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Icatibant

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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
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to market Firazyr in the European Union's 27 member states, as well as Switzerland, Liechtenstein and Iceland, making it the first product to be approved in all EU countries for the treatment of hereditary angioedema. In the US, the drug was granted FDA approval in August 2011.
249:)-2-amino]-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]-4-hydroxypyrrolidine-2-carbonyl]amino]acetyl]amino]-3-thiophen-2-ylpropanoyl]amino]-3-hydroxypropanoyl]-3,4-dihydro-1 194: 1081: 1276: 861: 149: 1033: 571:
C1CC2(C1)C(N2C(=O)3CC4=CC=CC=C4CN3C(=O)(CO)NC(=O)(CC5=CC=CS5)NC(=O)CNC(=O)6C(CN6C(=O)7CCCN7C(=O)(CCCN=C(N)N)NC(=O)(CCCN=C(N)N)N)O)C(=O)N(CCCN=C(N)N)C(=O)O
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Bradykinin is a peptide-based hormone that is formed locally in tissues, very often in response to a trauma. It increases vessel permeability,
61: 785: 563: 1026: 800: 928: 1019: 253:-isoquinoline-3-carbonyl]-2,3,3a,4,5,6,7,7a-octahydroindole-2-carbonyl]amino]-5-(diaminomethylideneamino)pentanoic acid 1261: 614: 583: 98: 693:
receptors. Icatibant acts as a bradykinin inhibitor by blocking the binding of native bradykinin to the bradykinin B
237: 179: 79: 1266: 316: 889:"Randomized Trial of Icatibant for Angiotensin-Converting Enzyme Inhibitor-Induced Upper Airway Angioedema" 367: 437: 786:
https://www.tga.gov.au/resources/prescription-medicines-registrations/icatibant-wkt-wockhardt-bio-pty-ltd
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Sinert R, Levy P, Bernstein JA, Body R, Sivilotti ML, Moellman J, et al. (September–October 2017).
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status in Australia, the EU, Switzerland, and the US for the treatment of hereditary angioedema (HAE).
994:"FDA Approves Shire's Firazyr (icatibant injection) for Acute Attacks of Hereditary Angioedema (HAE)" 834: 464: 1187: 1177: 135: 43: 658: 142: 862:"Jerini Receives European Commission Approval for Firazyr (Icatibant) in the Treatment of HAE" 417: 356: 1271: 1108: 922: 632: 307: 829: 271: 376: 993: 8: 1159: 262: 71: 468: 1072: 970: 943: 768: 678: 109: 975: 910: 760: 756: 207: 772: 296: 1164: 1011: 965: 955: 944:"Management of acute attacks of hereditary angioedema: potential role of icatibant" 900: 752: 485: 162: 1245: 689:, overheating and pain. These symptoms are mediated by activation of bradykinin B 681:
to contract. Bradykinin plays an important role as the mediator of pain. Surplus
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receptor. Little is known about the effects of icatibant on the bradykinin B
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deficiency. It is not effective in angioedema caused by medication from the
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is responsible for the typical symptoms of inflammation, such as swelling,
