Pirenzepine

Pirenzepine
Clinical data
Trade names	Gastrozepin
AHFS/Drugs.com	International Drug Names
ATC code	A02BX03 (WHO) ;
Identifiers
	IUPAC name 11-[(4-methylpiperazin-1-yl)acetyl]-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one;
CAS Number	28797-61-7 ;
PubChem CID	4848;
IUPHAR/BPS	328;
DrugBank	DB00670 ;
ChemSpider	4682 ;
UNII	3G0285N20N;
KEGG	D08389 ;
ChEBI	CHEBI:8247 ;
ChEMBL	ChEMBL9967 ;
CompTox Dashboard (EPA)	DTXSID7023487 ;
ECHA InfoCard	100.044.739
Chemical and physical data
Formula	C19H21N5O2
Molar mass	351.410 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C3c1ccccc1N(C(=O)CN2CCN(C)CC2)c4ncccc4N3;
	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) ; Key:RMHMFHUVIITRHF-UHFFFAOYSA-N ;
	(verify)

Pirenzepine (Gastrozepin), an M₁ selective antagonist, is used in the treatment of peptic ulcers, as it reduces gastric acid secretion and reduces muscle spasm. It is in a class of drugs known as muscarinic receptor antagonists; acetylcholine is the neurotransmitter of the parasympathetic nervous system which initiates the rest-and-digest state (as opposed to fight-or-flight), resulting in an increase in gastric motility and digestion; whereas pirenzepine would inhibit these actions and cause decreased gastric motility leading to delayed gastric emptying and constipation.^[1] It has no effects on the brain and spinal cord as it cannot diffuse through the blood–brain barrier.

Pirenzepine has been investigated for use in myopia control.^[2]^[3]

It promotes the homodimerization or oligomerisation of M₁ receptors.^[4]

^ Stolerman IP (2 August 2010). Encyclopedia of Psychopharmacology. Springer. p. 811. ISBN 978-3-540-68698-9. Retrieved 26 June 2013.
^ Czepita D (2005). "[Fundamentals of modern treatment of myopia]". Annales Academiae Medicae Stetinensis. 51 (2): 5–9. PMID 16519089.
^ Walline JJ, Lindsley KB, Vedula SS, Cotter SA, Mutti DO, Ng SM, Twelker JD (January 2020). "Interventions to slow progression of myopia in children". The Cochrane Database of Systematic Reviews. 1 (1): CD004916. doi:10.1002/14651858.CD004916.pub4. PMC 6984636. PMID 31930781.
^ Pediani JD, Ward RJ, Godin AG, Marsango S, Milligan G (June 2016). "Dynamic Regulation of Quaternary Organization of the M1 Muscarinic Receptor by Subtype-selective Antagonist Drugs". The Journal of Biological Chemistry. 291 (25): 13132–13146. doi:10.1074/jbc.M115.712562. PMC 4933229. PMID 27080256.

[Stolerman2010-1] Stolerman IP (2 August 2010). Encyclopedia of Psychopharmacology. Springer. p. 811. ISBN 978-3-540-68698-9. Retrieved 26 June 2013.

[2] Czepita D (2005). "[Fundamentals of modern treatment of myopia]". Annales Academiae Medicae Stetinensis. 51 (2): 5–9. PMID 16519089.

[3] Walline JJ, Lindsley KB, Vedula SS, Cotter SA, Mutti DO, Ng SM, Twelker JD (January 2020). "Interventions to slow progression of myopia in children". The Cochrane Database of Systematic Reviews. 1 (1): CD004916. doi:10.1002/14651858.CD004916.pub4. PMC 6984636. PMID 31930781.

[pmid27080256-4] Pediani JD, Ward RJ, Godin AG, Marsango S, Milligan G (June 2016). "Dynamic Regulation of Quaternary Organization of the M1 Muscarinic Receptor by Subtype-selective Antagonist Drugs". The Journal of Biological Chemistry. 291 (25): 13132–13146. doi:10.1074/jbc.M115.712562. PMC 4933229. PMID 27080256.

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