Profenamine

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Profenamine
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Clinical data
Trade namesParsidol, Parsidan, Parkisol, Parkin[citation needed]
AHFS/Drugs.comInternational Drug Names
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Pharmacokinetic data
Protein binding93%
Elimination half-life1 to 2 hours
Identifiers
  • N,N-Diethyl-1-(10H-phenothiazin-10-yl)propan-2-amine
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Chemical and physical data
FormulaC19H24N2S
Molar mass312.48 g·mol−1
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  • S2c1ccccc1N(c3c2cccc3)CC(N(CC)CC)C
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Profenamine (INN; also known as ethopropazine (BAN); sold under the trade name Parsidol and others) is a phenothiazine derivative used as an antiparkinsonian agent[1][2] 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:[3]

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Synthesis:[4] Patents:[5][6]

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

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  1. ^ Page Module:Citation/CS1/styles.css has no content."Prefenamine". drugs.com.
  2. ^ Page Module:Citation/CS1/styles.css has no content.Morton IK, Hall JM (1999). "Ethopropazine". Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Dordrecht: Springer Netherlands. p. 115. ISBN 9789401144391.
  3. ^ Debra Ellies, William Rosenberg, Page Template:Citation/styles.css has no content.WO 2010025135  (2010 to Osteogenex Inc.).
  4. ^ Charpentier, P. et al, Compt. Rend., 1951, 232, 415.
  5. ^ P. Carpentier, U.S. patent 2526118 (1950 to Societe desusines Chimiqiues).
  6. ^ Julius Nicholson Ashley, U.S. patent 2607773 (1952 to Societe des Bsines Chhniques Rhone).

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