal disorders NEC | 23 patients Disc. AE |
2400 mg single, oral Overdose Dose: 2400 mg Route: oral Route: single Dose: 2400 mg Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Renal disorders NEC | 23 patients Disc. AE |
2400 mg single, oral Overdose Dose: 2400 mg Route: oral Route: single Dose: 2400 mg Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Renal disorders NEC | 5 patients | 1200 mg 2 times / day steady, oral Higher than recommended Dose: 1200 mg, 2 times / day Route: oral Route: steady Dose: 1200 mg, 2 times / day Sources: |
unhealthy, mean 42 years Health Status: unhealthy Age Group: mean 42 years Sex: M+F Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 3.0 |
no | |||
Page: 3.0 |
no | |||
Page: 3.0 |
no | |||
Page: 3.0 |
no | |||
Page: 3.0 |
weak | |||
Page: 3.0 |
yes | yes (co-administration study) Comment: in the same study, clarithromycin AUC was increased by 53 ±36% and Cmax increased 22 ± 33% following coadministration with indinavir. Page: 3.0 |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/020685Orig1s000rev.pdf#page=145 Page: 145.0 |
weak | no (co-administration study) Comment: Coadministration of quinidine sulfate (CYP2D6 inhibitor) did not significantly alter the pharmacokinetics of indinavir Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/020685Orig1s000rev.pdf#page=145 Page: 145.0 |
||
Sources: https://pubmed.ncbi.nlm.nih.gov/9435299/ Page: - |
yes | |||
Page: 2.0 |
yes | yes (co-administration study) Comment: Clarithromycin (500 mg q12h) increased the AUC of indinavir (800 mg q8h) by 29±42% and increased Cmax by 18±44%. Page: 2.0 |
PubMed
Title | Date | PubMed |
---|---|---|
4-Aryl-2,4-dioxobutanoic acid inhibitors of HIV-1 integrase and viral replication in cells. | 2000 Dec 28 |
|
In vitro activity of human immunodeficiency virus protease inhibitors against Pneumocystis carinii. | 2000 May |
|
PMS-601, a new platelet-activating factor receptor antagonist that inhibits human immunodeficiency virus replication and potentiates zidovudine activity in macrophages. | 2000 Nov |
|
Tipranavir inhibits broadly protease inhibitor-resistant HIV-1 clinical samples. | 2000 Sep 8 |
|
CT appearances of HIV-related lipodystrophy syndrome. | 2001 Apr |
|
Intracellular concentration of the HIV protease inhibitors indinavir and saquinavir in human endothelial cells. | 2001 Apr |
|
Indinavir and systemic hypertension. | 2001 Apr 13 |
|
Differences in the intracellular accumulation of HIV protease inhibitors in vitro and the effect of active transport. | 2001 Apr 13 |
|
High prevalence of genotypic and phenotypic HIV-1 drug-resistant strains among patients receiving antiretroviral therapy in Abidjan, Côte d'Ivoire. | 2001 Apr 15 |
|
A phase II trial of dual protease inhibitor therapy: amprenavir in combination with indinavir, nelfinavir, or saquinavir. | 2001 Apr 15 |
|
[Didanosine as a capsule. A reliable drug in a new dosage form]. | 2001 Apr 2 |
|
Viral excretion in cervicovaginal secretions of HIV-1-infected women receiving antiretroviral therapy. | 2001 Feb |
|
[Long-term immunologic response in HIV-infected patients with CD4 cell counts = 50/mm3 when initiating protease inhibitor therapy]. | 2001 Feb |
|
Human immunodeficiency virus (HIV) protease inhibitors have no effect on hepatitis C virus (HCV) serum levels of HIV-HCV co-infected patients. | 2001 Feb |
|
Therapy with efavirenz plus indinavir in patients with extensive prior nucleoside reverse-transcriptase inhibitor experience: a randomized, double-blind, placebo-controlled trial. | 2001 Feb 1 |
|
[Bilateral hip necrosis, corticoids, and human immunodeficiency virus protease inhibitors]. | 2001 Jan |
|
The absence of hyperbilirubinaemia is highly predictive of treatment failure in advanced HIV-infected patients treated with indinavir. | 2001 Jan |
|
Effect of alpha1-acid glycoprotein on the intracellular accumulation of the HIV protease inhibitors saquinavir, ritonavir and indinavir in vitro. | 2001 Jan |
|
Indinavir, zidovudine, lamivudine: 3-year follow-up. | 2001 Jan 16 |
|
Efficacy, tolerance, and pharmacokinetics of the combination of stavudine, nevirapine, nelfinavir, and saquinavir as salvage regimen after ritonavir or indinavir failure. | 2001 Jan 20 |
|
Pathological fractures in AIDS patients with osteopenia and osteoporosis induced by antiretroviral therapy. | 2001 Jan 5 |
|
New developments in anti-HIV chemotherapy. | 2001 Jan-Feb |
|
Limits of deep salvage antiretroviral therapy with nelfinavir plus either efavirenz or nevirapine, in highly pre-treated patients with HIV disease. | 2001 Jun |
|
[Vertical trasmission of human immunodeficiency virus (HIV) and other sexually transmitted infections (STI)]. | 2001 Jun |
|
The HIV protease inhibitor indinavir decreases insulin- and contraction-stimulated glucose transport in skeletal muscle. | 2001 Jun |
|
The HIV protease inhibitor indinavir impairs sterol regulatory element-binding protein-1 intranuclear localization, inhibits preadipocyte differentiation, and induces insulin resistance. | 2001 Jun |
|
Severe lactic acidosis and thiamine administration in an HIV-infected patient on HAART. | 2001 Jun |
|
