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

Details

Stereochemistry ABSOLUTE
Molecular Formula C38H50N6O5.CH4O3S
Molecular Weight 766.946
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SAQUINAVIR MESYLATE

SMILES

CS(O)(=O)=O.[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=IRHXGOXEBNJUSN-YOXDLBRISA-N
InChI=1S/C38H50N6O5.CH4O3S/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;1-5(2,3)4/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);1H3,(H,2,3,4)/t26-,27+,30-,31-,32-,33+;/m0./s1

HIDE SMILES / InChI

Molecular Formula CH4O3S
Molecular Weight 96.106
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

1997
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
In-vitro tipranavir susceptibility of HIV-1 isolates with reduced susceptibility to other protease inhibitors.
2000 Jan 7
Synthesis and anti-HIV activity of prodrugs derived from saquinavir and indinavir.
2000 Mar
5,6-Dihydropyran-2-ones possessing various sulfonyl functionalities: potent nonpeptidic inhibitors of HIV protease.
2000 Mar 9
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
Generation of a flexible cell line with regulatable, high-level expression of HIV Gag/Pol particles capable of packaging HIV-derived vectors.
2001 Apr
An open-label randomized trial to evaluate different therapeutic strategies of combination therapy in HIV-1 infection: design, rationale, and methods of the initio trial.
2001 Apr
P-glycoprotein limits oral availability, brain, and fetal penetration of saquinavir even with high doses of ritonavir.
2001 Apr
Impact of HIV type 1 protease, reverse transcriptase, cleavage site, and p6 mutations on the virological response to quadruple therapy with saquinavir, ritonavir, and two nucleoside analogs.
2001 Apr 10
Determination of serum levels of thirteen human immunodeficiency virus-suppressing drugs by high-performance liquid chromatography.
2001 Apr 13
Determination of interaction kinetic constants for HIV-1 protease inhibitors using optical biosensor technology.
2001 Apr 15
[Improving the pharmacokinetics of protease inhibitors in a more innovative manner. HIV drugs administered in a more clever way].
2001 Apr 2
Antiretrovirals: simultaneous determination of five protease inhibitors and three nonnucleoside transcriptase inhibitors in human plasma by a rapid high-performance liquid chromatography--mass spectrometry assay.
2001 Aug
Pharmacokinetics and resistance mutations affect virologic response to ritonavir/saquinavir-containing regimens.
2001 Aug
Steady-state pharmacokinetics of twice-daily dosing of saquinavir plus ritonavir in HIV-1-infected individuals.
2001 Aug 1
HIV-protease inhibitors contribute to P-glycoprotein efflux function defect in peripheral blood lymphocytes from HIV-positive patients receiving HAART.
2001 Aug 1
[Resistance to protease inhibitors].
2001 Feb
Pharmacokinetics of ritonavir and saquinavir in a haemodialysis patient.
2001 Feb
[Long-term immunologic response in HIV-infected patients with CD4 cell counts
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
Ritonavir, efavirenz, and nelfinavir inhibit CYP2B6 activity in vitro: potential drug interactions with bupropion.
2001 Feb
Large hepatic mitochondrial DNA deletions associated with L-lactic acidosis and highly active antiretroviral therapy.
2001 Feb 16
Ritonavir-induced carbamazepine toxicity.
2001 Jan
The use of and response to second-line protease inhibitor regimens: results from the EuroSIDA study.
2001 Jan 26
New developments in anti-HIV chemotherapy.
2001 Jan-Feb
Maternal-fetal transfer of saquinavir studied in the ex vivo placental perfusion model.
2001 Jul
HIV protease inhibitors attenuate adherence of Candida albicans to epithelial cells in vitro.
