Icatibant

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Structural formula
Icatibant structural formula
General
Non-proprietary name Icatibant
other names

(2 S ) -2 - {[(3a S , 7a S ) -1- (2 - [(2 S ) -2 - {[(2 S ) -2 - ([2 - [{(4 R ) - 1- (1- (2 - {[(2 R ) -2-amino-5- (diaminomethylideneamino) pentanoyl] amino} -5- (diaminomethylideneamino) pentanoyl) pyrrolidine-2-carbonyl) -4-hydroxypyrrolidine-2-carbonyl } amino] acetyl] amino) -3-thiophen-2-ylpropanoyl] amino} -3-hydroxypropanoyl] -3,4-dihydro-1 H -isoquinoline-3-carbonyl) -2,3,3a, 4,5, 6,7,7a-octahydroindole-2-carbonyl] amino} -5- (diaminomethylidenamino) pentanoic acid ( IUPAC )

Molecular formula C 59 H 89 N 19 O 13 S.
External identifiers / databases
CAS number
  • 130308-48-4
  • 138614-30-9 ( icatibant acetate )
PubChem 6918173
ChemSpider 5293384
DrugBank DB06196
Wikidata Q902379
Drug information
ATC code

C01 EB19

Drug class

Bradykinin B 2 Receptors - Antagonist

properties
Molar mass 1304.52 g · mol -1
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Icatibant is a drug used to treat acute hereditary angioedema (HAE) attacks . It is made up of ten amino acid-like building blocks and has a similar structure to the body's own bradykinin and can therefore specifically bind to bradykinin B 2 receptors in its place ( peptidomimetic effect). Icatibant acts as an antagonist , that is, it blocks the B 2 receptors so that the effects of bradykinin are suppressed.

Bradykinin is a peptide- based hormone . It is produced locally in the tissues of the body, often in response to trauma . Bradykinin increases the permeability of the blood vessels, dilates the blood vessels, and causes the contraction of smooth muscle cells . The hormone also plays an essential role in mediating pain .

An increased local concentration of bradykinin is responsible for the typical symptoms of inflammation such as swelling, reddening, overheating and pain. These symptoms are mediated via the activation of bradykinin B 2 receptors. Since Icatibant also binds to B 2 receptors and displaces bradykinin, it forms a competitive B 2 antagonist that has an inhibitory effect on the receptor .

On July 11, 2008, the pharmaceutical company Jerini AG received approval from the European Commission for Firazyr , a solution for injection with the active ingredient icatibant, for the treatment of acute hereditary angioedema (HAE) attacks . This makes it the first form of therapy for the HAE indication to be approved in all EU countries. In Switzerland, approval was granted by Swissmedic on June 17, 2009. The injection solution is injected under the skin ( subcutaneously ). Icatibant is approved for self-use by the patient. It is available in 3 ml syringes with a concentration of 10 mg / ml.

Web links

Individual evidence

  1. ↑ a b Data sheet HOE 140, ≥94% from Sigma-Aldrich , accessed on February 17, 2013 ( PDF ).
  2. ↑ Public Assessment Report (EPAR) of the European Medicines Agency (EMA) on: Firazyr .