MedKoo Cat#: 314226 | Name: Icatibant
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Icatibant is a peptidomimetic drug consisting of ten amino acids, which is a selective and specific antagonist of bradykinin B2 receptors. It has been approved by the European Commission for the symptomatic treatment of acute attacks of hereditary angioedema (HAE) in adults with C1-esterase-inhibitor deficiency.

Chemical Structure

Icatibant
Icatibant
CAS#130308-48-4

Theoretical Analysis

MedKoo Cat#: 314226

Name: Icatibant

CAS#: 130308-48-4

Chemical Formula: C59H89N19O13S

Exact Mass: 1303.6608

Molecular Weight: 1304.54

Elemental Analysis: C, 54.32; H, 6.88; N, 20.40; O, 15.94; S, 2.46

Price and Availability

Size Price Availability Quantity
200mg USD 2,650.00
500mg USD 3,150.00
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Related CAS #
No Data
Synonym
Firazyr
IUPAC/Chemical Name
D-Arginyl-L-arginyl-L-prolyl-L[(4R)-4-hydroxyprolyl]-glycyl-L[3-(2-thienyl)alanyl]-L-seryl-D-(1,2,3,4-tetrahydroisoquinolin-3-ylcarbonyl)-L[(3aS,7aS)-octahydroindol-2-ylcarbonyl]-L-arginine
InChi Key
VDCFYALYBYCEPN-JXLPZLSSSA-N
InChi Code
InChI=1S/C59H89N19O13S/c60-36(13-5-19-68-57(62)63)49(83)73-40(15-6-20-69-58(64)65)51(85)75-21-7-16-44(75)54(88)76(52(86)42-25-34(80)28-71-42)29-47(81)77(50(84)37(61)26-35-12-8-22-92-35)46(30-79)55(89)78(53(87)43-24-32-10-3-4-14-38(32)72-43)45(56(90)91)18-17-39(74-59(66)67)48(82)41-23-31-9-1-2-11-33(31)27-70-41/h1-2,8-9,11-12,22,32,34,36-46,70-72,79-80H,3-7,10,13-21,23-30,60-61H2,(H,73,83)(H,90,91)(H4,62,63,68)(H4,64,65,69)(H4,66,67,74)/t32-,34+,36+,37-,38-,39?,40-,41?,42?,43?,44-,45-,46-/m0/s1
SMILES Code
N=C(N)NC(C(C1NCC2=C(C=CC=C2)C1)=O)CC[C@@H](C(O)=O)N(C([C@H](CO)N(C(CN(C([C@H]3N(C([C@H](CCCNC(N)=N)NC([C@@H](CCCNC(N)=N)N)=O)=O)CCC3)=O)C(C4NC[C@H](O)C4)=O)=O)C([C@H](CC5=CC=CS5)N)=O)=O)C(C6N[C@@]7([H])CCCC[C@@]7([H])C6)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO.
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Safety Data Sheet (SDS)
Biological target:
Icatibant (HOE-140) is a potent and specific peptide antagonist of bradykinin B2 receptor with IC50 and Ki of 1.07 nM and 0.798 nM respectively.
In vitro activity:
Ornithokinin and HOE140 at nanomolar concentrations stimulated intracellular inositol phosphate accumulation and induced a significant transient rise in intracelluar free Ca2+, whereas bradykinin was ineffective even at 100 nM. Hence the principal B2 receptor antagonist HOE140 is a potent agonist of the chicken kinin receptor. Reference: J Biol Chem. 1997 May 9;272(19):12475-81. https://pubmed.ncbi.nlm.nih.gov/9139696/
In vivo activity:
Subcutaneous administration of Icatibant (0.3 or 1.5 mg/kg) significantly suppressed shortening of the mouse large intestine and worsening of the general health. Oral administration of Icatibant (50 mg/kg) significantly suppressed shortening of the large intestine, the onset of diarrhea, and worsening of the general health. In addition, the oral treatment significantly inhibited the development of colitis that was observed histopathologically. Reference: Dig Dis Sci. 1999 Apr;44(4):845-51. https://pubmed.ncbi.nlm.nih.gov/10219847/
Solvent mg/mL mM
Solubility
Water 100.0 76.66
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 1,304.54 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Schroeder C, Beug H, Müller-Esterl W. Cloning and functional characterization of the ornithokinin receptor. Recognition of the major kinin receptor antagonist, HOE140, as a full agonist. J Biol Chem. 1997 May 9;272(19):12475-81. doi: 10.1074/jbc.272.19.12475. PMID: 9139696. 2. Hock FJ, Wirth K, Albus U, Linz W, Gerhards HJ, Wiemer G, Henke S, Breipohl G, König W, Knolle J, et al. Hoe 140 a new potent and long acting bradykinin-antagonist: in vitro studies. Br J Pharmacol. 1991 Mar;102(3):769-73. doi: 10.1111/j.1476-5381.1991.tb12248.x. PMID: 1364851; PMCID: PMC1917958. 3. Arai Y, Takanashi H, Kitagawa H, Wirth KJ, Okayasu I. Effect of icatibant, a bradykinin B2 receptor antagonist, on the development of experimental ulcerative colitis in mice. Dig Dis Sci. 1999 Apr;44(4):845-51. doi: 10.1023/a:1026694732602. PMID: 10219847. 4. Sgarra L, Coco C, Montagnani M, Potenza MA. Pulsatile antagonism on bradykinin 2-receptor (BK2R) by icatibant triggers the most effective kinin-dependent post-conditioning on rat hearts. Eur Rev Med Pharmacol Sci. 2019 May;23(10):4439-4447. doi: 10.26355/eurrev_201905_17953. PMID: 31173320.