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
Capillary electrophoretic separation of protease inhibitors used in human immunodeficiency virus therapy.
2001 Jul 13
High-performance liquid chromatographic assay to determine the plasma levels of HIV-protease inhibitors (amprenavir, indinavir, nelfinavir, ritonavir and saquinavir) and the non-nucleoside reverse transcriptase inhibitor (nevirapine) after liquid-liquid extraction.
2001 Jul 15
Synthesis of a chiral aziridine derivative as a versatile intermediate for HIV protease inhibitors.
2001 Jul 26
The effects of antiretroviral protease inhibitors on serum lipid levels in HIV-infected patients.
2001 Jun
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
Selection by AZT and rapid replacement in the absence of drugs of HIV type 1 resistant to multiple nucleoside analogs.
2001 Jun 10
Simultaneous determination of the HIV-protease inhibitors indinavir, amprenavir, ritonavir, saquinavir and nelfinavir in human plasma by reversed-phase high-performance liquid chromatography.
2001 Jun 15
The binding energetics of first- and second-generation HIV-1 protease inhibitors: implications for drug design.
2001 Jun 15
The safety and antiviral effect of protease inhibitors in children.
2001 Mar
A distinct binding mode of a hydroxyethylamine isostere inhibitor of HIV-1 protease.
2001 Mar
Elevated alpha-1-acid glycoprotein reduces the volume of distribution and systemic clearance of saquinavir.
2001 Mar
Regulation of expression of 11beta-hydroxysteroid dehydrogenase type 1 in adipose tissue: tissue-specific induction by cytokines.
2001 May
Clinical outcome among HIV-infected patients starting saquinavir hard gel compared to ritonavir or indinavir.
2001 May 25
Increased risk of lipodystrophy when nucleoside analogue reverse transcriptase inhibitors are included with protease inhibitors in the treatment of HIV-1 infection.
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
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
Novel low molecular weight spirodiketopiperazine derivatives potently inhibit R5 HIV-1 infection through their antagonistic effects on CCR5.
2001 Sep 14
Peptide mimetic HIV protease inhibitors are ligands for the orphan receptor SXR.
2001 Sep 7
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 Fri Dec 15 15:41:37 GMT 2023
Edited
by admin
on Fri Dec 15 15:41:37 GMT 2023
Record UNII
UHB9Z3841A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SAQUINAVIR MESYLATE
ORANGE BOOK   USAN   USP   USP-RS   VANDF  
USAN  
Official Name English
SAQUINAVIR MESILATE [EP MONOGRAPH]
Common Name English
SAQUINAVIR MESYLATE [USP MONOGRAPH]
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 MONOMETHANESULFONATE
Common Name English
RO 31-8959/003
Code English
SAQUINAVIR METHANESULFONATE SALT [MI]
Common Name English
SAQUINAVIR MESYLATE [USP-RS]
Common Name English
SAQUINAVIR MESILATE [JAN]
Common Name English
Saquinavir mesilate [WHO-DD]
Common Name English
SAQUINAVIR MESYLATE [USP IMPURITY]
Common Name English
SAQUINAVIR MESILATE [MART.]
Common Name English
SAQUINAVIR MESYLATE [VANDF]
Common Name English
SAQUINAVIR MESILATE
EP   JAN   MART.   WHO-DD   WHO-IP  
Common Name English
RO-318959003
Code English
RO-31-8959/003
Code English
SAQUINAVIR MESYLATE [USAN]
Common Name 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.))-, MONOMETHANESULPHONATE
Common Name 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.))-, MONOMETHANESULFONATE
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 MONOMETHANESULPHONATE
Common Name English
SAQUINAVIR MESILATE [WHO-IP]
Common Name English
SAQUINAVIR MESYLATE [ORANGE BOOK]
Common Name English
SAQUINAVIR METHANESULFONATE SALT
MI  