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In the EU, the approval by the European Commission (July 2008) allows
1202: 1197: 1062: 722: 282: 65: 631:, is a medication for the symptomatic treatment of acute attacks of 686: 397: 327: 93: 548: 1097: 865: 428: 1218: 539: 408: 453: 30: 893:
The Journal of Allergy and Clinical Immunology. In Practice
387: 886: 1229: 1041: 795: 793: 315: 654:, which is a selective and specific antagonist of 1277:Drugs developed by Takeda Pharmaceutical Company 1253: 801:"Firazyr- icatibant acetate injection, solution" 790: 295: 270: 824: 822: 1027: 856: 854: 97: 819: 221:In general: ℞ (Prescription only) 1034: 1020: 467: 355: 969: 959: 941: 904: 851: 375: 463: 335: 1254: 704: 668: 213: 1015: 743:"Icatibant: HOE 140, JE 049, JE049". 436: 416: 201: 88: 70: 161: 948:Vascular Health and Risk Management 396: 286: 13: 927:: CS1 maint: overridden setting ( 14: 1288: 188: 120: 1239: 757:10.2165/00126839-200405060-00006 502: 496: 29: 942:Longhurst HJ (September 2010). 709: 596:Key:QURWXBZNHXJZBE-SKXRKSCCSA-N 986: 935: 880: 779: 736: 514: 508: 490: 1: 729: 1042:Other hematological agents ( 627:, sold under the brand name 7: 10: 1293: 1193:Lovotibeglogene autotemcel 906:10.1016/j.jaip.2017.03.003 480:Chemical and physical data 1211: 1157: 1106: 1051: 835:European Medicines Agency 604: 579: 559: 537: 520: 484: 479: 447: 427: 407: 386: 366: 346: 326: 306: 281: 261: 233: 228: 178: 173: 148: 134: 108: 78: 60: 52: 42: 37: 28: 1262:Anti-inflammatory agents 1188:Exagamglogene autotemcel 1178:Betibeglogene autotemcel 996:(Press release). Shire 675:dilates blood vessels 637:C1-esterase-inhibitor 635:(HAE) in adults with 633:hereditary angioedema 1267:Peptide therapeutics 1160:sickle cell disease 1082:+desoxyribonuclease 899:(5): 1402–1409.e3. 839:. 17 September 2018 714:Icatibant received 705:Society and culture 679:smooth muscle cells 669:Mechanism of action 197:(Prescription only) 25: 16:Pharmaceutical drug 1073:Desoxyribonuclease 961:10.2147/vhrm.s4332 807:. 16 December 2019 751:(6): 343–8. 2004. 650:consisting of ten 21: 1227: 1226: 864:(Press release). 622: 621: 550:Interactive image 449:CompTox Dashboard 217: 205: 192: 124: 91: 1284: 1244: 1243: 1242: 1235: 1165:beta thalassemia 1036: 1029: 1022: 1013: 1012: 1006: 1005: 1003: 1001: 990: 984: 983: 973: 963: 939: 933: 932: 926: 918: 908: 884: 878: 877: 875: 873: 858: 849: 848: 846: 844: 826: 817: 816: 814: 812: 797: 788: 783: 777: 776: 745:Drugs in R&D 740: 618: 617: 610: 552: 532: 530: 516: 510: 504: 498: 492: 472: 471: 457: 455: 440: 420: 400: 379: 359: 339: 319: 299: 289: 288: 274: 215: 212: 203: 200: 190: 187: 165: 122: 119: 101: 90: 87: 74: 33: 26: 24: 20: 1292: 1291: 1287: 1286: 1285: 1283: 1282: 1281: 1252: 1251: 1250: 1240: 1238: 1230: 1228: 1223: 1207: 1162: 1153: 1110: 1102: 1047: 1040: 1010: 1009: 999: 997: 992: 991: 987: 940: 936: 920: 919: 885: 881: 871: 869: 860: 859: 852: 842: 840: 828: 827: 820: 810: 808: 799: 