Details of the Drug

General Information of Drug (ID: DMTUPZ2)

Drug Name
Ezlopitant
Synonyms
UNII-3L098A8MPY; 147116-64-1; CJ-11974; CHEMBL515966; 3L098A8MPY; Ezlopitant [USAN:INN]; Ezlopitant (USAN/INN); (2s,3s)-2-(diphenylmethyl)-n-(5-isopropyl-2-methoxybenzyl)quinuclidin-3-amine; AC1L4NQ6; SCHEMBL383011; AC1Q573W; SCHEMBL9069731; GTPL5751; BDBM50262567; CJ11974; (2S,3S)-2-benzhydryl-N-[(2-methoxy-5-propan-2-ylphenyl)methyl]-1-azabicyclo[222]octan-3-amine; CJ 11974; CJ-11, 974; D04122; 2beta-(Diphenylmethyl)-3beta-(2-methoxy-5-isopropylbenzylamino)-1beta,4beta-ethanopiperidine; Ezlopitant (USAN/INN); 2-benzhydryl-N-[(2-methoxy-5-propan-2-ylphenyl)methyl]-1-azabicyclo[222]octan-3-amine; CJ 11,974-01
Indication
Disease Entry ICD 11 Status REF
Irritable bowel syndrome DD91.0 Discontinued in Phase 2 [1]
Vomiting MD90 Discontinued in Phase 2 [1]
Pain MG30-MG3Z Investigative [2]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 454.6
Logarithm of the Partition Coefficient (xlogp) 6.5
Rotatable Bond Count (rotbonds) 8
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 3
Chemical Identifiers
Formula
C31H38N2O
IUPAC Name
(2S,3S)-2-benzhydryl-N-[(2-methoxy-5-propan-2-ylphenyl)methyl]-1-azabicyclo[2.2.2]octan-3-amine
Canonical SMILES
CC(C)C1=CC(=C(C=C1)OC)CN[C@@H]2[C@@H](N3CCC2CC3)C(C4=CC=CC=C4)C5=CC=CC=C5
InChI
InChI=1S/C31H38N2O/c1-22(2)26-14-15-28(34-3)27(20-26)21-32-30-25-16-18-33(19-17-25)31(30)29(23-10-6-4-7-11-23)24-12-8-5-9-13-24/h4-15,20,22,25,29-32H,16-19,21H2,1-3H3/t30-,31-/m0/s1
InChIKey
XPNMCDYOYIKVGB-CONSDPRKSA-N
Cross-matching ID
PubChem CID
188927
ChEBI ID
CHEMBL515966
CAS Number
147116-64-1
TTD ID
D01TBN
INTEDE ID
DR1782
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Substance-P receptor (TACR1) TTZPO1L NK1R_HUMAN Antagonist [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [4]
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Substrate [4]
Cytochrome P450 3A5 (CYP3A5) DEIBDNY CP3A5_HUMAN Substrate [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Irritable bowel syndrome
ICD Disease Classification DD91.0
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Substance-P receptor (TACR1) DTT TACR1 7.40E-01 0.02 0.07
Substance-P receptor (TACR1) DTT TACR1 8.57E-01 -0.02 -0.18
Cytochrome P450 3A5 (CYP3A5) DME CYP3A5 1.17E-01 -3.87E-02 -2.23E-01
Cytochrome P450 3A5 (CYP3A5) DME CYP3A5 9.74E-01 7.48E-03 1.37E-01
Cytochrome P450 2D6 (CYP2D6) DME CYP2D6 2.59E-01 6.29E-02 3.14E-01
Cytochrome P450 2D6 (CYP2D6) DME CYP2D6 4.84E-01 -8.38E-02 -8.46E-01
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 4.66E-01 4.25E-02 1.20E-01
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 4.75E-01 5.15E-02 3.64E-01
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: 5751).
2 Targeting pain-depressed behaviors in preclinical assays of pain and analgesia: drug effects on acetic acid-depressed locomotor activity in ICR mice. Life Sci. 2009 Aug 12;85(7-8):309-15.
3 Emerging drugs for chemotherapy-induced emesis. Expert Opin Emerg Drugs. 2006 Mar;11(1):137-51.
4 Metabolism of ezlopitant, a nonpeptidic substance P receptor antagonist, in liver microsomes: enzyme kinetics, cytochrome P450 isoform identity, and in vitro-in vivo correlation. Drug Metab Dispos. 2000 Sep;28(9):1069-76.