Details of the Drug

General Information of Drug (ID: DMSQ794)

Drug Name
PKI166
Synonyms
PKI-166; CGP-75166; 187724-61-4; NVP-PKI166; CHEMBL1914653; AC1OCFE0; UNII-9RIE5HW38P; 9RIE5HW38P; SCHEMBL177814; GTPL7642; CHEMBL1963502; ZINC23255; AOB1619; PKI-75166; BDBM50358046; NCGC00387215-02; AS-16676; KB-275097; PKI-166, > 4-[4-[[(1R)-1-phenylethyl]amino]-7H-pyrrolo[4,5-e]pyrimidin-6-yl]phenol
Indication
Disease Entry ICD 11 Status REF
Esophageal cancer 2B70 Discontinued in Phase 2 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 330.4
Logarithm of the Partition Coefficient (xlogp) 4.2
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 4
Chemical Identifiers
Formula
C20H18N4O
IUPAC Name
4-[4-[[(1R)-1-phenylethyl]amino]-7H-pyrrolo[2,3-d]pyrimidin-6-yl]phenol
Canonical SMILES
C[C@H](C1=CC=CC=C1)NC2=NC=NC3=C2C=C(N3)C4=CC=C(C=C4)O
InChI
InChI=1S/C20H18N4O/c1-13(14-5-3-2-4-6-14)23-19-17-11-18(24-20(17)22-12-21-19)15-7-9-16(25)10-8-15/h2-13,25H,1H3,(H2,21,22,23,24)/t13-/m1/s1
InChIKey
XRYJULCDUUATMC-CYBMUJFWSA-N
Cross-matching ID
PubChem CID
6918403
TTD ID
D07GFF

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Epidermal growth factor receptor (EGFR) TTGKNB4 EGFR_HUMAN Modulator [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Receptor tyrosine-protein kinase erbB-2 (ERBB2) OTOAUNCK ERBB2_HUMAN Gene/Protein Processing [3]
Solute carrier organic anion transporter family member 1B1 (SLCO1B1) OTNEN8QK SO1B1_HUMAN Gene/Protein Processing [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Esophageal cancer
ICD Disease Classification 2B70
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Epidermal growth factor receptor (EGFR) DTT EGFR 5.84E-05 0.32 0.55
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7642).
2 Epidermal growth factor receptor inhibitor PKI-166 governs cardiovascular protection without beneficial effects on the kidney in hypertensive 5/6 nephrectomized rats.J Pharmacol Exp Ther.2013 Jun;345(3):393-403.
3 Cooperation between fibroblast growth factor receptor-4 and ErbB2 in regulation of cyclin D1 translation. J Biol Chem. 2004 Nov 26;279(48):50004-11. doi: 10.1074/jbc.M404252200. Epub 2004 Sep 17.
4 Hepatic transport of PKI166, an epidermal growth factor receptor kinase inhibitor of the pyrrolo-pyrimidine class, and its main metabolite, ACU154. Drug Metab Dispos. 2004 Nov;32(11):1272-8. doi: 10.1124/dmd.104.000497. Epub 2004 Jul 27.