icatibant

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icatibant

GtoPdb Ligand ID: 667

Synonyms: D-Arg-[Hyp³,Thi⁵,D-Tic⁷,Oic⁸]BK | Firazyr® | HOE 140 | HOE140

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.
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).

View interactive charts of activity data across species

2D Structure

SMILES / InChI / InChIKey

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

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Structurally Similar Ligands
lonodelestat
terlipressin
carbetocin Targets OT receptor
mersacidin
davalintide Targets AMY₃ receptor; CT receptor
motixafortide Targets CXCR4
OSTN (81-102) Targets chemerin receptor 2
Pomc (141-162) Targets GPR68
CARTPT (76-96) Targets GPR68
OSTN (115-133) Targets GPR68
oryzatensin Targets C3a receptor
casoxin C Targets C3a receptor
AUNP-12 Targets programmed cell death 1 (CD279)
C391 Targets PAR2
TP508 Targets integrin αVβ3
rotigaptide
zyklophin Targets δ receptor; κ receptor; μ receptor
pepcan-12 Targets CB₁ receptor; CB₂ receptor
vosoritide Targets Guanylyl cyclase-B
cenderitide Targets Guanylyl cyclase-A; Guanylyl cyclase-B
NM4-C₁₆ Targets NMU1 receptor; NMU2 receptor
peptide ligand 2 [PMID: 19055415] Targets integrin, alpha 3 subunit (antigen CD49C, alpha 3 subunit of VLA-3 receptor)
Dup-714 Targets coagulation factor II, thrombin; plasminogen activator, tissue type
Elabela/Toddler-11 Targets apelin receptor
Elabela/Toddler-21 Targets apelin receptor
Elabela/Toddler-32 Targets apelin receptor
MM07 Targets apelin receptor
A(9-26)INSL3 Targets RXFP2
compound 8d [PMID: 24999562] Targets NMU1 receptor
conopeptide Y-PI1 Targets K_v1.6
neurotensin-(8-13)
angiotensin-(1-9) Targets Angiotensin-converting enzyme 2
CGEN-856 Targets MAS1
calcitonin (salmon) Targets AM₁ receptor; AM₂ receptor; AMY₁ receptor; AMY₃ receptor; CGRP receptor; CT receptor
corticotropin zinc hydroxide Targets MC₂ receptor
TRV027 Targets AT₁ receptor
angiotensin A Targets AT₁ receptor; AT₂ receptor
bivalirudin Targets coagulation factor II, thrombin
lepirudin Targets coagulation factor II, thrombin
desirudin Targets coagulation factor II, thrombin
CRAMP Targets FPR2/ALX
V3 peptide Targets FPR2/ALX
alarin Targets GAL₁ receptor; GAL₂ receptor; GAL₃ receptor
galanin(10-29) (pig) Targets GAL₁ receptor; GAL₂ receptor; GAL₃ receptor
galanin(10-29) (rat/mouse) Targets GAL₁ receptor; GAL₂ receptor
galanin(3-29) (rat/mouse) Targets GAL₁ receptor; GAL₂ receptor; GAL₃ receptor
galanin(3-29) (pig) Targets GAL₁ receptor; GAL₂ receptor; GAL₃ receptor
galanin(7-29) (pig) Targets GAL₁ receptor; GAL₂ receptor; GAL₃ receptor
alamandine
FLPLAR Targets C3a receptor
degarelix Targets GnRH₁ receptor
[¹²⁵I]angiotensin-(1-7) (human, mouse, rat) Targets MAS1
LL-37 Targets FPR2/ALX; P2X7
[³H]d[D-Arg⁸]VP
angiotensin IV Targets AT₁ receptor
galanin(5-29) (pig) Targets GAL₂ receptor
ABS-201 Targets NTS₁ receptor
α-conotoxin GI Targets nicotinic acetylcholine receptor α1 subunit
α-conotoxin PnIA Targets nicotinic acetylcholine receptor α3 subunit; nicotinic acetylcholine receptor α5 subunit
α-conotoxin AuIB Targets nicotinic acetylcholine receptor α3 subunit
CGP42112 Targets AT₂ receptor
R-954 Targets B₁ receptor
ganirelix Targets GnRH₁ receptor
BODIPY^® TMR-NMU
iturelix Targets GnRH₁ receptor
[Pro³⁴]NPY Targets Y₁ receptor
[³H]SP (human, mouse, rat) Targets NK₁ receptor
[³H]neurotensin (human, mouse, rat)
[³H]Lys-[Leu⁸][des-Arg⁹]BK Targets B₁ receptor
[³H]Lys-[des-Arg⁹]BK Targets B₁ receptor
[³H]BK (human, mouse, rat) Targets B₂ receptor
[¹²⁵I]SP (human, mouse, rat) Targets NK₁ receptor
[¹²⁵I]PYY-(3-36) (human) Targets Y₂ receptor
[¹²⁵I]PP (human) Targets Y₄ receptor
[¹²⁵I]orexin A (human, mouse, rat)
[¹²⁵I]NPFF Targets NPFF1 receptor; NPFF2 receptor
[¹²⁵I]motilin (human) Targets motilin receptor
[¹²⁵I]CT (salmon) Targets CT receptor
[¹²⁵I]CT (human) Targets CT receptor
[¹²⁵I]αCGRP (human) Targets AMY₁ receptor; CGRP receptor
[¹²⁵I][Tyr⁸]bradykinin Targets B₂ receptor
α-neodynorphin
β-endorphin Targets δ receptor; κ receptor; μ receptor
β-endorphin Targets δ receptor; κ receptor; μ receptor
endomorphin-2 Targets μ receptor
[des-octanoyl]ghrelin Targets ghrelin receptor
apelin-17 Targets apelin receptor
chemerin C-terminal peptide Targets CCRL2; chemerin receptor 1; chemerin receptor 2
FPYVAE peptide [PMID: 20494585] Targets hydroxymethylglutaryl-CoA reductase
ω-conotoxin GVIA Targets Ca_v2.1; Ca_v2.2
angiotensin II Targets AT₁ receptor; AT₂ receptor; Angiotensin-converting enzyme; K_2P3.1
helodermin Targets VPAC₁ receptor; VPAC₂ receptor
d[Pen¹,Tyr(Me)²]AVP Targets V_1A receptor; V_1B receptor; V₂ receptor
d(CH₂)₅[Tyr(Me)²]AVP Targets OT receptor; V_1A receptor; V_1B receptor; V₂ receptor
d(CH₂)₅[Tyr(Et)²,Val⁴,des-Gly⁹]AVP Targets V_1A receptor; V_1B receptor; V₂ receptor
atosiban Targets OT receptor; V_1A receptor; V_1B receptor; V₂ receptor
desmopressin Targets OT receptor; V_1A receptor; V_1B receptor; V₂ receptor
dAVP Targets OT receptor; V_1A receptor; V_1B receptor; V₂ receptor
[Val⁴]AVP Targets V_1A receptor; V_1B receptor; V₂ receptor
[Phe³]OT Targets OT receptor; V_1A receptor; V₂ receptor
[³H]OT (human, mouse, rat) Targets OT receptor; V_1A receptor; V_1B receptor; V₂ receptor
[³H]AVP (human, mouse, rat) Targets OT receptor; V_1A receptor; V_1B receptor; V₂ receptor
oxytocin Targets OT receptor; V_1A receptor; V_1B receptor; V₂ receptor
LVP Targets V_1A receptor; V_1B receptor; V₂ receptor
arginine vasotocin Targets OT receptor; V_1A receptor; V_1B receptor; V₂ receptor
vasopressin Targets OATP3A1; OT receptor; V_1A receptor; V_1B receptor; V₂ receptor
GR138676 Targets NK₃ receptor
substance P Targets MRGPRX2; NK₁ receptor; NK₂ receptor; NK₃ receptor
septide Targets NK₁ receptor
physalaemin Targets NK₁ receptor
kassinin Targets NK₁ receptor; NK₃ receptor
eledoisin Targets NK₁ receptor; NK₃ receptor
PrRP-(24-31) (human) Targets PrRP receptor
peptide III-BTD Targets NOP receptor
PL017 Targets μ receptor
E2078 Targets κ receptor
β-neoendorphin Targets κ receptor
β-endorphin Targets δ receptor; κ receptor; μ receptor
dynorphin A-(1-13) Targets δ receptor; κ receptor; μ receptor
dynorphin-(1-11) Targets δ receptor; κ receptor; μ receptor
α-neoendorphin Targets δ receptor; κ receptor
neurotensin Targets NTS₁ receptor; NTS₂ receptor
[¹²⁵I]neurotensin (human, mouse, rat) Targets NTS₁ receptor; NTS₂ receptor
Thr¹⁰contulakin-G Targets NTS₁ receptor; NTS₂ receptor
JMV449 Targets NTS₁ receptor
PP-(20-36) (human) Targets Y₄ receptor
PP-(2-36) (human) Targets Y₄ receptor
PP-(13-36) (human) Targets Y₄ receptor
NPY-(2-36) Targets Y₁ receptor; Y₂ receptor; Y₄ receptor; Y₅ receptor
PYY-(3-36) (pig) Targets Y₂ receptor
[³H]NPY (human, mouse, rat) Targets Y₁ receptor
[¹²⁵I]PYY (pig) Targets Y₁ receptor; Y₄ receptor
[¹²⁵I]NPY (human, mouse, rat) Targets Y₁ receptor; Y₂ receptor
PYY-(13-36) (mouse, rat, pig) Targets Y₁ receptor; Y₂ receptor; Y₄ receptor; Y₅ receptor
NPY-(3-36) (pig) Targets Y₁ receptor; Y₂ receptor; Y₄ receptor; Y₅ receptor
NPY-(2-36) (pig) Targets Y₁ receptor; Y₂ receptor; Y₄ receptor
