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=C4C=CC=C5

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 8297	47.9 µM [Ki]
Human immunodeficiency virus type 1 protease 35 Target ID: CHEMBL243 Sources: http://www.drugbank.ca/drugs/DB00224	Inhibitor 8297	0.37 nM [Ki]
Leishmania amazonensis 8 Target ID: CHEMBL612877 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22579524	Inhibitor 8297	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 8429	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
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 1737 inhibitor 1587	inhibitor 1767	inhibitor 1852 substrate 1217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2E1 882 CYP2B6 810	P-gp 1537

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020685s078lbl.pdf#page=3 Page: 3.0	no
CYP2B6 1001	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020685s078lbl.pdf#page=3 Page: 3.0	no
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020685s078lbl.pdf#page=3 Page: 3.0	no
CYP2E1 970	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020685s078lbl.pdf#page=3 Page: 3.0	no
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020685s078lbl.pdf#page=3 Page: 3.0	weak
CYP3A4 1925	inhibitor 3277 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 1217	substrate 3367 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 1537	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9435299/ Page: -	yes
CYP3A4 1737	substrate 3367 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
In vitro and in vivo anticandidal activity of human immunodeficiency virus protease inhibitors.	1999 Aug	10395861
4-Aryl-2,4-dioxobutanoic acid inhibitors of HIV-1 integrase and viral replication in cells.	2000 Dec 28	11150161
In-vitro tipranavir susceptibility of HIV-1 isolates with reduced susceptibility to other protease inhibitors.	2000 Jan 7	10714580
Inhibition of HIV-1 protease by a boron-modified polypeptide.	2000 Oct 1	10974201
CT appearances of HIV-related lipodystrophy syndrome.	2001 Apr	11387159
Virologic outcome and predictors of virologic failure of highly active antiretroviral therapy containing protease inhibitors.	2001 Apr	11359661
Effects of grapefruit juice on pharmacokinetic exposure to indinavir in HIV-positive subjects.	2001 Apr	11304900
Long-term virologic and immunologic responses in human immunodeficiency virus type 1-infected children treated with indinavir, zidovudine, and lamivudine.	2001 Apr 1	11237839
Determination of serum levels of thirteen human immunodeficiency virus-suppressing drugs by high-performance liquid chromatography.	2001 Apr 13	11355843
High prevalence of genotypic and phenotypic HIV-1 drug-resistant strains among patients receiving antiretroviral therapy in Abidjan, Côte d'Ivoire.	2001 Apr 15	11391173
Chemotherapy for human immunodeficiency virus-associated non-Hodgkin's lymphoma in combination with highly active antiretroviral therapy.	2001 Apr 15	11304769
Sensitive and rapid method for the simultaneous quantification of the HIV-protease inhibitors indinavir, nelfinavir, ritonavir, and saquinavir in human plasma by reversed-phase liquid chromatography.	2001 Feb	11206045
Ritonavir, efavirenz, and nelfinavir inhibit CYP2B6 activity in vitro: potential drug interactions with bupropion.	2001 Feb	11159797
[Anti-infection prophylaxis after sexual assault. Experience of the Raymond Poincaré-Garches Hospital].	2001 Feb 17	11252969
The absence of hyperbilirubinaemia is highly predictive of treatment failure in advanced HIV-infected patients treated with indinavir.	2001 Jan	11177479
Efficacy, tolerance, and pharmacokinetics of the combination of stavudine, nevirapine, nelfinavir, and saquinavir as salvage regimen after ritonavir or indinavir failure.	2001 Jan 20	11177388
Pathological fractures in AIDS patients with osteopenia and osteoporosis induced by antiretroviral therapy.	2001 Jan 5	11192861
New developments in anti-HIV chemotherapy.	2001 Jan-Feb	11347962
Hypercholesterolemia in a health care worker receiving thyroxine after postexposure prophylaxis for human immunodeficiency virus infection.	2001 Jun 1	11340537
Effect of indinavir on the pharmacokinetics of rifampicin in HIV-infected patients.	2001 Mar	11291758
A retrospective, cohort-based survey of patients using twice-daily indinavir + ritonavir combinations: pharmacokinetics, safety, and efficacy.	2001 Mar 1	11242194
Indinavir, nevirapine, stavudine, and lamivudine for human immunodeficiency virus-infected, amprenavir-experienced subjects: AIDS Clinical Trials Group protocol 373.	2001 Mar 1	11181147
Abacavir-lamivudine-zidovudine vs indinavir-lamivudine-zidovudine in antiretroviral-naive HIV-infected adults: A randomized equivalence trial.	2001 Mar 7	11231744
[Simultaneous quantitative determination of amprenavir and indinavir in human plasma by high-performance liquid chromatography].	2001 Mar-Apr	11282520
An LC-MS-MS method for the determination of indinavir, an HIV-1 protease inhibitor, in human plasma.	2001 May	11275438
Low incidence of genotypic and phenotypic resistance in paediatric HIV-infected patients on long-term first-line antiretroviral triple therapy.	2001 May 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 May 25	11399998
Sexual dysfunction associated with protease inhibitor containing highly active antiretroviral treatment.	2001 May 25	11399984

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 15 16:03:37 GMT 2023` Edited by `admin` on `Fri Dec 15 16:03:37 GMT 2023`
Record UNII	9MG78X43ZT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

INDINAVIR ANHYDROUS

Common 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

INDINAVIR [MI]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000175889