U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C38H50N6O5
Molecular Weight 670.8408
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SAQUINAVIR

SMILES

[H][C@@]12CCCC[C@]1([H])CN(C[C@@H](O)[C@H](CC3=CC=CC=C3)NC(=O)[C@H](CC(N)=O)NC(=O)C4=CC=C5C=CC=CC5=N4)[C@@H](C2)C(=O)NC(C)(C)C

InChI

InChIKey=QWAXKHKRTORLEM-UGJKXSETSA-N
InChI=1S/C38H50N6O5/c1-38(2,3)43-37(49)32-20-26-14-7-8-15-27(26)22-44(32)23-33(45)30(19-24-11-5-4-6-12-24)41-36(48)31(21-34(39)46)42-35(47)29-18-17-25-13-9-10-16-28(25)40-29/h4-6,9-13,16-18,26-27,30-33,45H,7-8,14-15,19-23H2,1-3H3,(H2,39,46)(H,41,48)(H,42,47)(H,43,49)/t26-,27+,30-,31-,32-,33+/m0/s1

HIDE SMILES / InChI

Molecular Formula C38H50N6O5
Molecular Weight 670.8408
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.drugbank.ca/drugs/DB01232 | http://reference.medscape.com/drug/invirase-saquinavir-342628 | https://www.drugs.com/cdi/saquinavir.html | https://www.ncbi.nlm.nih.gov/pubmed/20950334

Saquinavir (brand names Invirase and Fortovase) is an antiretroviral drug used together with other medications to treat or prevent HIV/AIDS. Saquinavir is an inhibitor of HIV protease. HIV protease is an enzyme required for the proteolytic cleavage of viral polyprotein precursors into individual functional proteins found in infectious HIV. Saquinavir is a peptide-like substrate analog that binds to the protease active site and inhibits the activity of the enzyme. Saquinavir inhibition prevents cleavage of the viral polyproteins resulting in the formation of immature noninfectious virus particles. The most frequent adverse events with saquinavir in either formulation are mild gastrointestinal symptoms, including diarrhea, nausea, loose stools & abdominal discomfort. Invirase is better tolerated than Fortovase.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.5 nM [IC50]
0.4 nM [IC50]
0.4 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FORTOVASE

Approved Use

INDICATIONS & USAGE INVIRASE in combination with ritonavir and other antiretroviral agents is indicated for the treatment of HIV-1 infection in adults (over the age of 16 years). The following points should be considered when initiating therapy with INVIRASE: – The twice daily administration of INVIRASE in combination with ritonavir is supported by safety data from the MaxCmin 1 trial [see Adverse Reactions (6.1)

Launch Date

8.7886083E11
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
21747 ng × h/mL
1200 mg 3 times / day steady-state, oral
dose: 1200 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
SAQUINAVIR unknown
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1000 mg 2 times / day multiple, oral
Recommended
Dose: 1000 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1000 mg, 2 times / day
Co-administed with::
ritonavir(100 mg; 2/day)
Sources:
unhealthy, adult
n = 148
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Population Size: 148
Sources:
Other AEs: Diabetes mellitus, Lipodystrophy...
Other AEs:
Diabetes mellitus (3%)
Lipodystrophy (5%)
Nausea (11%)
Vomiting (7%)
Diarrhea (8%)
Abdominal pain (6%)
Constipation (2%)
Fatigue (6%)
Fever (3%)
Back pain (2%)
Pneumonia (5%)
Bronchitis (3%)
Influenza (3%)
Sinusitis (3%)
Rash (3%)
Pruritus (3%)
Dry lips (2%)
Eczema (2%)
Sources:
1600 mg 1 times / day multiple, oral
Dose: 1600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1600 mg, 1 times / day
Co-administed with::
ritonavir(100 mg; 1/day)
Sources:
unhealthy, adult
n = 81
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Sex: M+F
Population Size: 81
Sources:
Other AEs: Nausea, Vomiting...