neuropeptide Y Targets PrRP receptor; Y₁ receptor; Y₂ receptor; Y₄ receptor; Y₅ receptor
Y-RFRP-3 Targets NPFF1 receptor; NPFF2 receptor
1DMe Targets NPFF1 receptor; NPFF2 receptor
[¹²⁵I]neuromedin U-8 (pig) Targets NMU1 receptor; NMU2 receptor
[¹²⁵I]neuromedin U-23 (rat) Targets NMU1 receptor; NMU2 receptor
[¹²⁵I]neuromedin U-25 (human) Targets NMU1 receptor; NMU2 receptor
neuromedin U-8 Targets NMU1 receptor; NMU2 receptor
neuromedin U-8 Targets NMU1 receptor; NMU2 receptor
motilin-(2-22) (human) Targets motilin receptor
motilin-(1-19) (human) Targets motilin receptor
motilin-(1-13) (human) Targets motilin receptor
motilin-(1-12) (human) Targets motilin receptor	No image available
motilin-(1-11) (human) Targets motilin receptor	No image available
motilin Targets motilin receptor	No image available
motilin Targets motilin receptor	No image available
motilin Targets motilin receptor	No image available
[Leu¹³]motilin (human) Targets motilin receptor	No image available
ACTH-(11-24) Targets MC₂ receptor	No image available
cetrorelix Targets GnRH₁ receptor	No image available
antarelix Targets GnRH₁ receptor	No image available
abarelix Targets GnRH₁ receptor	No image available
[¹²⁵I]cetrorelix Targets GnRH₁ receptor	No image available
humanin Targets FPR2/ALX; FPR3	No image available
[¹²⁵I]urocortin 1 (mouse, rat) Targets CRF₁ receptor; CRF₂ receptor	No image available
T140 Targets CXCR4	No image available
CXCL12-(1-9) Targets CXCR4	No image available
CXCL12-(1-17) Targets CXCR4	No image available
AM-(22-52) (human) Targets AM₁ receptor; AM₂ receptor	No image available
α-CGRP-(8-37) (rat) Targets AM₁ receptor; AM₂ receptor; CGRP receptor	No image available
α-CGRP-(8-37) (human) Targets AM₁ receptor; AM₂ receptor; AMY₁ receptor; AMY₃ receptor; CGRP receptor	No image available
Tyr⁰α-CGRP (human) Targets AMY₁ receptor; AMY₂ receptor	No image available
CT-(8-32) (salmon) Targets AMY₁ receptor; AMY₃ receptor; CT receptor	No image available
AC187 Targets AMY₁ receptor; AMY₃ receptor; CT receptor	No image available
NPC-567 Targets B₂ receptor	No image available
NPC-349 Targets B₂ receptor	No image available
labradimil Targets B₂ receptor	No image available
NPC 17731 Targets B₁ receptor; B₂ receptor	No image available
kallidin Targets B₁ receptor; B₂ receptor	No image available
bradykinin Targets B₁ receptor; B₂ receptor	No image available
[des-Pro⁸,des-Phe⁹,des-Arg¹⁰]kallidin Targets B₁ receptor	No image available
[des-Phe⁹,des-Arg¹⁰]kallidin Targets B₁ receptor	No image available
[des-Arg⁹]bradykinin Targets B₁ receptor; B₂ receptor	No image available
[des-Arg¹¹]T-kinin Targets B₁ receptor	No image available
[des-Arg¹⁰]kallidin Targets B₁ receptor; B₂ receptor	No image available
[Sar,D-Phe⁸,des-Arg⁹]bradykinin Targets B₁ receptor	No image available
[Leu⁸,des-Arg⁹]bradykinin Targets B₁ receptor	No image available
T-kinin Targets B₁ receptor; B₂ receptor	No image available
Met-Lys-bradykinin Targets B₁ receptor; B₂ receptor	No image available
Lys-kallidin Targets B₁ receptor	No image available
apelin-13 Targets apelin receptor	No image available
[¹²⁵I]apelin-13 Targets apelin receptor	No image available
saralasin Targets AT₂ receptor	No image available
[¹²⁵I]CGP42112 Targets AT₂ receptor	No image available
angiotensin III Targets AT₁ receptor; AT₂ receptor	No image available
angiotensin I Targets Angiotensin-converting enzyme; Angiotensin-converting enzyme 2	No image available
angiotensin-(1-7) Targets MAS1; AT₂ receptor	No image available