Iprazochrome

Iprazochrome
Clinical data
Trade names	Divascan
Other names	[(3-hydroxy-1-isopropyl-6-oxo-2,3-dihydroindol-5-ylidene)amino]urea
AHFS/Drugs.com	International Drug Names
ATC code	N02CX03 (WHO) ;
Identifiers
	IUPAC name 3-hydroxy-1-isopropylindoline-5,6-dione 5-semicarbazone;
CAS Number	7248-21-7 ;
PubChem CID	6381821;
ChemSpider	4903581 ;
UNII	903A9K181P;
KEGG	D07297 ;
ChEMBL	ChEMBL2104324 ;
CompTox Dashboard (EPA)	DTXSID70864030 ;
Chemical and physical data
Formula	C12H16N4O3
Molar mass	264.285 g·mol−1
3D model (JSmol)	Interactive image;
	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- ; Key:XZKVIDLLLOUTSS-ZSOIEALJSA-N ;
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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).

Chemically, it is a derivative of adrenochrome, which is a product of adrenaline oxidation. And it is a derivative of carbazochrome as well.

Mechanism of action

It is a serotonin antagonist^[1] both in vitro and in vivo (it is a 5-HT_2D 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. It's achieves its full efficacy after 3 months of treatment.

Side effects

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

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 (C_max) 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

^ ^a ^b Hampf G (1989). "Effect of serotonin antagonists on patients with atypical facial pain". Journal of Craniomandibular Disorders. 3 (4): 211–212. PMID 2639158.
^ Wiedemann M, de Lima VM, Hanke W (April 1996). "Effects of antimigraine drugs on retinal spreading depression". Naunyn-Schmiedeberg's Archives of Pharmacology. 353 (5): 552–556. doi:10.1007/BF00169175. PMID 8740149. S2CID 6932302.

[pmid2639158-1] Hampf G (1989). "Effect of serotonin antagonists on patients with atypical facial pain". Journal of Craniomandibular Disorders. 3 (4): 211–212. PMID 2639158.

[2] Wiedemann M, de Lima VM, Hanke W (April 1996). "Effects of antimigraine drugs on retinal spreading depression". Naunyn-Schmiedeberg's Archives of Pharmacology. 353 (5): 552–556. doi:10.1007/BF00169175. PMID 8740149. S2CID 6932302.

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