| Stereochemistry | ABSOLUTE |
| Molecular Formula | C59H89N19O13S |
| Molecular Weight | 1304.522 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 12 / 12 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12C[C@]([H])(N(C(=O)[C@@]3([H])CC4=C(CN3C(=O)[C@H](CO)NC(=O)[C@H](CC5=CC=CS5)NC(=O)CNC(=O)[C@]6([H])C[C@@H](O)CN6C(=O)[C@@H]7CCCN7C(=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
InChI
InChIKey=QURWXBZNHXJZBE-SKXRKSCCSA-N
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
| Molecular Formula | C59H89N19O13S |
| Molecular Weight | 1304.522 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 12 / 12 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Icatibant (trade name 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. Icatibant currently has orphan drug status in the United States and FDA approved on August 25, 2011. Icatibant inhibits bradykinin from binding the B2 receptor
and thereby treats the clinical symptoms of an acute, episodic attack of HAE.
CNS Activity
Originator
Approval Year
AUC
Doses
AEs
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
Drug as victim
Tox targets
Sourcing
PubMed
Patents
Sample Use Guides
30 mg administered by subcutaneous (SC) injection in the
abdominal area. Additional doses may be administered at intervals of at least 6 hours if response is inadequate or if symptoms recur. No more than 3 doses may be administered in any 24 hour period.
Route of Administration:
Other
In vitro studies indicated Hoe 140 as a highly potent bradykinin antagonist. In isolated organ preparations Hoe 140 inhibited bradykinin-induced contractions concentration dependently, with IC50-values in the guinea-pig ileum preparation of 11 mM. In the rat uterus preparation the IC50 value for Hoe 140 was 4.9 nM. In the guinea-pig isolated pulmonary artery IC50 was 5.4 nM. In cultured bovine endothelial cells, Hoe 140 antagonized (IC50 = 100 nM) bradykinin-induced endothelium-derived relaxing factor (EDRF) release and the bradykinin-induced increase in cytosolic free calcium (IC50 = 1 nM).
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