Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C36H47N5O4.C2H6O.H2O4S |
| Molecular Weight | 757.936 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCO.OS(O)(=O)=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=QDNVAYDEAGXHTB-NOYQBWMBSA-N
InChI=1S/C36H47N5O4.C2H6O.H2O4S/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;1-2-3;1-5(2,3)4/h4-15,21,28-29,31-33,42-43H,16-20,22-24H2,1-3H3,(H,38,44)(H,39,45);3H,2H2,1H3;(H2,1,2,3,4)/t28-,29+,31+,32-,33+;;/m1../s1
| Molecular Formula | H2O4S |
| Molecular Weight | 98.078 |
| 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 |
| Molecular Formula | C2H6O |
| Molecular Weight | 46.0684 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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
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
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1287617 |
47.9 µM [Ki] | ||
Target ID: CHEMBL243 Sources: http://www.drugbank.ca/drugs/DB00224 |
0.37 nM [Ki] | ||
Target ID: CHEMBL612877 |
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 Date8.2555201E11 |
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 |
|---|---|---|---|---|
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 |
|
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 |
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: Page: 20 |
unhealthy, adult n = 23 Health Status: unhealthy Condition: HIV-1 Age Group: adult Sex: unknown Population Size: 23 Sources: Page: 20 |
Disc. AE: Renal disorders NEC, Gastrointestinal disorders NEC... AEs leading to discontinuation/dose reduction: Renal disorders NEC (23 patients) Sources: Page: 20Gastrointestinal 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: 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: Page: 97 |
Other AEs: Renal disorders NEC... Other AEs: Renal disorders NEC (5 patients) Sources: 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: Page: 20 |
unhealthy, adult n = 23 Health Status: unhealthy Condition: HIV-1 Age Group: adult Sex: unknown Population Size: 23 Sources: 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: Page: 20 |
unhealthy, adult n = 23 Health Status: unhealthy Condition: HIV-1 Age Group: adult Sex: unknown Population Size: 23 Sources: 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: 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: Page: 97 |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| weak | ||||
| 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 |
|---|---|---|---|---|
| weak | no (co-administration study) Comment: Coadministration of quinidine sulfate (CYP2D6 inhibitor) did not significantly alter the pharmacokinetics of indinavir Page: 145.0 |
|||
Page: - |
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 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Non-active site changes elicit broad-based cross-resistance of the HIV-1 protease to inhibitors. | 1999 Aug 20 |
|
| Design and fast synthesis of C-terminal duplicated potent C(2)-symmetric P1/P1'-modified HIV-1 protease inhibitors. | 1999 Sep 23 |
|
| Glutathione oxidation and PTPase inhibition by hydrogen peroxide in Caco-2 cell monolayer. | 2000 Aug |
|
| BMS-232632, a highly potent human immunodeficiency virus protease inhibitor that can be used in combination with other available antiretroviral agents. | 2000 Aug |
|
| 5,6-Dihydropyran-2-ones possessing various sulfonyl functionalities: potent nonpeptidic inhibitors of HIV protease. | 2000 Mar 9 |
|
| In vitro resistance profile of the human immunodeficiency virus type 1 protease inhibitor BMS-232632. | 2000 Sep |
|
| Identification of MK-944a: a second clinical candidate from the hydroxylaminepentanamide isostere series of HIV protease inhibitors. | 2000 Sep 7 |
|
| Tipranavir inhibits broadly protease inhibitor-resistant HIV-1 clinical samples. | 2000 Sep 8 |
|
| Saquinavir soft gelatin capsule: a comparative safety review. | 2001 |
|
| Comparison of P-triglyceride levels among patients with human immunodeficiency virus on randomized treatment with ritonavir, indinavir or ritonavir/saquinavir. | 2001 |
|
| Smaller amounts of antiretroviral drugs are needed when combined with an active ribozyme against HIV-1. | 2001 Apr |
|
| Effects of grapefruit juice on pharmacokinetic exposure to indinavir in HIV-positive subjects. | 2001 Apr |
|
| Gynecomastia associated with highly active antiretroviral therapy. | 2001 Apr |
|
| Intracellular concentration of the HIV protease inhibitors indinavir and saquinavir in human endothelial cells. | 2001 Apr |
|
| Long-term virologic and immunologic responses in human immunodeficiency virus type 1-infected children treated with indinavir, zidovudine, and lamivudine. | 2001 Apr 1 |
|
| 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 |
|
| Chemotherapy for human immunodeficiency virus-associated non-Hodgkin's lymphoma in combination with highly active antiretroviral therapy. | 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 |
|
| [Acute porphyria and indinavir]. | 2001 Feb |
|
| [Long-term immunologic response in HIV-infected patients with CD4 cell counts | 2001 Feb |
|
| Switch of protease inhibitor-containing HAART in routine clinical practice: a four-year prospective observational study. | 2001 Feb |
|
| 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 |
|
| 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 |
|
| [Anti-infection prophylaxis after sexual assault. Experience of the Raymond Poincaré-Garches Hospital]. | 2001 Feb 17 |
|
| Economic analysis of initial HIV treatment. Efavirenz- versus indinavir-containing triple therapy. | 2001 Jan |
|
| The use of and response to second-line protease inhibitor regimens: results from the EuroSIDA study. | 2001 Jan 26 |
|
| [Vertical trasmission of human immunodeficiency virus (HIV) and other sexually transmitted infections (STI)]. | 2001 Jun |
|
| Hypercholesterolemia in a health care worker receiving thyroxine after postexposure prophylaxis for human immunodeficiency virus infection. | 2001 Jun 1 |
|
| Effect of indinavir on the pharmacokinetics of rifampicin in HIV-infected patients. | 2001 Mar |
|
| Resolution of microsporidial keratoconjunctivitis in an AIDS patient treated with highly active antiretroviral therapy. | 2001 Mar |
|
| A retrospective, cohort-based survey of patients using twice-daily indinavir + ritonavir combinations: pharmacokinetics, safety, and efficacy. | 2001 Mar 1 |
|
| Sequencing of protease inhibitor therapy: insights from an analysis of HIV phenotypic resistance in patients failing protease inhibitors. | 2001 Mar 30 |
|
| Secreted aspartic proteases of Candida albicans, Candida tropicalis, Candida parapsilosis and Candida lusitaniae. Inhibition with peptidomimetic inhibitors. | 2001 May |
|
| Regulation of expression of 11beta-hydroxysteroid dehydrogenase type 1 in adipose tissue: tissue-specific induction by cytokines. | 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 |
|
| 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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 01:41:09 UTC 2023
by
admin
on
Sat Dec 16 01:41:09 UTC 2023
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| Record UNII |
34OB95C8AE
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| Record Status |
Validated (UNII)
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| Record Version |
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34OB95C8AE
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11954281
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100000176917
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PARENT -> SALT/SOLVATE | |||
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ANHYDROUS->SOLVATE | |||
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BASIS OF STRENGTH->SUBSTANCE |
anhydrous and ethanol-free substance
ASSAY (HPLC)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
For the calculation of contents, multiply the peak areas by 1.8
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |
