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

Stem definitionDrug idCAS RN
HIV protease inhibitors 1893 159989-64-7

Description:

MoleculeDescription

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:

DoseUnitRoute
2.25 g O

ADMET properties:

PropertyValueReference
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):

PropertyDescriptionValueUnitConfidenceSimilarity
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
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:

DateAgencyCompanyOrphan
March 14, 1997 FDA AGOURON

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
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 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 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 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 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:

SourceCodeDescription
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
amprenaviratazanavirdarunavirensitrelvirfosamprenavirindinavirnirmatrelvirritonavirsaquinavirtipranavir

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

DiseaseRelationSNOMED_IDDOID
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 levelDissociation constantType (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:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])		Mechanism
action		Bioact sourceMoA source
Beta-3 adrenergic receptor GPCR Ki 4.59 DRUG MATRIX
Multidrug resistance protein 1 Transporter IC50 4.70 CHEMBL
Sodium-dependent noradrenaline transporter Transporter Ki 5.06 DRUG MATRIX
Mu-type opioid receptor GPCR Ki 5.23 DRUG MATRIX
D(1A) dopamine receptor GPCR Ki 5.19 DRUG MATRIX
Cytochrome P450 3A4 Enzyme IC50 5.70 DRUG MATRIX
Sodium-dependent dopamine transporter Transporter Ki 4.91 DRUG MATRIX
Adenosine receptor A3 GPCR Ki 5.08 DRUG MATRIX
Kappa-type opioid receptor GPCR Ki 4.84 DRUG MATRIX
ATP-binding cassette sub-family G member 2 Transporter IC50 4.90 CHEMBL
Delta-type opioid receptor GPCR Ki 4.63 DRUG MATRIX
Epidermal growth factor receptor Kinase IC50 4.26 DRUG MATRIX
Tyrosine-protein kinase Lck Kinase IC50 4.10 DRUG MATRIX
Tyrosine-protein kinase Fyn Kinase IC50 5.10 DRUG MATRIX
Thromboxane-A synthase Enzyme IC50 4.68 DRUG MATRIX
Mitogen-activated protein kinase 3 Kinase IC50 4.65 DRUG MATRIX
Mitogen-activated protein kinase 14 Kinase IC50 4.74 DRUG MATRIX
Substance-K receptor GPCR Ki 5.01 DRUG MATRIX
Muscarinic acetylcholine receptor M5 GPCR Ki 4.21 DRUG MATRIX
Pol polyprotein Enzyme INHIBITOR Ki 11 CHEMBL CHEMBL
Gag-Pol polyprotein Polyprotein WOMBAT-PK
Androgen receptor Transcription factor Ki 4.62 DRUG MATRIX
Arachidonate 15-lipoxygenase Enzyme IC50 4.86 DRUG MATRIX
Progesterone receptor Transcription factor Ki 5.24 DRUG MATRIX
Protease Enzyme Ki 10.15 CHEMBL
Protease Enzyme Ki 8.49 CHEMBL
Protease Enzyme Ki 8.68 CHEMBL

External reference:

IDSource
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:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
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