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Revision as of 13:43, 22 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 447765362 of page Icatibant for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CAS_number').  Latest revision as of 05:15, 15 September 2024 edit Whywhenwhohow (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers49,178 edits refs, links, templates 
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{{Short description|Pharmaceutical drug}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Use dmy dates|date=April 2020}}
{{cs1 config |name-list-style=vanc |display-authors=6}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
⚫ | IUPAC_name = (2S)-2-<nowiki>amino]-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-<BR/>2-carbonyl]-4-hydroxypyrrolidine-2-carbonyl]amino]acetyl]amino]-<BR/>3-thiophen-2-ylpropanoyl]amino]-3-hydroxypropanoyl]<BR/>3,4-dihydro-1H-isoquinoline-3-carbonyl]<BR/>2,3,3a,4,5,6,7,7a-octahydroindole-2-carbonyl]amino]-<BR/>5-(diaminomethylideneamino)pentanoic acid
| Watchedfields = changed
⚫ | image = Icatibant.png
| verifiedrevid = 461936569
⚫ | image = Icatibant.svg
| width = 300
| alt =
| caption =


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename = Firazyr
| Drugs.com = {{drugs.com|international|icatibant}} | Drugs.com = {{drugs.com|monograph|icatibant-acetate}}
| licence_EU = Firazyr | MedlinePlus =
| licence_US = Icatibant | DailyMedID = Icatibant
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_AU = C
| pregnancy_US = C
| pregnancy_category = | pregnancy_category =
⚫ | routes_of_administration = ]
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
⚫ | ATC_prefix = B06
⚫ | ATC_suffix = AC02
⚫ | ATC_supplemental =

| legal_AU = S4
| legal_AU_comment = <ref>https://www.tga.gov.au/resources/prescription-medicines-registrations/icatibant-wkt-wockhardt-bio-pty-ltd</ref>
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> | legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
| legal_US = Rx-only | legal_US = Rx-only
| legal_US_comment = <ref name="Firazyr FDA label" />
⚫ | legal_status =
| legal_EU = Rx-only
⚫ | routes_of_administration = subcutaneous
| legal_EU_comment = <ref name="Firazyr EPAR" />
⚫ | legal_status = Rx-only


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
Line 24: Line 38:
| metabolism = | metabolism =
| elimination_half-life = | elimination_half-life =
| excretion = | excretion =


<!--Identifiers--> <!--Identifiers-->
| index2_label = as salt
⚫ | CAS_number = <!-- blanked - oldvalue: 130308-48-4 -->
| CAS_number_Ref = {{cascite|changed|??}}
⚫ | ATC_prefix = C01
⚫ | CAS_number = 130308-48-4
⚫ | ATC_suffix = EB19
⚫ | PubChem = 6918173
⚫ | ATC_supplemental =
⚫ | PubChem = 71364
| IUPHAR_ligand = 667 | IUPHAR_ligand = 667
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB06196 | DrugBank = DB06196
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 16736634 | ChemSpiderID = 16736634
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 68556
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7PG89G35Q7 | UNII = 7PG89G35Q7
| KEGG2 = D04492
| ChEMBL = <!-- blanked - oldvalue: 375218 -->
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1743581
| synonyms = Hoe 140, JE 049<ref>{{cite journal | title = Icatibant: HOE 140, JE 049, JE049 | journal = Drugs in R&D | volume = 5 | issue = 6 | pages = 343–8 | year = 2004 | pmid = 15563238 | doi = 10.2165/00126839-200405060-00006 | s2cid = 25491021 }}</ref>