In vitro protocol:
1. Schroeder C, Beug H, Müller-Esterl W. Cloning and functional characterization of the ornithokinin receptor. Recognition of the major kinin receptor antagonist, HOE140, as a full agonist. J Biol Chem. 1997 May 9;272(19):12475-81. doi: 10.1074/jbc.272.19.12475. PMID: 9139696. 2. Hock FJ, Wirth K, Albus U, Linz W, Gerhards HJ, Wiemer G, Henke S, Breipohl G, König W, Knolle J, et al. Hoe 140 a new potent and long acting bradykinin-antagonist: in vitro studies. Br J Pharmacol. 1991 Mar;102(3):769-73. doi: 10.1111/j.1476-5381.1991.tb12248.x. PMID: 1364851; PMCID: PMC1917958.
In vivo protocol:
1. Arai Y, Takanashi H, Kitagawa H, Wirth KJ, Okayasu I. Effect of icatibant, a bradykinin B2 receptor antagonist, on the development of experimental ulcerative colitis in mice. Dig Dis Sci. 1999 Apr;44(4):845-51. doi: 10.1023/a:1026694732602. PMID: 10219847. 2. Sgarra L, Coco C, Montagnani M, Potenza MA. Pulsatile antagonism on bradykinin 2-receptor (BK2R) by icatibant triggers the most effective kinin-dependent post-conditioning on rat hearts. Eur Rev Med Pharmacol Sci. 2019 May;23(10):4439-4447. doi: 10.26355/eurrev_201905_17953. PMID: 31173320.
 1: Kawalec P, Holko P, Paszulewicz A, Obtułowicz K. [Administration of conestat alfa, human C1 esterase inhibitor and icatibant in the treatment of acute angioedema attacks in adults with hereditary angioedema due to C1 esterase inhibitor deficiency. Treatment comparison based on systematic review results]. Pneumonol Alergol Pol. 2013;81(2):95-104. Review. Polish. PubMed PMID: 23420425. 2: Cole SW, Lundquist LM. Icatibant for the treatment of hereditary angioedema. Ann Pharmacother. 2013 Jan;47(1):49-55. doi: 10.1345/aph.1R423. Epub 2012 Dec 18. Review. PubMed PMID: 23249729. 3: Charignon D, Späth P, Martin L, Drouet C. Icatibant , the bradykinin B2 receptor antagonist with target to the interconnected kinin systems. Expert Opin Pharmacother. 2012 Oct;13(15):2233-47. doi: 10.1517/14656566.2012.723692. Epub 2012 Sep 13. Review. PubMed PMID: 22970904. 4: Drake D. Towards evidence-based emergency medicine: best BETs from the Manchester Royal Infirmary. Management of adult patients with icatibant in hereditary angioedema. Emerg Med J. 2011 Aug;28(8):720-1. doi: 10.1136/emermed-2011-200396-4. Review. PubMed PMID: 21788245. 5: Bouillet L. Icatibant in hereditary angioedema: news and challenges. Expert Rev Clin Immunol. 2011 May;7(3):267-72. doi: 10.1586/eci.11.16. Review. PubMed PMID: 21595592. 6: Icatibant. Attacks of hereditary angioedema: continue to use C1 esterase inhibitor. Prescrire Int. 2010 Nov;19(110):245-7. Review. PubMed PMID: 21284353. 7: Longhurst HJ. Management of acute attacks of hereditary angioedema: potential role of icatibant. Vasc Health Risk Manag. 2010 Sep 7;6:795-802. Review. PubMed PMID: 20859548; PubMed Central PMCID: PMC2941790. 8: Gras J. Icatibant for hereditary angioedema. Drugs Today (Barc). 2009 Dec;45(12):855-64. doi: 1396674/dot.2009.45.12.1424267. Review. PubMed PMID: 20135020. 9: Cruden NL, Newby DE. Therapeutic potential of icatibant (HOE-140, JE-049). Expert Opin Pharmacother. 2008 Sep;9(13):2383-90. doi: 10.1517/14656566.9.13.2383 . Review. PubMed PMID: 18710362. 10: Icatibant: HOE 140, JE 049, JE049. Drugs R D. 2005;6(4):239-44. Review. PubMed PMID: 15991885.