Icatibant acetateProduct ingredient for Icatibant
- Name
- Icatibant acetate
- Drug Entry
- Icatibant
Icatibant is a synthetic decapeptide with 5 nonproteinogenic amino acid antagonist targeting the B2 receptors with a similar affinity to bradykinin. It is resistant to bradykinin-cleaving enzyme degradation and has a potency of 2-3 times higher than earlier B2 receptors antagonists, thus representing a new class of medication.1,4 It was investigated as a potential treatment of hereditary angioedema (HAE) as bradykinin was implicated in HAE swelling; specifically, mice lacking B2 receptors showed reduced swelling, thus demonstrating bradykinin involvement in the disease pathophysiology.1,5
Icatibant was approved by the FDA on August 25, 2011, and by the EMA in 2008 as a treatment for hereditary angioedema.8,9 The FDA approval was based on positive results obtained from 3 double-blind, randomized, controlled clinical trials known as FAST 1, 2, and 3, where a median time to almost complete symptom relief was observed to be 8 hours compared to 36 hours for the placebo treatment.8
- Accession Number
- DBSALT000097
- Structure
- Synonyms
- Icatibant acetate
- UNII
- 325O8467XK
- CAS Number
- 138614-30-9
- Weight
- Average: 1364.59
Monoisotopic: 1363.681924545 - Chemical Formula
- C61H93N19O15S
- InChI Key
- HKMZRZUEADSZDQ-DZJWSCHMSA-N
- InChI
- InChI=1S/C59H89N19O13S.C2H4O2/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;1-2(3)4/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);1H3,(H,3,4)/t33-,35+,37+,38-,39-,40-,41-,42-,43-,44-,45-,46+;/m0./s1
- IUPAC Name
- (2S)-2-{[(2S,3aS,7aS)-1-[(3R)-2-[(2S)-2-[(2S)-2-(2-{[(2S,4R)-1-[(2S)-1-[(2S)-2-[(2R)-2-amino-5-carbamimidamidopentanamido]-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]-4-hydroxypyrrolidin-2-yl]formamido}acetamido)-3-(thiophen-2-yl)propanamido]-3-hydroxypropanoyl]-1,2,3,4-tetrahydroisoquinoline-3-carbonyl]-octahydro-1H-indol-2-yl]formamido}-5-carbamimidamidopentanoic acid; acetic acid
- SMILES
- CC(O)=O.[H][C@]12C[C@]([H])(N(C(=O)[C@@]3([H])CC4=C(CN3C(=O)[C@H](CO)NC(=O)[C@H](CC3=CC=CS3)NC(=O)CNC(=O)[C@]3([H])C[C@@H](O)CN3C(=O)[C@@H]3CCCN3C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](N)CCCNC(N)=N)C=CC=C4)[C@@]1([H])CCCC2)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O
- External Links
- PubChem Compound
- 70678897
- ChemSpider
- 5293383
- ChEBI
- 68564
- ChEMBL
- CHEMBL2028852
- Wikipedia
- Icatibant
- Predicted Properties
Property Value Source Water Solubility 0.0362 mg/mL ALOGPS logP -2.2 ALOGPS logP -7.7 Chemaxon logS -4.6 ALOGPS pKa (Strongest Acidic) 3.46 Chemaxon pKa (Strongest Basic) 12.48 Chemaxon Physiological Charge 3 Chemaxon Hydrogen Acceptor Count 23 Chemaxon Hydrogen Donor Count 18 Chemaxon Polar Surface Area 516.22 Å2 Chemaxon Rotatable Bond Count 30 Chemaxon Refractivity 363.79 m3·mol-1 Chemaxon Polarizability 135.35 Å3 Chemaxon Number of Rings 7 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon