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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
Structure of INDINAVIR

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

HIDE SMILES / InChI

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

Description
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

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

Curator's Comment: # Merck & Co

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
47.9 µM [Ki]
0.37 nM [Ki]
100.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CRIXIVAN®

Approved Use

CRIXIVAN in combination with antiretroviral agents is indicated for the treatment of HIV infection.

Launch Date

1996
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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)
Gastrointestinal disorders NEC (23 patients)
Sources:
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...
Other AEs:
Renal disorders NEC (5 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
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

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
weak
no (co-administration study)
Comment: Coadministration of quinidine sulfate (CYP2D6 inhibitor) did not significantly alter the pharmacokinetics of indinavir
Page: 145.0
yes
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
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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
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

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
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 Mon Mar 31 18:07:14 GMT 2025
Edited
by admin
on Mon Mar 31 18:07:14 GMT 2025
Record UNII
5W6YA9PKKH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
INDINAVIR MONOHYDRATE
WHO-DD  
Preferred Name English
INDINAVIR
USAN   VANDF  
USAN  
Official Name English
INDINAVIR [USP-RS]
Common Name English
INDINAVIR [USAN]
Common Name English
(?R,?S,2S)-?-Benzyl-2-(tert-butylcarbamoyl)-?-hydroxy-N-[(1S,2R)-2-hydroxy-1-indanyl]-4-(3-pyridylmethyl)-1-piperazinevaleramide monohydrate
Common Name English
INDINAVIR SYSTEM SUITABILITY [USP-RS]
Common Name English
Indinavir monohydrate [WHO-DD]
Common Name English
INDINAVIR SYSTEM SUITABILITY
USP-RS  
Common Name English
INDINAVIR [VANDF]
Common Name English
D-ERYTHRO-PENTONAMIDE, 2,3,5-TRIDEOXY-N-(2,3-DIHYDRO-2-HYDROXY-1H-INDEN-1-YL)-5-(2-(((1,1-DIMETHYLETHYL)AMINO)CARBONYL)-4-(3-PYRIDINYLMETHYL)-1-PIPERAZINYL)-2-(PHENYLMETHYL)-, MONOHYDRATE, (1(1S,2R),5(S))-
Common Name English
Classification Tree Code System Code
LIVERTOX NBK548674
Created by admin on Mon Mar 31 18:07:14 GMT 2025 , Edited by admin on Mon Mar 31 18:07:14 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 6.4.2.3
Created by admin on Mon Mar 31 18:07:14 GMT 2025 , Edited by admin on Mon Mar 31 18:07:14 GMT 2025
WHO-ATC J05AE02
Created by admin on Mon Mar 31 18:07:14 GMT 2025 , Edited by admin on Mon Mar 31 18:07:14 GMT 2025
NCI_THESAURUS C97366
Created by admin on Mon Mar 31 18:07:14 GMT 2025 , Edited by admin on Mon Mar 31 18:07:14 GMT 2025
WHO-VATC QJ05AE02
Created by admin on Mon Mar 31 18:07:14 GMT 2025 , Edited by admin on Mon Mar 31 18:07:14 GMT 2025
Code System Code Type Description
RXCUI
114289
Created by admin on Mon Mar 31 18:07:14 GMT 2025 , Edited by admin on Mon Mar 31 18:07:14 GMT 2025
PRIMARY RxNorm
PUBCHEM
5484730
Created by admin on Mon Mar 31 18:07:14 GMT 2025 , Edited by admin on Mon Mar 31 18:07:14 GMT 2025
PRIMARY
WIKIPEDIA
INDINAVIR
Created by admin on Mon Mar 31 18:07:14 GMT 2025 , Edited by admin on Mon Mar 31 18:07:14 GMT 2025
PRIMARY
EPA CompTox
DTXSID7023144
Created by admin on Mon Mar 31 18:07:14 GMT 2025 , Edited by admin on Mon Mar 31 18:07:14 GMT 2025
PRIMARY
USAN
II-15
Created by admin on Mon Mar 31 18:07:14 GMT 2025 , Edited by admin on Mon Mar 31 18:07:14 GMT 2025
PRIMARY
ChEMBL
CHEMBL115
Created by admin on Mon Mar 31 18:07:14 GMT 2025 , Edited by admin on Mon Mar 31 18:07:14 GMT 2025
PRIMARY
DAILYMED
5W6YA9PKKH
Created by admin on Mon Mar 31 18:07:14 GMT 2025 , Edited by admin on Mon Mar 31 18:07:14 GMT 2025
PRIMARY
CHEBI
44032
Created by admin on Mon Mar 31 18:07:14 GMT 2025 , Edited by admin on Mon Mar 31 18:07:14 GMT 2025
PRIMARY
NCI_THESAURUS
C66877
Created by admin on Mon Mar 31 18:07:14 GMT 2025 , Edited by admin on Mon Mar 31 18:07:14 GMT 2025
PRIMARY
CAS
180683-37-8
Created by admin on Mon Mar 31 18:07:14 GMT 2025 , Edited by admin on Mon Mar 31 18:07:14 GMT 2025
PRIMARY
DRUG CENTRAL
1437
Created by admin on Mon Mar 31 18:07:14 GMT 2025 , Edited by admin on Mon Mar 31 18:07:14 GMT 2025
PRIMARY
LACTMED
Indinavir
Created by admin on Mon Mar 31 18:07:14 GMT 2025 , Edited by admin on Mon Mar 31 18:07:14 GMT 2025
PRIMARY
MESH
D019469
Created by admin on Mon Mar 31 18:07:14 GMT 2025 , Edited by admin on Mon Mar 31 18:07:14 GMT 2025
PRIMARY
FDA UNII
5W6YA9PKKH
Created by admin on Mon Mar 31 18:07:14 GMT 2025 , Edited by admin on Mon Mar 31 18:07:14 GMT 2025
PRIMARY
RS_ITEM_NUM
1339178
Created by admin on Mon Mar 31 18:07:14 GMT 2025 , Edited by admin on Mon Mar 31 18:07:14 GMT 2025
PRIMARY
DRUG BANK
DB00224
Created by admin on Mon Mar 31 18:07:14 GMT 2025 , Edited by admin on Mon Mar 31 18:07:14 GMT 2025
PRIMARY
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