Other AEs:
Nausea (22.2%)
Vomiting (6.2%)
Diarrhea (4.9%)
Abdominal pain (2.5%)
Diarrhea aggravated (2.5%)
Esophageal reflux (2.5%)
Fatigue (2.5%)
Dizziness (excl vertigo) (1.2%)
Dermatitis (1.2%)
Decreased appetite (3.7%)
Headache (2.5%)
Insomnia (1.2%)
Weakness (2.5%)
Depression (2.5%)
Anxiety (1.2%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Nausea 11%
1000 mg 2 times / day multiple, oral
Recommended
Dose: 1000 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1000 mg, 2 times / day
Co-administed with::
ritonavir(100 mg; 2/day)
Sources:
unhealthy, adult
n = 148
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Population Size: 148
Sources:
Back pain 2%
1000 mg 2 times / day multiple, oral
Recommended
Dose: 1000 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1000 mg, 2 times / day
Co-administed with::
ritonavir(100 mg; 2/day)
Sources:
unhealthy, adult
n = 148
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Population Size: 148
Sources:
Constipation 2%
1000 mg 2 times / day multiple, oral
Recommended
Dose: 1000 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1000 mg, 2 times / day
Co-administed with::
ritonavir(100 mg; 2/day)
Sources:
unhealthy, adult
n = 148
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Population Size: 148
Sources:
Dry lips 2%
1000 mg 2 times / day multiple, oral
Recommended
Dose: 1000 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1000 mg, 2 times / day
Co-administed with::
ritonavir(100 mg; 2/day)
Sources:
unhealthy, adult
n = 148
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Population Size: 148
Sources:
Eczema 2%
1000 mg 2 times / day multiple, oral
Recommended
Dose: 1000 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1000 mg, 2 times / day
Co-administed with::
ritonavir(100 mg; 2/day)
Sources:
unhealthy, adult
n = 148
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Population Size: 148
Sources:
Bronchitis 3%
1000 mg 2 times / day multiple, oral
Recommended
Dose: 1000 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1000 mg, 2 times / day
Co-administed with::
ritonavir(100 mg; 2/day)
Sources:
unhealthy, adult
n = 148
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Population Size: 148
Sources:
Diabetes mellitus 3%
1000 mg 2 times / day multiple, oral
Recommended
Dose: 1000 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1000 mg, 2 times / day
Co-administed with::
ritonavir(100 mg; 2/day)
Sources:
unhealthy, adult
n = 148
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Population Size: 148
Sources:
Fever 3%
1000 mg 2 times / day multiple, oral
Recommended
Dose: 1000 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1000 mg, 2 times / day
Co-administed with::
ritonavir(100 mg; 2/day)
Sources:
unhealthy, adult
n = 148
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Population Size: 148
Sources:
Influenza 3%
1000 mg 2 times / day multiple, oral
Recommended
Dose: 1000 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1000 mg, 2 times / day
Co-administed with::
ritonavir(100 mg; 2/day)
Sources:
unhealthy, adult
n = 148
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Population Size: 148
Sources:
Pruritus 3%
1000 mg 2 times / day multiple, oral
Recommended
Dose: 1000 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1000 mg, 2 times / day
Co-administed with::
ritonavir(100 mg; 2/day)
Sources:
unhealthy, adult
n = 148
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Population Size: 148
Sources:
Rash 3%
1000 mg 2 times / day multiple, oral
Recommended
Dose: 1000 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1000 mg, 2 times / day
Co-administed with::
ritonavir(100 mg; 2/day)
Sources:
unhealthy, adult
n = 148
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Population Size: 148
Sources:
Sinusitis 3%
1000 mg 2 times / day multiple, oral
Recommended
Dose: 1000 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1000 mg, 2 times / day
Co-administed with::
ritonavir(100 mg; 2/day)
Sources:
unhealthy, adult
n = 148
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Population Size: 148
