Dioxopromethazine

Last updated
Dioxopromethazine
Dioxopromethazine.svg
9,9-Dioxopromethazine (model) 3D.png
Clinical data
Trade names Prothanon
Other names9,9-Dioxopromethazine
Drug class antihistamine; 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
Formula C17H20N2O2S
Molar mass 316.42 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, commonly used in the form of hydrochloride or hydrogels, especially as eye drops [1] [2] [3] . 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. [4] [5]

Contents

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. [3] [5] [6] [7]

Side effects

Adverse effects after consumption or use include photoallergic contact dermatitis or other severe allergic skin lesions, followed by a persistent photoreaction. [8]

References

  1. ↑ Capkova, Z.; Hudecová, T.; Hatrík, S.; Havránek, E.; Vitková, Z. "[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. ISSN   1210-7816. PMID   15369230.
  2. ↑ Lun, Jia; Zhang, Wenying; Zhao, Yu; Song, Yongbo; Guo, Xingjie. "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. ISSN   1520-6017. PMID   33940025.
  3. 1 2 Lun, Jia; Zhang, Wenying; Zhao, Yu; Song, Yongbo; Guo, Xingjie (2021-08-01). "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. ISSN   0022-3549.
  4. ↑ Capkova, Z.; Hudecová, T.; Hatrík, S.; Havránek, E.; Vitková, Z. "[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. ISSN   1210-7816. PMID   15369230.
  5. 1 2 Mikuš, Peter; Valášková, Iva; Havránek, Emil (2003-09-19). "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. ISSN   0731-7085.
  6. ↑ Li, Yunhui; Wang, Chunyan; Sun, Jinying; Zhou, Yongchang; You, Tianyan; Wang, Erkang; Fung, YingSing (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.
  7. ↑ Graupner, O. K.; Kálmán, E. V. (1972-12-01). "Die Flimmer-Verschmelzungs-Frequenz unter dem Einflu\ verschiedener Pharmaka". Psychopharmacologia (in German). 27 (4): 343–347. doi:10.1007/BF00429387. ISSN   1432-2072.
  8. ↑ Schauder, S. "Dioxopromethazine-induced photoallergic contact dermatitis followed by persistent light reaction". American Journal of Contact Dermatitis: Official Journal of the American Contact Dermatitis Society. 9 (3): 182–187. ISSN   1046-199X. PMID   9744913.
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