Icatibant

Icatibant
Clinical data
Trade names	Firazyr
Other names	Hoe 140, JE 049
AHFS/Drugs.com	Monograph
License data	US DailyMed: Icatibant;
Pregnancy; category	AU: C;
Routes of; administration	Subcutaneous
ATC code	B06AC02 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); US: ℞-only; EU: Rx-only; In general: ℞ (Prescription only);
Identifiers
	IUPAC name (2S)-2-[[(2S,3aS,7aS)-1-[(3R)-2-[(2S)-2-[[(2S)-2-[[2-[[(2S,4R)-1-[(2S)-1-[(2S)-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;
CAS Number	130308-48-4 ;
PubChem CID	6918173;
IUPHAR/BPS	667;
DrugBank	DB06196 ;
ChemSpider	16736634 ;
UNII	7PG89G35Q7;
KEGG	as salt: D04492;
ChEBI	CHEBI:68556 ;
ChEMBL	ChEMBL1743581 ;
CompTox Dashboard (EPA)	DTXSID20903963 ;
Chemical and physical data
Formula	C59H89N19O13S
Molar mass	1304.54 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CC[C@H]2[C@@H](C1)C[C@H](N2C(=O)[C@H]3CC4=CC=CC=C4CN3C(=O)[C@H](CO)NC(=O)[C@H](CC5=CC=CS5)NC(=O)CNC(=O)[C@@H]6C[C@H](CN6C(=O)[C@@H]7CCCN7C(=O)[C@H](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;
	InChI InChI=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 ; Key:QURWXBZNHXJZBE-SKXRKSCCSA-N ;
	(what is this?) (verify)

Icatibant, sold under the brand name Firazyr, is a medication for the symptomatic treatment of acute attacks of hereditary angioedema (HAE) in adults with C1-esterase-inhibitor deficiency.^[5]^[3]^[4] It is not effective in angioedema caused by medication from the ACE inhibitor class.^[6]

It is a peptidomimetic consisting of ten amino acids, which is a selective and specific antagonist of bradykinin B₂ receptors.

^ "Icatibant: HOE 140, JE 049, JE049". Drugs in R&D. 5 (6): 343–8. 2004. doi:10.2165/00126839-200405060-00006. PMID 15563238. S2CID 25491021.
^ https://www.tga.gov.au/resources/prescription-medicines-registrations/icatibant-wkt-wockhardt-bio-pty-ltd
^ ^a ^b "Firazyr- icatibant acetate injection, solution". DailyMed. 16 December 2019. Retrieved 17 April 2020.
^ ^a ^b "Firazyr EPAR". European Medicines Agency (EMA). 17 September 2018. Retrieved 17 April 2020.
^ "Jerini Receives European Commission Approval for Firazyr (Icatibant) in the Treatment of HAE" (Press release). Jerini AG. 15 July 2008. Retrieved 22 July 2008.
^ Sinert R, Levy P, Bernstein JA, Body R, Sivilotti ML, Moellman J, et al. (September–October 2017). "Randomized Trial of Icatibant for Angiotensin-Converting Enzyme Inhibitor-Induced Upper Airway Angioedema". The Journal of Allergy and Clinical Immunology. In Practice. 5 (5): 1402–1409.e3. doi:10.1016/j.jaip.2017.03.003. PMID 28552382.{{cite journal}}: CS1 maint: overridden setting (link)

[1] "Icatibant: HOE 140, JE 049, JE049". Drugs in R&D. 5 (6): 343–8. 2004. doi:10.2165/00126839-200405060-00006. PMID 15563238. S2CID 25491021.

[2] ttps://www.tga.gov.au/resources/prescription-medicines-registrations/icatibant-wkt-wockhardt-bio-pty-ltd

[Firazyr_FDA_label-3] "Firazyr- icatibant acetate injection, solution". DailyMed. 16 December 2019. Retrieved 17 April 2020.

[Firazyr_EPAR-4] "Firazyr EPAR". European Medicines Agency (EMA). 17 September 2018. Retrieved 17 April 2020.

[Jerini2008-5] "Jerini Receives European Commission Approval for Firazyr (Icatibant) in the Treatment of HAE" (Press release). Jerini AG. 15 July 2008. Retrieved 22 July 2008.

[6] Sinert R, Levy P, Bernstein JA, Body R, Sivilotti ML, Moellman J, et al. (September–October 2017). "Randomized Trial of Icatibant for Angiotensin-Converting Enzyme Inhibitor-Induced Upper Airway Angioedema". The Journal of Allergy and Clinical Immunology. In Practice. 5 (5): 1402–1409.e3. doi:10.1016/j.jaip.2017.03.003. PMID 28552382.{{cite journal}}: CS1 maint: overridden setting (link)

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