nelfinavir ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | 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 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 50 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

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 504.45 48.50 182 1658 155365 63331817
Pregnancy 208.43 48.50 66 1774 36770 63450412
Stillbirth 200.47 48.50 45 1795 6705 63480477
Viral mutation identified 186.49 48.50 34 1806 1776 63485406
Caesarean section 172.82 48.50 48 1792 16984 63470198
Abortion spontaneous 124.75 48.50 48 1792 47147 63440035
Drug resistance 120.88 48.50 39 1801 22894 63464288
Premature baby 120.57 48.50 38 1802 20697 63466485
Foetal exposure during pregnancy 119.59 48.50 42 1798 31920 63455262
Maternal drugs affecting foetus 102.90 48.50 25 1815 5217 63481965
Hypertriglyceridaemia 93.58 48.50 24 1816 6235 63480947
Blood lactic acid increased 85.87 48.50 23 1817 7063 63480119
Pathogen resistance 78.63 48.50 21 1819 6377 63480805
Lipodystrophy acquired 73.25 48.50 15 1825 1437 63485745
Premature labour 64.73 48.50 21 1819 12483 63474699
Normal newborn 64.26 48.50 19 1821 8322 63478860
Virologic failure 63.93 48.50 14 1826 1848 63485334
Live birth 63.81 48.50 25 1815 25605 63461577
Atrial septal defect 63.19 48.50 18 1822 6920 63480262
Abortion induced 60.41 48.50 19 1821 10223 63476959
Multiple-drug resistance 58.95 48.50 16 1824 5154 63482028
Patent ductus arteriosus 57.22 48.50 15 1825 4235 63482947
Foetal death 55.04 48.50 18 1822 10962 63476220
Trisomy 21 51.04 48.50 9 1831 386 63486796

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 500.42 35.44 104 3211 3240 34950376
Mitochondrial toxicity 421.50 35.44 87 3228 2612 34951004
Exposure during pregnancy 379.44 35.44 100 3215 8834 34944782
Progressive external ophthalmoplegia 374.16 35.44 71 3244 1364 34952252
Eyelid ptosis 365.95 35.44 89 3226 5677 34947939
Diplopia 251.48 35.44 84 3231 16759 34936857
Foetal exposure during pregnancy 233.74 35.44 99 3216 38002 34915614
Viral mutation identified 120.06 35.44 32 3283 2922 34950694
Virologic failure 119.46 35.44 33 3282 3447 34950169
Pathogen resistance 116.76 35.44 41 3274 9441 34944175
Ophthalmoplegia 109.41 35.44 27 3288 1813 34951803
Premature baby 103.68 35.44 46 3269 19587 34934029
Hydrocele 77.22 35.44 21 3294 2066 34951550
Maternal drugs affecting foetus 76.21 35.44 24 3291 3941 34949675
Hypertriglyceridaemia 72.42 35.44 28 3287 8420 34945196
Cryptorchism 63.83 35.44 18 3297 2023 34951593
Caesarean section 62.79 35.44 18 3297 2146 34951470
Drug resistance 60.57 35.44 35 3280 25892 34927724
Blood lactic acid increased 56.60 35.44 22 3293 6706 34946910
Lipoatrophy 54.21 35.44 12 3303 499 34953117
Optic nerve neoplasm 54.09 35.44 8 3307 28 34953588
Neonatal disorder 53.49 35.44 13 3302 817 34952799
Multiple-drug resistance 50.78 35.44 19 3296 5220 34948396
Pregnancy 49.14 35.44 10 3305 276 34953340
Anaemia neonatal 48.12 35.44 10 3305 307 34953309
Cardiac murmur 46.65 35.44 20 3295 7817 34945799
Hyperlactacidaemia 44.72 35.44 15 3300 3001 34950615
Dyslipidaemia 44.21 35.44 19 3296 7469 34946147
Hypospadias 43.84 35.44 15 3300 3186 34950430
Astrocytoma, low grade 43.82 35.44 7 3308 45 34953571
Congenital anomaly 42.26 35.44 12 3303 1381 34952235

