fosamprenavir 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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 Bocci G, Oprea TI, Benet LZ
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
BA (Bioavailability) 35 %

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2A,ACVR2B,ACVRL1,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK4,CDK5,CDK9,DDR1,DYRK1B,EGFR,EIF2AK3,EPHB4,ERBB2,GRK2,GRK3,GSK3B,ITK,JAK2,JAK3,KDR,MAP2K6,MAP3K14,MAP3K21,MAP3K7,MAPK10,MAPK12,MAPK7,MAPK9,MAPKAPK2,MTOR,NTRK2,PDK1,PDK2,PIK3CB,PIM2,PLK1,PRKDC,SIK2,SIK3,STK33,SYK,TEK,TGFBR1,TTK,ZAP70 50
kinase-selectivity-class AURKA,AXL,CDK9,EPHB4,ERBB2,GRK2,MAP2K6,MAPK7,SIK2,TEK 10
mdck-mdr1-bcrp-efflux MDCK-MDR1-BCRP efflux ratio 0.333 High 0.81
pfas-class PFAS structural alert (1 = True, 0 = False) 0
rat-kpuu-brain Rat brain Kpuu 0.001 % High 0.81

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 122.78 110.02 17 196 2008 90626226

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 74.30 51.47 16 694 3434 42617191
Virologic failure 71.97 51.47 16 694 3978 42616647
Heart transplant rejection 55.82 51.47 11 699 1523 42619102
Blood HIV RNA increased 55.42 51.47 11 699 1580 42619045
Cystitis noninfective 53.01 51.47 9 701 545 42620080
Viral mutation identified 52.67 51.47 12 698 3319 42617306

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
Viral mutation identified 124.56 47.31 22 694 4397 110584186
Lipodystrophy acquired 117.42 47.31 21 695 4503 110584080
Virologic failure 96.21 47.31 18 698 4934 110583649
Drug resistance 94.43 47.31 28 688 56346 110532237
CSF HIV escape syndrome 73.80 47.31 10 706 347 110588236
Blood HIV RNA increased 62.30 47.31 11 705 2177 110586406
Drug interaction 47.48 47.31 33 683 500150 110088433
Nephropathy toxic 47.43 47.31 14 702 27464 110561119

FDA Adverse Event Reporting System (Pediatric)

None

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 D000084762 Viral Protease Inhibitors
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000904 Antibiotics, Antitubercular
MeSH PA D000995 Antitubercular 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
MeSH PA D044966 Anti-Retroviral Agents
FDA EPC N0000175889 Protease Inhibitor
FDA MoA N0000182141 Cytochrome P450 3A4 Inhibitors
FDA MoA N0000185506 Cytochrome P450 3A4 Inducers
FDA MoA N0000191264 P-Glycoprotein Inducers
CHEBI has role CHEBI:22587 antiviral agent
CHEBI has role CHEBI:35660 HIV protease inhibitor
CHEBI has role CHEBI:36044 antiviral drug
CHEBI has role CHEBI:64946 anti-HIV agent
CHEBI has role CHEBI:50266 prodrug

Related Drugs by ATC class:

J05AE Protease inhibitors 10 drugs
amprenaviratazanavirdarunavirensitrelvirindinavirnelfinavirnirmatrelvirritonavirsaquinavirtipranavir

Drug Use | Suggest Off label Use Form| |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




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

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
4021158 VANDF
4021412 VANDF
C1176315 UMLSCUI
CHEBI:82941 CHEBI
478 PDB_CHEM_ID
CHEMBL1664 ChEMBL_ID
CHEMBL1200734 ChEMBL_ID
DB01319 DRUGBANK_ID
C426859 MESH_SUPPLEMENTAL_RECORD_UI
12682 IUPHAR_LIGAND_ID
8011 INN_ID
WOU1621EEG UNII
131536 PUBCHEM_CID
228656 RXNORM
17646 MMSL
262160 MMSL
64492 MMSL
8067 MMSL
d04428 MMSL
d04901 MMSL
004510 NDDF
004511 NDDF
007752 NDDF
116088006 SNOMEDCT_US
387006009 SNOMEDCT_US
407017006 SNOMEDCT_US
407018001 SNOMEDCT_US
412393004 SNOMEDCT_US
C0754188 UMLSCUI
DB00701 DRUGBANK_ID
65016 PUBCHEM_CID
7751 INN_ID
C095108 MESH_SUPPLEMENTAL_RECORD_UI
CHEBI:40050 CHEBI
WOU1621EEG INXIGHT DRUGS

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 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 24 sections