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Tox | Related Drugs | BioActivity |

Stem definition	Drug id	CAS RN
HIV protease inhibitors	1893	159989-64-7

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: nelfinavir viracept nelfinavir mesylate nelfinavir mesilate	A potent HIV protease inhibitor. It is used in combination with other antiviral drugs in the treatment of HIV in both adults and children. 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: 567.79 Formula: C32H45N3O4S CLOGP: 5.84 LIPINSKI: 2 HAC: 7 HDO: 4 TPSA: 101.90 ALOGS: -5.47 ROTB: 10 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

nelfinavir
viracept
nelfinavir mesylate
nelfinavir mesilate

A potent HIV protease inhibitor. It is used in combination with other antiviral drugs in the treatment of HIV in both adults and children. 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: 567.79
Formula: C32H45N3O4S
CLOGP: 5.84
LIPINSKI: 2
HAC: 7
HDO: 4
TPSA: 101.90
ALOGS: -5.47
ROTB: 10

Status: OFP

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

Drug dosage:

Dose	Unit	Route
2.25	g	O

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	62.90 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	50 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Predicted pharmacokinetic/toxicological properties (PK-AZ):

Property	Description	Value	Unit	Confidence	Similarity
azlogd74	LogD at pH 7.4	4.849		High	1
caco2-efflux	Caco-2 efflux ratio (BA/AB)	4.159		High	1
caco2-intrinsic-papp	Caco-2 intrinsic apparent permeability	14.622	10^-6 cm/s	High	1
dh-clint	Dog hepatocyte intrinsic clearance	66.069	uL/min/10^6 cells	High	1
dppb	Dog plasma protein binding (% unbound)	0.660	%	High	1
fcs-ppb	Fetal calf serum protein binding (% unbound)	1.390	%	High	1
herg	hERG pIC50	5.058	pIC50	High	1
hh-clint	Human hepatocyte intrinsic clearance	169.044	uL/min/10^6 cells	High	1
hlm-clint	Human liver microsomal intrinsic clearance	296.483	uL/min/mg protein	High	1
hppb	Human plasma protein binding (% unbound)	0.570	%	High	1
kinase-safety-class	ACVR2A,ACVR2B,AKT2,AKT3,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK2,CDK5,CDK9,DDR1,DYRK1B,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,ITK,JAK2,JAK3,MAP2K6,MAP3K21,MAP3K7,MAPK10,MAPK7,MAPK9,MAPKAPK2,MET,MTOR,NTRK2,PDK1,PDK2,PDK4,PDPK1,PIK3CA,PIK3CB,PIM2,PRKCD,PRKDC,SIK2,SIK3,STK33,SYK,TEK,TGFBR1,TTK,ZAP70	50
kinase-selectivity-class	AXL,BRAF,GRK2	3
mdck-mdr1-efflux	MDCK-MDR1 efflux ratio	9.268		High	1
mh-clint	Mouse hepatocyte intrinsic clearance	207.970		High	1
mppb	Mouse plasma protein binding (% unbound)	0.830		High	1
nih-mdck-mdr1-efflux	NIH MDCK-MDR1 efflux ratio	33.113		High	1
pfas-class	PFAS structural alert (1 = True, 0 = False)	0
pld-class	Phospholipidosis risk class (1 = positive, 0 = negative)	1		High	1
pppb	Pig plasma protein binding (% unbound)	1.990	%	High	1
rh-clint	Rat hepatocyte intrinsic clearance	295.121	uL/min/10^6 cells	High	1
rh-fuinc	Rat hepatocyte fraction unbound in incubation	4.450	%	High	1
rppb	Rat plasma protein binding (% unbound)	0.650	%	High	1
solubility-dd	Solubility at pH 7.4 in DMSO	2.547	uM	High	1

Approvals:

Date	Agency	Company	Orphan
March 14, 1997	FDA	AGOURON

FDA Adverse Event Reporting System (Female)

