INDINAVIR

US Previously Marketed

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 Search

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=C4C=CC=C5

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
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 14 Target ID: CHEMBL1287617 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16118329	Inhibitor 8146	47.9 µM [Ki]
Human immunodeficiency virus type 1 protease 35 Target ID: CHEMBL243 Sources: http://www.drugbank.ca/drugs/DB00224	Inhibitor 8146	0.37 nM [Ki]
Leishmania amazonensis 8 Target ID: CHEMBL612877 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22579524	Inhibitor 8146	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 8307	CRIXIVAN® Approved Use CRIXIVAN in combination with antiretroviral agents is indicated for the treatment of HIV infection. Launch Date 8.2555201E11

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
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
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

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 Page: 20	unhealthy, adult n = 23 Health Status: unhealthy Condition: HIV-1 Age Group: adult Sex: unknown Population Size: 23 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020685s073lbl.pdf Page: 20	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 Page: 20
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/ Page: 97	unhealthy, mean 42 years n = 5 Health Status: unhealthy Condition: HIV-1 Age Group: mean 42 years Sex: M+F Population Size: 5 Sources: https://pubmed.ncbi.nlm.nih.gov/10513637/ Page: 97	Other AEs: Renal disorders NEC... Other AEs: Renal disorders NEC (5 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/10513637/ Page: 97

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 Page: 20	unhealthy, adult n = 23 Health Status: unhealthy Condition: HIV-1 Age Group: adult Sex: unknown Population Size: 23 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020685s073lbl.pdf Page: 20
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 Page: 20	unhealthy, adult n = 23 Health Status: unhealthy Condition: HIV-1 Age Group: adult Sex: unknown Population Size: 23 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020685s073lbl.pdf Page: 20
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/ Page: 97	unhealthy, mean 42 years n = 5 Health Status: unhealthy Condition: HIV-1 Age Group: mean 42 years Sex: M+F Population Size: 5 Sources: https://pubmed.ncbi.nlm.nih.gov/10513637/ Page: 97

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1670 inhibitor 1532	inhibitor 1695	inhibitor 1789 substrate 1168

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1463 CYP2E1 846 CYP2B6 770	P-gp 1491

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 1620	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020685s078lbl.pdf#page=3 Page: 3.0	no
CYP2B6 946	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020685s078lbl.pdf#page=3 Page: 3.0	no
CYP2C9 1747	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020685s078lbl.pdf#page=3 Page: 3.0	no
CYP2E1 929	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020685s078lbl.pdf#page=3 Page: 3.0	no
CYP2D6 1826	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020685s078lbl.pdf#page=3 Page: 3.0	weak
CYP3A4 1857	inhibitor 3185 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 1168	substrate 3264 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 1491	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/9435299/ Page: -	yes
CYP3A4 1670	substrate 3264 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
BLD Pharm	BD134557	http://www.bldpharm.com/products/150378-17-9.html
BioSynth	J-008694	https://www.biosynth.com/en/products/all-products/products/J-008694.html
CSNpharm	CSN11198	https://www.csnpharm.com/products/indinavir.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
DC Chemicals	DC8906	http://www.dcchemicals.com/product_show-Indinavir.html
Glentham Life Sciences	GP8542	http://www.glentham.com/products/product/GP8542/
Hairui	HR130052	http://www.hairuichem.com/en/product/150378-17-9.html
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
eNovation Chemicals	D591373	https://www.enovationchem.com/ProductDetails.asp?ProductID=D591373
eNovation Chemicals	D674369	https://www.enovationchem.com/ProductDetails.asp?ProductID=D674369
iChemical	EBD41965	http://www.ichemical.com/chemicals/cas-150378-17-9

PubMed

Title	Date	PubMed
4-Aryl-2,4-dioxobutanoic acid inhibitors of HIV-1 integrase and viral replication in cells.	2000 Dec 28	11150161
Anti-toxoplasma activities of antiretroviral drugs and interactions with pyrimethamine and sulfadiazine in vitro.	2000 Sep	10952623
The emerging roles of non-nucleoside reverse transcriptase inhibitors in antiretroviral therapy.	2001	11217868
Virologic outcome and predictors of virologic failure of highly active antiretroviral therapy containing protease inhibitors.	2001 Apr	11359661
Intracellular concentration of the HIV protease inhibitors indinavir and saquinavir in human endothelial cells.	2001 Apr	11266428
Differences in the intracellular accumulation of HIV protease inhibitors in vitro and the effect of active transport.	2001 Apr 13	11371681
[Indinavir-ritonavir combination: pharmacologic results and tolerance in patients infected by HIV].	2001 Apr 21	11360738
[Acute porphyria and indinavir].	2001 Feb	11275609
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	11133370
[Bilateral hip necrosis, corticoids, and human immunodeficiency virus protease inhibitors].	2001 Jan	11256248
Paronychia in association with indinavir treatment.	2001 Jan	11118393
Indinavir, zidovudine, lamivudine: 3-year follow-up.	2001 Jan 16	11177322
Changes in host cell molecules acquired by circulating HIV-1 in patients treated with highly active antiretroviral therapy and interleukin-2.	2001 Jan 5	11192851
Limits of deep salvage antiretroviral therapy with nelfinavir plus either efavirenz or nevirapine, in highly pre-treated patients with HIV disease.	2001 Jun	11397623
Severe lactic acidosis and thiamine administration in an HIV-infected patient on HAART.	2001 Jun	11368826
Hypercholesterolemia in a health care worker receiving thyroxine after postexposure prophylaxis for human immunodeficiency virus infection.	2001 Jun 1	11340537
The binding energetics of first- and second-generation HIV-1 protease inhibitors: implications for drug design.	2001 Jun 15	11396919
Anti-AIDS drugs available 'at cost'.	2001 Mar 15	11268163
Competition prompts drug companies to cut antiretroviral drug prices.	2001 Mar 17	11265962
Abacavir-lamivudine-zidovudine vs indinavir-lamivudine-zidovudine in antiretroviral-naive HIV-infected adults: A randomized equivalence trial.	2001 Mar 7	11231744
P1/P1' modified HIV protease inhibitors as tools in two new sensitive surface plasmon resonance biosensor screening assays.	2001 May	11297905
An LC-MS-MS method for the determination of indinavir, an HIV-1 protease inhibitor, in human plasma.	2001 May	11275438
Is indinavir crystalluria an indicator for indinavir stone formation?	2001 May 25	11400000
Low incidence of genotypic and phenotypic resistance in paediatric HIV-infected patients on long-term first-line antiretroviral triple therapy.	2001 May 25	11399999
Indinavir hair concentration in highly active antiretroviral therapy-treated patients: association with viral load and drug resistance.	2001 May 4	11399971

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 `Fri Dec 16 18:01:51 UTC 2022` Edited by `admin` on `Fri Dec 16 18:01:51 UTC 2022`
Record UNII	5W6YA9PKKH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

INDINAVIR

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

Common Name

English

INDINAVIR MONOHYDRATE

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