Dioxopromethazine

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Wikipedia

Dioxopromethazine
Clinical data
Trade namesProthanon
Other names9,9-Dioxopromethazine
Drug classantihistamine; antitussive
Legal status
Legal status
  • generally not controlled
Identifiers
  • 1-(5,5-dioxophenothiazin-10-yl)-N,N-dimethylpropan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H20N2O2S
Molar mass316.42 g·mol−1
3D model (JSmol)
  • CC(CN1C2=CC=CC=C2S(=O)(=O)C3=CC=CC=C31)N(C)C
  • InChI=1S/C17H20N2O2S/c1-13(18(2)3)12-19-14-8-4-6-10-16(14)22(20,21)17-11-7-5-9-15(17)19/h4-11,13H,12H2,1-3H3
  • Key:FDXKCOBAFGSMDJ-UHFFFAOYSA-N

Dioxopromethazine, sold under the trade name Prothanon (Lat. Dioxopromethazinum), is an phenothiazine antihistamine, which is widely used in clinical practice in the form of a racemate for the treatment of respiratory diseases or allergic diseases, commonly used in the form of hydrochloride or hydrogels, especially as eye drops[1][2] It was first developed and synthesized in the German Democratic Republic in 1967 and later introduced into clinical practice. It was widely used from the 1970s to 1990s, after which there was a proposal to remove Dioxopromethazine from the pharmaceutical market.[1][3]

Pharmacology

Pharmacodynamics

Dioxopromethazine — is histamine H1-receptor antagonist that decreases elevated permeability of capillaries and their dilatation induced by histamine released upon allergic reaction. This is a medicament belonging to the group of first-generation antihistamines and phenothiazine derivatives, exhibits antihistamine, as well as antiallergic and anti-inflammatory activity, and was also used as an antitussive agent of equal strength to codeine, or approximately 6-11 times more powerful. Exhibits local anesthetic activity, has a moderate sedative effect, through the mechanism of influence on the central nervous system.[2][3][4][5]

Side effects

Adverse effects after consumption or use include photoallergic contact dermatitis or other severe allergic skin lesions, followed by a persistent photoreaction.[6]

References

  1. 1 2 Capkova Z, Hudecová T, Hatrík S, Havránek E, Vitková Z (July 2004). "[A study of the stability of dioxopromethazine in aqueous solutions and ophthalmic instillation]". Ceska a Slovenska Farmacie: Casopis Ceske Farmaceuticke Spolecnosti a Slovenske Farmaceuticke Spolecnosti. 53 (4): 187–191. PMID 15369230.
  2. 1 2 Lun J, Zhang W, Zhao Y, Song Y, Guo X (August 2021). "Enantiomeric Separation of Dioxopromethazine and its Stereoselective Pharmacokinetics in Rats by HPLC-MS/MS". Journal of Pharmaceutical Sciences. 110 (8): 3082–3090. doi:10.1016/j.xphs.2021.04.015. PMID 33940025.
  3. 1 2 Mikus P, Valásková I, Havránek E (September 2003). "Chiral separation of dioxopromethazine in eye drops by CZE with charged cyclodextrin". Journal of Pharmaceutical and Biomedical Analysis. 33 (2): 157–164. doi:10.1016/S0731-7085(03)00254-1. PMID 12972080.
  4. ↑ Li Y, Wang C, Sun J, Zhou Y, You T, Wang E, et al. (2005-09-26). "Determination of dioxopromethazine hydrochloride by capillary electrophoresis with electrochemiluminescence detection". Analytica Chimica Acta. 550 (1): 40–46. doi:10.1016/j.aca.2005.06.045. ISSN 0003-2670.
  5. ↑ Graupner OK, Kálmán EV (1972-12-01). "[Effects of various drugs on flicker fusion frequency. II. Phenothiazine derivatives (with reference to the dependence of the results on the chronological course of experiments]". Psychopharmacologia (in German). 27 (4): 343–347. doi:10.1007/BF00429387. PMID 4405388.
  6. ↑ Schauder S (September 1998). "Dioxopromethazine-induced photoallergic contact dermatitis followed by persistent light reaction". American Journal of Contact Dermatitis. 9 (3): 182–187. PMID 9744913.