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))
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.
The HELM annotation is PEPTIDE1{[dR].(R,[dR]).(P,[dP]).[*C(=O)C1C[C@H](CN1*)O |$_R2;;;;;;;;_R1;$|].G.[Thi].S.[*C(=O)C1Cc2ccccc2CN1* |$_R2;;;;;;;;;;;;;_R1$|].[*C(=O)C1C[C@@H]2CCCC[C@@H]2N1* |$_R2;;;;;;;;;;;;_R1$|].R}$$$$V2.0 (from PubChem).
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2D Structure
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SMILES / InChI / InChIKey
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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
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Design and synthesis of potent bradykinin agonists containing a benzothiazepine moiety.
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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/
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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)
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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.
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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.
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