fosamprenavir Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
HIV protease inhibitors 1240 226700-79-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • fos-amprenavir
  • GW433908
  • GW-433908
  • telzir
  • fosamprenavir
  • amprenavir phosphate
  • fosamprenavir calcium
a prodrug of the protease inhibitor amprenavir
  • Molecular weight: 585.61
  • Formula: C25H36N3O9PS
  • CLOGP: 2.50
  • LIPINSKI: 2
  • HAC: 12
  • HDO: 4
  • TPSA: 177.72
  • ALOGS: -2.93
  • ROTB: 13
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
1.40 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.31 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 67.81 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

Approvals:

DateAgencyCompanyOrphan
Oct. 20, 2003 FDA VIIV HLTHCARE

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
Viral mutation identified 91.16 46.94 17 714 1882 46683449
Exposure during pregnancy 89.18 46.94 40 691 108172 46577159
Drug resistance 70.85 46.94 21 710 17347 46667984
Abortion spontaneous 66.08 46.94 25 706 43621 46641710
Lipodystrophy acquired 56.71 46.94 11 720 1494 46683837

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 90.54 25.62 25 2077 3535 29946841
Virologic failure 56.75 25.62 17 2085 3202 29947174
Immune reconstitution inflammatory syndrome 46.18 25.62 19 2083 9082 29941294
Hypertriglyceridaemia 44.84 25.62 18 2084 8080 29942296
Heart transplant rejection 42.24 25.62 11 2091 1242 29949134
Viral mutation identified 38.33 25.62 12 2090 2614 29947762
Mitochondrial cytopathy 36.07 25.62 7 2095 206 29950170
Hyperlactacidaemia 34.28 25.62 11 2091 2595 29947781
Myositis 31.16 25.62 15 2087 10362 29940014
Drug resistance 29.28 25.62 18 2084 20115 29930261
Adrenogenital syndrome 28.79 25.62 5 2097 78 29950298
Portal hypertension 26.35 25.62 10 2092 3863 29946513
Hypercholesterolaemia 25.94 25.62 12 2090 7580 29942796

Pharmacologic Action:

SourceCodeDescription
ATC J05AE07 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
FDA EPC N0000175889 Protease Inhibitor
CHEBI has role CHEBI:50266 prodrugs

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Human immunodeficiency virus infection indication 86406008 DOID:526
Prevention of HIV Infection after Exposure off-label use
Hypercholesterolemia contraindication 13644009
Myocardial infarction contraindication 22298006 DOID:5844
Hereditary factor VIII deficiency disease contraindication 28293008 DOID:12134
Hypertensive disorder contraindication 38341003 DOID:10763
Hereditary factor IX deficiency disease contraindication 41788008 DOID:12259
Hemolytic anemia contraindication 61261009 DOID:583
Chronic type B viral hepatitis contraindication 61977001
Lipodystrophy contraindication 71325002 DOID:811
Diabetes mellitus contraindication 73211009 DOID:9351
Hyperglycemia contraindication 80394007 DOID:4195
Kidney stone contraindication 95570007
Chronic hepatitis C contraindication 128302006
Liver function tests abnormal contraindication 166603001
Disease of liver contraindication 235856003 DOID:409
Hypertriglyceridemia contraindication 302870006
Cardiovascular event risk contraindication 395112001
Breastfeeding (mother) contraindication 413712001
Disorder of coronary artery contraindication 414024009
Obesity contraindication 414916001 DOID:9970
Ketoacidosis in diabetes mellitus contraindication 420422005 DOID:1837
Smokes tobacco daily contraindication 449868002

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 1.13 acidic
pKa2 6.35 acidic
pKa3 1.8 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
Pol polyprotein Enzyme INHIBITOR CHEMBL CHEMBL
Gag-Pol polyprotein Polyprotein WOMBAT-PK

External reference:

IDSource
4021412 VUID
N0000148827 NUI
D02497 KEGG_DRUG
226700-81-8 SECONDARY_CAS_RN
4021412 VANDF
C1176315 UMLSCUI
CHEBI:82941 CHEBI
CHEMBL1664 ChEMBL_ID
CHEMBL1200734 ChEMBL_ID
DB01319 DRUGBANK_ID
131536 PUBCHEM_CID
C426859 MESH_SUPPLEMENTAL_RECORD_UI
8011 INN_ID
WOU1621EEG UNII
358262 RXNORM
17646 MMSL
262160 MMSL
64492 MMSL
d04901 MMSL
004510 NDDF
004511 NDDF
407017006 SNOMEDCT_US
407018001 SNOMEDCT_US
412393004 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Fosamprenavir Calcium HUMAN PRESCRIPTION DRUG LABEL 1 0378-3520 TABLET, FILM COATED 700 mg ORAL ANDA 27 sections
LEXIVA HUMAN PRESCRIPTION DRUG LABEL 1 49702-207 TABLET, FILM COATED 700 mg ORAL NDA 26 sections
LEXIVA HUMAN PRESCRIPTION DRUG LABEL 1 49702-208 SUSPENSION 50 mg ORAL NDA 26 sections
LEXIVA HUMAN PRESCRIPTION DRUG LABEL 1 53808-0281 TABLET, FILM COATED 700 mg ORAL NDA 26 sections
LEXIVA HUMAN PRESCRIPTION DRUG LABEL 1 53808-1010 TABLET, FILM COATED 700 mg ORAL NDA 25 sections
Fosamprenavir Calcium HUMAN PRESCRIPTION DRUG LABEL 1 63304-583 TABLET, COATED 700 mg ORAL ANDA 25 sections