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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL175691
CHEMBL175691
Compound Name RILPIVIRINE
ChEMBL Synonyms TMC278 HYDROCHLORIDE | RILPIVIRINE | TMC-278 | EDURANT | R 278474 | RILPIVIRINE HYDROCHLORIDE
Max Phase 4 (Approved)
Trade Names EDURANT
Molecular Formula C22H18N6

Additional synonyms for CHEMBL175691 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES Cc1cc(\C=C\C#N)cc(C)c1Nc2ccnc(Nc3ccc(cc3)C#N)n2
Standard InChI InChI=1S/C22H18N6/c1-15-12-18(4-3-10-23)13-16(2)21(15)27-20- ...
Download InChI
Standard InChI Key YIBOMRUWOWDFLG-ONEGZZNKSA-N

Sources

  • British National Formulary
  • Orange Book
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL175691

Molecule Features

CHEMBL175691 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:N Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Human immunodeficiency virus type 1 reverse transcriptase inhibitor Human immunodeficiency virus type 1 reverse transcriptase DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
HIV InfectionsD015658EFO:0000180HIV-1 infection3ClinicalTrials
HIV InfectionsD015658EFO:0000764HIV infection4ClinicalTrials
DailyMed
DailyMed
DailyMed
DailyMed
Insulin ResistanceD007333EFO:0002614insulin resistance1ClinicalTrials
Hepatitis CD006526EFO:0003047hepatitis C infection1ClinicalTrials
Acquired Immunodeficiency SyndromeD000163EFO:0000765AIDS3ClinicalTrials

Clinical Data

ClinicalTrials.gov RILPIVIRINE
The Cochrane Collaboration RILPIVIRINE

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL175691. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL3905 Tyrosine-protein kinase Lyn Homo sapiens 0.997
CHEMBL2480 Tyrosine-protein kinase LCK Mus musculus 0.990
CHEMBL267 Tyrosine-protein kinase SRC Homo sapiens 0.985
CHEMBL4179 c-Jun N-terminal kinase 2 Homo sapiens 0.983
CHEMBL2366516 Reverse transcriptase Human immunodeficiency virus 1 0.955
CHEMBL2073 Tyrosine-protein kinase YES Homo sapiens 0.798
CHEMBL301 Cyclin-dependent kinase 2 Homo sapiens 0.440
CHEMBL258 Tyrosine-protein kinase LCK Homo sapiens 0.427
CHEMBL279 Vascular endothelial growth factor receptor 2 Homo sapiens 0.374



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL2480 Tyrosine-protein kinase LCK Mus musculus 1.000
CHEMBL4179 c-Jun N-terminal kinase 2 Homo sapiens 0.999
CHEMBL3905 Tyrosine-protein kinase Lyn Homo sapiens 0.990
CHEMBL2366516 Reverse transcriptase Human immunodeficiency virus 1 0.987
CHEMBL2041 Tyrosine-protein kinase receptor RET Homo sapiens 0.960
CHEMBL4367 Tyrosine-protein kinase TXK Homo sapiens 0.950
CHEMBL267 Tyrosine-protein kinase SRC Homo sapiens 0.945
CHEMBL2073 Tyrosine-protein kinase YES Homo sapiens 0.904
CHEMBL301 Cyclin-dependent kinase 2 Homo sapiens 0.866
CHEMBL4600 Serine/threonine-protein kinase PAK 1 Homo sapiens 0.815
CHEMBL258 Tyrosine-protein kinase LCK Homo sapiens 0.634
CHEMBL308 Cyclin-dependent kinase 1 Homo sapiens 0.631
CHEMBL4203 Dual specificity protein kinase CLK4 Homo sapiens 0.629
CHEMBL279 Vascular endothelial growth factor receptor 2 Homo sapiens 0.579
CHEMBL1841 Tyrosine-protein kinase FYN Homo sapiens 0.521
CHEMBL3024 Serine/threonine-protein kinase PLK1 Homo sapiens 0.482
CHEMBL262 Glycogen synthase kinase-3 beta Homo sapiens 0.445
CHEMBL2007 Platelet-derived growth factor receptor alpha Homo sapiens 0.377
CHEMBL4225 Dual specificity protein kinase CLK2 Homo sapiens 0.287

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
366.4 366.1593 4.99 5 97.42 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
6 2 0 6 2 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 5.25 4.53 4.53 3 28 0.62

Structural Alerts

There are 4 structural alerts for CHEMBL175691. To view alerts please click here.

Compound Cross References

ATC J - ANTIINFECTIVES FOR SYSTEMIC USE
J05 - ANTIVIRALS FOR SYSTEMIC USE
J05A - DIRECT ACTING ANTIVIRALS
J05AG - Non-nucleoside reverse transcriptase inhibitors
J05AG05 - rilpivirine

ChemSpider ChemSpider:YIBOMRUWOWDFLG-ONEGZZNKSA-N
DailyMed rilpivirine hydrochloride
Wikipedia Rilpivirine

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL175691



ACToR 500287-72-9
BindingDB 222178
Brenda 146979 61803 165598
ChEBI 68606
ChemicalBook CB81454833
DrugBank DB08864
DrugCentral 4174
eMolecules 10663308
EPA CompTox Dashboard DTXSID10198189
FDA SRS FI96A8X663
Human Metabolome Database HMDB0061725
LINCS LSM-45777
MolPort MolPort-006-170-051
Nikkaji J2.576.528A J2.980.206H
PDBe T27
PubChem 6451164
PubChem: Thomson Pharma 14926256
SureChEMBL SCHEMBL385113
ZINC ZINC000001554274

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/YIBOMRUWOWDFLG-ONEGZZNKSA-N spacer
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