amprenavir indications/contra

Stem definitionDrug idCAS RN
HIV protease inhibitors 200 161814-49-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • amprenavir
  • agenerase
  • angenerase
  • samprenavir
; RN refers to (3S-(3R*(1S*,2R*)))-isomer; fosamprenavir is a prodrug
  • Molecular weight: 505.63
  • Formula: C25H35N3O6S
  • CLOGP: 3.29
  • LIPINSKI: 1
  • HAC: 9
  • HDO: 3
  • TPSA: 131.19
  • ALOGS: -4.01
  • ROTB: 11

Drug dosage:

DoseUnitRoute
1.20 g O

Approvals:

DateAgencyCompanyOrphan
Oct. 20, 2000 EMA
April 15, 1999 FDA GLAXOSMITHKLINE

FDA Adverse Event Reporting System

None

Pharmacologic Action:

scroll-->
SourceCodeDescription
ATC J05AE05 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIVIRALS FOR SYSTEMIC USE
DIRECT ACTING ANTIVIRALS
Protease inhibitors
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
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D019380 Anti-HIV Agents
MeSH PA D000890 Anti-Infective Agents
MeSH PA D044966 Anti-Retroviral Agents
MeSH PA D000904 Antibiotics, Antitubercular
MeSH PA D000995 Antitubercular 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:36044 antiviral drug

Drug Use (View source of the data)

scroll-->
DiseaseRelationSNOMED_IDDOID
Human immunodeficiency virus infection indication 86406008 DOID:526
Acquired hemolytic anemia contraindication 4854004
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
Blood coagulation disorder contraindication 64779008 DOID:1247
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
Familial hypercholesterolemia - homozygous contraindication 238078005
Hypertriglyceridemia contraindication 302870006
Cardiovascular event risk contraindication 395112001
Autoimmune hemolytic anemia contraindication 413603009 DOID:718
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
Vitamin K Deficiency Induced Hypoprothrombinemia contraindication
Prevention of HIV Infection after Exposure off-label use

Acid dissociation constants calculated using MoKa v3.0.0

scroll-->
Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.6 acidic
pKa2 1.64 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

scroll-->
TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Cytochrome P450 3A4 Enzyme IC50 6 DRUG MATRIX
Thromboxane-A synthase Enzyme IC50 5.17 DRUG MATRIX
Cathepsin D Enzyme IC50 4.82 CHEMBL
Pol polyprotein Enzyme INHIBITOR Ki 10.40 CHEMBL CHEMBL
Gag-Pol polyprotein Polyprotein WOMBAT-PK

External reference:

scroll-->
IDSource
4021158 VUID
N0000148609 NUI
C0754188 UMLSCUI
D00894 KEGG_DRUG
CHEMBL116 ChEMBL_ID
5S0W860XNR UNII
7751 INN_ID
DB00701 DRUGBANK_ID
228656 RXNORM
116088006 SNOMEDCT_US
387006009 SNOMEDCT_US
d04428 MMSL
8067 MMSL
4021158 VANDF
N0000148609 NDFRT
N0000004336 NDFRT
007752 NDDF
65016 PUBCHEM_CID
C095108 MESH_SUPPLEMENTAL_RECORD_UI
CHEBI:40050 CHEBI
478 PDB_CHEM_ID

Pharmaceutical products:

None