Hypercholesterolemia in a health care worker receiving thyroxine after postexposure prophylaxis for human immunodeficiency virus infection. | 2001 Jun 1 |
|
The binding energetics of first- and second-generation HIV-1 protease inhibitors: implications for drug design. | 2001 Jun 15 |
|
A comprehensive account on the role of efflux transporters in the gastrointestinal absorption of 13 commonly used substrate drugs in humans. | 2001 Mar |
|
Resolution of microsporidial keratoconjunctivitis in an AIDS patient treated with highly active antiretroviral therapy. | 2001 Mar |
|
Alterations in T cell phenotype and human immunodeficiency virus type 1-specific cytotoxicity after potent antiretroviral therapy. | 2001 Mar 1 |
|
Indinavir, nevirapine, stavudine, and lamivudine for human immunodeficiency virus-infected, amprenavir-experienced subjects: AIDS Clinical Trials Group protocol 373. | 2001 Mar 1 |
|
Anti-AIDS drugs available 'at cost'. | 2001 Mar 15 |
|
Competition prompts drug companies to cut antiretroviral drug prices. | 2001 Mar 17 |
|
Sequencing of protease inhibitor therapy: insights from an analysis of HIV phenotypic resistance in patients failing protease inhibitors. | 2001 Mar 30 |
|
Assessment of active transport of HIV protease inhibitors in various cell lines and the in vitro blood--brain barrier. | 2001 Mar 9 |
|
P1/P1' modified HIV protease inhibitors as tools in two new sensitive surface plasmon resonance biosensor screening assays. | 2001 May |
|
An LC-MS-MS method for the determination of indinavir, an HIV-1 protease inhibitor, in human plasma. | 2001 May |
|
Residual human immunodeficiency virus type 1 infection in lymphoid tissue during highly active antiretroviral therapy: quantitation and virus characterization. | 2001 May 1 |
|
Treatment of primary human immunodeficiency virus type 1 infection with potent antiretroviral therapy reduces frequency of rapid progression to AIDS. | 2001 May 15 |
|
Is indinavir crystalluria an indicator for indinavir stone formation? | 2001 May 25 |
|
Low incidence of genotypic and phenotypic resistance in paediatric HIV-infected patients on long-term first-line antiretroviral triple therapy. | 2001 May 25 |
|
'Do HIV-infected injecting drug users over-report adherence to highly active antiretroviral therapy?' A comparison between patients' self-reports and serum protease inhibitor concentrations in the French Manif 2000 cohort study. | 2001 May 25 |
|
Sexual dysfunction associated with protease inhibitor containing highly active antiretroviral treatment. | 2001 May 25 |
|
Clinical outcome among HIV-infected patients starting saquinavir hard gel compared to ritonavir or indinavir. | 2001 May 25 |
|
Metabolic effects of indinavir in healthy HIV-seronegative men. | 2001 May 4 |
|
Indinavir hair concentration in highly active antiretroviral therapy-treated patients: association with viral load and drug resistance. | 2001 May 4 |
|
[Effective in HIV: dual combination with indinavir and ritonavir]. | 2001 May 4 |
|
Simultaneous determination of the HIV protease inhibitors indinavir, amprenavir, saquinavir, ritonavir and nelfinavir in human plasma by high-performance liquid chromatography. | 2001 May 5 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/indinavir.html
Usual Adult Dose for HIV Infection
800 mg orally every 8 hours or indinavir 800 mg plus ritonavir 100 to 200 mg orally every 12 hours
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15456083
Indinavir (10 nM) gave 14% inhibition of HIV replication alone and 81% in combination with P-gp/MRP inhibitors.
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:07:14 GMT 2025
by
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Mon Mar 31 18:07:14 GMT 2025
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Record UNII |
5W6YA9PKKH
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Record Status |
Validated (UNII)
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LIVERTOX |
NBK548674
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WHO-ESSENTIAL MEDICINES LIST |
6.4.2.3
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WHO-ATC |
J05AE02
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NCI_THESAURUS |
C97366
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WHO-VATC |
QJ05AE02
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114289
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5484730
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INDINAVIR
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DTXSID7023144
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II-15
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CHEMBL115
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5W6YA9PKKH
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44032
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C66877
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180683-37-8
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1437
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Indinavir
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D019469
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1339178
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DB00224
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