AMPRENAVIR

Search structure
Trade Names:
Synonyms:
Status: Approved (1999)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: J05AE05
UNII: 5S0W860XNR

Structure
InChI Key YMARZQAQMVYCKC-OEMFJLHTSA-N
Smile CC(C)CN(C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)c1ccc(N)cc1
InChI
InChI=1S/C25H35N3O6S/c1-18(2)15-28(35(31,32)22-10-8-20(26)9-11-22)16-24(29)23(14-19-6-4-3-5-7-19)27-25(30)34-21-12-13-33-17-21/h3-11,18,21,23-24,29H,12-17,26H2,1-2H3,(H,27,30)/t21-,23-,24+/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C25H35N3O6S
Molecular Weight 505.64
AlogP 2.4
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 11.0
Polar Surface Area 131.19
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 35.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Human immunodeficiency virus type 1 protease inhibitor FDA
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- - - 260-370 -
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A5
- - - 200 -
Enzyme Protease Aspartic protease Aspartic protease AA clan Aspartic protease A1A subfamily
- 15200 - - -
Enzyme Protease Aspartic protease Aspartic protease AA clan Aspartic protease A2A subfamily
- 1-440 1 0-225 -
Enzyme Protease Cysteine protease Cysteine protease PAC clan Cysteine protease C3A subfamily
- - - 0-600 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 16
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 25000-44800 - - -

Metabolites

visNetwork

Indications

Mesh Heading Maximum Phase Mesh ID Reference
HIV Infections 3 D015658 ClinicalTrials
Acquired Immunodeficiency Syndrome 1 D000163 ClinicalTrials

Related Entries

MCS

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Gastrointestinal disorders Diarrhoea 60.0
Endocrine disorders Hyperglycaemia 58.0
Investigations Blood triglycerides increased 56.0
Gastrointestinal disorders Diarrhoea 56.0
Metabolism and nutrition disorders Hypertriglyceridaemia 56.0
Endocrine disorders Hyperglycaemia 53.0
Investigations Blood triglycerides increased 52.0
Metabolism and nutrition disorders Hypertriglyceridaemia 52.0
Investigations Blood triglycerides increased 47.0
Metabolism and nutrition disorders Hypertriglyceridaemia 47.0
Endocrine disorders Hyperglycaemia 44.0
Gastrointestinal disorders Diarrhoea 41.0
Endocrine disorders Hyperglycaemia 41.0
Investigations Blood triglycerides increased 40.0
Metabolism and nutrition disorders Hypertriglyceridaemia 40.0
Gastrointestinal disorders Diarrhoea 32.0
Nervous system disorders Paraesthesia 31.0
Nervous system disorders Paraesthesia 30.0
Gastrointestinal disorders Vomiting 24.0
Skin and subcutaneous tissue disorders Dermatitis 20.0
Skin and subcutaneous tissue disorders Rash 20.0
Gastrointestinal disorders Vomiting 20.0
Skin and subcutaneous tissue disorders Dermatitis 18.0
Gastrointestinal disorders Diarrhoea 18.0
Skin and subcutaneous tissue disorders Rash 18.0
Skin and subcutaneous tissue disorders Dermatitis 15.0
Metabolism and nutrition disorders Hypercholesterolaemia 15.0
Skin and subcutaneous tissue disorders Rash 15.0
Nervous system disorders Paraesthesia 14.0
Psychiatric disorders Affective disorder 13.0
Metabolism and nutrition disorders Hypercholesterolaemia 13.0
Nervous system disorders Paraesthesia 12.0
Gastrointestinal disorders Vomiting 11.0
Skin and subcutaneous tissue disorders Dermatitis 10.0
Metabolism and nutrition disorders Hypercholesterolaemia 10.0
Nervous system disorders Paraesthesia 10.0
Skin and subcutaneous tissue disorders Rash 10.0
Psychiatric disorders Affective disorder 9.0
Metabolism and nutrition disorders Hypercholesterolaemia 9.0
Nervous system disorders Paraesthesia 9.0
Skin and subcutaneous tissue disorders Dermatitis 8.0
Skin and subcutaneous tissue disorders Rash 8.0
Gastrointestinal disorders Nausea 7.0
Psychiatric disorders Affective disorder 6.0
Gastrointestinal disorders Diarrhoea 5.0
Gastrointestinal disorders Nausea 5.0
Psychiatric disorders Affective disorder 4.0
Nervous system disorders Headache 4.0
Gastrointestinal disorders Nausea 4.0
Gastrointestinal disorders Vomiting 4.0
Skin and subcutaneous tissue disorders Dermatitis 3.0
Nervous system disorders Headache 3.0
Skin and subcutaneous tissue disorders Rash 3.0
Gastrointestinal disorders Abdominal pain 2.0
General disorders and administration site conditions Asthenia 2.0
Skin and subcutaneous tissue disorders Dermatitis 2.0
General disorders and administration site conditions Fatigue 2.0
Gastrointestinal disorders Gastrointestinal pain 2.0
Nervous system disorders Headache 2.0
Nervous system disorders Paraesthesia 2.0
Skin and subcutaneous tissue disorders Rash 2.0
Gastrointestinal disorders Vomiting 2.0
Gastrointestinal disorders Abdominal pain 1.0
General disorders and administration site conditions Asthenia 1.0
General disorders and administration site conditions Fatigue 1.0
Gastrointestinal disorders Gastrointestinal pain 1.0
Nervous system disorders Paraesthesia 1.0

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Immune system disorders
28.57
Endocrine disorders
14.29
Eye disorders
14.29
General disorders and administration site conditions
14.29
Metabolism and nutrition disorders
14.29
Skin and subcutaneous tissue disorders
14.29

Cross References

Resources Reference
CAS NUMBER 161814-49-9
ChEBI 40050
ChEMBL CHEMBL116
DrugBank DB00701
DrugCentral 200
FDA SRS 5S0W860XNR
Human Metabolome Database HMDB0014839
KEGG C08086
PDB 478
PharmGKB PA448422
PubChem 65016
SureChEMBL SCHEMBL34151
ZINC ZINC000003809192
CONTENTS