Sources:
Lipodystrophy 5%
1000 mg 2 times / day multiple, oral
Recommended
Dose: 1000 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1000 mg, 2 times / day
Co-administed with::
ritonavir(100 mg; 2/day)
Sources:
unhealthy, adult
n = 148
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Population Size: 148
Sources:
Pneumonia 5%
1000 mg 2 times / day multiple, oral
Recommended
Dose: 1000 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1000 mg, 2 times / day
Co-administed with::
ritonavir(100 mg; 2/day)
Sources:
unhealthy, adult
n = 148
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Population Size: 148
Sources:
Abdominal pain 6%
1000 mg 2 times / day multiple, oral
Recommended
Dose: 1000 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1000 mg, 2 times / day
Co-administed with::
ritonavir(100 mg; 2/day)
Sources:
unhealthy, adult
n = 148
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Population Size: 148
Sources:
Fatigue 6%
1000 mg 2 times / day multiple, oral
Recommended
Dose: 1000 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1000 mg, 2 times / day
Co-administed with::
ritonavir(100 mg; 2/day)
Sources:
unhealthy, adult
n = 148
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Population Size: 148
Sources:
Vomiting 7%
1000 mg 2 times / day multiple, oral
Recommended
Dose: 1000 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1000 mg, 2 times / day
Co-administed with::
ritonavir(100 mg; 2/day)
Sources:
unhealthy, adult
n = 148
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Population Size: 148
Sources:
Diarrhea 8%
1000 mg 2 times / day multiple, oral
Recommended
Dose: 1000 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1000 mg, 2 times / day
Co-administed with::
ritonavir(100 mg; 2/day)
Sources:
unhealthy, adult
n = 148
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Population Size: 148
Sources:
Anxiety 1.2%
1600 mg 1 times / day multiple, oral
Dose: 1600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1600 mg, 1 times / day
Co-administed with::
ritonavir(100 mg; 1/day)
Sources:
unhealthy, adult
n = 81
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Sex: M+F
Population Size: 81
Sources:
Dermatitis 1.2%
1600 mg 1 times / day multiple, oral
Dose: 1600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1600 mg, 1 times / day
Co-administed with::
ritonavir(100 mg; 1/day)
Sources:
unhealthy, adult
n = 81
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Sex: M+F
Population Size: 81
Sources:
Dizziness (excl vertigo) 1.2%
1600 mg 1 times / day multiple, oral
Dose: 1600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1600 mg, 1 times / day
Co-administed with::
ritonavir(100 mg; 1/day)
Sources:
unhealthy, adult
n = 81
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Sex: M+F
Population Size: 81
Sources:
Insomnia 1.2%
1600 mg 1 times / day multiple, oral
Dose: 1600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1600 mg, 1 times / day
Co-administed with::
ritonavir(100 mg; 1/day)
Sources:
unhealthy, adult
n = 81
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Sex: M+F
Population Size: 81
Sources:
Abdominal pain 2.5%
1600 mg 1 times / day multiple, oral
Dose: 1600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1600 mg, 1 times / day
Co-administed with::
ritonavir(100 mg; 1/day)
Sources:
unhealthy, adult
n = 81
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Sex: M+F
Population Size: 81
Sources:
Depression 2.5%
1600 mg 1 times / day multiple, oral
Dose: 1600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1600 mg, 1 times / day
Co-administed with::
ritonavir(100 mg; 1/day)
Sources:
unhealthy, adult
n = 81
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Sex: M+F
Population Size: 81
Sources:
Diarrhea aggravated 2.5%
1600 mg 1 times / day multiple, oral
Dose: 1600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1600 mg, 1 times / day
Co-administed with::
ritonavir(100 mg; 1/day)
Sources:
unhealthy, adult
n = 81
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Sex: M+F
