Icatibant (Standard)

CAT: 0804-HY-17446R-01Size: 1 mgDry Ice: NoHazardous: No

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CAT#:0804-HY-17446R-01Size:1 mg

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Description

Icatibant (Standard) is the analytical standard of Icatibant. This product is intended for research and analytical applications. 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[1][2][3].

CAS Number

130308-48-4

Product Name Alternative

HOE 140 (Standard)

UNSPSC

12352209

Target

Bradykinin Receptor; Reference Standards

Type

Reference Standards

Related Pathways

GPCR/G Protein; Others

Field of Research

Endocrinology

Assay Protocol

https://www.medchemexpress.com/icatibant-standard.html

Smiles

[H][C@]1(C[C@@H](C(N[C@H](C(O)=O)CCCNC(N)=N)=O)N2C([C@@H]3N(C([C@H](CO)NC([C@H](CC4=CC=CS4)NC(CNC([C@@H]5C[C@@H](O)CN5C([C@H]6N(C([C@H](CCCNC(N)=N)NC([C@H](N)CCCNC(N)=N)=O)=O)CCC6)=O)=O)=O)=O)=O)CC7=C(C=CC=C7)C3)=O)[C@]2([H])CCCC1

Molecular Formula

C59H89N19O13S

Molecular Weight

1304.52

References & Citations

[1]Hock FJ, et al. Hoe 140 a new potent and long acting bradykinin-antagonist: in vitro studies. Br J Pharmacol. 1991 Mar;102 (3) :769-73.|[2]Y Arai, et al. 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.|[3]Marie-Thérèse Bawolak, et al The Bradykinin B2 Receptor Antagonist Icatibant (Hoe 140) Blocks Aminopeptidase N at Micromolar Concentrations: Off-Target Alterations of Signaling Mediated by the Bradykinin B1 and Angiotensin Receptors. Eur J Pharmacol. 2006 Dec 3;551 (1-3) :108-11.

Shipping Conditions

Room temperature

Scientific Category

Reference Standards

Chemical Information

Icatibant

Icatibant is a synthetic decapeptide with 5 nonproteinogenic amino acid antagonist targeting the B2 receptors with a similar affinity to bradykinin. It is resistant to bradykinin-cleaving enzyme degradation and has a potency of 2-3 times higher than earlier B2 receptors antagonists, thus representing a new class of medication. It was investigated as a potential treatment of hereditary angioedema (HAE) as bradykinin was implicated in HAE swelling; specifically, mice lacking B2 receptors showed reduced swelling, thus demonstrating bradykinin involvement in the disease pathophysiology. Icatibant was approved by the FDA on August 25, 2011, and by the EMA in 2008 as a treatment for hereditary angioedema. The FDA approval was based on positive results obtained from 3 double-blind, randomized, controlled clinical trials known as FAST 1, 2, and 3, where a median time to almost complete symptom relief was observed to be 8 hours compared to 36 hours for the placebo treatment.

CAS Number	130308-48-4
PubChem CID	6918173
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
Molecular Formula	C59H89N19O13S
Molecular Weight	1304.5
XLogP	-6.4
Topological Polar Surface Area	552
Hydrogen Bond Donor Count	15
Hydrogen Bond Acceptor Count	18
Rotatable Bond Count	30
Heavy Atom Count	92
Formal Charge	0
Complexity	2720

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

InChIKey

QURWXBZNHXJZBE-SKXRKSCCSA-N

Chemical Structure

2D Structure

CAS: 130308-48-4

CID: 6918173

Formula: C59H89N19O13S

MW: 1304.5

Interactive 3D Structure

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View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	1304.5
XLogP3	-6.4
Hydrogen Bond Donor Count	15
Hydrogen Bond Acceptor Count	18
Rotatable Bond Count	30
Exact Mass	1303.66079514
Monoisotopic Mass	1303.66079514
Topological Polar Surface Area	552 Å²
Heavy Atom Count	92
Formal Charge	0
Complexity	2720
Isotope Atom Count	0
Defined Atom Stereocenter Count	12
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

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