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.
  • 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 712.39 133.70 160 389 25059 2332477
Pregnancy 276.83 133.70 61 488 7888 2349648
Viral mutation identified 208.79 133.70 29 520 226 2357310
Stillbirth 204.90 133.70 36 513 1405 2356131
Caesarean section 178.93 133.70 38 511 4043 2353493
Abortion spontaneous 166.40 133.70 45 504 13400 2344136
Premature baby 158.55 133.70 33 516 3171 2354365
Foetal exposure during pregnancy 153.04 133.70 35 514 5217 2352319
Maternal drugs affecting foetus 150.15 133.70 28 521 1519 2356017
Hypertriglyceridaemia 144.79 133.70 25 524 871 2356665

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
Exposure during pregnancy 601.13 67.36 111 613 2706 1743351
Lipodystrophy acquired 446.33 67.36 65 659 308 1745749
Mitochondrial toxicity 303.18 67.36 43 681 159 1745898
Eyelid ptosis 302.60 67.36 51 673 686 1745371
Progressive external ophthalmoplegia 281.85 67.36 35 689 25 1746032
Foetal exposure during pregnancy 252.24 67.36 63 661 6296 1739761
Premature baby 193.59 67.36 44 680 2898 1743159
Diplopia 177.47 67.36 40 684 2530 1743527
Cryptorchism 154.70 67.36 26 698 337 1745720
Cardiac murmur 146.51 67.36 30 694 1192 1744865
Osteonecrosis 145.28 67.36 37 687 3925 1742132
Hypertriglyceridaemia 123.47 67.36 26 698 1183 1744874
Immune reconstitution inflammatory syndrome 106.10 67.36 24 700 1525 1744532
Abdominal hernia 106.08 67.36 19 705 362 1745695
Maternal drugs affecting foetus 101.45 67.36 22 702 1149 1744908
Drug resistance 98.06 67.36 26 698 3204 1742853
Abdominal distension 92.76 67.36 29 695 6415 1739642
Congenital anomaly 91.03 67.36 17 707 411 1745646
Hyperlipidaemia 87.36 67.36 22 702 2207 1743850
Caesarean section 84.88 67.36 17 707 598 1745459
Lipoatrophy 83.27 67.36 13 711 101 1745956
Cachexia 81.90 67.36 18 706 998 1745059
Optic nerve neoplasm 74.57 67.36 9 715 3 1746054
Hepatic function abnormal 73.96 67.36 25 699 7049 1739008
Ophthalmoplegia 73.71 67.36 13 711 225 1745832
Hyperlactacidaemia 73.31 67.36 14 710 382 1745675
Hypospadias 67.93 67.36 14 710 568 1745489
Viral mutation identified 67.71 67.36 13 711 365 1745692

Pharmacologic Action:

SourceCodeDescription
ATC J05AE04 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIVIRALS FOR SYSTEMIC USE
DIRECT ACTING ANTIVIRALS
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
CHEBI has role CHEBI:35610 antineoplastic agent
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
C0525005 UMLSCUI
D00899 KEGG_DRUG
108706004 SNOMEDCT_US
4024050 VANDF
006408 NDDF
134527 RXNORM
373445001 SNOMEDCT_US
5162 MMSL
d04118 MMSL
98D603VP8V UNII
159989-65-8 SECONDARY_CAS_RN
CHEMBL584 ChEMBL_ID
CHEMBL1205 ChEMBL_ID
DB00220 DRUGBANK_ID
7494 INN_ID
CHEBI:7496 CHEBI
D019888 MESH_DESCRIPTOR_UI
64143 PUBCHEM_CID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
VIRACEPT HUMAN PRESCRIPTION DRUG LABEL 1 52959-289 TABLET, FILM COATED 250 mg ORAL NDA 14 sections
Viracept HUMAN PRESCRIPTION DRUG LABEL 1 53808-0809 TABLET, FILM COATED 625 mg ORAL NDA 14 sections
VIRACEPT HUMAN PRESCRIPTION DRUG LABEL 1 63010-010 TABLET, FILM COATED 250 mg ORAL NDA 19 sections
VIRACEPT HUMAN PRESCRIPTION DRUG LABEL 1 63010-027 TABLET, FILM COATED 625 mg ORAL NDA 19 sections