icatibant   Click here for help

GtoPdb Ligand ID: 667

Synonyms: D-Arg-[Hyp3,Thi5,D-Tic7,Oic8]BK | Firazyr® | HOE 140 | HOE140
Approved drug Immunopharmacology Ligand
icatibant is an approved drug (EMA (2008), FDA (2011))
Compound class: Peptide or derivative
Comment: Synthetic analogue of bradykinin. There is some ambiguity in the literature and on online resources as to the exact chemical structure and stereochemistry of icatibant.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES OC[C@@H](C(=O)N1Cc2ccccc2CC1C(=O)N1[C@H]2CCCC[C@H]2CC1C(=O)N[C@H](C(=O)O)CCCN=C(N)N)NC(=O)[C@H](Cc1cccs1)NC(=O)CNC(=O)C1C[C@H](CN1C(=O)C1CCCN1C(=O)C(NC(=O)[C@@H](CCCN=C(N)N)N)CCCN=C(N)N)O
Isomeric SMILES OC[C@@H](C(=O)N1Cc2ccccc2CC1C(=O)N1[C@H]2CCCC[C@H]2CC1C(=O)N[C@H](C(=O)O)CCCN=C(N)N)NC(=O)[C@H](Cc1cccs1)NC(=O)CNC(=O)C1C[C@H](CN1C(=O)C1CCCN1C(=O)C(NC(=O)[C@@H](CCCN=C(N)N)N)CCCN=C(N)N)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
InChI Key QURWXBZNHXJZBE-MCDGZUPGSA-N
References
1. Amblard M, Daffix I, Bedos P, Bergé G, Pruneau D, Paquet JL, Luccarini JM, Bélichard P, Dodey P, Martinez J. (1999)
Design and synthesis of potent bradykinin agonists containing a benzothiazepine moiety.
J Med Chem, 42 (20): 4185-92. [PMID:10514288]
2. Anderson M. 
We are finally unravelling the mystery of what causes severe covid-19.
Accessed on 22/09/2020. Modified on 22/09/2020. New Scientist, https://institutions.newscientist.com/article/2253987-we-are-finally-unravelling-the-mystery-of-what-causes-severe-covid-19/
3. Aramori I, Zenkoh J, Morikawa N, O'Donnell N, Asano M, Nakamura K, Iwami M, Kojo H, Notsu Y. (1997)
Novel subtype-selective nonpeptide bradykinin receptor antagonists FR167344 and FR173657.
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4. Bastian S, Loillier B, Paquet JL, Pruneau D. (1997)
Stable expression of human kinin B1 receptor in 293 cells: pharmacological and functional characterization.
Br J Pharmacol, 122 (2): 393-9. [PMID:9313952]
5. Burgess GM, Perkins MN, Rang HP, Campbell EA, Brown MC, McIntyre P, Urban L, Dziadulewicz EK, Ritchie TJ, Hallett A et al.. (2000)
Bradyzide, a potent non-peptide B(2) bradykinin receptor antagonist with long-lasting oral activity in animal models of inflammatory hyperalgesia.
Br J Pharmacol, 129 (1): 77-86. [PMID:10694205]
6. De Falco L, Fioravanti A, Galeazzi M, Tenti S. (2013)
Bradykinin and its role in osteoarthritis.
Reumatismo, 65 (3): 97-104. [PMID:23884024]
7. Garvin MR, Alvarez C, Miller JI, Prates ET, Walker AM, Amos BK, Mast AE, Justice A, Aronow B, Jacobson D. (2020)
A mechanistic model and therapeutic interventions for COVID-19 involving a RAS-mediated bradykinin storm.
Elife, 9. DOI: 10.7554/eLife.59177 [PMID:32633718]
8. Gobeil F, Pheng LH, Badini I, Nguyen-Le XK, Pizard A, Rizzi A, Blouin D, Regoli D. (1996)
Receptors for kinins in the human isolated umbilical vein.
Br J Pharmacol, 118 (2): 289-94. [PMID:8735629]
9. Hess JF, Borkowski JA, MacNeil T, Stonesifer GY, Fraher J, Strader CD, Ransom RW. (1994)
Differential pharmacology of cloned human and mouse B2 bradykinin receptors.
Mol Pharmacol, 45: 1-8. [PMID:8302267]
10. Jones C, Phillips E, Davis C, Arbuckle J, Yaqoob M, Burgess GM, Docherty RJ, Webb M, Bevan SJ, McIntyre P. (1999)
Molecular characterisation of cloned bradykinin B1 receptors from rat and human.
Eur J Pharmacol, 374: 423-433. [PMID:10422787]
11. Robinson EL, Alkass K, Bergmann O, Maguire JJ, Roderick HL, Davenport AP. (2020)
Genes encoding ACE2, TMPRSS2 and related proteins mediating SARS-CoV-2 viral entry are upregulated with age in human cardiomyocytes.
J Mol Cell Cardiol, 147: 88-91. [PMID:32818486]
12. Roche JA, Roche R. (2020)
A hypothesized role for dysregulated bradykinin signaling in COVID-19 respiratory complications.
FASEB J, 34 (6): 7265-7269. [PMID:32359101]
13. van de Veerdonk FL, Kouijzer IJE, de Nooijer AH, van der Hoeven HG, Maas C, Netea MG, Brüggemann RJM. (2020)
Outcomes Associated With Use of a Kinin B2 Receptor Antagonist Among Patients With COVID-19.
JAMA Netw Open, 3 (8): e2017708. [PMID:32789513]