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
Exposure during pregnancy	484.54	48.42	182	1731	238228	90388306
Viral mutation identified	240.99	48.42	41	1872	1984	90624550
Stillbirth	210.27	48.42	45	1868	7398	90619136
Pregnancy	199.09	48.42	67	1846	61980	90564554
Caesarean section	183.74	48.42	48	1865	18529	90608005
Abortion spontaneous	133.21	48.42	48	1865	54008	90572526
Premature baby	125.30	48.42	38	1875	25039	90601495
Drug resistance	122.15	48.42	39	1874	30410	90596124
Foetal exposure during pregnancy	120.43	48.42	42	1871	42933	90583601
Pathogen resistance	115.08	48.42	28	1885	8087	90618447
Maternal drugs affecting foetus	111.20	48.42	25	1888	5130	90621404
Virologic failure	107.33	48.42	21	1892	2203	90624331
Hypertriglyceridaemia	95.61	48.42	24	1889	7865	90618669
Blood lactic acid increased	88.21	48.42	23	1890	8755	90617779
Lipodystrophy acquired	77.36	48.42	15	1898	1499	90625035
Premature labour	74.23	48.42	22	1891	13354	90613180
Atrial septal defect	65.78	48.42	18	1895	8216	90618318
Abortion induced	63.56	48.42	19	1894	11869	90614665
Multiple-drug resistance	62.12	48.42	17	1896	7759	90618775
Patent ductus arteriosus	60.86	48.42	15	1898	4554	90621980
Trisomy 21	52.56	48.42	9	1904	449	90626085
Normal newborn	50.96	48.42	19	1894	23343	90603191
Foetal death	49.43	48.42	18	1895	20705	90605829

FDA Adverse Event Reporting System (Male)

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	539.46	37.51	108	3278	3342	42614607
Mitochondrial toxicity	421.44	37.51	84	3302	2531	42615418
Exposure during pregnancy	401.37	37.51	100	3286	8448	42609501
Progressive external ophthalmoplegia	387.89	37.51	71	3315	1340	42616609
Eyelid ptosis	368.83	37.51	89	3297	6572	42611377
Diplopia	238.73	37.51	81	3305	20235	42597714
Foetal exposure during pregnancy	229.95	37.51	99	3287	47212	42570737
Virologic failure	130.11	37.51	35	3351	3959	42613990
Viral mutation identified	121.86	37.51	32	3354	3299	42614650
Ophthalmoplegia	119.53	37.51	29	3357	2171	42615778
Pathogen resistance	116.29	37.51	41	3345	11409	42606540
Premature baby	107.46	37.51	47	3339	23106	42594843
Maternal drugs affecting foetus	81.16	37.51	24	3362	3815	42614134
Hydrocele	76.46	37.51	21	3365	2562	42615387
Hypertriglyceridaemia	72.31	37.51	28	3358	10098	42607851
Blood lactic acid increased	71.10	37.51	26	3360	8013	42609936
Cryptorchism	67.11	37.51	18	3368	2009	42615940
Caesarean section	66.42	37.51	18	3368	2088	42615861
Lipoatrophy	57.98	37.51	12	3374	433	42617516
Drug resistance	57.28	37.51	35	3351	34213	42583736
Optic nerve neoplasm	55.50	37.51	8	3378	28	42617921
Multiple-drug resistance	54.96	37.51	21	3365	7301	42610648
Pregnancy	51.56	37.51	10	3376	258	42617691
Neonatal disorder	50.87	37.51	12	3374	795	42617154
Dyslipidaemia	49.84	37.51	21	3365	9397	42608552
Congenital anomaly	47.80	37.51	13	3373	1528	42616421
Anaemia neonatal	47.27	37.51	10	3376	402	42617547
Hypospadias	44.85	37.51	15	3371	3552	42614397
Hyperlactacidaemia	41.39	37.51	15	3371	4501	42613448
Cardiac murmur	40.69	37.51	20	3366	12755	42605194
Astrocytoma, low grade	39.95	37.51	7	3379	101	42617848

FDA Adverse Event Reporting System (Geriatric)

