TIPRANAVIR

Search structure
Trade Names:
Synonyms:
Status: Approved (2005)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: J05AE09
UNII: ZZT404XD09

Structure
InChI Key SUJUHGSWHZTSEU-FYBSXPHGSA-N
Smile CCC[C@@]1(CCc2ccccc2)CC(O)=C([C@H](CC)c2cccc(NS(=O)(=O)c3ccc(C(F)(F)F)cn3)c2)C(=O)O1
InChI
InChI=1S/C31H33F3N2O5S/c1-3-16-30(17-15-21-9-6-5-7-10-21)19-26(37)28(29(38)41-30)25(4-2)22-11-8-12-24(18-22)36-42(39,40)27-14-13-23(20-35-27)31(32,33)34/h5-14,18,20,25,36-37H,3-4,15-17,19H2,1-2H3/t25-,30-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C31H33F3N2O5S
Molecular Weight 602.68
AlogP 7.33
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 11.0
Polar Surface Area 105.59
Molecular species ACID
Aromatic Rings 3.0
Heavy Atoms 42.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Human immunodeficiency virus type 1 protease inhibitor DailyMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Protease Aspartic protease Aspartic protease AA clan Aspartic protease A1A subfamily
- - - 15000 -
Enzyme Protease Aspartic protease Aspartic protease AA clan Aspartic protease A2A subfamily
- 30-30 - 0-0 -
Enzyme Protease Cysteine protease Cysteine protease PAC clan Cysteine protease C3A subfamily
- - - 0 -
Enzyme Protease Metallo protease Metallo protease MAE clan Metallo protease M2 family
- - - - 31
Enzyme Protease Metallo protease Metallo protease MAE clan Metallo protease M48A subfamily
- 1200 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 109

Indications

Mesh Heading Maximum Phase Mesh ID Reference
HIV Infections 4 D015658 ClinicalTrials

Related Entries

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Gastrointestinal disorders Diarrhoea 13.4
Investigations Alanine aminotransferase increased 9.6
Investigations Body temperature increased 6.4
Gastrointestinal disorders Nausea 6.4
Investigations Aspartate aminotransferase increased 6.1
Investigations Amylase increased 6.0
Investigations Alanine aminotransferase increased 5.9
Investigations White blood cell count decreased 5.7
General disorders and administration site conditions Asthenia 5.6
General disorders and administration site conditions Fatigue 5.6
Respiratory, thoracic and mediastinal disorders Cough 5.5
Skin and subcutaneous tissue disorders Dermatitis 5.5
Skin and subcutaneous tissue disorders Rash 5.5
Gastrointestinal disorders Vomiting 5.5
Investigations Body temperature increased 5.4
Investigations Amylase increased 4.5
Gastrointestinal disorders Nausea 4.5
Nervous system disorders Headache 4.2
Gastrointestinal disorders Vomiting 4.1
Investigations Aspartate aminotransferase increased 4.0
Skin and subcutaneous tissue disorders Dermatitis 3.8
Skin and subcutaneous tissue disorders Rash 3.8
Respiratory, thoracic and mediastinal disorders Epistaxis 3.7
Nervous system disorders Insomnia 3.7
Gastrointestinal disorders Diarrhoea 3.6
Investigations White blood cell count decreased 3.6
Gastrointestinal disorders Abdominal pain 3.4
Gastrointestinal disorders Gastrointestinal pain 3.4
Gastrointestinal disorders Abdominal pain upper 2.3
Blood and lymphatic system disorders Anaemia 2.3
Investigations Weight decreased 2.2
Investigations Blood triglycerides increased 2.0
Metabolism and nutrition disorders Hypertriglyceridaemia 2.0
Nervous system disorders Neuropathy peripheral 2.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 1.8
Musculoskeletal and connective tissue disorders Myalgia 1.8
Metabolism and nutrition disorders Dehydration 1.1
Cardiac disorders Dyspnoea 1.0
Blood and lymphatic system disorders Neutropenia 1.0
Metabolism and nutrition disorders Hyperlipidaemia 0.8
Investigations Alanine aminotransferase increased 0.5
Investigations Gamma-glutamyltransferase increased 0.4

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Congenital, familial and genetic disorders
23.31
Pregnancy, puerperium and perinatal conditions
9.02
Gastrointestinal disorders
8.83
Nervous system disorders
7.89
Musculoskeletal and connective tissue disorders
6.77
Investigations
5.83
Renal and urinary disorders
5.83
Reproductive system and breast disorders
4.89
Skin and subcutaneous tissue disorders
4.7
Metabolism and nutrition disorders
3.76
Infections and infestations
3.38
Injury, poisoning and procedural complications
3.38
General disorders and administration site conditions
2.63
Hepatobiliary disorders
2.44
Psychiatric disorders
2.44

Cross References

Resources Reference
CAS NUMBER 174484-41-4
ChEBI 63628
ChEMBL CHEMBL222559
DrugBank DB00932
DrugCentral 3609
EPA CompTox DTXSID6048622
FDA SRS ZZT404XD09
KEGG D08605
PDB TPV
PubChem 54682461
SureChEMBL SCHEMBL40629
ZINC ZINC000100016058
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