Common Name English
INVIRASE
Brand Name English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS INVIRASE (AUTHORIZED: HIV INFECTIONS)
Created by admin on Fri Dec 15 15:41:37 GMT 2023 , Edited by admin on Fri Dec 15 15:41:37 GMT 2023
NCI_THESAURUS C97366
Created by admin on Fri Dec 15 15:41:37 GMT 2023 , Edited by admin on Fri Dec 15 15:41:37 GMT 2023
Code System Code Type Description
WHO INTERNATIONAL PHARMACOPEIA
SAQUINAVIR MESYLATE
Created by admin on Fri Dec 15 15:41:37 GMT 2023 , Edited by admin on Fri Dec 15 15:41:37 GMT 2023
PRIMARY Description: A white or almost white powder. Solubility: Very slightly soluble in water and sparingly soluble in methanol R. Category: Antiretroviral (Protease Inhibitor). Storage: Saquinavir mesilate should be kept in a tightly-closed container, protected from light. Additional information: Saquinavir mesilate is slightly hygroscopic. Definition: Saquinavir mesilate contains not less than 98.5 % and not more than 101.0 % of C38H50N6O5.CH4O3S calculated with reference to the dried substance. Manufacture: The production method must be evaluated to determine the potential for formation of alkyl mesilates, which is particularly likely to occur if the reaction medium contains lower alcohols. Where necessary, the production method is validated to demonstrate that alkyl mesilates are not detectable in the final product.
RXCUI
859857
Created by admin on Fri Dec 15 15:41:37 GMT 2023 , Edited by admin on Fri Dec 15 15:41:37 GMT 2023
PRIMARY RxNorm
DAILYMED
UHB9Z3841A
Created by admin on Fri Dec 15 15:41:37 GMT 2023 , Edited by admin on Fri Dec 15 15:41:37 GMT 2023
PRIMARY
RS_ITEM_NUM
1609829
Created by admin on Fri Dec 15 15:41:37 GMT 2023 , Edited by admin on Fri Dec 15 15:41:37 GMT 2023
PRIMARY
SMS_ID
100000091808
Created by admin on Fri Dec 15 15:41:37 GMT 2023 , Edited by admin on Fri Dec 15 15:41:37 GMT 2023
PRIMARY
CAS
149845-06-7
Created by admin on Fri Dec 15 15:41:37 GMT 2023 , Edited by admin on Fri Dec 15 15:41:37 GMT 2023
PRIMARY
NCI_THESAURUS
C1602
Created by admin on Fri Dec 15 15:41:37 GMT 2023 , Edited by admin on Fri Dec 15 15:41:37 GMT 2023
PRIMARY
USAN
GG-17
Created by admin on Fri Dec 15 15:41:37 GMT 2023 , Edited by admin on Fri Dec 15 15:41:37 GMT 2023
PRIMARY
FDA UNII
UHB9Z3841A
Created by admin on Fri Dec 15 15:41:37 GMT 2023 , Edited by admin on Fri Dec 15 15:41:37 GMT 2023
PRIMARY
PUBCHEM
60934
Created by admin on Fri Dec 15 15:41:37 GMT 2023 , Edited by admin on Fri Dec 15 15:41:37 GMT 2023
PRIMARY
EVMPD
SUB12572MIG
Created by admin on Fri Dec 15 15:41:37 GMT 2023 , Edited by admin on Fri Dec 15 15:41:37 GMT 2023
PRIMARY
EPA CompTox
DTXSID9023835
Created by admin on Fri Dec 15 15:41:37 GMT 2023 , Edited by admin on Fri Dec 15 15:41:37 GMT 2023
PRIMARY
MERCK INDEX
m9776
Created by admin on Fri Dec 15 15:41:37 GMT 2023 , Edited by admin on Fri Dec 15 15:41:37 GMT 2023
PRIMARY Merck Index
DRUG BANK
DBSALT002836
Created by admin on Fri Dec 15 15:41:37 GMT 2023 , Edited by admin on Fri Dec 15 15:41:37 GMT 2023
PRIMARY
ChEMBL
CHEMBL114
Created by admin on Fri Dec 15 15:41:37 GMT 2023 , Edited by admin on Fri Dec 15 15:41:37 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
correction factors: for the calculation of content, multiply the peak areas of the following impurity by the corresponding correction factor: impurity A = 0.5
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
Water: maximum 1.0 per cent, determined on 0.250 g.
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
correction factors: for the calculation of content, multiply the peak areas of the following impurity by the corresponding correction factor: impurity B = 0.5
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY