RILPIVIRINE

Search structure
Trade Names:
Synonyms:
Status: Approved (2011)
Entry Type: Small molecule
Molecule Category: Parent
ATC: J05AG05
UNII: FI96A8X663

Structure
InChI Key YIBOMRUWOWDFLG-ONEGZZNKSA-N
Smile Cc1cc(/C=C/C#N)cc(C)c1Nc1ccnc(Nc2ccc(C#N)cc2)n1
InChI
InChI=1S/C22H18N6/c1-15-12-18(4-3-10-23)13-16(2)21(15)27-20-9-11-25-22(28-20)26-19-7-5-17(14-24)6-8-19/h3-9,11-13H,1-2H3,(H2,25,26,27,28)/b4-3+

Physicochemical Descriptors

Property Name Value
Molecular Formula C22H18N6
Molecular Weight 366.43
AlogP 4.99
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 5.0
Polar Surface Area 97.42
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 28.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Human immunodeficiency virus type 1 reverse transcriptase inhibitor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 1 Cytochrome P450 family 1A Cytochrome P450 1A2
- 9110-9110 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C19
- 335-340 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- 346-350 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2D Cytochrome P450 2D6
- 3410-3410 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- 2170-2170 - - -
Enzyme Hydrolase
0.2-3.55 0.24-1000 - - -
Enzyme Transferase
- - - - -36.34-5.68
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- - - - -12.72-5.73
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 500-3310 - - -
Transporter Primary active transporter ATP-binding cassette ABCG subfamily
- 1500 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Acquired Immunodeficiency Syndrome 3 D000163 ClinicalTrials
Hepatitis C 1 D006526 ClinicalTrials
Insulin Resistance 1 D007333 ClinicalTrials

Related Entries

MCS

Salt
Mixture

Side Effects from Label

Side effects Relative Frequency (%) Labels
Skin and subcutaneous tissue disorders Dermatitis 11.0
Skin and subcutaneous tissue disorders Rash 11.0
Cardiac disorders Dizziness 7.0
Psychiatric disorders Depression 5.0
Dysthymic disorder 5.0
Nervous system disorders Abnormal dreams 4.0
Psychiatric disorders Depression 4.0
Dysthymic disorder 4.0
Nervous system disorders Headache 4.0
Nervous system disorders Insomnia 4.0
Nervous system disorders Headache 3.5
Skin and subcutaneous tissue disorders Dermatitis 3.0
Nervous system disorders Headache 3.0
Nervous system disorders Insomnia 3.0
Gastrointestinal disorders Nausea 3.0
Skin and subcutaneous tissue disorders Rash 3.0
Investigations Aspartate aminotransferase increased 2.3
Skin and subcutaneous tissue disorders Dermatitis 2.3
Skin and subcutaneous tissue disorders Rash 2.3
Gastrointestinal disorders Abdominal pain 2.0
Nervous system disorders Abnormal dreams 2.0
General disorders and administration site conditions Asthenia 2.0
General disorders and administration site conditions Fatigue 2.0
Gastrointestinal disorders Gastrointestinal pain 2.0
Gastrointestinal disorders Vomiting 2.0
Investigations Alanine aminotransferase increased 1.6
Investigations White blood cell count decreased 1.2
Cardiac disorders Dizziness 1.0
Gastrointestinal disorders Nausea 1.0
Gastrointestinal disorders Vomiting 1.0
Investigations Lipase increased 0.9
Investigations Blood bilirubin increased 0.7
Investigations Haemoglobin decreased 0.1
Investigations Platelet count decreased 0.1

Cross References

Resources Reference
CAS NUMBER 500287-72-9
ChEBI 68606
ChEMBL CHEMBL175691
DrugBank DB08592
DrugCentral 4174
EPA CompTox DTXSID10198189
FDA SRS FI96A8X663
Human Metabolome Database HMDB0061725
PDB T27
PubChem 6451164
SureChEMBL SCHEMBL385113
ZINC ZINC000001554274
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