nelfinavir 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 ┬ÁM/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 593.70 40.72 214 2061 107998 46575789
Pregnancy 238.55 40.72 77 2198 27060 46656727
Stillbirth 214.23 40.72 52 2223 6439 46677348
Caesarean section 157.54 40.72 50 2225 16553 46667234
Viral mutation identified 155.39 40.72 32 2243 1867 46681920
Abortion spontaneous 133.23 40.72 57 2218 43589 46640198
Premature baby 109.95 40.72 39 2236 18073 46665714
Foetal exposure during pregnancy 103.23 40.72 43 2232 30704 46653083
Drug resistance 100.13 40.72 36 2239 17332 46666455
Maternal drugs affecting foetus 97.88 40.72 27 2248 5491 46678296
Hypertriglyceridaemia 96.99 40.72 27 2248 5677 46678110
Blood lactic acid increased 88.10 40.72 25 2250 5632 46678155
Live birth 81.18 40.72 27 2248 10303 46673484
Normal newborn 77.80 40.72 23 2252 5978 46677809
Foetal death 77.36 40.72 25 2250 8718 46675069
Pathogen resistance 73.24 40.72 22 2253 6038 46677749
Abortion induced 69.53 40.72 24 2251 10236 46673551
Premature labour 63.50 40.72 23 2252 11276 46672511
Multiple-drug resistance 61.81 40.72 16 2259 2549 46681238
Atrial septal defect 59.67 40.72 19 2256 6313 46677474
Lipodystrophy acquired 59.64 40.72 14 2261 1491 46682296
Trisomy 21 58.60 40.72 11 2264 394 46683393
Patent ductus arteriosus 55.33 40.72 16 2259 3846 46679941
Virologic failure 45.56 40.72 12 2263 2043 46681744
Maternal exposure during pregnancy 44.33 40.72 38 2237 102511 46581276
Neonatal disorder 41.80 40.72 9 2266 648 46683139

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 464.78 29.20 106 4056 3454 29944862
Exposure during pregnancy 445.56 29.20 124 4038 9137 29939179
Mitochondrial toxicity 350.37 29.20 79 4083 2435 29945881
Eyelid ptosis 326.82 29.20 86 4076 5102 29943214
Progressive external ophthalmoplegia 296.39 29.20 61 4101 1205 29947111
Foetal exposure during pregnancy 200.36 29.20 99 4063 36772 29911544
Diplopia 199.02 29.20 74 4088 13698 29934618
Premature baby 115.47 29.20 53 4109 16638 29931678
Lipoatrophy 106.52 29.20 23 4139 574 29947742
Ophthalmoplegia 98.43 29.20 25 4137 1279 29947037
Extraocular muscle paresis 94.90 29.20 20 4142 443 29947873
Hypertriglyceridaemia 83.14 29.20 34 4128 8064 29940252
Hydrocele 78.41 29.20 23 4139 2021 29946295
Cryptorchism 69.33 29.20 20 4142 1657 29946659
Osteonecrosis 69.12 29.20 37 4125 16098 29932218
Maternal drugs affecting foetus 65.44 29.20 24 4138 4249 29944067
Hyperlactacidaemia 64.68 29.20 21 4141 2585 29945731
Caesarean section 64.54 29.20 20 4142 2117 29946199
Viral mutation identified 60.49 29.20 20 4142 2606 29945710
Optic nerve neoplasm 58.47 29.20 9 4153 27 29948289
Hyperlipidaemia 54.30 29.20 30 4132 13877 29934439
Pregnancy 53.40 29.20 11 4151 217 29948099
Portal hypertension 52.89 29.20 20 4142 3853 29944463
Virologic failure 52.72 29.20 19 4143 3200 29945116
Neonatal disorder 51.81 29.20 14 4148 912 29947404
Cardiac murmur 51.31 29.20 23 4139 6811 29941505
Congenital anomaly 51.25 29.20 15 4147 1307 29947009
Drug resistance 48.88 29.20 32 4130 20101 29928215
Hypospadias 48.37 29.20 17 4145 2662 29945654
Astrocytoma, low grade 47.50 29.20 8 4154 48 29948268
Multiple-drug resistance 46.82 29.20 17 4145 2924 29945392
Immune reconstitution inflammatory syndrome 45.04 29.20 23 4139 9078 29939238
Nodular regenerative hyperplasia 45.01 29.20 12 4150 742 29947574
Facial wasting 44.79 29.20 9 4153 156 29948160
Pathogen resistance 43.80 29.20 22 4140 8388 29939928
Blood lactic acid increased 41.80 29.20 19 4143 5811 29942505
HIV infection 39.60 29.20 13 4149 1655 29946661
Anaemia neonatal 39.55 29.20 9 4153 287 29948029
Gynaecomastia 38.14 29.20 20 4142 8331 29939985
Sickle cell disease 35.13 29.20 7 4155 116 29948200
Cachexia 33.56 29.20 17 4145 6594 29941722
Abdominal hernia 33.11 29.20 13 4149 2768 29945548
Foetal distress syndrome 33.00 29.20 10 4152 981 29947335
Mitochondrial cytopathy 31.30 29.20 7 4155 206 29948110
Neutropenia neonatal 29.42 29.20 8 4154 533 29947783

Pharmacologic Action:

SourceCodeDescription
ATC J05AE04 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIVIRALS FOR SYSTEMIC USE
DIRECT ACTING ANTIVIRALS
Protease inhibitors
FDA MoA N0000000246 HIV Protease 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
CHEBI has role CHEBI:35610 cytostatic
CHEBI has role CHEBI:35660 hiv protease inhibitors
FDA EPC N0000175889 Protease Inhibitor
FDA MoA N0000190114 Cytochrome P450 3A Inhibitors

Drug Use (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

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
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 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
Delta-type opioid receptor GPCR Ki 4.63 DRUG MATRIX
Epidermal growth factor receptor Kinase IC50 4.25 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
Multidrug resistance protein 1 Transporter IC50 4.70 CHEMBL
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
SARS-CoV-2 Virus INHIBITOR EC50 5.53 SCIENTIFIC LITERATURE
Protease Enzyme Ki 10.15 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 63010-027 TABLET, FILM COATED 625 mg ORAL NDA 29 sections