Population Size: 81
Sources:
Esophageal reflux 2.5%
1600 mg 1 times / day multiple, oral
Dose: 1600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1600 mg, 1 times / day
Co-administed with::
ritonavir(100 mg; 1/day)
Sources:
unhealthy, adult
n = 81
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Sex: M+F
Population Size: 81
Sources:
Fatigue 2.5%
1600 mg 1 times / day multiple, oral
Dose: 1600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1600 mg, 1 times / day
Co-administed with::
ritonavir(100 mg; 1/day)
Sources:
unhealthy, adult
n = 81
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Sex: M+F
Population Size: 81
Sources:
Headache 2.5%
1600 mg 1 times / day multiple, oral
Dose: 1600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1600 mg, 1 times / day
Co-administed with::
ritonavir(100 mg; 1/day)
Sources:
unhealthy, adult
n = 81
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Sex: M+F
Population Size: 81
Sources:
Weakness 2.5%
1600 mg 1 times / day multiple, oral
Dose: 1600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1600 mg, 1 times / day
Co-administed with::
ritonavir(100 mg; 1/day)
Sources:
unhealthy, adult
n = 81
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Sex: M+F
Population Size: 81
Sources:
Nausea 22.2%
1600 mg 1 times / day multiple, oral
Dose: 1600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1600 mg, 1 times / day
Co-administed with::
ritonavir(100 mg; 1/day)
Sources:
unhealthy, adult
n = 81
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Sex: M+F
Population Size: 81
Sources:
Decreased appetite 3.7%
1600 mg 1 times / day multiple, oral
Dose: 1600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1600 mg, 1 times / day
Co-administed with::
ritonavir(100 mg; 1/day)
Sources:
unhealthy, adult
n = 81
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Sex: M+F
Population Size: 81
Sources:
Diarrhea 4.9%
1600 mg 1 times / day multiple, oral
Dose: 1600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1600 mg, 1 times / day
Co-administed with::
ritonavir(100 mg; 1/day)
Sources:
unhealthy, adult
n = 81
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Sex: M+F
Population Size: 81
Sources:
Vomiting 6.2%
1600 mg 1 times / day multiple, oral
Dose: 1600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1600 mg, 1 times / day
Co-administed with::
ritonavir(100 mg; 1/day)
Sources:
unhealthy, adult
n = 81
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: adult
Sex: M+F
Population Size: 81
Sources:
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
little [IC50 >100 uM]
little [IC50 >100 uM]
little [IC50 >100 uM]
negligible [IC50 >100 uM]
negligible [IC50 >100 uM]
weak [Ki 1.8 uM]
yes [IC50 1.8 uM]
yes [IC50 13 uM]
yes [IC50 2.1 uM]
yes [IC50 2.14 uM]
yes [IC50 27.4 uM]
yes [IC50 4.1 uM]
yes [IC50 5.3 uM]
yes [IC50 5.5 uM]
yes [IC50 54 uM]
yes [IC50 8 uM]
yes [IC50 8.3 uM]
yes [Ki 0.6 uM]
yes [Ki 24 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 <10 uM]
yes
yes
yes
yes (co-administration study)
Comment: Coadministration with ritonavir (CYP3A4 inhibitor): mean saquinavir AUC value was seven fold greater than mean value observed after administration of saquinavir alone.
Page: 13,19
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Unexplained thrombosis in HIV-infected patients receiving protease inhibitors: report of seven cases.
1999 Dec
Structural and kinetic analyses of the protease from an amprenavir-resistant human immunodeficiency virus type 1 mutant rendered resistant to saquinavir and resensitized to amprenavir.
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
Inhibitory effect of human immunodeficiency virus protease inhibitors on multidrug resistance transporter P-glycoproteins.
2000 Dec
Increasing cerebrospinal fluid chemokine concentrations despite undetectable cerebrospinal fluid HIV RNA in HIV-1-infected patients receiving antiretroviral therapy.
2000 Dec 15
In-vitro tipranavir susceptibility of HIV-1 isolates with reduced susceptibility to other protease inhibitors.
