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

Stem definition	Drug id	CAS RN
HIV protease inhibitors	2422	127779-20-8

Description:

Molecule	Description
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

Molecule

Description

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:

Dose	Unit	Route
1.80	g	O

ADMET properties:

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

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Approvals:

Date	Agency	Company	Orphan
Dec. 6, 1995	FDA	HOFFMANN LA ROCHE
Oct. 3, 1996	EMA	ROCHE REGISTRATION GMBH

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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

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FDA Adverse Event Reporting System (Pediatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Hypertriglyceridaemia	35.68	35.03	7	16	66	89703

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Pharmacologic Action:

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Source	Code	Description
ATC	J05AE01	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Protease inhibitors
CHEBI has role	CHEBI:35660	HIV protease inhibitors
CHEBI has role	CHEBI:36044	antiviral drugs
FDA EPC	N0000175889	Protease Inhibitor
FDA MoA	N0000000246	HIV Protease Inhibitors
FDA MoA	N0000190114	Cytochrome P450 3A Inhibitors
MeSH PA	D019380	Anti-HIV Agents
MeSH PA	D000890	Anti-Infective Agents
MeSH PA	D044966	Anti-Retroviral Agents
MeSH PA	D000998	Antiviral Agents

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
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

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	11.89	acidic
pKa2	12.53	acidic
pKa3	12.89	acidic
pKa4	7.46	Basic
pKa5	4.9	Basic

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Orange Book patent data (new drug applications)

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Orange Book exclusivity data (new drug applications)

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Type	Activity value (-log[M])	Bioact source
Cytochrome P450 3A4	Enzyme	P08684	CP3A4_HUMAN	IC50	5.82	WOMBAT-PK
Multidrug resistance protein 1	Transporter	P08183	MDR1_HUMAN	IC50	4.92	WOMBAT-PK
5-hydroxytryptamine receptor 1A	GPCR	P08908	5HT1A_HUMAN	Ki	5.61	DRUG MATRIX
D(3) dopamine receptor	GPCR	P35462	DRD3_HUMAN	Ki	5.28	DRUG MATRIX
Canalicular multispecific organic anion transporter 1	Transporter	Q92887	MRP2_HUMAN	IC50	4.70	WOMBAT-PK
Sodium-dependent dopamine transporter	Transporter	Q01959	SC6A3_HUMAN	Ki	4.56	DRUG MATRIX
Kappa-type opioid receptor	GPCR	P41145	OPRK_HUMAN	Ki	5.56	DRUG MATRIX
Multidrug resistance-associated protein 1	Transporter	P33527	MRP1_HUMAN			WOMBAT-PK
ATP-binding cassette sub-family G member 2	Transporter	Q9UNQ0	ABCG2_HUMAN	IC50	4.71	CHEMBL
Delta-type opioid receptor	GPCR	P41143	OPRD_HUMAN	Ki	5.00	DRUG MATRIX

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External reference:

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ID	Source
ROC	PDB_CHEM_ID
005089	NDDF
005090	NDDF
108700005	SNOMEDCT_US
108701009	SNOMEDCT_US
11448	MMSL
149845-06-7	SECONDARY_CAS_RN
16538	MMSL
203674	RXNORM
372530001	SNOMEDCT_US

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
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

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