Dacemazine
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| Formula | C16H16N2OS |
| Molar mass | 284.38 g·mol−1 |
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Dacemazine (INN, also known as Ahistan and Histantine)[1] is a phenothiazine derivative which acts as a histamine antagonist at the H1 subtype. First described in 1951, it was never marketed as a drug on its own, although a combination of dacemazine and di-tert-butylnaphthalenesulfonate was sold as an antispasmodic and antitussive under the trade name Codopectyl.[1] It was also assessed as a possible anticancer drug.[2]
Synthesis
Amide formation between phenothiazine (1) and chloroacetyl chloride (2) gives 10-(chloroacetyl)-phenothiazine (3). The subsequent displacement of the remaining halogen with dimethylamine (4) completes the synthesis of dacemazine (5).
References
- ^ a b Triggle DJ, Ganellin CR, MacDonald F (1996). Dictionary of Pharmacological Agents. Vol. 1. Boca Raton: Chapman & Hall/CRC. p. 711. ISBN 978-0-412-46630-4.
- ^ Karolyhazy G, Havas I, Jancso G, Kapas L, Sellei C (August 1952). "[The anticarcinogenic effect of dimethylaminoacetyl-phentiazide (ahistan)]". Kiserletes Orvostudomany (in Romanian). 4 (4): 260–262. PMID 13023855.
- ^ Dahlbom R, Ekstrand T, Rubin I, Saluste E, Stjernholm R, Ehrensvärd G (1951). "10-Aminoacylphenothiazines. I. Aminoacetyl and Aminopropionyl Derivatives". Acta Chemica Scandinavica. 5: 102–114. doi:10.3891/acta.chem.scand.05-0102.
- ^ Wassermann N, Ionescu M, Cuiban L, Panaiteslu T, Gheorghiu M, Arhip C (1959). "Syntheses of phenothiazine drugs". Revistade Chimie. 10. Bucharest, Romania: 81–85.
- ^ Kano H, Makisumi Y (1957). "Phenothiazine derivatives. II. Synthesis of 10-(alkylaminoacetyl)phenothiazines". Shionogi Kenkyusho Nempo [Annual Report of Shionogi Research Laboratory] (in Japanese). 7: 511–516. Abstract in: Chem Abstr. 1958;52:10094.
- ^ US 2694705, Cusic JW, "N-(Hydroxyalkylaminoalkanoyl)phenothiazines", issued 16 Novmember 1954, assigned to G.D. Searle & Co.