saquinavir 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
HIV protease inhibitors 2422 127779-20-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • invirase
  • saquinavir methanesulfonate
  • saquinavir
  • sequinavir
  • fortovase
  • saquinavir mesylate
  • saquinavir mesilate
An HIV protease inhibitor which acts as an analog of an HIV protease cleavage site. It is a highly specific inhibitor of HIV-1 and HIV-2 proteases, and also inhibits CYTOCHROME P-450 CYP3A. There was some evidence of in vitro activity against SARS-CoV-2, but no clinical trial data was found to support use in the treatment of COVID-19.
  • Molecular weight: 670.86
  • Formula: C38H50N6O5
  • CLOGP: 4.73
  • LIPINSKI: 2
  • HAC: 11
  • HDO: 5
  • TPSA: 166.75
  • ALOGS: -5.43
  • ROTB: 13

  • Status: OFM

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
1.80 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.08 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 2 % Benet LZ, Broccatelli F, Oprea TI
Vd (Volume of distribution) 3.60 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 13 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.03 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 13 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Dec. 6, 1995 FDA HOFFMANN LA ROCHE

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Viral mutation identified 161.48 52.00 26 584 1603 50602911
Drug resistance 117.24 52.00 30 580 18959 50585555
Pregnancy 65.30 52.00 21 589 29556 50574958
Foetal exposure during pregnancy 62.75 52.00 20 590 27339 50577175
Exposure during pregnancy 53.80 52.00 27 583 120988 50483526

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Lipodystrophy acquired 692.65 33.61 134 2620 2960 29568813
Mitochondrial toxicity 642.96 33.61 121 2633 2290 29569483
Eyelid ptosis 528.32 33.61 117 2637 5069 29566704
Diplopia 416.97 33.61 117 2637 13401 29558372
Progressive external ophthalmoplegia 318.57 33.61 61 2693 1256 29570517
Ophthalmoplegia 122.72 33.61 29 2725 1653 29570120
Dysphagia 90.93 33.61 59 2695 54867 29516906
Virologic failure 89.04 33.61 25 2729 2822 29568951
Pathogen resistance 66.86 33.61 26 2728 8090 29563683
Hypertriglyceridaemia 61.76 33.61 24 2730 7451 29564322
Multiple-drug resistance 56.62 33.61 19 2735 3881 29567892
Viral mutation identified 52.04 33.61 16 2738 2472 29569301
Blood lactic acid increased 42.32 33.61 17 2737 5749 29566024
Foetal exposure during pregnancy 38.62 33.61 29 2725 33838 29537935
CD4 lymphocytes decreased 36.50 33.61 11 2743 1587 29570186
Dyslipidaemia 34.80 33.61 15 2739 6046 29565727

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Lipodystrophy acquired 733.20 35.03 129 2524 3898 64492181
Mitochondrial toxicity 727.85 35.03 121 2532 2585 64493494
Eyelid ptosis 547.06 35.03 116 2537 9409 64486670
Diplopia 427.89 35.03 116 2537 26649 64469430
Progressive external ophthalmoplegia 367.91 35.03 61 2592 1266 64494813
Viral mutation identified 204.50 35.03 43 2610 3303 64492776
Ophthalmoplegia 127.08 35.03 28 2625 2674 64493405
Drug resistance 125.57 35.03 49 2604 35053 64461026
Virologic failure 114.86 35.03 27 2626 3439 64492640
Dysphagia 96.60 35.03 58 2595 106754 64389325
Pathogen resistance 84.49 35.03 28 2625 12515 64483564
Multiple-drug resistance 66.63 35.03 20 2633 6482 64489597
Ergot poisoning 49.80 35.03 8 2645 134 64495945
Foetal exposure during pregnancy 42.56 35.03 13 2640 4463 64491616
Dyslipidaemia 40.55 35.03 15 2638 9227 64486852
Immune reconstitution inflammatory syndrome 39.60 35.03 16 2637 12454 64483625
Hyperlactacidaemia 37.40 35.03 12 2641 4832 64491247

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC J05AE01 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIVIRALS FOR SYSTEMIC USE
DIRECT ACTING ANTIVIRALS
Protease inhibitors
FDA MoA N0000000246 HIV Protease Inhibitors
FDA EPC N0000175889 Protease Inhibitor
FDA MoA N0000190114 Cytochrome P450 3A Inhibitors
CHEBI has role CHEBI:35660 HIV protease inhibitors
CHEBI has role CHEBI:36044 antiviral drugs
MeSH PA D019380 Anti-HIV Agents
MeSH PA D000890 Anti-Infective Agents
MeSH PA D044966 Anti-Retroviral Agents
MeSH PA D000998 Antiviral Agents
MeSH PA D065692 Cytochrome P-450 CYP3A Inhibitors
MeSH PA D065607 Cytochrome P-450 Enzyme Inhibitors
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D017320 HIV Protease Inhibitors
MeSH PA D065606 Metabolic Side Effects of Drugs and Substances
MeSH PA D011480 Protease Inhibitors
MeSH PA D000084762 Viral Protease Inhibitors

