Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C34H36Cl2N6O5S.2CH4O3S |
| Molecular Weight | 903.869 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CS(O)(=O)=O.CS(O)(=O)=O.CC1=NC2=C(C=CC=C2OCC3=C(Cl)C(=CC=C3Cl)S(=O)(=O)N4CCC[C@H]4C(=O)NCCCNC(=O)C5=CC=C(C=C5)C(N)=N)C(C)=C1
InChI
InChIKey=YTTYYRCGZDOABP-LPCSYZHESA-N
InChI=1S/C34H36Cl2N6O5S.2CH4O3S/c1-20-18-21(2)41-31-24(20)6-3-8-28(31)47-19-25-26(35)13-14-29(30(25)36)48(45,46)42-17-4-7-27(42)34(44)40-16-5-15-39-33(43)23-11-9-22(10-12-23)32(37)38;2*1-5(2,3)4/h3,6,8-14,18,27H,4-5,7,15-17,19H2,1-2H3,(H3,37,38)(H,39,43)(H,40,44);2*1H3,(H,2,3,4)/t27-;;/m0../s1
Anatibant was a selective small-molecule antagonist of the bradykinin B2 receptor that was undergoing clinical development with Xytis and Fournier for the treatment of brain injuries. Anatibant reduces brain oedema in animal TBI models. Noserious toxicity was found in Phase 1 clinical trials. Following subcutaneous administration of clinically relevant doses, there were no systemic effects but there was pain, inflammation and nodule formation at the injection site. Anatibant inhibits the binding of BK to the B2 receptor. After subcutaneous injection Anatibant is bio-available and crosses the BBB.
CNS Activity
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Pharmacological profile of LF 16-0687, a new potent non-peptide bradykinin B2 receptor antagonist. | 1999 Sep |
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| The N-terminal of icatibant and bradykinin interact with the same Asp residues in the human B2 receptor. | 2004 May 3 |
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| A single dose, three-arm, placebo-controlled, phase I study of the bradykinin B2 receptor antagonist Anatibant (LF16-0687Ms) in patients with severe traumatic brain injury. | 2005 Dec |
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| Autoradiographic analysis of mouse brain kinin B1 and B2 receptors after closed head trauma and ability of Anatibant mesylate to cross the blood-brain barrier. | 2006 May |
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| Anatibant, a selective non-peptide bradykinin B2 receptor antagonist, reduces intracranial hypertension and histopathological damage after experimental traumatic brain injury. | 2009 Apr 24 |
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| Response to: The BRAIN TRIAL: a randomised, placebo controlled trial of a Bradykinin B2 receptor antagonist (Anatibant) in patients with traumatic brain injury. | 2009 Dec 3 |
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| The BRAIN TRIAL: a randomised, placebo controlled trial of a Bradykinin B2 receptor antagonist (Anatibant) in patients with traumatic brain injury. | 2009 Dec 3 |
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| Inhibition of bradykinin B2 receptors before, not after onset of experimental subarachnoid hemorrhage prevents brain edema formation and improves functional outcome. | 2009 Jul |
Patents
Sample Use Guides
At 8-12 h after traumatic brain injury (9.9 +/- 2.8 h), patients received a single subcutaneous injection of Anatibant (3.75 mg or 22.5 mg, n = 10 each)
Route of Administration:
Other
Anatibant (LF 16-0687) bound to the human, rat and guinea-pig recombinant B2 receptor expressed in CHO cells giving K(i) values of 0.67 nM, 1.74 nM and 1.37 nM, respectively. It also bound to the native BK B2 receptor from human umbilical vein (HUV), rat uterus (RU) and guinea-pig ileum (GPI) giving K(i) values of 0.89 nM, 0.28 nM and 0.98 nM, respectively. It inhibited BK-induced IP1, IP2 and IP3 formation in INT407 cells yielding pK(B) values of 8.5, 8.6 and 8.7, respectively. In isolated organs experiments, LF 16-0687 behaved as a competitive antagonist of BK-mediated contractions giving pA2 values of 9.1 in HUV, 7.7 in RU and 9.1 in GPI.
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1332585-65-5
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16I7ZY06ZY
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100000183822
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21968583
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ACTIVE MOIETY
SUBSTANCE RECORD
