ANATIBANT MESYLATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C34H36Cl2N6O5S.CH4O3S
Molecular Weight	807.764
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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=XSDHLAGTQUKMIQ-YCBFMBTMSA-N

InChI=1S/C34H36Cl2N6O5S.CH4O3S/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;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);1H3,(H,2,3,4)/t27-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	CH4O3S
Molecular Weight	96.106
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C34H36Cl2N6O5S
Molecular Weight	711.658
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://adisinsight.springer.com/drugs/800009281 | https://www.ncbi.nlm.nih.gov/pubmed/19958521

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
Response to: The BRAIN TRIAL: a randomised, placebo controlled trial of a Bradykinin B2 receptor antagonist (Anatibant) in patients with traumatic brain injury.	2009-12-03	19958522
The BRAIN TRIAL: a randomised, placebo controlled trial of a Bradykinin B2 receptor antagonist (Anatibant) in patients with traumatic brain injury.	2009-12-03	19958521
Inhibition of bradykinin B2 receptors before, not after onset of experimental subarachnoid hemorrhage prevents brain edema formation and improves functional outcome.	2009-07	19487935
Anatibant, a selective non-peptide bradykinin B2 receptor antagonist, reduces intracranial hypertension and histopathological damage after experimental traumatic brain injury.	2009-04-24	19429066
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.	2006-05	16689671
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.	2005-12	16379582
The N-terminal of icatibant and bradykinin interact with the same Asp residues in the human B2 receptor.	2004-05-03	15140628
Pharmacological profile of LF 16-0687, a new potent non-peptide bradykinin B2 receptor antagonist.	1999-09	10596852

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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.

Substance Class	Chemical Created by `admin` on `Tue Apr 01 21:13:08 GMT 2025` Edited by `admin` on `Tue Apr 01 21:13:08 GMT 2025`
Record UNII	SD3N4DR0VY
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ANATIBANT MESYLATE

Common Name

English

ANATIBANT MESILATE

Preferred Name

English

2-PYRROLIDINECARBOXAMIDE, N-(3-((4-(AMINOIMINOMETHYL)BENZOYL)AMINO)PROPYL)-1-((2,4-DICHLORO-3-(((2,4-DIMETHYL-8-QUINOLINYL)OXY)METHYL)PHENYL)SULFONYL)-, (2S)-, METHANESULFONATE (1:1)

Systematic Name

English

Code System Code Type Description

FDA UNII

SD3N4DR0VY