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
Oct. 3, 1996 EMA ROCHE REGISTRATION GMBH
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 176.19 58.35 28 655 1782 63486557
Drug resistance 124.69 58.35 32 651 22901 63465438
Genotype drug resistance test positive 74.53 58.35 11 672 422 63487917
Pregnancy 63.08 58.35 21 662 36815 63451524
Foetal exposure during pregnancy 61.90 58.35 20 663 31942 63456397
Blood HIV RNA increased 61.45 58.35 10 673 729 63487610

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 761.83 32.91 144 2724 3200 34950863
Mitochondrial toxicity 708.40 32.91 131 2737 2568 34951495
Eyelid ptosis 586.58 32.91 127 2741 5639 34948424
Diplopia 451.31 32.91 127 2741 16716 34937347
Progressive external ophthalmoplegia 358.95 32.91 67 2801 1368 34952695
Ophthalmoplegia 145.12 32.91 33 2835 1807 34952256
Virologic failure 110.08 32.91 30 2838 3450 34950613
Dysphagia 103.40 32.91 64 2804 62317 34891746
Pathogen resistance 84.18 32.91 31 2837 9451 34944612
Viral mutation identified 82.05 32.91 23 2845 2931 34951132
Hypertriglyceridaemia 61.86 32.91 24 2844 8424 34945639
Multiple-drug resistance 53.48 32.91 19 2849 5220 34948843
Blood lactic acid increased 48.85 32.91 19 2849 6709 34947354
Drug resistance 43.84 32.91 27 2841 25900 34928163
Foetal exposure during pregnancy 38.84 32.91 29 2839 38072 34915991
CD4 lymphocytes decreased 36.95 32.91 11 2857 1730 34952333
Immune reconstitution inflammatory syndrome 34.41 32.91 16 2852 8743 34945320
Dyslipidaemia 33.58 32.91 15 2853 7473 34946590

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 811.27 35.69 139 2686 4186 79737377
Mitochondrial toxicity 799.62 35.69 131 2694 2983 79738580
Eyelid ptosis 604.84 35.69 126 2699 10918 79730645
Diplopia 465.91 35.69 126 2699 33340 79708223
Progressive external ophthalmoplegia 414.70 35.69 67 2758 1378 79740185
Viral mutation identified 233.89 35.69 48 2777 3810 79737753
Drug resistance 152.56 35.69 57 2768 42156 79699407
Ophthalmoplegia 151.88 35.69 32 2793 2880 79738683
Virologic failure 124.26 35.69 29 2796 4162 79737401
Dysphagia 110.68 35.69 63 2762 122073 79619490
Pathogen resistance 88.94 35.69 29 2796 14313 79727250
Blood HIV RNA increased 66.95 35.69 15 2810 1793 79739770
Multiple-drug resistance 63.59 35.69 20 2805 8788 79732775
Genotype drug resistance test positive 54.75 35.69 12 2813 1296 79740267
Ergot poisoning 50.93 35.69 8 2817 135 79741428
Immune reconstitution inflammatory syndrome 43.82 35.69 17 2808 13824 79727739
Foetal exposure during pregnancy 41.17 35.69 13 2812 5777 79735786
Dyslipidaemia 39.37 35.69 15 2810 11618 79729945
Hyperlactacidaemia 37.46 35.69 12 2813 5583 79735980
Hepatitis B DNA increased 37.04 35.69 8 2817 807 79740756

FDA Adverse Event Reporting System (Pediatric)

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
Hypertriglyceridaemia 35.68 35.03 7 16 66 89703

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 | Suggest Off label Use Form| |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
ATP-binding cassette sub-family G member 2 Transporter IC50 4.71 CHEMBL
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