Icatibant

Drugbox
IUPAC_name = (2S)-2- [(3aS,7aS)-1- [2- [(2S)-2- [(2S)-
2- [2- [(4R)-1- [1- [2- [(2R)-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-1H-isoquinoline-3-carbonyl]
2,3,3a,4,5,6,7,7a-octahydroindole-2-carbonyl] amino] -
5-(diaminomethylideneamino)pentanoic acid

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CAS_number = 130308-48-4
CAS_supplemental =
ATC_prefix = C01
ATC_suffix = EB19
ATC_supplemental =
PubChem = 71364
DrugBank =
C=59|H=89|N=19|O=13|S=1
molecular_weight = 1304.52 g/mol
smiles = C1CC [C@H] 2 [C@@H] (C1)CC(N2C(=O)C3CC4=CC=CC=C4CN3C(=O) [C@H] (CO)NC(=O) [C@H] (CC5=CC=CS5)NC(=O)CNC(=O)C6C [C@H] (CN6C(=O)C7CCCN7C(=O)C(CCCN=C(N)N)NC(=O) [C@@H] (CCCN=C(N)N)N)O)C(=O)N [C@@H] (CCCN=C(N)N)C(=O)O
bioavailability =
protein_bound =
metabolism =
elimination_half-life =
excretion =
pregnancy_AU =
pregnancy_US =
pregnancy_category=
legal_AU =
legal_CA =
legal_UK =
legal_US =
legal_status =
routes_of_administration = subcutaneous
licence_EU = Firazyr

Icatibant (trade name Firazyr) is a peptidomimetic drug consisting of ten amino acids, which is an effective and specific antagonist of bradykinin B2 receptors. It has been approved for use in hereditary angioedema, and is under investigation for a number of other conditions in which bradykinin is thought to play a significant role.

Mode of action

Bradykinin is a peptide-based hormone that is formed locally in tissues, very often in response to a trauma. It increases vessel permeability, dilates blood vessels and causes smooth muscle cells to contract. Bradykinin plays an important role in the mediation of pain. Surplus bradykinin is responsible for the typical symptoms of inflammation, such as swelling, redness, overheating and pain. These symptoms are mediated by activation of bradykinin B2 receptors. Icatibant displaces bradykinin from B2 receptors and has an inhibitory effect on the receptor for a relatively long time.

Approval

Firazyr currently has orphan drug status in the United States and in the European Union and is developed by Jerini AG in order to treat acute episodes of hereditary angioedema within the framework of clinical studies.

In July 2008 icatibant was approved by the European Medicines Agency for the treatment of acute episodes of hereditary angioedema.cite press release | title = Jerini Receives European Commission Approval for Firazyr® (Icatibant) in the Treatment of HAE | publisher = Jerini AG | date = 2008-07-15 | url = http://www.jerini.com/cms/en/05-news-events/05-01-corporate-news/05-01-07-newsarchive-2008/08-07-15_EU_Approval.php?back=true | accessdate = 2008-07-22] The approval allows Jerini to market Firazyr in the European's Union 27 member states, making it the firts product to be approved in all EU countries for the treatment of HAE. The U.S. Food and Drug Administration, however, has declined Jerini's license application for the American market in April 2008. [cite press release | title = Jerini Receives Positive CHMP Opinion Recommending European Approval for Icatibant in the Treatment of HAE; FDA Issues Not Approvable Letter | publisher = Jerini AG | date = 2008-04-24 | url=http://www.jerini.com/cms/en/05-news-events/05-01-corporate-news/05-01-07-newsarchive-2008/08-07-15_EU_Approval.php?back=true | accessdate = 2008-07-22] Therefore it is not available in the United States.

References