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

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

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
Renin-angiotensin system inhibition in a patient having an overdose of HIV protease inhibitor.
1999 Oct 1
In-vitro tipranavir susceptibility of HIV-1 isolates with reduced susceptibility to other protease inhibitors.
2000 Jan 7
Novel inhibitors of HIV protease: design, synthesis and biological evaluation of picomolar inhibitors containing cyclic P1/P2 scaffolds.
2000 Jun 5
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
Analysis of HIV-1 mutation patterns in patients failing antiretroviral therapy.
2001
High prevalence of genotypic and phenotypic HIV-1 drug-resistant strains among patients receiving antiretroviral therapy in Abidjan, Côte d'Ivoire.
2001 Apr 15
A phase II trial of dual protease inhibitor therapy: amprenavir in combination with indinavir, nelfinavir, or saquinavir.
2001 Apr 15
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
Antiviral drugs: current state of the art.
2001 Aug
Comparison of virologic, immunologic, and clinical response to five different initial protease inhibitor-containing and nevirapine-containing regimens.
2001 Aug 1
[Resistance to protease inhibitors].
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
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 ADAM study continued: maintenance therapy after 50 weeks of induction therapy.
2001 Jan 5
New developments in anti-HIV chemotherapy.
2001 Jan-Feb
Structure-based design of non-peptide HIV protease inhibitors.
2001 Jan-Feb
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
Prognostic factors of combined viral load and CD4+ cell count responses under triple antiretroviral therapy, Aquitaine cohort, 1996-1998.
2001 Jun 1
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
Challenges of antiretroviral treatment in transient and drug-using populations: the SUN study.
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
Sequencing of protease inhibitor therapy: insights from an analysis of HIV phenotypic resistance in patients failing protease inhibitors.
2001 Mar 30
The interaction of saquinavir (soft gelatin capsule) with ketoconazole, erythromycin and rifampicin: comparison of the effect in healthy volunteers and in HIV-infected patients.
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
Novel low molecular weight spirodiketopiperazine derivatives potently inhibit R5 HIV-1 infection through their antagonistic effects on CCR5.
2001 Sep 14
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 23:10:31 UTC 2023
Edited
by admin
on Wed Jul 05 23:10:31 UTC 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 Wed Jul 05 23:10:31 UTC 2023 , Edited by admin on Wed Jul 05 23:10:31 UTC 2023
NCI_THESAURUS C97366
Created by admin on Wed Jul 05 23:10:31 UTC 2023 , Edited by admin on Wed Jul 05 23:10:31 UTC 2023
Code System Code Type Description
WHO INTERNATIONAL PHARMACOPEIA
SAQUINAVIR MESYLATE
Created by admin on Wed Jul 05 23:10:31 UTC 2023 , Edited by admin on Wed Jul 05 23:10:31 UTC 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 Wed Jul 05 23:10:31 UTC 2023 , Edited by admin on Wed Jul 05 23:10:31 UTC 2023
PRIMARY RxNorm
DAILYMED
UHB9Z3841A
Created by admin on Wed Jul 05 23:10:31 UTC 2023 , Edited by admin on Wed Jul 05 23:10:31 UTC 2023
PRIMARY
RS_ITEM_NUM
1609829
Created by admin on Wed Jul 05 23:10:31 UTC 2023 , Edited by admin on Wed Jul 05 23:10:31 UTC 2023
PRIMARY
SMS_ID
100000091808
Created by admin on Wed Jul 05 23:10:31 UTC 2023 , Edited by admin on Wed Jul 05 23:10:31 UTC 2023
PRIMARY
CAS
149845-06-7
Created by admin on Wed Jul 05 23:10:31 UTC 2023 , Edited by admin on Wed Jul 05 23:10:31 UTC 2023
PRIMARY
NCI_THESAURUS
C1602
Created by admin on Wed Jul 05 23:10:31 UTC 2023 , Edited by admin on Wed Jul 05 23:10:31 UTC 2023
PRIMARY
USAN
GG-17
Created by admin on Wed Jul 05 23:10:31 UTC 2023 , Edited by admin on Wed Jul 05 23:10:31 UTC 2023
PRIMARY
FDA UNII
UHB9Z3841A
Created by admin on Wed Jul 05 23:10:31 UTC 2023 , Edited by admin on Wed Jul 05 23:10:31 UTC 2023
PRIMARY
PUBCHEM
60934
Created by admin on Wed Jul 05 23:10:31 UTC 2023 , Edited by admin on Wed Jul 05 23:10:31 UTC 2023
PRIMARY
EVMPD
SUB12572MIG
Created by admin on Wed Jul 05 23:10:31 UTC 2023 , Edited by admin on Wed Jul 05 23:10:31 UTC 2023
PRIMARY
EPA CompTox
DTXSID9023835
Created by admin on Wed Jul 05 23:10:31 UTC 2023 , Edited by admin on Wed Jul 05 23:10:31 UTC 2023
PRIMARY
MERCK INDEX
M9776
Created by admin on Wed Jul 05 23:10:31 UTC 2023 , Edited by admin on Wed Jul 05 23:10:31 UTC 2023
PRIMARY Merck Index
DRUG BANK
DBSALT002836
Created by admin on Wed Jul 05 23:10:31 UTC 2023 , Edited by admin on Wed Jul 05 23:10:31 UTC 2023
PRIMARY
ChEMBL
CHEMBL114
Created by admin on Wed Jul 05 23:10:31 UTC 2023 , Edited by admin on Wed Jul 05 23:10:31 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
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