<!--Chemical data-->
⚫ | IUPAC_name = (2''S'')-2-<nowiki>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-(diaminomethylideneamino)pentanoic acid
| C=59 | H=89 | N=19 | O=13 | S=1 | C=59 | H=89 | N=19 | O=13 | S=1
⚫ | smiles = C1CC2(C1)C(N2C(=O)3CC4=CC=CC=C4CN3C(=O)(CO)NC(=O)(CC5=CC=CS5)NC(=O)CNC(=O)6C(CN6C(=O)7CCCN7C(=O)(CCCN=C(N)N)NC(=O)(CCCN=C(N)N)N)O)C(=O)N(CCCN=C(N)N)C(=O)O
| molecular_weight = 1304.52 g/mol
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫ | smiles = C1CC2(C1)CC(N2C(=O)C3CC4=CC=CC=C4CN3C(=O)(CO)NC(=O)(CC5=CC=CS5)NC(=O)CNC(=O)C6C(CN6C(=O)C7CCCN7C(=O)C(CCCN=C(N)N)NC(=O)(CCCN=C(N)N)N)O)C(=O)N(CCCN=C(N)N)C(=O)O
| StdInChI = 1S/C59H89N19O13S/c60-37(14-5-19-67-57(61)62)48(82)72-38(15-6-20-68-58(63)64)52(86)75-22-8-18-43(75)54(88)77-30-35(80)26-44(77)50(84)70-28-47(81)71-40(27-36-13-9-23-92-36)49(83)74-41(31-79)53(87)76-29-34-12-2-1-10-32(34)24-46(76)55(89)78-42-17-4-3-11-33(42)25-45(78)51(85)73-39(56(90)91)16-7-21-69-59(65)66/h1-2,9-10,12-13,23,33,35,37-46,79-80H,3-8,11,14-22,24-31,60H2,(H,70,84)(H,71,81)(H,72,82)(H,73,85)(H,74,83)(H,90,91)(H4,61,62,67)(H4,63,64,68)(H4,65,66,69)/t33-,35+,37+,38-,39-,40-,41-,42-,43-,44-,45?,46+/m0/s1 | StdInChI = 1S/C59H89N19O13S/c60-37(14-5-19-67-57(61)62)48(82)72-38(15-6-20-68-58(63)64)52(86)75-22-8-18-43(75)54(88)77-30-35(80)26-44(77)50(84)70-28-47(81)71-40(27-36-13-9-23-92-36)49(83)74-41(31-79)53(87)76-29-34-12-2-1-10-32(34)24-46(76)55(89)78-42-17-4-3-11-33(42)25-45(78)51(85)73-39(56(90)91)16-7-21-69-59(65)66/h1-2,9-10,12-13,23,33,35,37-46,79-80H,3-8,11,14-22,24-31,60H2,(H,70,84)(H,71,81)(H,72,82)(H,73,85)(H,74,83)(H,90,91)(H4,61,62,67)(H4,63,64,68)(H4,65,66,69)/t33-,35+,37+,38-,39-,40-,41-,42-,43-,44-,45-,46+/m0/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = QURWXBZNHXJZBE-OVZQYVDUSA-N | StdInChIKey = QURWXBZNHXJZBE-SKXRKSCCSA-N
}} }}

'''Icatibant''', sold under the brand name '''Firazyr''', is a medication for the symptomatic treatment of acute attacks of ] (HAE) in adults with ] deficiency.<ref name=Jerini2008>{{cite press release|title=Jerini Receives European Commission Approval for Firazyr (Icatibant) in the Treatment of HAE |publisher=] |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 |access-date=2008-07-22 }}{{dead link|date=April 2017 |bot=InternetArchiveBot |fix-attempted=yes }}</ref><ref name="Firazyr FDA label">{{cite web | title=Firazyr- icatibant acetate injection, solution | website=DailyMed | date=16 December 2019 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=ed6657ca-ab68-477a-9968-e12dc928b540 | access-date=17 April 2020}}</ref><ref name="Firazyr EPAR">{{cite web | title=Firazyr EPAR | website=] (EMA) | date=17 September 2018 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/firazyr | access-date=17 April 2020}}</ref> It is not effective in angioedema caused by medication from the ] class.<ref>{{cite journal | vauthors = Sinert R, Levy P, Bernstein JA, Body R, Sivilotti ML, Moellman J, Schranz J, Baptista J, Kimura A, Nothaft W | display-authors = 6 | title = Randomized Trial of Icatibant for Angiotensin-Converting Enzyme Inhibitor-Induced Upper Airway Angioedema | journal = The Journal of Allergy and Clinical Immunology. In Practice | volume = 5 | issue = 5 | pages = 1402–1409.e3 | date = September–October 2017 | pmid = 28552382 | doi = 10.1016/j.jaip.2017.03.003 | doi-access = free }}</ref>

It is a ] consisting of ten ]s, which is a selective and specific antagonist of ] ].

==Mechanism 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, ] and causes ]s to contract. Bradykinin plays an important role as the mediator of pain. Surplus ] is responsible for the typical symptoms of inflammation, such as swelling, ], overheating and pain. These symptoms are mediated by activation of bradykinin B<sub>2</sub> receptors. Icatibant acts as a bradykinin inhibitor by blocking the binding of native bradykinin to the bradykinin B<sub>2</sub> receptor. Little is known about the effects of icatibant on the bradykinin B<sub>1</sub> receptor.

== Society and culture ==
=== Legal status ===
Icatibant received ] status in Australia, the EU, Switzerland, and the US for the treatment of hereditary angioedema (HAE).<ref>{{cite journal | vauthors = Longhurst HJ | title = Management of acute attacks of hereditary angioedema: potential role of icatibant | journal = Vascular Health and Risk Management | volume = 6 | pages = 795–802 | date = September 2010 | pmid = 20859548 | pmc = 2941790 | doi = 10.2147/vhrm.s4332 | doi-access = free }}</ref>

In the EU, the approval by the European Commission (July 2008) allows ] to market Firazyr in the European Union's 27 member states, as well as Switzerland, Liechtenstein and Iceland, making it the first product to be approved in all EU countries for the treatment of hereditary angioedema.<ref name="Jerini2008"/> In the US, the drug was granted FDA approval in August 2011.<ref>{{cite press release|url=http://www.shire.com/shireplc/en/media/shirenews?id=520 |title=FDA Approves Shire's Firazyr (icatibant injection) for Acute Attacks of Hereditary Angioedema (HAE) |publisher=Shire |access-date=2011-08-28}}</ref>

== References ==
{{Reflist}}

{{Other hematological agents}}
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