Icatibant acetate | CAS# 138614-30-9 | Biochemical

MedKoo Cat#: 575457 | Name: Icatibant acetate

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Description:

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

Icatibant acetate 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 acetate

CAS#138614-30-9

Theoretical Analysis

MedKoo Cat#: 575457

Name: Icatibant acetate

CAS#: 138614-30-9

Chemical Formula: C61H93N19O15S

Exact Mass:

Molecular Weight: 1364.59

Elemental Analysis: C, 53.69; H, 6.87; N, 19.50; O, 17.59; S, 2.35

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 300.00	2 Weeks
5mg	USD 750.00	2 Weeks

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Related CAS #

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Synonym

Firazyr; HOE 140; HOE140; HOE-140; Icatibant acetate

IUPAC/Chemical Name

L-Arginine, D-arginyl-L-arginyl-L-prolyl-trans-4-hydroxy-L-prolylglycyl-3-(2-thienyl)-L-alanyl-L-seryl-D-1,2,3,4-tetrahydro-3-isoquinolinecarbonyl-L-(2alpha,3abeta,7abeta)-octahydro-1H-indole-2-carbonyl-, acetate (salt)

InChi Key

HKMZRZUEADSZDQ-DZJWSCHMSA-N

InChi Code

InChI=1S/C59H89N19O13S.C2H4O2/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;1-2(3)4/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);1H3,(H,3,4)/t33-,35+,37+,38-,39-,40-,41-,42-,43-,44-,45-,46+;/m0./s1

SMILES Code

CC(=O)O.N[C@H](CCCNC(=N)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N1CCC[C@H]1C(=O)N2C[C@H](O)C[C@H]2C(=O)NCC(=O)N[C@@H](Cc3cccs3)C(=O)N[C@@H](CO)C(=O)N4Cc5ccccc5C[C@@H]4C(=O)N6[C@H]7CCCC[C@H]7C[C@H]6C(=O)N[C@@H](CCCNC(=N)N)C(=O)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

Product Data

Instruction

View handling instruction

Biological target:

Icatibant acetate (HOE-140 acetate) is a potent and specific peptide antagonist of bradykinin B2 receptor with an 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
	DMSO	65.0	47.63
	Ethanol	0.3	0.18
	PBS (pH 7.2)	10.0	7.33

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 1,364.59 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.

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:

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. Hock, F.J., Wirth, K., Albus, U., et al. Hoe 140 a new potent and long acting bradykinin-antagonist: In vitro studies. Br. J. Pharmacol. 102(3), 769-773 (1991). 2. Han, E.D., MacFarlane, R.C., Mulligan, A.N., et al. Increased vascular permeability in C1 inhibitor-deficient mice mediated by the bradykinin type 2 receptor. J. Clin. Invest. 109(8), 1057-1063 (2002).