Profenamine
{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 464215203
| IUPAC_name = N,N-Diethyl-1-(10H-phenothiazin-10-yl)propan-2-amine
| image = Profenamine.svg
| tradename = Parsidol, Parsidan, Parkisol, Parkin{{fact|date=April 2025}}
| Drugs.com = {{drugs.com|international|profenamine}}
| pregnancy_AU =
| pregnancy_US =
| legal_AU =
| legal_UK =
| legal_US =
| protein_bound = 93%
| elimination_half-life = 1 to 2 hours
| IUPHAR_ligand = 7181
| CAS_number_Ref = {{cascite|changed|CAS}}
| CAS_number = 522-00-9
| ATC_prefix = N04
| ATC_suffix = AA05
| PubChem = 3290
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00392
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 3174
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = 7WI4P02YN1
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 313639
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1206
| C=19 | H=24 | N=2 | S=1
| smiles = S2c1ccccc1N(c3c2cccc3)CC(N(CC)CC)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C19H24N2S/c1-4-20(5-2)15(3)14-21-16-10-6-8-12-18(16)22-19-13-9-7-11-17(19)21/h6-13,15H,4-5,14H2,1-3H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = CDOZDBSBBXSXLB-UHFFFAOYSA-N
}}
Profenamine (INN; also known as ethopropazine (BAN); sold under the trade name Parsidol and others) is a phenothiazine derivative used as an antiparkinsonian agent{{Cite web | url = https://www.drugs.com/international/profenamine.html | title = Prefenamine | publisher = drugs.com}}{{cite book | vauthors = Morton IK, Hall JM | chapter = Ethopropazine | chapter-url = https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA115 | page = 115 |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms |date=1999 |publisher=Springer Netherlands |location=Dordrecht |isbn=9789401144391}} that has anticholinergic, antihistamine, and antiadrenergic actions. It is also used in the alleviation of the extrapyramidal syndrome induced by drugs such as other phenothiazine compounds, but, like other compounds with antimuscarinic properties, is of no value against tardive dyskinesia.
Synthesis
For promoting bone growth:Debra Ellies, William Rosenberg, {{Cite patent|WO|2010025135}} (2010 to Osteogenex Inc.).
File:Profenamine synthesis.svg
The alkylation between phenothiazine [92-84-2] (1) and 1-Diethylamino-2-chloropropane [761-21-7] (2) in the presence of Sodium amide gives ethopropazine (3).
- The aziridinium salt helps to rationalize why a rearrangement product is observed (ala methadone). This was also observewd for Aceprometazine.
References
{{Reflist}}
{{Antiparkinson}}
{{Navboxes
| title = Pharmacodynamics
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{{Acetylcholine metabolism and transport modulators}}
{{Adrenergic receptor modulators}}
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{{Tricyclics}}
Category:H1 receptor antagonists
Category:Muscarinic antagonists
Category:Diethylamino compounds
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