Piprozolin

Piprozolin
Clinical data
ATC code	A05AX01 (WHO) ;
Identifiers
	IUPAC name Ethyl (2Z)-2-(3-ethyl-4-oxo-5-piperidin-1-yl-1,3-thiazolidin-2-ylidene)acetate;
CAS Number	17243-64-0;
PubChem CID	5911905;
ChemSpider	4744588 ;
UNII	7786W0VV8M;
ChEMBL	ChEMBL2105231;
CompTox Dashboard (EPA)	DTXSID70864757 ;
ECHA InfoCard	100.037.512
Chemical and physical data
Formula	C14H22N2O3S
Molar mass	298.40 g·mol−1
	InChI InChI=1S/C14H22N2O3S/c1-3-16-11(10-12(17)19-4-2)20-14(13(16)18)15-8-6-5-7-9-15/h10,14H,3-9H2,1-2H3/b11-10- ; Key:UAXYBJSAPFTPNB-KHPPLWFESA-N ;
	(verify)

Piprozolin (or piprozoline) is a medication for bile therapy.^[1]^[2]

Synthesis

Compared to fenclozic acid, piprozolin shows choleretic rather than anti-inflammatory activity. That is, the compound is useful in those conditions where the flow of bile is to be increased.

Condensation of ethyl mercaptoacetate with ethyl cyanoacetate leads to thiazolinone (4); an intermediate such as 3, involving addition of the mercaptide to the nitrile function can reasonably be invoked. M/ethylation with di(m)ethyl sulfate proceeds on nitrogen with the concomitant shift of the enamine to afford olefin (5). Bromination of the active methylene (6) followed by displacement of halogen by piperidine affords the choleretic piprozolin (7).

References

^ Koss FW, Vollmer KO, Herrmann M (August 1972). "[Research with experimental animals on the mechanism of action of the new choleretic, 3-ethyl-4-oxo-5-piperidino-delta 2, alpha-thiazolidine-acetic acid ethyl ester (Piprozolin)]". Archives Internationales de Pharmacodynamie et de Therapie. 198 (2): 333–46. PMID 5074733.
^ "Piprozolin". Drugs-about.com.
^ Satzinger (1975). "Substituierte 2-Methylen-thiazolidone-(4)". Justus Liebigs Annalen der Chemie. 665: 150–165. doi:10.1002/jlac.19636650118.
^ DE 2414345, Satzinger G, Herrmann M, Vollmer K, issued 1975, assigned to Goeecke
^ US 3971794, Satzinger G, Herrmann M, Vollmer K, issued 1976, assigned to Warner-Lambert

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[1] Koss FW, Vollmer KO, Herrmann M (August 1972). "[Research with experimental animals on the mechanism of action of the new choleretic, 3-ethyl-4-oxo-5-piperidino-delta 2, alpha-thiazolidine-acetic acid ethyl ester (Piprozolin)]". Archives Internationales de Pharmacodynamie et de Therapie. 198 (2): 333–46. PMID 5074733.

[2] "Piprozolin". Drugs-about.com.

[3] Satzinger (1975). "Substituierte 2-Methylen-thiazolidone-(4)". Justus Liebigs Annalen der Chemie. 665: 150–165. doi:10.1002/jlac.19636650118.

[4] DE 2414345, Satzinger G, Herrmann M, Vollmer K, issued 1975, assigned to Goeecke

[5] US 3971794, Satzinger G, Herrmann M, Vollmer K, issued 1976, assigned to Warner-Lambert

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v t e Bile and liver therapy (A05)
Bile therapy	bile acid Chenodeoxycholic acid Cholic acid Obeticholic acid Ursodeoxycholic acid Ursodoxicoltaurine Cyclobutyrol Elafibranor Hymecromone Maralixibat chloride Menbutone Nicotinyl methylamide Odevixibat Piprozolin Seladelpar
Liver therapy	Arginine glutamate Citiolone Epomediol Glycyrrhizin Metadoxine Methionine Ornithine oxoglutarate Phospholipids Silymarin Tidiacic arginine