amprenavir ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

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

  • Status: OFM

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
1.20 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.04 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 1 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 67.81 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

Approvals:

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

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

FDA Adverse Event Reporting System (Geriatric)

None

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC J05AE05 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIVIRALS FOR SYSTEMIC USE
DIRECT ACTING ANTIVIRALS
Protease inhibitors
FDA MoA N0000000246 HIV Protease Inhibitors
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
MeSH PA D000084762 Viral 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
CHEBI has role CHEBI:35660 HIV protease inhibitors
CHEBI has role CHEBI:36044 antiviral drugs

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
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




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

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:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Thromboxane-A synthase Enzyme IC50 5.17 DRUG MATRIX
Cathepsin D Enzyme IC50 4.82 CHEMBL
Cytochrome P450 3A4 Enzyme IC50 6 DRUG MATRIX
Pol polyprotein Enzyme INHIBITOR Ki 10.40 CHEMBL CHEMBL
Gag-Pol polyprotein Polyprotein WOMBAT-PK
Protease Enzyme Ki 10.44 CHEMBL
Protease Unclassified Ki 10.52 CHEMBL
Protease Unclassified Ki 9.82 CHEMBL

External reference:

IDSource
4021158 VUID
N0000148609 NUI
D00894 KEGG_DRUG
228655 RXNORM
C0754188 UMLSCUI
CHEBI:40050 CHEBI
478 PDB_CHEM_ID
CHEMBL116 ChEMBL_ID
DB00701 DRUGBANK_ID
C095108 MESH_SUPPLEMENTAL_RECORD_UI
12681 IUPHAR_LIGAND_ID
7751 INN_ID
5S0W860XNR UNII
65016 PUBCHEM_CID
29919 MMSL
8067 MMSL
d04428 MMSL
116088006 SNOMEDCT_US
387006009 SNOMEDCT_US
4021158 VANDF
007752 NDDF

Pharmaceutical products:

None