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Human immunodeficiency virus infection indication 86406008 DOID:526
Alcoholism contraindication 7200002
Hypercholesterolemia contraindication 13644009
Cirrhosis of liver contraindication 19943007 DOID:5082
Complete atrioventricular block contraindication 27885002
Hereditary factor VIII deficiency disease contraindication 28293008 DOID:12134
Torsades de pointes contraindication 31722008
Hereditary factor IX deficiency disease contraindication 41788008 DOID:12259
Hypokalemia contraindication 43339004
Viral hepatitis C contraindication 50711007 DOID:1883
Hepatic failure contraindication 59927004
Chronic type B viral hepatitis contraindication 61977001
Diabetes mellitus contraindication 73211009 DOID:9351
Hyperglycemia contraindication 80394007 DOID:4195
Prolonged QT interval contraindication 111975006
Chronic hepatitis C contraindication 128302006
Liver function tests abnormal contraindication 166603001
Hypomagnesemia contraindication 190855004
Second degree atrioventricular block contraindication 195042002
Disease of liver contraindication 235856003 DOID:409
Hypertriglyceridemia contraindication 302870006
Breastfeeding (mother) contraindication 413712001
Congenital long QT syndrome contraindication 442917000




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 11.89 acidic
pKa2 12.53 acidic
pKa3 12.89 acidic
pKa4 7.46 Basic
pKa5 4.9 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Cytochrome P450 3A4 Enzyme IC50 5.82 WOMBAT-PK
Multidrug resistance protein 1 Transporter IC50 4.92 WOMBAT-PK
5-hydroxytryptamine receptor 1A GPCR Ki 5.61 DRUG MATRIX
D(3) dopamine receptor GPCR Ki 5.28 DRUG MATRIX
Canalicular multispecific organic anion transporter 1 Transporter IC50 4.70 WOMBAT-PK
Sodium-dependent dopamine transporter Transporter Ki 4.56 DRUG MATRIX
Kappa-type opioid receptor GPCR Ki 5.56 DRUG MATRIX
Multidrug resistance-associated protein 1 Transporter WOMBAT-PK
Delta-type opioid receptor GPCR Ki 5.00 DRUG MATRIX
Vasopressin V1a receptor GPCR Ki 5.15 DRUG MATRIX
Thromboxane-A synthase Enzyme IC50 5.66 DRUG MATRIX
Substance-K receptor GPCR Ki 5.68 DRUG MATRIX
Mu-type opioid receptor GPCR Ki 5.41 DRUG MATRIX
Pol polyprotein Enzyme INHIBITOR Ki 10.40 CHEMBL CHEMBL
Gag-Pol polyprotein Polyprotein Ki 10.19 WOMBAT-PK
5-hydroxytryptamine receptor 1A GPCR IC50 5.37 CHEMBL
Protease Enzyme IC50 9.30 CHEMBL
Protease Enzyme Ki 10.40 CHEMBL
Chloroquine resistance transporter Transporter IC50 4.89 CHEMBL
Protease Unclassified Ki 9.66 CHEMBL
Protease Unclassified Ki 8.54 CHEMBL

External reference:

IDSource
D00429 KEGG_DRUG
149845-06-7 SECONDARY_CAS_RN
4020939 VANDF
4021118 VANDF
C0286738 UMLSCUI
CHEBI:63621 CHEBI
ROC PDB_CHEM_ID
CHEMBL114 ChEMBL_ID
CHEMBL282042 ChEMBL_ID
D019258 MESH_DESCRIPTOR_UI
DB01232 DRUGBANK_ID
C508896 MESH_SUPPLEMENTAL_RECORD_UI
4813 IUPHAR_LIGAND_ID
7098 INN_ID
L3JE09KZ2F UNII
441243 PUBCHEM_CID
203674 RXNORM
11448 MMSL
16538 MMSL
5146 MMSL
5442 MMSL
7880 MMSL
d03860 MMSL
005089 NDDF
005090 NDDF
108700005 SNOMEDCT_US
108701009 SNOMEDCT_US
372530001 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Invirase HUMAN PRESCRIPTION DRUG LABEL 1 0004-0244 TABLET, FILM COATED 500 mg ORAL NDA 30 sections
Invirase HUMAN PRESCRIPTION DRUG LABEL 1 53808-0674 TABLET, FILM COATED 500 mg ORAL NDA 26 sections