Details of the Drug

General Information of Drug (ID: DMJSKUI)

Drug Name

Norcisapride

Synonyms

Norcisapride; 84946-16-7; CHEMBL1748; 4-Amino-5-chloro-2-methoxy-N-(3-methoxy-4-piperidyl)benzamide; 4-amino-5-chloro-2-methoxy-N-(3-methoxy-4-piperidinyl)benzamide; (4-Amino-5-chloro-2-methoxy)-N-[3-methoxy(4-piperidyl)]benzamide; 4-amino-5-chloro-2-methoxy-N-(3-methoxypiperidin-4-yl)benzamide; Benzamide,4-amino-5-chloro-2-methoxy-N-[(3S,4R)-3-methoxy-4-piperidinyl]-, hydrochloride(1:1); EINECS 284-619-3; AC1MI81F; SCHEMBL593405; CTK4E8653; OMLDMGPCWMBPAN-UHFFFAOYSA-N; BDBM50301927; AKOS030254741; API0006151; DB-076176

Indication

Disease Entry	ICD 11	Status	REF
Gastroesophageal reflux disease	DA22.Z	Discontinued in Phase 2	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

313.78

Logarithm of the Partition Coefficient (xlogp)

0.8

Rotatable Bond Count (rotbonds)

4

Hydrogen Bond Donor Count (hbonddonor)

3

Hydrogen Bond Acceptor Count (hbondacc)

5

Chemical Identifiers

Formula: C14H20ClN3O3
IUPAC Name: 4-amino-5-chloro-2-methoxy-N-(3-methoxypiperidin-4-yl)benzamide
Canonical SMILES: COC1CNCCC1NC(=O)C2=CC(=C(C=C2OC)N)Cl
InChI: InChI=1S/C14H20ClN3O3/c1-20-12-6-10(16)9(15)5-8(12)14(19)18-11-3-4-17-7-13(11)21-2/h5-6,11,13,17H,3-4,7,16H2,1-2H3,(H,18,19)
InChIKey: OMLDMGPCWMBPAN-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 3019427
CAS Number: 84946-16-7
TTD ID: D0K1SZ
INTEDE ID: DR1780

Combinatorial Drugs (CBD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
5-HT 3A receptor (HTR3A)	TTPC4TU	5HT3A_HUMAN	Inhibitor	[2]
5-HT 4 receptor (HTR4)	TT07C3Y	5HT4R_HUMAN	Inhibitor	[2]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)_{Main DME}	DE4LYSA	CP3A4_HUMAN	Substrate	[3]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Cytochrome P450 3A4 (CYP3A4)	OTQGYY83	CP3A4_HUMAN	Biotransformations	[3]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Gastroesophageal reflux disease

ICD Disease Classification

DA22.Z

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
5-HT 4 receptor (HTR4)	DTT	HTR4	6.16E-01	-0.03	-0.24
Cytochrome P450 3A4 (CYP3A4)	DME	CYP3A4	1.76E-01	1.26E-01	8.27E-01

Molecular Expression Atlas (MEA)

MEA Detail

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References

1	Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800007174)
2	mu-Opioid/5-HT4 dual pharmacologically active agents-efforts towards an effective opioid analgesic with less GI and respiratory side effects (Part I). Bioorg Med Chem Lett. 2009 Oct 1;19(19):5679-83.
3	Cytochrome P450 Involvement in the biotransformation of cisapride and racemic norcisapride in vitro: differential activity of individual human CYP3A isoforms. Drug Metab Dispos. 2001 Dec;29(12):1548-54.