798: 791: 784: 780: 742: 741: 737: 732: 712: 707: 700: 696: 692: 671: 662: 613: 611: 608:(what is this?) 605: 600: 597: 592: 587: 586: 575: 572: 567: 566: 555: 528: 526: 513: 507: 501: 495: 475: 451: 443: 423: 403: 382: 362: 342: 322: 302: 285: 277: 257: 254: 241: 240: 224: 169: 137: 130: 111: 104: 56:Hoe 140, JE 049 17: 12: 11: 5: 1290: 1280: 1279: 1274: 1269: 1264: 1249: 1248: 1225: 1224: 1222: 1221: 1215: 1213: 1209: 1208: 1206: 1205: 1200: 1195: 1190: 1185: 1180: 1174: 1172: 1158:Drugs used in 1155: 1154: 1152: 1151: 1146: 1141: 1136: 1131: 1126: 1120: 1118: 1107:Drugs used in 1104: 1103: 1101: 1100: 1095: 1090: 1085: 1075: 1070: 1065: 1059: 1057: 1049: 1048: 1039: 1038: 1031: 1024: 1016: 1008: 1007: 985: 934: 879: 868:. 15 July 2008 850: 830:"Firazyr EPAR" 818: 789: 778: 734: 733: 731: 728: 711: 708: 706: 703: 698: 694: 690: 670: 667: 660: 648:peptidomimetic 620: 619: 602: 601: 599: 598: 595: 593: 590: 582: 581: 580: 577: 576: 574: 573: 570: 562: 561: 560: 557: 556: 554: 553: 545: 543: 535: 534: 524: 518: 517: 511: 505: 499: 493: 488: 482: 481: 477: 476: 474: 473: 465:DTXSID20903963 460: 458: 445: 444: 442: 441: 433: 431: 425: 424: 422: 421: 413: 411: 405: 404: 402: 401: 395:as salt:  392: 390: 384: 383: 381: 380: 372: 370: 364: 363: 361: 360: 352: 350: 344: 343: 341: 340: 332: 330: 324: 323: 321: 320: 312: 310: 304: 303: 301: 300: 292: 290: 279: 278: 276: 275: 267: 265: 259: 258: 256: 255: 244: 236: 235: 234: 231: 230: 226: 225: 223: 222: 219: 210: 198: 184: 182: 176: 175: 171: 170: 168: 167: 154: 152: 146: 145: 140: 138:administration 132: 131: 129: 128: 126: 116: 114: 106: 105: 103: 102: 84: 82: 76: 75: 68: 58: 57: 54: 50: 49: 46: 40: 39: 35: 34: 15: 9: 6: 4: 3: 2: 1289: 1278: 1275: 1273: 1270: 1268: 1265: 1263: 1260: 1259: 1257: 1247: 1237: 1236: 1233: 1220: 1217: 1216: 1214: 1210: 1204: 1201: 1199: 1196: 1194: 1191: 1189: 1186: 1184: 1183:Crizanlizumab 1181: 1179: 1176: 1175: 1173: 1170: 1166: 1161: 1156: 1150: 1147: 1145: 1142: 1140: 1137: 1135: 1134:Conestat alfa 1132: 1130: 1127: 1125: 1122: 1121: 1119: 1116: 1112: 1105: 1099: 1096: 1094: 1093:Streptokinase 1091: 1089: 1088:Hyaluronidase 1086: 1083: 1079: 1076: 1074: 1071: 1069: 1066: 1064: 1061: 1060: 1058: 1055: 1050: 1045: 1037: 1032: 1030: 1025: 1023: 1018: 1017: 1014: 995: 989: 981: 977: 972: 967: 962: 957: 953: 949: 945: 938: 930: 924: 916: 912: 907: 902: 898: 894: 890: 883: 867: 863: 857: 855: 838: 836: 831: 825: 823: 806: 802: 796: 794: 787: 782: 774: 770: 766: 762: 758: 754: 750: 746: 739: 735: 727: 724: 719: 717: 702: 688: 684: 680: 676: 666: 664: 657: 653: 649: 644: 642: 641:ACE inhibitor 638: 634: 630: 626: 616: 609: 603: 594: 589: 588: 585: 578: 569: 568: 565: 558: 551: 547: 546: 544: 541: 536: 525: 523: 519: 489: 487: 483: 478: 470: 466: 462: 461: 459: 450: 446: 439: 438:ChEMBL1743581 435: 434: 432: 430: 426: 419: 415: 414: 412: 410: 406: 399: 394: 393: 391: 389: 385: 378: 374: 373: 371: 369: 365: 358: 354: 353: 351: 349: 345: 338: 334: 333: 331: 329: 325: 318: 