Iprazochrome

Iprazochrome is an antimigraine agent used for prophylaxis of the attacks. It is also indicated for diabetic retinopathy (both treatment and prevention in people with type-2 diabetes).

Iprazochrome
Clinical data
Trade namesDivascan
Other names[(3-hydroxy-1-isopropyl-6-oxo-2,3-dihydroindol-5-ylidene)amino]urea
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
IUPAC name
  • 3-hydroxy-1-isopropylindoline-5,6-dione 5-semicarbazone
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H16N4O3
Molar mass264.285 g·mol−1
3D model (JSmol)
SMILES
  • CC(C)N1CC(C2=C/C(=N/NC(=O)N)/C(=O)C=C21)O
InChI
  • InChI=1S/C12H16N4O3/c1-6(2)16-5-11(18)7-3-8(14-15-12(13)19)10(17)4-9(7)16/h3-4,6,11,18H,5H2,1-2H3,(H3,13,15,19)/b14-8- N
  • Key:XZKVIDLLLOUTSS-ZSOIEALJSA-N N
 NY (what is this?)  (verify)

Chemically, it is a derivative of adrenochrome, which is a product of adrenaline oxidation.

Mechanism of action

It is a serotonin antagonist[1] both in vitro and in vivo (it is a 5-HT2D receptor antagonist). It also neutralises other vasoactive compounds such as bradykinin, histamine, and others.

This drug decreases the permeability and fragility of blood vessels, which reduces the number of migraine days and attenuates the symptoms associated with this condition, but it does not eliminate them altogether.

In animal models, iprazochrome was shown not to decrease the spreading depression velocity, which is a feature of other antimigraine agents and is thought to be one of the essential causes of classical migraines.[2]

Dose

For migraines, 1-3 tabletes (each tablet contains 2.5 mg of iprazochrome) are taken three times a day. An abortive medication is recommended in the first weeks of treatment.

For diabetic retinopaty, 2 tablets are taken three times a day. If the initial treatment was successful, it can be reduced to 1 tablet three times a day.

The effect of this medication is usually seen after a month. Its achieves its full efficacy after 3 months of treatment.

Side effects

It can work as an anorectic and can cause skin allergic reactions after dicontinuing.

This drug was also shown to induce pain in patients with atypical facial pain.[1]

Pharmacokinetics

Absorption

After taking the drug on empty stomach, it is rapidly absorbed. Peak serum concentration (Cmax) is achieved after 1 hour, but its effect on blood vessels is seen only after 3 hours.

Elimination

The half-life of iprazochrome is 2.2 hours. It is metabolised renally and 20% is eliminated in an unchanged form.

There are two known metabolites of iprazochrome: an indole derivative (detected in urine) and a 6-hydroxy derivative (detected in feces).

References
  1. Hampf G (1989). "Effect of serotonin antagonists on patients with atypical facial pain". Journal of Craniomandibular Disorders. 3 (4): 211–2. PMID 2639158.
  2. Wiedemann, Meike; de Lima, Vera M. Fernandes; Hanke, Wolfgang (1996-04-01). "Effects of antimigraine drugs on retinal spreading depression". Naunyn-Schmiedeberg's Archives of Pharmacology. 353 (5): 552–556. doi:10.1007/BF00169175. ISSN 1432-1912.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.