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]
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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
CAS Number: 73736-50-2
TTD ID: D0C9UF
INTEDE ID: DR1859

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]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 2J2 (CYP2J2)_{Main DME}	DERSX5P	CP2J2_HUMAN	Substrate	[3]

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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]

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Molecular Interaction Atlas (MIA)

MIA Detail

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)

MEA Detail

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.