Ethopropazine

Title: Ethopropazine
CAS Registry Number: 522-00-9
CAS Name: N,N-Diethyl-a-methyl-10H-phenothiazine-10-ethanamine
Additional Names: 10-(2-diethylaminopropyl)phenothiazine; 10-(2-diethylamino-2-methylethyl)phenothiazine; 2-diethylamino-1-propyl-N-dibenzoparathiazine; phenopropazine; profenamine
Manufacturers' Codes: RP-3356; W-483
Trademarks: Isothazine; Isothiazine; Parkin (Yoshitomi)
Molecular Formula: C19H24N2S
Molecular Weight: 312.47
Percent Composition: C 73.03%, H 7.74%, N 8.97%, S 10.26%
Literature References: Anticholinergic. Prepd from Grignard complexes of diethylaminopropyl halide and phenothiazine: S. S. Berg, J. N. Ashley, US 2607773 (1952 to Rhône-Poulenc). Pharmacology: M. E. Farquharson, R. G. Johnston, Br. J. Pharmacol. 14, 559 (1959). Pharmacokinetics: M. Maboudian-Esfahani, D. R. Brocks, Biopharm. Drug Dispos. 20, 159 (1999). HPLC determn in plasma: eidem, J. Chromatogr. B 715, 417 (1998).
Properties: Crystals, mp 53-55°. Usually obtained as an oil because of contamination with 10-(2-diethylamino-1-methylethyl)phenothiazine.
Melting point: mp 53-55°
Derivative Type: Hydrochloride
CAS Registry Number: 1094-08-2
Trademarks: Dibutil (Bayer); Lysivane (M & B); Pardisol; Parphezein; Parphezin; Parsidol (Warner-Chilcott; Specia); Parsitan; Parsotil; Rodipal
Molecular Formula: C19H24N2S.HCl
Molecular Weight: 348.93
Percent Composition: C 65.40%, H 7.22%, N 8.03%, S 9.19%, Cl 10.16%
Properties: Crystals from ethylene dichloride, mp 223-225° (some decompn). Lower melting points reported are caused by admixture with 10-(2-diethylamino-1-methylethyl)phenothiazine-HCl which melts at 166-168°. One gram dissolves in 400 ml water at 20°, in 20 ml water at 40°. Sol in ethanol, chloroform. Soly in abs ethanol at 25° = 1.0 g/30 ml. Sparingly sol in acetone. Practically insol in ether, benzene. pH of a 5% aq soln is about 5.8. LD50 s.c. in mice: 670 mg/kg (Farquharson, Johnston).
Melting point: mp 223-225° (some decompn)
Toxicity data: LD50 s.c. in mice: 670 mg/kg (Farquharson, Johnston)
Therap-Cat: Antiparkinsonian.
Keywords: Antiparkinsonian; Antimuscarinic.
Ethosuximide Ethoxazene Ethoxyquin Ethoxysulfuron Ethoxzolamide

Profenamine
Profenamine.svg
Systematic (IUPAC) name
N,N-diethyl-1-(10H-phenothiazin-10-yl)propan-2-amine
Clinical data
AHFS/Drugs.com International Drug Names
Legal status  ?
Pharmacokinetic data
Protein binding 93%
Half-life 1 to 2 hours
Identifiers
CAS number 1094-08-2 YesY
ATC code N04AA05
PubChem CID 3290
DrugBank DB00392
ChemSpider 3174 YesY
UNII O00T1I1VRN YesY
ChEBI CHEBI:313639 YesY
ChEMBL CHEMBL1206 YesY
Chemical data
Formula C19H24N2S 
Mol. mass 312.473 g/mol
 YesY (what is this?)  (verify)

Profenamine (INN, trade names Parsidol, Parsidan, Parkin), also known as ethopropazine (BAN), is a phenothiazine derivative used as an antiparkinsonian agent 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.