Icatibant (acetate)

Icatibant is a synthetic peptide antagonist of the bradykinin B2 receptor with IC50 and Ki values of 1.07 and 0.798 nM, respectively, in guinea pig ileal cell membranes. It inhibits bradykinin-induced contractions in isolated guinea pig ileum and pulmonary arteries as well as in rat uterus (IC50s = 11, 5.4, and 4.9 nM, respectively). In vivo, icatibant inhibits bronchoconstriction induced by bradykinin (Cay-37408) in a guinea pig model (ID50s = 13.4 and 31.8 pmol/kg, i.v., for pulmonary resistance and dynamic lung compliance, respectively). Icatibant (30 µg, i.v.) also reduces vascular permeability in the footpad and intestine in a mouse model of hereditary angioedema. Formulations containing icatibant have been used for the treatment of hereditary angioedema.Formal Name: D-arginyl-L-arginyl-L-prolyl-(4R)-4-hydroxy-L-prolylglycyl-3-(2-thienyl)-L-alanyl-L-seryl-(3R)-1,2,3,4-tetrahydro-3-isoquinolinecarbonyl-(2S,3aS,7aS)-octahydro-1H-indole-2-carbonyl-L-arginine, acetate. CAS Number: 138614-30-9. Synonyms: HOE 140. Molecular Formula: C59H89N19O13S . XC2H4O2. Formula Weight: 1304.5. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 30 mg/ml, DMSO: 30 mg/ml, Ethanol: 0.25 mg/ml, PBS (pH 7.2): 10 mg/ml. SMILES: O=C(N1[C@](CCCC2)([H])[C@]2([H])C[C@H]1C(N[C@H](C(O)=O)CCCNC(N)=N)=O)[C@@H]3N(C([C@H](CO)NC([C@H](CC4=CC=CS4)NC(CNC([C@@H]5C[C@@H](O)CN5C([C@H]6N(C([C@@H](NC([C@H](N)CCCNC(N)=N)=O)CCCNC(N)=N)=O)CCC6)=O)=O)=O)=O)=O)CC7=C(C=CC=C7)C3.OC(C)=O. InChi Code: 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-,. InChi Key: HKMZRZUEADSZDQ-DZJWSCHMSA-N.