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
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
B2 receptor Primary target of this compound Hs Antagonist Antagonist 8.4 pA2 - 8
pA2 8.4 [8]
B2 receptor Primary target of this compound Hs Antagonist Antagonist 10.2 pKi - 1
pKi 10.2 (Ki 6.4x10-11 M) [1]
B2 receptor Rn Antagonist Antagonist 10.0 – 10.3 pKi - 5
pKi 10.0 – 10.3 [5]
B2 receptor Mm Antagonist Antagonist 9.6 pKi - 9
pKi 9.6 [9]
B1 receptor Hs Antagonist Antagonist 6.4 – 7.0 pKi - 4,10
pKi 6.4 – 7.0 [4,10]
B1 receptor Rn Antagonist Antagonist 6.1 – 6.4 pKi - 10
pKi 6.1 – 6.4 [10]
B2 receptor Primary target of this compound Hs Antagonist Antagonist 8.0 – 9.4 pIC50 - 3,9
pIC50 8.0 – 9.4 [3,9]
Ligand mentioned in the following text fields