2000 Jan 7
Drug resistance and drug combination features of the human immunodeficiency virus inhibitor, BCH-10652 [(+/-)-2'-deoxy-3'-oxa-4'-thiocytidine, dOTC].
2000 Jul
In vitro activity of human immunodeficiency virus protease inhibitors against Pneumocystis carinii.
2000 May
A mutation in human immunodeficiency virus type 1 protease, N88S, that causes in vitro hypersensitivity to amprenavir.
2000 May
Inhibition of HIV-1 protease by a boron-modified polypeptide.
2000 Oct 1
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
Comparison of P-triglyceride levels among patients with human immunodeficiency virus on randomized treatment with ritonavir, indinavir or ritonavir/saquinavir.
2001
Analysis of HIV-1 mutation patterns in patients failing antiretroviral therapy.
2001
Generation of a flexible cell line with regulatable, high-level expression of HIV Gag/Pol particles capable of packaging HIV-derived vectors.
2001 Apr
P-glycoprotein limits oral availability, brain, and fetal penetration of saquinavir even with high doses of ritonavir.
2001 Apr
Determination of serum levels of thirteen human immunodeficiency virus-suppressing drugs by high-performance liquid chromatography.
2001 Apr 13
[Improving the pharmacokinetics of protease inhibitors in a more innovative manner. HIV drugs administered in a more clever way].
2001 Apr 2
Antiviral drugs: current state of the art.
2001 Aug
Pharmacology and clinical experience with saquinavir.
2001 Feb
Pharmacokinetics of ritonavir and saquinavir in a haemodialysis patient.
2001 Feb
Ritonavir, efavirenz, and nelfinavir inhibit CYP2B6 activity in vitro: potential drug interactions with bupropion.
2001 Feb
Progressive human immunodeficiency virus-specific immune recovery with prolonged viral suppression.
2001 Feb 15
Large hepatic mitochondrial DNA deletions associated with L-lactic acidosis and highly active antiretroviral therapy.
2001 Feb 16
Ritonavir-induced carbamazepine toxicity.
2001 Jan
Effect of alpha1-acid glycoprotein on the intracellular accumulation of the HIV protease inhibitors saquinavir, ritonavir and indinavir in vitro.
2001 Jan
Pilot study of a combination of highly active antiretroviral therapy and cytokines to induce HIV-1 remission.
2001 Jan 1
Patterns of resistance mutations to antiretroviral drugs in extensively treated HIV-1-infected patients with failure of highly active antiretroviral therapy.
2001 Jan 1
Efficacy, tolerance, and pharmacokinetics of the combination of stavudine, nevirapine, nelfinavir, and saquinavir as salvage regimen after ritonavir or indinavir failure.
2001 Jan 20
The use of and response to second-line protease inhibitor regimens: results from the EuroSIDA study.
2001 Jan 26
Predictors of protease inhibitor-associated adverse events.
2001 Jul
Combination therapy with saquinavir soft gelatin capsules in children with human immunodeficiency virus infection.
2001 Jul
CMVR diagnoses and progression of CD4 cell counts and HIV viral load measurements in HIV patients on HAART.
2001 Jul
Synthesis of a chiral aziridine derivative as a versatile intermediate for HIV protease inhibitors.
2001 Jul 26
The effect of fluconazole on ritonavir and saquinavir pharmacokinetics in HIV-1-infected individuals.
2001 Jun
Prognostic factors of combined viral load and CD4+ cell count responses under triple antiretroviral therapy, Aquitaine cohort, 1996-1998.
2001 Jun 1
Effect of ritonavir/saquinavir on stereoselective pharmacokinetics of methadone: results of AIDS Clinical Trials Group (ACTG) 401.
2001 Jun 1
The effect of nevirapine in combination with nelfinavir in heavily pretreated HIV-1-infected patients: a prospective, open-label, controlled, randomized study.
2001 Jun 1
A comprehensive account on the role of efflux transporters in the gastrointestinal absorption of 13 commonly used substrate drugs in humans.
2001 Mar
The safety and antiviral effect of protease inhibitors in children.
