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Icatibant

Icatibant (Firazyr) is a synthetic peptidomimetic drug consisting of ten amino acids, and acts as an effective and specific antagonist of bradykinin B2 receptors. It has been approved in the EU for use in hereditary angioedema, and is under investigation for a number of other conditions in which bradykinin is thought to play a significant role.

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CAT No: 10-101-163

CAS No: 130308-48-4

Synonyms/Alias: Icatibant;130308-48-4;Firazyr;icatibanto;HOE 140;UNII-7PG89G35Q7;7PG89G35Q7;Hoechst 140;DTXSID20903963;HOE140;Icatibant [INN];(R)-ARGINYL-(S)-ARGINYL-(S)-PROLYL-(2S,4R)-(4-HYDROXYPROLYL)GLYCYL-(S)-(3-(2-THIENYL)ALANYL)-(S)-SERYL-(R)-((1,2,3,4-TETRAHYDRO-3-ISOQUINOLYL)CARBONYL)-(2S,3AS,7AS)-((HEXAHYDRO-2-INDOLINYL)CARBONYL)-(S)-ARGININE;Icatibant [INN:BAN];icatibantum;icatibant-acetate;D-Arg-(Hyp3,Thi5,D-Tic7,Oic8)BK;JE 049;Icatibant (Standard);Icatibant HOE 140;ICATIBANT [MI];ICATIBANT [VANDF];HOE-140 (Icatibant);ICATIBANT [WHO-DD];ICATIBANT [EMA EPAR];HOE 140 TFA;CHEMBL2028850;SCHEMBL21495177;B06AC02;DTXCID901331902;BDBM50403371;BDBM50406750;HY-17446R;AKOS040741862;AT24149;CS-3381;DB06196;NCGC00390805-02;DA-64221;HY-17446;HOE 140, >=94%;EN300-18166877;Q902379;BRD-K63772874-001-01-4;BRD-K63772874-001-02-2;L-ARGININE, D-ARGINYL-L-ARGINYL-L-PROLYL-TRANS-4-HYDROXY-L-PROLYLGLYCYL-3-(2-THIENYL)-L-ALANYL-L-SERYL-D-1,2,3,4-TETRAHYDRO-3-ISOQUINOLINECARBONYL-L-(2.ALPHA.,3A.BETA.,7A.BETA.)-OCTAHYDRO-1H-INDOLE-2-CARBONYL-;L-Arginine, D-arginyl-L-arginyl-L-prolyl-trans-4-hydroxy-L-prolylglycyl-3-(2-thienyl)-L-alanyl-L-seryl-D-1,2,3,4-tetrahydro-3-isoquinolinecarbonyl-L-(2alpha,3abeta,7abeta)-octahydro-1H-indole-2-carbonyl-;

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Specification Technical Data Publications Customer reviews and Q&A
M.F/FormulaC59H89N19O13S
M.W/Mr.1304.5
SequenceOne Letter Code:RRPXGXSXXR
Three Letter Code:H-D-Arg-Arg-Pro-Hyp-Gly-2Thi-Ser-D-Tic-Oic-Arg-OH
Labeling TargetB2 bradykinin receptor
ApplicationApproved for use in acute attacks of hereditary angioedema (HAE). Investigated for use/treatment in angioedema, liver disease, and burns and burn infections.
AppearanceSolid powder
Purity>98% (or refer to the Certificate of Analysis)
ActivityAntagonist
Biological ActivityIcatibant (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.
Areas of InterestHereditary angioedema
FunctionsType 1 angiotensin receptor binding
TargetBradykinin Receptor
Source#Synthetic
Long-term Storage ConditionsSoluble in DMSO.
Shipping ConditionShipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Short-term Storage ConditionsDry, dark and at 0 - 4 °C
Solubility-20 °C
OrganismHuman
InChIInChI=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 KeyQURWXBZNHXJZBE-SKXRKSCCSA-N
BoilingPointN/A
ShelfLife>2 years if stored properly
References

Icatibant (also called JE049 or HOE140) is a synthetic decapeptide that has a similar structure as bradykinin but contains 5 nonproteinogenic amino acids (D-Arg, L-Hyp, L-Thi, D-Tic, and L-Oic). It is stable and not degraded by bradykinin-cleaving enzymes like carboxypeptidase N (or kininase I) and angiotensin converting enzyme (or kininase II). The study drug was provided by the Jerini AG (Berlin, Germany).

Treatment of acute edema attacks in hereditary angioedema with a bradykinin receptor-2 antagonist (Icatibant)

Icatibant is a selective bradykinin B2 receptor antagonist with, like bradykinin itself, an affinity for the B2 receptor. It does not interact with bradykinin B1 receptors or other peptide receptors. Icatibant reverses increased vascular permeability in C1 esterase inhibitor–knockout mice, inhibits bradykinin-induced vasodilation in humans and, in a phase 1 study, showed dose- and time-dependent inhibition of bradykinin-induced effects in vivo. In a phase 2 study, symptoms improved significantly after open-label treatment with icatibant in 15 patients with hereditary angioedema having acute cutaneous or abdominal attacks.

Icatibant, a New Bradykinin-Receptor Antagonist, in Hereditary Angioedema

Melting PointN/A

1. Myotropic activity and immunolocalization of selected neuropeptides of the burying beetle Nicrophorus vespilloides (Coleoptera: Silphidae)

2. C-peptide and its C-terminal fragments improve erythrocyte deformability in type 1 diabetes patients

3. Cell-based adhesion assays for isolation of snake venom’s integrin antagonists

4. Multifunctional peptide-oligonucleotide conjugate promoted sensitive electrochemical biosensing of cardiac troponin I

5. Effect of Short-Term Desiccation, Recovery Time, and CAPA-PVK Neuropeptide on the Immune System of the Burying Beetle Nicrophorus vespilloides

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