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 597.91 35.18 111 3397 4214 79736666
Mitochondrial toxicity 501.71 35.18 91 3417 3023 79737857
Progressive external ophthalmoplegia 435.14 35.18 72 3436 1373 79739507
Eyelid ptosis 371.12 35.18 88 3420 10956 79729924
Viral mutation identified 281.03 35.18 58 3450 3800 79737080
Diplopia 258.15 35.18 84 3424 33382 79707498
Exposure during pregnancy 245.68 35.18 109 3399 101023 79639857
Stillbirth 172.47 35.18 39 3469 3916 79736964
Virologic failure 170.22 35.18 39 3469 4152 79736728
Drug resistance 168.53 35.18 65 3443 42148 79698732
Pregnancy 165.59 35.18 57 3451 26794 79714086
Pathogen resistance 165.23 35.18 49 3459 14293 79726587
Multiple-drug resistance 123.18 35.18 35 3473 8773 79732107
Caesarean section 115.17 35.18 36 3472 12499 79728381
Ophthalmoplegia 112.36 35.18 26 3482 2886 79737994
Abortion spontaneous 102.09 35.18 41 3467 29466 79711414
Premature baby 76.02 35.18 20 3488 3760 79737120
Optic nerve neoplasm 61.17 35.18 8 3500 24 79740856
Lipoatrophy 59.83 35.18 12 3496 677 79740203
Normal newborn 59.49 35.18 19 3489 7053 79733827
Dyslipidaemia 57.58 35.18 21 3487 11612 79729268
Foetal exposure during pregnancy 54.71 35.18 17 3491 5773 79735107
Maternal drugs affecting foetus 44.10 35.18 11 3497 1672 79739208
Abortion induced 43.40 35.18 15 3493 7094 79733786
Osteonecrosis 43.35 35.18 23 3485 31072 79709808
HIV-associated neurocognitive disorder 42.00 35.18 8 3500 344 79740536
Live birth 41.48 35.18 19 3489 18725 79722155
Astrocytoma, low grade 40.59 35.18 6 3502 52 79740828
Blood HIV RNA increased 38.44 35.18 10 3498 1798 79739082
Hypertriglyceridaemia 38.22 35.18 16 3492 12724 79728156

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
CHEBI has role CHEBI:35610 antineoplastic agents
CHEBI has role CHEBI:35660 HIV protease inhibitors
FDA EPC N0000175889 Protease Inhibitor
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
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D017320 HIV Protease Inhibitors
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
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




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ 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
D(1A) dopamine receptor GPCR Ki 5.19 DRUG MATRIX
Cytochrome P450 3A4 Enzyme IC50 5.70 DRUG MATRIX
Multidrug resistance protein 1 Transporter IC50 4.70 CHEMBL
Sodium-dependent noradrenaline transporter Transporter Ki 5.06 DRUG MATRIX
Muscarinic acetylcholine receptor M5 GPCR Ki 4.21 DRUG MATRIX
Beta-3 adrenergic receptor GPCR Ki 4.59 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
Mu-type opioid receptor GPCR Ki 5.23 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 Unclassified Ki 8.49 CHEMBL
Protease Unclassified 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
1UN PDB_CHEM_ID
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

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 29 sections
VIRACEPT HUMAN PRESCRIPTION DRUG LABEL 1 63010-010 TABLET, FILM COATED 250 mg ORAL NDA 29 sections
VIRACEPT HUMAN PRESCRIPTION DRUG LABEL 1 63010-027 TABLET, FILM COATED 625 mg ORAL NDA 29 sections
VIRACEPT HUMAN PRESCRIPTION DRUG LABEL 1 63010-027 TABLET, FILM COATED 625 mg ORAL NDA 29 sections