2001 Mar
Elevated alpha-1-acid glycoprotein reduces the volume of distribution and systemic clearance of saquinavir.
2001 Mar
Sequencing of protease inhibitor therapy: insights from an analysis of HIV phenotypic resistance in patients failing protease inhibitors.
2001 Mar 30
Structure-activity studies of FIV and HIV protease inhibitors containing allophenylnorstatine.
2001 May
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
Simultaneous determination of the HIV protease inhibitors indinavir, amprenavir, saquinavir, ritonavir and nelfinavir in human plasma by high-performance liquid chromatography.
2001 May 5
Combined hydroxypropyl-beta-cyclodextrin and poly(alkylcyanoacrylate) nanoparticles intended for oral administration of saquinavir.
2001 May 7
[Drug interactions with antiretroviral agents].
2001 May-Jun
Mismatched double-stranded RNA (polyI-polyC(12)U) is synergistic with multiple anti-HIV drugs and is active against drug-sensitive and drug-resistant HIV-1 in vitro.
2001 Sep
Patents

Sample Use Guides

1000 mg (with ritonavir 100 mg) PO q12hr, or in combination with ritonavir-enhanced lopinavir Treatment-naïve patients: Initial dose: 500 mg PO BID plus ritonavir 100 mg BID x 7 days, THEN increase to 1000mg/100mg PO BID
Route of Administration: Oral
In vitro antiviral activity of saquinavir was assessed in lymphoblastoid and monocytic cell lines and in peripheral blood lymphocytes. Saquinavir inhibited HIV activity in both acutely and chronically infected cells. IC50 and IC90 values (50% and 90% inhibitory concentrations) were in the range of 1 to 30 nM and 5 to 80 nM, respectively. In the presence of 40% human serum, the mean IC50 of saquinavir against laboratory strain HIV-1 RF in MT4 cells was 37.7± 5nM representing a 4-fold increase in the IC50 value. In cell culture, saquinavir demonstrated additive to synergistic effects against HIV-1 in combination with reverse transcriptase inhibitors (didanosine, lamivudine, nevirapine, stavudine, zalcitabine and zidovudine) without enhanced cytotoxicity. Saquinavir in combination with the protease inhibitors amprenavir, atazanavir, or lopinavir resulted in synergistic antiviral activity. Saquinavir displayed antiviral activity in vitro against HIV-1 clades A-H (IC50 ranged from 0.9 to 2.5 nM). The IC50 and IC90 values of saquinavir against HIV-2 isolates in vitro ranged from 0.25 nM to 14.6 nM and 4.65 nM to 28.6 nM respectively.
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:07:37 UTC 2023
Edited
by admin
on Wed Jul 05 23:07:37 UTC 2023
Record UNII
L3JE09KZ2F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SAQUINAVIR
EMA EPAR   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   VANDF   WHO-DD   WHO-IP  
USAN   INN  
Official Name English
RO 31-8959/000
Code English
SAQUINAVIR [JAN]
Common Name English
SAQUINAVIRUM [WHO-IP LATIN]
Common Name English
SAQUINAVIR [ORANGE BOOK]
Common Name English
SAQUINAVIR [VANDF]
Common Name English
SAQUINAVIR [USAN]
Common Name English
SAQUINAVIR [HSDB]
Common Name English
RO-31-8959/000
Code English
BUTANEDIAMIDE, N(SUP 1)-(3-(3-(((1,1-DIMETHYLETHYL)AMINO)CARBONYL)OCTAHYDRO-2(1H)-ISOQUINOLINYL)-2-HYDROXY-1-(PHENYLMETHYL)PROPYL)-2-((2-QUINOLINYLCARBONYL)AMINO)-, (3S-(2(1R*(R*),2S*),3.ALPHA.,4A.BETA.,8A.BETA.))-
Common Name English
Saquinavir [WHO-DD]
Common Name English
(S)-N-[(IS)-I-[(1R)-2-[(3S,4aS,8aS)-3-(tert-Butylcarbamoyl)octahydro-2(1H)-isoquinolyl]-1-hydroxyethyl]phenethyl]-2-quinaldamidosuccinamide
Common Name English
SAQUINAVIR [USP IMPURITY]
Common Name English
SAQUINAVIR [WHO-IP]
Common Name English
SAQUINAVIR [EMA EPAR]
Common Name English
(S)-N-((.ALPHA.S)-.ALPHA.-((1R)-2-((3S,4AS,8AS)-3-(TERT-BUTYLCARBAMOYL)OCTAHYDRO-2(1H)-ISOQUINOLYL)-1-HYDROXYETHYL)PHENETHYL)-2-QUINALDAMIDOSUCCINAMIDE
Common Name English
saquinavir [INN]
Common Name English
SAQUINAVIR [MART.]
Common Name English
SCH-52852
Code English
SAQUINAVIR [MI]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175889
Created by admin on Wed Jul 05 23:07:37 UTC 2023 , Edited by admin on Wed Jul 05 23:07:37 UTC 2023
NDF-RT N0000000246
Created by admin on Wed Jul 05 23:07:37 UTC 2023 , Edited by admin on Wed Jul 05 23:07:37 UTC 2023
WHO-VATC QJ05AE01
Created by admin on Wed Jul 05 23:07:37 UTC 2023 , Edited by admin on Wed Jul 05 23:07:37 UTC 2023
EMA ASSESSMENT REPORTS INVIRASE (AUHTORIZED: HIV INFECTIONS)
Created by admin on Wed Jul 05 23:07:37 UTC 2023 , Edited by admin on Wed Jul 05 23:07:37 UTC 2023
EMA ASSESSMENT REPORTS FORTOVASE (WITHDRAWN: HIV INFECTIONS)
Created by admin on Wed Jul 05 23:07:37 UTC 2023 , Edited by admin on Wed Jul 05 23:07:37 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 6.4.2.3
Created by admin on Wed Jul 05 23:07:37 UTC 2023 , Edited by admin on Wed Jul 05 23:07:37 UTC 2023
WHO-ATC J05AE01
Created by admin on Wed Jul 05 23:07:37 UTC 2023 , Edited by admin on Wed Jul 05 23:07:37 UTC 2023
NCI_THESAURUS C97366
Created by admin on Wed Jul 05 23:07:37 UTC 2023 , Edited by admin on Wed Jul 05 23:07:37 UTC 2023
LIVERTOX NBK548019
Created by admin on Wed Jul 05 23:07:37 UTC 2023 , Edited by admin on Wed Jul 05 23:07:37 UTC 2023
Code System Code Type Description
INN
7098
Created by admin on Wed Jul 05 23:07:37 UTC 2023 , Edited by admin on Wed Jul 05 23:07:37 UTC 2023
PRIMARY
NCI_THESAURUS
C29444
Created by admin on Wed Jul 05 23:07:37 UTC 2023 , Edited by admin on Wed Jul 05 23:07:37 UTC 2023
PRIMARY
IUPHAR
4813
Created by admin on Wed Jul 05 23:07:37 UTC 2023 , Edited by admin on Wed Jul 05 23:07:37 UTC 2023
PRIMARY
DRUG BANK
DB01232
Created by admin on Wed Jul 05 23:07:37 UTC 2023 , Edited by admin on Wed Jul 05 23:07:37 UTC 2023
PRIMARY
WIKIPEDIA
SAQUINAVIR
Created by admin on Wed Jul 05 23:07:37 UTC 2023 , Edited by admin on Wed Jul 05 23:07:37 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
SAQUINAVIR
Created by admin on Wed Jul 05 23:07:37 UTC 2023 , Edited by admin on Wed Jul 05 23:07:37 UTC 2023
PRIMARY Description: A white or almost white powder. Solubility: Practically insoluble in water and soluble in methanol. Category: Antiretroviral (Protease Inhibitor). Storage: Saquinavir should be kept at 2-8?C in a tightly closed container, protected from light. Additional information: Saquinavir is slightly hygroscopic. Requirements: Saquinavir contains not less than 98.5 % and not more than 101.0 % of C38H50N6O5, calculated with reference to the dried substance.
FDA UNII
L3JE09KZ2F
Created by admin on Wed Jul 05 23:07:37 UTC 2023 , Edited by admin on Wed Jul 05 23:07:37 UTC 2023
PRIMARY
ChEMBL
CHEMBL114
Created by admin on Wed Jul 05 23:07:37 UTC 2023 , Edited by admin on Wed Jul 05 23:07:37 UTC 2023
PRIMARY
NDF-RT
N0000190114
Created by admin on Wed Jul 05 23:07:37 UTC 2023 , Edited by admin on Wed Jul 05 23:07:37 UTC 2023
PRIMARY Cytochrome P450 3A Inhibitors [MoA]
USAN
JJ-79
Created by admin on Wed Jul 05 23:07:37 UTC 2023 , Edited by admin on Wed Jul 05 23:07:37 UTC 2023
PRIMARY
DRUG CENTRAL
2422
Created by admin on Wed Jul 05 23:07:37 UTC 2023 , Edited by admin on Wed Jul 05 23:07:37 UTC 2023
PRIMARY
CHEBI
63621
Created by admin on Wed Jul 05 23:07:37 UTC 2023 , Edited by admin on Wed Jul 05 23:07:37 UTC 2023
PRIMARY
EVMPD
SUB10446MIG
Created by admin on Wed Jul 05 23:07:37 UTC 2023 , Edited by admin on Wed Jul 05 23:07:37 UTC 2023
PRIMARY
RXCUI
83395
Created by admin on Wed Jul 05 23:07:37 UTC 2023 , Edited by admin on Wed Jul 05 23:07:37 UTC 2023
PRIMARY RxNorm
PUBCHEM
441243
Created by admin on Wed Jul 05 23:07:37 UTC 2023 , Edited by admin on Wed Jul 05 23:07:37 UTC 2023
PRIMARY
LACTMED
Saquinavir
Created by admin on Wed Jul 05 23:07:37 UTC 2023 , Edited by admin on Wed Jul 05 23:07:37 UTC 2023
PRIMARY
MERCK INDEX
M9776
Created by admin on Wed Jul 05 23:07:37 UTC 2023 , Edited by admin on Wed Jul 05 23:07:37 UTC 2023
PRIMARY Merck Index
DAILYMED
L3JE09KZ2F
Created by admin on Wed Jul 05 23:07:37 UTC 2023 , Edited by admin on Wed Jul 05 23:07:37 UTC 2023
PRIMARY
MESH
D019258
Created by admin on Wed Jul 05 23:07:37 UTC 2023 , Edited by admin on Wed Jul 05 23:07:37 UTC 2023
PRIMARY
EPA CompTox
DTXSID6044012
Created by admin on Wed Jul 05 23:07:37 UTC 2023 , Edited by admin on Wed Jul 05 23:07:37 UTC 2023
PRIMARY
SMS_ID
100000089169
Created by admin on Wed Jul 05 23:07:37 UTC 2023 , Edited by admin on Wed Jul 05 23:07:37 UTC 2023
PRIMARY
HSDB
7161
Created by admin on Wed Jul 05 23:07:37 UTC 2023 , Edited by admin on Wed Jul 05 23:07:37 UTC 2023
PRIMARY
CAS
127779-20-8
Created by admin on Wed Jul 05 23:07:37 UTC 2023 , Edited by admin on Wed Jul 05 23:07:37 UTC 2023
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
SUBSTRATE USED: ESTRONE-3-SULFATE
TRANSPORTER -> SUBSTRATE
BINDER->LIGAND
BINDING
METABOLIC ENZYME -> SUBSTRATE
TRANSPORTER -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC