INDINAVIR ANHYDROUS

US Previously Marketed

First approved in 1996

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C36H47N5O4
Molecular Weight	613.7895
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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=CBVCZFGXHXORBI-PXQQMZJSSA-N

InChI=1S/C36H47N5O4/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)/t28-,29+,31+,32-,33+/m1/s1

HIDE SMILES / InChI

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
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
UDP-glucuronosyltransferase 1-1 15 Target ID: CHEMBL1287617 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16118329	Inhibitor 8504	47.9 µM [Ki]
Human immunodeficiency virus type 1 protease 36 Target ID: CHEMBL243 Sources: http://www.drugbank.ca/drugs/DB00224	Inhibitor 8504	0.37 nM [Ki]
Leishmania amazonensis 8 Target ID: CHEMBL612877 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22579524	Inhibitor 8504	100.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
HIV infection 21 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020685s073lbl.pdf	Primary		Approved 8583	CRIXIVAN® Approved Use CRIXIVAN in combination with antiretroviral agents is indicated for the treatment of HIV infection. Launch Date 1996

C_max

Value	Dose	Co-administered	Analyte	Population
12617 nM DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020685s078lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020685s078lbl.pdf	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	Analyte	Population
30691 nM × h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020685s078lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020685s078lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020685s078lbl.pdf	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
40% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020685s078lbl.pdf	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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020685s073lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020685s073lbl.pdf	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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020685s073lbl.pdf
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: https://pubmed.ncbi.nlm.nih.gov/10513637/	unhealthy, mean 42 years Health Status: unhealthy Age Group: mean 42 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10513637/	Other AEs: Renal disorders NEC... Other AEs: Renal disorders NEC (5 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/10513637/

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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020685s073lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020685s073lbl.pdf
Renal disorders NEC	23 patients Disc. AE	2400 mg single, oral Overdose Dose: 2400 mg Route: oral Route: single Dose: 2400 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020685s073lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020685s073lbl.pdf
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: https://pubmed.ncbi.nlm.nih.gov/10513637/	unhealthy, mean 42 years Health Status: unhealthy Age Group: mean 42 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10513637/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252	inhibitor 2438	inhibitor 2507 substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2E1 1060 CYP2B6 926	P-gp 2052

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020685s078lbl.pdf#page=3 Page: 3.0	no
CYP2B6 1160	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020685s078lbl.pdf#page=3 Page: 3.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020685s078lbl.pdf#page=3 Page: 3.0	no
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020685s078lbl.pdf#page=3 Page: 3.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020685s078lbl.pdf#page=3 Page: 3.0	weak
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020685s078lbl.pdf#page=3 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. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020685s078lbl.pdf#page=3 Page: 3.0

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP2D6 1388	substrate 4014 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
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9435299/ Page: -	yes
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020685s078lbl.pdf#page=2 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%. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020685s078lbl.pdf#page=2 Page: 2.0

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-0207	http://www.3bsc.com/index/pro_info.php?id=19563
AA Blocks	AA001MH2	https://www.aablocks.com/goods/Goods/detail?id=AA001MH2
AHH Chemical co.,ltd	API-1193	http://www.ahhchemical.com/product/API-1193.html
AK Scientific, Inc. (AKSCI)	69104	http://www.aksci.com/item_detail.php?cat=69104
Aurora Fine Chemicals LLC	A13.111.810	http://online.aurorafinechemicals.com/info?ID=A13.111.810
AvaChem Scientific	2152B	http://www.avachem.com/productSearch.asp?2152B
BioSynth	J-008694	https://www.biosynth.com/en/products/all-products/products/J-008694.html
BLD Pharm	BD134557	http://www.bldpharm.com/products/150378-17-9.html
Chem Scene	CS-2930	http://www.chemscene.com/150378-17-9.html
ChemMol	30107683	http://www.chemmol.com/chemmol/30107683.html
ChemMol	99047026	http://www.chemmol.com/chemmol/99047026.html
Chemspace	CSSB00000053661	https://chem-space.com/CSSB00000053661
CSNpharm	CSN11198	https://www.csnpharm.com/products/indinavir.html
DC Chemicals	DC8906	http://www.dcchemicals.com/product_show-Indinavir.html
eNovation Chemicals	D591373	https://www.enovationchem.com/ProductDetails.asp?ProductID=D591373
eNovation Chemicals	D674369	https://www.enovationchem.com/ProductDetails.asp?ProductID=D674369
Glentham Life Sciences	GP8542	http://www.glentham.com/products/product/GP8542/
Hairui	HR130052	http://www.hairuichem.com/en/product/150378-17-9.html
iChemical	EBD41965	http://www.ichemical.com/chemicals/cas-150378-17-9
Lab Network	LN00202000	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00202000
Matrix Scientific	99281	https://www.matrixscientific.com/099281.html
MedChem Express	HY-B0689	https://www.medchemexpress.com/indinavir.html
OChem	7422	http://www.ocheminc.com/index.php?act=psearch&pid=378I179
Parchem	29155	http://www.parchem.com/chemical-supplier-distributor/Indinavir-019155.aspx
Smolecule	S530618	http://www.smolecule.com/products/s530618
THE BioTek	bt-271014	https://www.thebiotek.com/product/inhibitors/bt-271014
Yuhao Chemical	RT5885	http://www.chemyuhao.com/150378-17-9.html

PubMed

Title	Date	PubMed
The binding energetics of first- and second-generation HIV-1 protease inhibitors: implications for drug design.	2001-06-15	11396919
Hypercholesterolemia in a health care worker receiving thyroxine after postexposure prophylaxis for human immunodeficiency virus infection.	2001-06-01	11340537
Limits of deep salvage antiretroviral therapy with nelfinavir plus either efavirenz or nevirapine, in highly pre-treated patients with HIV disease.	2001-06	11397623
[Vertical trasmission of human immunodeficiency virus (HIV) and other sexually transmitted infections (STI)].	2001-06	11395690
The HIV protease inhibitor indinavir decreases insulin- and contraction-stimulated glucose transport in skeletal muscle.	2001-06	11375341
The HIV protease inhibitor indinavir impairs sterol regulatory element-binding protein-1 intranuclear localization, inhibits preadipocyte differentiation, and induces insulin resistance.	2001-06	11375339
Severe lactic acidosis and thiamine administration in an HIV-infected patient on HAART.	2001-06	11368826
Is indinavir crystalluria an indicator for indinavir stone formation?	2001-05-25	11400000
Low incidence of genotypic and phenotypic resistance in paediatric HIV-infected patients on long-term first-line antiretroviral triple therapy.	2001-05-25	11399999
'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.	2001-05-25	11399998
Sexual dysfunction associated with protease inhibitor containing highly active antiretroviral treatment.	2001-05-25	11399984
Clinical outcome among HIV-infected patients starting saquinavir hard gel compared to ritonavir or indinavir.	2001-05-25	11399982
Treatment of primary human immunodeficiency virus type 1 infection with potent antiretroviral therapy reduces frequency of rapid progression to AIDS.	2001-05-15	11319682
New developments in anti-HIV chemotherapy.	2001-05-12	11347962
Simultaneous determination of the HIV protease inhibitors indinavir, amprenavir, saquinavir, ritonavir and nelfinavir in human plasma by high-performance liquid chromatography.	2001-05-05	11393736
Metabolic effects of indinavir in healthy HIV-seronegative men.	2001-05-04	11399973
Indinavir hair concentration in highly active antiretroviral therapy-treated patients: association with viral load and drug resistance.	2001-05-04	11399971
[Effective in HIV: dual combination with indinavir and ritonavir].	2001-05-04	11381644
Residual human immunodeficiency virus type 1 infection in lymphoid tissue during highly active antiretroviral therapy: quantitation and virus characterization.	2001-05-01	11375053
Residual human immunodeficiency virus (HIV) Type 1 RNA and DNA in lymph nodes and HIV RNA in genital secretions and in cerebrospinal fluid after suppression of viremia for 2 years.	2001-05-01	11294662
Secreted aspartic proteases of Candida albicans, Candida tropicalis, Candida parapsilosis and Candida lusitaniae. Inhibition with peptidomimetic inhibitors.	2001-05	11322888
Regulation of expression of 11beta-hydroxysteroid dehydrogenase type 1 in adipose tissue: tissue-specific induction by cytokines.	2001-05	11316764
P1/P1' modified HIV protease inhibitors as tools in two new sensitive surface plasmon resonance biosensor screening assays.	2001-05	11297905
An LC-MS-MS method for the determination of indinavir, an HIV-1 protease inhibitor, in human plasma.	2001-05	11275438
[Indinavir-ritonavir combination: pharmacologic results and tolerance in patients infected by HIV].	2001-04-21	11360738
High prevalence of genotypic and phenotypic HIV-1 drug-resistant strains among patients receiving antiretroviral therapy in Abidjan, Côte d'Ivoire.	2001-04-15	11391173
A phase II trial of dual protease inhibitor therapy: amprenavir in combination with indinavir, nelfinavir, or saquinavir.	2001-04-15	11391165
Chemotherapy for human immunodeficiency virus-associated non-Hodgkin's lymphoma in combination with highly active antiretroviral therapy.	2001-04-15	11304769
Indinavir and systemic hypertension.	2001-04-13	11371700
Differences in the intracellular accumulation of HIV protease inhibitors in vitro and the effect of active transport.	2001-04-13	11371681
Determination of serum levels of thirteen human immunodeficiency virus-suppressing drugs by high-performance liquid chromatography.	2001-04-13	11355843
[Simultaneous quantitative determination of amprenavir and indinavir in human plasma by high-performance liquid chromatography].	2001-04-03	11282520
[Didanosine as a capsule. A reliable drug in a new dosage form].	2001-04-02	11373794
CT appearances of HIV-related lipodystrophy syndrome.	2001-04	11387159
Virologic outcome and predictors of virologic failure of highly active antiretroviral therapy containing protease inhibitors.	2001-04	11359661
Smaller amounts of antiretroviral drugs are needed when combined with an active ribozyme against HIV-1.	2001-04	11319914
Effects of grapefruit juice on pharmacokinetic exposure to indinavir in HIV-positive subjects.	2001-04	11304900
Gynecomastia associated with highly active antiretroviral therapy.	2001-04	11302408
Intracellular concentration of the HIV protease inhibitors indinavir and saquinavir in human endothelial cells.	2001-04	11266428
Sequencing of protease inhibitor therapy: insights from an analysis of HIV phenotypic resistance in patients failing protease inhibitors.	2001-03-30	11316998
Anti-AIDS drugs available 'at cost'.	2001-03-15	11268163
A comprehensive account on the role of efflux transporters in the gastrointestinal absorption of 13 commonly used substrate drugs in humans.	2001-03	11396754
Incidence and clinical relevance of the interactions and side effects of Hypericum preparations.	2001-03	11315759
HIV/AIDS case histories: indinavir crystalluria.	2001-03	11313030
Effect of indinavir on the pharmacokinetics of rifampicin in HIV-infected patients.	2001-03	11291758
Viral excretion in cervicovaginal secretions of HIV-1-infected women receiving antiretroviral therapy.	2001-02	11305478
[Acute porphyria and indinavir].	2001-02	11275609
Saquinavir soft gelatin capsule: a comparative safety review.	2001	11347724
Comparison of P-triglyceride levels among patients with human immunodeficiency virus on randomized treatment with ritonavir, indinavir or ritonavir/saquinavir.	2001	11345223
Delavirdine: clinical pharmacokinetics and drug interactions.	2001	11327199

Patents

Sample Use Guides

In Vivo Use Guide

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

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 18:17:46 GMT 2025` Edited by `admin` on `Mon Mar 31 18:17:46 GMT 2025`
Record UNII	9MG78X43ZT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

INDINAVIR ANHYDROUS

Common Name

English

INDINAVIR [MI]

Preferred Name

English

(.ALPHA.R,.GAMMA.S,2S)-.ALPHA.-BENZYL-2-(TERT-BUTYLCARBAMOYL)-.GAMMA.-HYDROXY-N-((1S,2R)-2-HYDROXY-1-INDANYL)-4-(3-PYRIDYLMETHYL)-1-PIPERAZINEVALERAMIDE

Common Name

English

indinavir [INN]

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)-, (1(1S,2R),5(S))-

Common Name

English

Indinavir [WHO-DD]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000175889