Details of the Drug

General Information of Drug (ID: DMP6M1N)

Drug Name

Pirenzepine

Synonyms

Gasteril; Gastrotsepin; Gastrozepin; Pirenzepin; Pirenzepina; Pirenzepinum; Pyrenzepine; Ulcosan; Pirenzepine Gastrozepin; Gastrozepin (TN); L-S 519; Pirenzepina [INN-Spanish]; Pirenzepine (INN); Pirenzepine [INN:BAN]; Pirenzepinum [INN-Latin]; 11-((4-Methyl-1-piperazinyl)acetyl)-5,11-dihydro-6H-pyrido(2,3-b)(1,4)benzodiazepin-6-one; 11-[(4-methylpiperazin-1-yl)acetyl]-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one; 11-[2-(4-methylpiperazin-1-yl)acetyl]-5H-pyrido[2,3-b][1,4]benzodiazepin-6-one; 5,11-Dihydro-11-((4-methyl-1-piperazinyl)acetyl)-6H-pyrido(2,3-b)(1,4)benzodiazepin-6-one

Indication

Disease Entry	ICD 11	Status	REF
Peptic ulcer	DA61	Approved	[1]
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Therapeutic Class

Antiulcer Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

351.4

Logarithm of the Partition Coefficient (xlogp)

0.1

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [2]
Clearance: The drug present in the plasma can be removed from the body at the rate of 2.77 mL/min/kg [3]
Elimination: 43% of drug is excreted from urine in the unchanged form [2]
Half-life: The concentration or amount of drug in body reduced by one-half in 11.1 hours [3]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 7.11417 micromolar/kg/day [4]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 1.71 L/kg [3]
Water Solubility: The ability of drug to dissolve in water is measured as 50 mg/mL [2]

Chemical Identifiers

Formula: C19H21N5O2
IUPAC Name: 11-[2-(4-methylpiperazin-1-yl)acetyl]-5H-pyrido[2,3-b][1,4]benzodiazepin-6-one
Canonical SMILES: CN1CCN(CC1)CC(=O)N2C3=CC=CC=C3C(=O)NC4=C2N=CC=C4
InChI: InChI=1S/C19H21N5O2/c1-22-9-11-23(12-10-22)13-17(25)24-16-7-3-2-5-14(16)19(26)21-15-6-4-8-20-18(15)24/h2-8H,9-13H2,1H3,(H,21,26)
InChIKey: RMHMFHUVIITRHF-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 4848
ChEBI ID: CHEBI:8247
CAS Number: 28797-61-7
DrugBank ID: DB00670
TTD ID: D0T0LM
VARIDT ID: DR01428

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Muscarinic acetylcholine receptor M1 (CHRM1)	TTZ9SOR	ACM1_HUMAN	Antagonist	[5]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
P-glycoprotein 1 (ABCB1)	DTUGYRD	MDR1_HUMAN	Substrate	[6]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Muscarinic acetylcholine receptor M1 (CHRM1)	OTKW3E6B	ACM1_HUMAN	Protein Interaction/Cellular Processes	[7]

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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

Peptic ulcer

ICD Disease Classification

DA61

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Muscarinic acetylcholine receptor M1 (CHRM1)	DTT	CHRM1	5.59E-01	0.19	0.41
P-glycoprotein 1 (ABCB1)	DTP	P-GP	6.54E-01	1.95E-01	4.04E-01

Molecular Expression Atlas (MEA)

MEA Detail

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: 328).
2	BDDCS applied to over 900 drugs
3	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
5	Negative crosstalk between M1 and M2 muscarinic autoreceptors involves endogenous adenosine activating A1 receptors at the rat motor endplate. Neurosci Lett. 2009 Aug 14;459(3):127-31.
6	Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs. J Pharmacol Exp Ther. 2002 Dec;303(3):1029-37.
7	Fluorescent pirenzepine derivatives as potential bitopic ligands of the human M1 muscarinic receptor. J Med Chem. 2004 Aug 12;47(17):4300-15. doi: 10.1021/jm040800a.