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	648.53	38.89	115	3624	4409	110581151
Mitochondrial toxicity	501.63	38.89	88	3651	3157	110582403
Progressive external ophthalmoplegia	455.28	38.89	72	3667	1348	110584212
Eyelid ptosis	377.64	38.89	88	3651	13239	110572321
Viral mutation identified	330.62	38.89	65	3674	4354	110581206
Diplopia	249.02	38.89	81	3658	41813	110543747
Virologic failure	229.76	38.89	49	3690	4903	110580657
Exposure during pregnancy	223.50	38.89	110	3629	167314	110418246
Pathogen resistance	199.27	38.89	56	3683	17616	110567944
Drug resistance	192.05	38.89	72	3667	56302	110529258
Stillbirth	179.76	38.89	39	3700	4225	110581335
Pregnancy	147.98	38.89	58	3681	51009	110534551
Multiple-drug resistance	135.89	38.89	39	3700	13196	110572364
Ophthalmoplegia	124.89	38.89	28	3711	3522	110582038
Caesarean section	121.04	38.89	36	3703	13781	110571779
Abortion spontaneous	106.58	38.89	41	3698	34241	110551319
Portal hypertension	86.62	38.89	25	3714	8612	110576948
Premature baby	76.27	38.89	20	3719	4835	110580725
HIV-associated neurocognitive disorder	76.07	38.89	13	3726	395	110585165
Dyslipidaemia	67.69	38.89	24	3715	15941	110569619
Lipoatrophy	63.97	38.89	12	3727	622	110584938
Optic nerve neoplasm	63.28	38.89	8	3731	24	110585536
Foetal exposure during pregnancy	54.77	38.89	17	3722	7488	110578072
Maternal drugs affecting foetus	47.42	38.89	11	3728	1606	110583954
Osteonecrosis	47.29	38.89	23	3716	33718	110551842
Abortion induced	45.50	38.89	15	3724	8004	110577556
Treatment noncompliance	45.02	38.89	29	3710	72961	110512599
Normal newborn	43.44	38.89	19	3720	21877	110563683
Blood HIV RNA increased	39.15	38.89	10	3729	2178	110583382
Blood lactic acid increased	38.94	38.89	16	3723	15805	110569755

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
ATC	J05AE04	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:22587	antiviral agent
CHEBI has role	CHEBI:35610	antineoplastic agent
CHEBI has role	CHEBI:35660	HIV protease inhibitor
CHEBI has role	CHEBI:64946	anti-HIV agent
MeSH PA	D000890	Anti-Infective Agents
MeSH PA	D000998	Antiviral Agents
MeSH PA	D004791	Enzyme Inhibitors
MeSH PA	D011480	Protease Inhibitors
MeSH PA	D017320	HIV Protease Inhibitors
MeSH PA	D019380	Anti-HIV Agents

Related Drugs by ATC class:

J05AE Protease inhibitors 10 drugs

amprenavir atazanavir darunavir ensitrelvir fosamprenavir indinavir nirmatrelvir ritonavir saquinavir tipranavir

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

Disease	Relation	SNOMED_ID	DOID
Human immunodeficiency virus infection	indication	86406008	DOID:526
Depressive disorder	contraindication	35489007
Diarrhea	contraindication	62315008
Diabetes mellitus	contraindication	73211009	DOID:9351
Hyperglycemia	contraindication	80394007	DOID:4195
Hemophilia	contraindication	90935002
Disease of liver	contraindication	235856003	DOID:409
Pregnancy, function	contraindication	289908002
Breastfeeding (mother)	contraindication	413712001

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	8.66	acidic
pKa2	11.97	acidic
pKa3	6.63	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Beta-3 adrenergic receptor	GPCR	P13945	ADRB3_HUMAN		Ki	4.59	DRUG MATRIX
Multidrug resistance protein 1	Transporter	P08183	MDR1_HUMAN		IC50	4.70	CHEMBL
Sodium-dependent noradrenaline transporter	Transporter	P23975	SC6A2_HUMAN		Ki	5.06	DRUG MATRIX
Mu-type opioid receptor	GPCR	P35372	OPRM_HUMAN		Ki	5.23	DRUG MATRIX
D(1A) dopamine receptor	GPCR	P21728	DRD1_HUMAN		Ki	5.19	DRUG MATRIX
Cytochrome P450 3A4	Enzyme	P08684	CP3A4_HUMAN		IC50	5.70	DRUG MATRIX
Sodium-dependent dopamine transporter	Transporter	Q01959	SC6A3_HUMAN		Ki	4.91	DRUG MATRIX
Adenosine receptor A3	GPCR	P0DMS8	AA3R_HUMAN		Ki	5.08	DRUG MATRIX
Kappa-type opioid receptor	GPCR	P41145	OPRK_HUMAN		Ki	4.84	DRUG MATRIX
ATP-binding cassette sub-family G member 2	Transporter	Q9UNQ0	ABCG2_HUMAN		IC50	4.90	CHEMBL
Delta-type opioid receptor	GPCR	P41143	OPRD_HUMAN		Ki	4.63	DRUG MATRIX
Epidermal growth factor receptor	Kinase	P00533	EGFR_HUMAN		IC50	4.26	DRUG MATRIX
Tyrosine-protein kinase Lck	Kinase	P06239	LCK_HUMAN		IC50	4.10	DRUG MATRIX
Tyrosine-protein kinase Fyn	Kinase	P06241	FYN_HUMAN		IC50	5.10	DRUG MATRIX
Thromboxane-A synthase	Enzyme	P24557	THAS_HUMAN		IC50	4.68	DRUG MATRIX
Mitogen-activated protein kinase 3	Kinase	P27361	MK03_HUMAN		IC50	4.65	DRUG MATRIX
Mitogen-activated protein kinase 14	Kinase	Q16539	MK14_HUMAN		IC50	4.74	DRUG MATRIX
Substance-K receptor	GPCR	P21452	NK2R_HUMAN		Ki	5.01	DRUG MATRIX
Muscarinic acetylcholine receptor M5	GPCR	P08912	ACM5_HUMAN		Ki	4.21	DRUG MATRIX
Pol polyprotein	Enzyme		Q72874_9HIV1	INHIBITOR	Ki	11	CHEMBL	CHEMBL
Gag-Pol polyprotein	Polyprotein		POL_HV1BR				WOMBAT-PK
Androgen receptor	Transcription factor		ANDR_RAT		Ki	4.62	DRUG MATRIX
Arachidonate 15-lipoxygenase	Enzyme		LOX15_RABIT		IC50	4.86	DRUG MATRIX
Progesterone receptor	Transcription factor		Q690N0_BOVIN		Ki	5.24	DRUG MATRIX
Protease	Enzyme		Q9YQ12_9HIV1		Ki	10.15	CHEMBL
Protease	Enzyme		O90781_9PLVG		Ki	8.49	CHEMBL
Protease	Enzyme		Q9YQ30_9PLVG		Ki	8.68	CHEMBL

External reference:

ID	Source
4024050	VUID
N0000022055	NUI
D00899	KEGG_DRUG
159989-65-8	SECONDARY_CAS_RN
4021010	VANDF
4024050	VANDF
C0525005	UMLSCUI
CHEBI:7496	CHEBI
CHEMBL584	ChEMBL_ID
CHEMBL1205	ChEMBL_ID
D019888	MESH_DESCRIPTOR_UI
DB00220	DRUGBANK_ID
11090	IUPHAR_LIGAND_ID
7494	INN_ID
HO3OGH5D7I	UNII
64143	PUBCHEM_CID
134526	RXNORM
5162	MMSL
9815	MMSL
d04118	MMSL
006408	NDDF
006409	NDDF
108706004	SNOMEDCT_US
108707008	SNOMEDCT_US
373445001	SNOMEDCT_US
1UN	PDB_CHEM_ID
HO3OGH5D7I	INXIGHT DRUGS

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
VIRACEPT	HUMAN PRESCRIPTION DRUG LABEL	1	52959-289	TABLET, FILM COATED	250 mg	ORAL	NDA	26 sections
Viracept	HUMAN PRESCRIPTION DRUG LABEL	1	53808-0809	TABLET, FILM COATED	625 mg	ORAL	NDA	25 sections
VIRACEPT	HUMAN PRESCRIPTION DRUG LABEL	1	63010-010	TABLET, FILM COATED	250 mg	ORAL	NDA	31 sections
VIRACEPT	HUMAN PRESCRIPTION DRUG LABEL	1	63010-027	TABLET, FILM COATED	625 mg	ORAL	NDA	31 sections

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nelfinavir 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Description:

Drug dosage:

ADMET properties:

Predicted pharmacokinetic/toxicological properties (PK-AZ):

Approvals:

FDA Adverse Event Reporting System (Female)

FDA Adverse Event Reporting System (Male)

FDA Adverse Event Reporting System (Geriatric)

FDA Adverse Event Reporting System (Pediatric)

Pharmacologic Action:

Related Drugs by ATC class:

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

🐶 Veterinary Drug Use

🐶 Veterinary products

Acid dissociation constants calculated using MoKa v3.0.0

Orange Book patent data (new drug applications)

Orange Book exclusivity data (new drug applications)

Bioactivity Summary:

External reference:

Pharmaceutical products: