Profenamine

Profenamine (INN; also known as ethopropazine (BAN); trade names Parsidol, Parsidan, Parkin) 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.

Profenamine
Clinical data
Trade namesParsidol, Parsidan, Parkin
AHFS/Drugs.comInternational Drug Names
ATC code
Pharmacokinetic data
Protein binding93%
Elimination half-life1 to 2 hours
Identifiers
IUPAC name
  • N,N-Diethyl-1-(10H-phenothiazin-10-yl)propan-2-amine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.007.566
Chemical and physical data
FormulaC19H24N2S
Molar mass312.48 g·mol−1
3D model (JSmol)
SMILES
  • S2c1ccccc1N(c3c2cccc3)CC(N(CC)CC)C
InChI
  • InChI=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 Y
  • Key:CDOZDBSBBXSXLB-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Synthesis

For promoting bone growth:[3]

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
  1. "Prefenamine". drugs.com.
  2. 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, WO 2010025135 (2010 to Osteogenex Inc.).
  4. Charpentier, P. et al, Compt. Rend., 1951, 232, 415.
  5. P. Carpentier, U.S. Patent 2,526,118 (1950 to Societe desusines Chimiqiues).
  6. Julius Nicholson Ashley, U.S. Patent 2,607,773 (1952 to Societe des Bsines Chhniques Rhone).
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