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

See full entry for Icatibant

Accession Number

DBSALT000097

Structure

Similar Structures

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

Icatibant acetateProduct ingredient for Icatibant

Structure for Icatibant acetate (DBSALT000097)