Fenoverine

Fenoverine
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	A03AX05 (WHO) ;
Identifiers
	IUPAC name 2-[4-(Benzo[d][1,3]dioxol-5-ylmethyl)piperazin-1-yl]-1-(10H-phenothiazin-10-yl)ethanone;
CAS Number	37561-27-6;
PubChem CID	72098;
ChemSpider	65083;
UNII	N274ZQ6PZJ;
KEGG	D07095 ;
ChEMBL	ChEMBL1512949;
CompTox Dashboard (EPA)	DTXSID8046296 ;
ECHA InfoCard	100.048.666
Chemical and physical data
Formula	C26H15N3O3S
Molar mass	449.48 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CN(CCN1CC2=CC3=C(C=C2)OCO3)CC(=O)N4C5=CC=CC=C5SC6=CC=CC=C64;
	InChI InChI=1S/C26H25N3O3S/c30-26(29-20-5-1-3-7-24(20)33-25-8-4-2-6-21(25)29)17-28-13-11-27(12-14-28)16-19-9-10-22-23(15-19)32-18-31-22/h1-10,15H,11-14,16-18H2; Key:UBAJTZKNDCEGKL-UHFFFAOYSA-N;
	(verify)

Fenoverine (INN) is an antispasmodic [also known as spasmolytics] drug,[1] which acts by inhibiting calcium channels[2] [much in the same way as traditional calcium channel blockers, which are used as antianginal drugs]. In the case of Fenoverine, the relaxation occurs in abdominal / intestinal smooth mucles, while in case of antianginal drugs, the relaxation occurs in coronary vessels. Notably Fenoverine does not act as an antianginal agent.

Toxicity

Fenoverine is known to cause rhabdomyolysis.[2][3]

Synthesis

Note that the synthesis involves MDBZP agent.

Patent:[4]

Acylation of phenothiazine (1) with chloroacetyl chloride [79-04-9] (2) gives 10-(Chloroacetyl)-Phenothiazine [786-50-5] (3). Displacement of the remaining halogen upon addition of 1-Piperonylpiperazine [32231-06-4] (4) in pyridine completes the synthesis of Fenoverine (5).

References

Martínez-Vázquez MA, Vázquez-Elizondo G, González-González JA, Gutiérrez-Udave R, Maldonado-Garza HJ, Bosques-Padilla FJ (2012). "Effect of antispasmodic agents, alone or in combination, in the treatment of Irritable Bowel Syndrome: systematic review and meta-analysis". Revista De Gastroenterologia De Mexico. 77 (2): 82–90. doi:10.1016/j.rgmx.2012.04.002. PMID 22672854.
Chariot P, Ratiney R, Le Maguet F, Fourestié V, Astier A, Gherardi R (August 1995). "Fenoverine-induced rhabdomyolysis". Hum Exp Toxicol. 14 (8): 654–656. doi:10.1177/096032719501400805. PMID 7576832.
Cho J, Na J, Bae E, Lee TW, Jang HN, Cho HS, Chang SH, Park DJ (April 2020). "The incidence, risk factors, and clinical outcomes of rhabdomyolysis associated with fenoverine prescription: a retrospective study in South Korea (1999-2014)". BMC Pharmacol Toxicol. 21 (1): 30. doi:10.1186/s40360-020-00408-3. PMC 7183697. PMID 32334639.
Buzas Andre & Pierre Rene, FR2092639 (1972).

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[pmid22672854-1] Martínez-Vázquez MA, Vázquez-Elizondo G, González-González JA, Gutiérrez-Udave R, Maldonado-Garza HJ, Bosques-Padilla FJ (2012). "Effect of antispasmodic agents, alone or in combination, in the treatment of Irritable Bowel Syndrome: systematic review and meta-analysis". Revista De Gastroenterologia De Mexico. 77 (2): 82–90. doi:10.1016/j.rgmx.2012.04.002. PMID 22672854.

[Chariot_1995-2] Chariot P, Ratiney R, Le Maguet F, Fourestié V, Astier A, Gherardi R (August 1995). "Fenoverine-induced rhabdomyolysis". Hum Exp Toxicol. 14 (8): 654–656. doi:10.1177/096032719501400805. PMID 7576832.

[Cho_2020-3] Cho J, Na J, Bae E, Lee TW, Jang HN, Cho HS, Chang SH, Park DJ (April 2020). "The incidence, risk factors, and clinical outcomes of rhabdomyolysis associated with fenoverine prescription: a retrospective study in South Korea (1999-2014)". BMC Pharmacol Toxicol. 21 (1): 30. doi:10.1186/s40360-020-00408-3. PMC 7183697. PMID 32334639.

[4] Buzas Andre & Pierre Rene, FR2092639 (1972).