ANATIBANT

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C34H36Cl2N6O5S
Molecular Weight	711.658
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC(C)=C2C=CC=C(OCC3=C(Cl)C(=CC=C3Cl)S(=O)(=O)N4CCC[C@H]4C(=O)NCCCNC(=O)C5=CC=C(C=C5)C(N)=N)C2=N1

InChI

InChIKey=XUHBBTKJWIBQMY-MHZLTWQESA-N

InChI=1S/C34H36Cl2N6O5S/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/h3,6,8-14,18,27H,4-5,7,15-17,19H2,1-2H3,(H3,37,38)(H,39,43)(H,40,44)/t27-/m0/s1

HIDE SMILES / InChI

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

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 `Fri Dec 15 17:19:51 GMT 2023` Edited by `admin` on `Fri Dec 15 17:19:51 GMT 2023`
Record UNII	CLO4JRD21F
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ANATIBANT

Official Name

English

anatibant [INN]

Common Name

English

(2S)-N-(3-(4-CARBAMIMIDOYLBENZAMIDO)PROPYL)-1-(2,4-DICHLORO-3-((2,4-DIMETHYL-8-QUINOLYLOXY)METHYL)PHENYLSULFONYL)PYRROLIDINE-2-CARBOXAMIDE

Common Name

English

XY-2405

Code

English

Classification Tree Code System Code

EU-Orphan Drug

EU/3/04/188