Details of the Drug

General Information of Drug (ID: DM58XJN)

Drug Name
Desmethylastemizole
Synonyms
O-Desmethyl Astemizole; 73736-50-2; UNII-L460QHM1YN; L460QHM1YN; CHEMBL60796; Demethylastemizole; 4-[2-[4-[[1-[(4-fluorophenyl)methyl]benzimidazol-2-yl]amino]piperidin-1-yl]ethyl]phenol; Desmethylasteizole; R-44-271; R 44 271; O-Demethylastemizole; O-Desmethylastemizole; AC1L4F06; SCHEMBL1152697; CTK8G2140; DTXSID10224058; LAGYWHSFHIMTPE-UHFFFAOYSA-N; ZINC13537287; BDBM50131433; AKOS030240026; Phenol, 4-(2-(4-((1-((4-fluorophenyl)methyl)-1H-benzimidazol-2-yl)amino)-1-piperidinyl)ethyl)-; FT-0666079; R 44271; DESMETHEYLASTEMIZOLE
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 444.5
Logarithm of the Partition Coefficient (xlogp) 5.6
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C27H29FN4O
IUPAC Name
4-[2-[4-[[1-[(4-fluorophenyl)methyl]benzimidazol-2-yl]amino]piperidin-1-yl]ethyl]phenol
Canonical SMILES
C1CN(CCC1NC2=NC3=CC=CC=C3N2CC4=CC=C(C=C4)F)CCC5=CC=C(C=C5)O
InChI
InChI=1S/C27H29FN4O/c28-22-9-5-21(6-10-22)19-32-26-4-2-1-3-25(26)30-27(32)29-23-14-17-31(18-15-23)16-13-20-7-11-24(33)12-8-20/h1-12,23,33H,13-19H2,(H,29,30)
InChIKey
LAGYWHSFHIMTPE-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
155805
ChEBI ID
CHEMBL60796
CAS Number
73736-50-2
TTD ID
D0C9UF
INTEDE ID
DR1859
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Voltage-gated potassium channel Kv11.1 (KCNH2) TTQ6VDM KCNH2_HUMAN Blocker [2]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2J2 (CYP2J2)
Main DME 		DERSX5P CP2J2_HUMAN Substrate [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Potassium voltage-gated channel subfamily H member 1 (KCNH1) OTZZXWER KCNH1_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 Discovery agent
ICD Disease Classification N.A.
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Cytochrome P450 2J2 (CYP2J2) DME CYP2J2 6.32E-01 -4.03E-02 -1.63E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Prediction of hERG potassium channel affinity by traditional and hologram qSAR methods. Bioorg Med Chem Lett. 2003 Aug 18;13(16):2773-5.
2 Block of HERG potassium channels by the antihistamine astemizole and its metabolites desmethylastemizole and norastemizole. J Cardiovasc Electrophysiol. 1999 Jun;10(6):836-43.
3 Involvement of CYP2J2 on the intestinal first-pass metabolism of antihistamine drug, astemizole. Drug Metab Dispos. 2002 Nov;30(11):1240-5.
4 A clinical drug library screen identifies astemizole as an antimalarial agent. Nat Chem Biol. 2006 Aug;2(8):415-6. doi: 10.1038/nchembio806. Epub 2006 Jul 2.