Piprozolin: Difference between revisions

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			{{Short description\|Chemical compound}}
	{{Wikify\|date=December 2010}}

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	\| metabolism =		\| metabolism =
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	\| excretion =		\| excretion =

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	\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}		\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
	\| DrugBank =		\| DrugBank =
			\| ChEMBL = 2105231
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	\| ChemSpiderID = 4744588		\| ChemSpiderID = 4744588
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	<!--Chemical data-->		<!--Chemical data-->
	\| C=14 \| H=22 \| N=2 \| O=3 \| S=1		\| C=14 \| H=22 \| N=2 \| O=3 \| S=1
	\| molecular_weight = 298.40 g/mol
	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChI = 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-		\| StdInChI = 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-
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			'''Piprozolin''' (or '''piprozoline''') is a ] for ] therapy.<ref>{{cite journal \| vauthors = Koss FW, Vollmer KO, Herrmann M \| title = \| journal = Archives Internationales de Pharmacodynamie et de Therapie \| volume = 198 \| issue = 2 \| pages = 333–46 \| date = August 1972 \| pmid = 5074733 }}</ref><ref>{{cite web \| work = Drugs-about.com \| url = http://drugs-about.com/ing/piprozolin.html \| title = Piprozolin }}</ref>
	'''Piprozolin''' (or '''piprozoline''') is a molecule used in ] therapy.

			==Synthesis==
			Compared to ], piprozolin shows ] rather than anti-inflammatory activity. That is, the compound is useful in those conditions where the flow of bile is to be increased.
			] \| gdate = 1976}}</ref>]]
			Condensation of ] with ] leads to ] ('''4'''); an intermediate such as '''3''', involving addition of the ] to the nitrile function can reasonably be invoked. M/ethylation with di(m)] proceeds on nitrogen with the concomitant shift of the enamine to afford olefin ('''5'''). Bromination of the active ] ('''6''') followed by displacement of halogen by piperidine affords the ] piprozolin ('''7''').

			== References ==
			{{reflist}}

	{{Bile and liver therapy}}		{{Bile and liver therapy}}

	]		]
	]		]
	]		]
	]		]


	{{gastrointestinal-drug-stub}}		{{gastrointestinal-drug-stub}}

Latest revision as of 13:31, 2 April 2023

Chemical compound Pharmaceutical compound

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
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.

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). "". 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

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 Resmetirom Silymarin Tidiacic arginine

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