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Revision as of 13:27, 10 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report← Previous edit Latest revision as of 13:31, 2 April 2023 edit undoEntranced98 (talk | contribs)Extended confirmed users, Pending changes reviewers, Rollbackers171,176 edits Importing Wikidata short description: "Chemical compound"Tag: Shortdesc helper 
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{{Short description|Chemical compound}}
{{Wikify|date=December 2010}}
{{Drugbox
| Watchedfields = changed
⚫ | verifiedrevid = 444056288
⚫ | IUPAC_name = Ethyl (2''Z'')-2-(3-ethyl-4-oxo-5-piperidin-1-yl-1,3-thiazolidin-2-ylidene)acetate
| image = Piprozolin.png


<!--Clinical data-->
{{unreferenced|date=December 2010}}
| tradename =
⚫ | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫ | pregnancy_US = <!-- A / B / C / D / X -->
⚫ | pregnancy_category =
⚫ | legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
⚫ | legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
⚫ | legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
⚫ | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
⚫ | legal_status =
⚫ | routes_of_administration =


<!--Pharmacokinetic data-->
{{drugbox
⚫ | bioavailability =
⚫ | protein_bound =
⚫ | metabolism =
⚫ | elimination_half-life =
⚫ | excretion =

<!--Identifiers-->
⚫ | CAS_number = 17243-64-0
⚫ | ATC_prefix = A05
⚫ | ATC_suffix = AX01
⚫ | PubChem = 5911905
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
⚫ | DrugBank =
| ChEMBL = 2105231
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | ChemSpiderID = 4744588
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7786W0VV8M | UNII = 7786W0VV8M

⚫ | verifiedrevid = 444056288
<!--Chemical data-->
⚫ | IUPAC_name = Ethyl (2''Z'')-2-(3-ethyl-4-oxo-5-piperidin-1-yl-1,3-thiazolidin-2-ylidene)acetate
| image = Piprozolin.png | C=14 | H=22 | N=2 | O=3 | S=1
⚫ | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫ | CAS_number = 17243-64-0
⚫ | ATC_prefix = A05
⚫ | ATC_suffix = AX01
⚫ | PubChem = 5911905
| CASNo = 63250-48-6
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | ChemSpiderID = 4744588
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫ | StdInChIKey = UAXYBJSAPFTPNB-KHPPLWFESA-N
| SMILES = O=C(OCC)\C=C1/SC(C(=O)N1CC)N2CCCCC2
⚫ | 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-
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫ | StdInChIKey = UAXYBJSAPFTPNB-KHPPLWFESA-N
⚫ | DrugBank =
| C=14|H=22|N=2|O=3|S=1
| molecular_weight = 298.40 g/mol
⚫ | bioavailability =
⚫ | protein_bound =
⚫ | metabolism =
⚫ | elimination_half-life =
⚫ | excretion =
⚫ | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫ | pregnancy_US = <!-- A / B / C / D / X -->
⚫ | pregnancy_category=
⚫ | legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
⚫ | legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
⚫ | legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
⚫ | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
⚫ | legal_status =
⚫ | routes_of_administration =
}} }}


'''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
Identifiers
IUPAC name
  • Ethyl (2Z)-2-(3-ethyl-4-oxo-5-piperidin-1-yl-1,3-thiazolidin-2-ylidene)acetate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.037.512 Edit this at Wikidata
Chemical and physical data
FormulaC14H22N2O3S
Molar mass298.40 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.

Piprozolin synthesis:

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

  1. Koss FW, Vollmer KO, Herrmann M (August 1972). "". 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 
Bile and liver therapy (A05)
Bile therapy
Liver therapy
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