314: 313: 311: 309: 305: 298: 294: 293: 291: 284: 280: 273: 269: 268: 266: 264: 260: 252: 248: 243: 242: 239: 232: 227: 220: 218: Rx-only 211: 209: 199: 196: 186: 185: 183: 181: 177: 172: 164: 159: 156: 155: 153: 151: 147: 144: 141: 139: 133: 127: 118: 117: 115: 113: 107: 100: 95: 86: 85: 83: 81: 77: 73: 69: 67: 63: 59: 55: 51: 47: 45: 41: 38:Clinical data 36: 32: 27: 19: 1272:Orphan drugs 1143: 1129:C1-inhibitor 1124:Berotralstat 1078:Fibrinolysin 1068:Chymotrypsin 998:. Retrieved 988: 951: 947: 937: 923:cite journal 896: 892: 882: 870:. Retrieved 841:. Retrieved 833: 809:. Retrieved 804: 781: 748: 744: 738: 720: 713: 710:Legal status 672: 645: 628: 624: 623: 612:   606:   250: 246: 180:Legal status 174:Legal status 143:Subcutaneous 80:License data 18: 1149:Lanadelumab 1139:Ecallantide 954:: 795–802. 716:orphan drug 677:and causes 652:amino acids 533: g·mol 418:CHEBI:68556 272:130308-48-4 229:Identifiers 53:Other names 44:Trade names 1256:Categories 1111:angioedema 1109:hereditary 730:References 701:receptor. 683:bradykinin 656:bradykinin 538:3D model ( 522:Molar mass 377:7PG89G35Q7 348:ChemSpider 308:IUPHAR/BPS 263:CAS Number 238:IUPAC name 1203:Voxelotor 1198:Mitapivat 1144:Icatibant 1063:Bromelain 1052:Enzymes ( 1000:28 August 866:Jerini AG 663:receptors 625:Icatibant 136:Routes of 110:Pregnancy 99:Icatibant 72:Monograph 66:Drugs.com 23:Icatibant 1246:Medicine 980:20859548 915:28552382 843:17 April 811:17 April 805:DailyMed 773:25491021 765:15563238 646:It is a 615:(verify) 357:16736634 328:DrugBank 150:ATC code 112:category 94:DailyMed 1098:Trypsin 971:2941790 872:22 July 687:redness 643:class. 629:Firazyr 486:Formula 337:DB06196 297:6918173 283:PubChem 166:) 160: ( 158:B06AC02 125: C 96::  48:Firazyr 1232:Portal 1212:Others 978:  968:  913:  771:  763:  723:Jerini 564:SMILES 429:ChEMBL 398:D04492 208:℞-only 206: 193: 92:  1219:Hemin 1169:B06AX 1115:B06AC 1054:B06AA 837:(EMA) 769:S2CID 584:InChI 540:JSmol 409:ChEBI 1163:and 1002:2011 976:PMID 929:link 911:PMID 874:2008 845:2020 813:2020 761:PMID 388:KEGG 368:UNII 62:AHFS 1044:B06 966:PMC 956:doi 901:doi 753:doi 531:.54 529:304 454:EPA 317:667 287:CID 163:WHO 1258:: 974:. 964:. 950:. 946:. 925:}} 921:{{ 909:. 895:. 891:. 853:^ 832:. 821:^ 803:. 792:^ 767:. 759:. 747:. 665:. 512:13 506:19 500:89 494:59 245:(2 214:EU 202:US 195:S4 189:AU 121:AU 89:US 1234:: 1171:) 1167:( 1117:) 1113:( 1084:) 1080:( 1056:) 1046:) 1035:e 1028:t 1021:v 1004:. 982:. 958:: 952:6 931:) 917:. 903:: 897:5 876:. 847:. 815:. 775:. 755:: 749:5 699:1 695:2 691:2 661:2 659:B 542:) 527:1 515:S 509:O 503:N 497:H 491:C 456:) 452:( 251:H 247:S 216:: 204:: 191:: 123:: 64:/

Index


Trade names
AHFS
Drugs.com
Monograph
License data
DailyMed
Icatibant
Pregnancy
category

Routes of
administration

Subcutaneous
ATC code
B06AC02
WHO
Legal status
S4
℞-only
IUPAC name
CAS Number
130308-48-4
PubChem
6918173
IUPHAR/BPS
667
DrugBank
DB06196
ChemSpider
16736634
UNII
7PG89G35Q7

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