Buloxibutid

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H29N3O4S2
Molecular Weight	475.624
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCOC(=O)NS(=O)(=O)C1=C(C=C(CC(C)C)S1)C2=CC=C(CN3C=CN=C3)C=C2

InChI

InChIKey=XTEOJPUYZWEXFI-UHFFFAOYSA-N

InChI=1S/C23H29N3O4S2/c1-4-5-12-30-23(27)25-32(28,29)22-21(14-20(31-22)13-17(2)3)19-8-6-18(7-9-19)15-26-11-10-24-16-26/h6-11,14,16-17H,4-5,12-13,15H2,1-3H3,(H,25,27)

HIDE SMILES / InChI

Molecular Formula	C23H29N3O4S2
Molecular Weight	475.624
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15537354
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25560767 | https://www.ncbi.nlm.nih.gov/pubmed/19029468

Compound M24 is a selective angiotensin II AT2 receptor agonist with a Ki value of 0.4 nM for the AT2 receptor. Compound enhances in vivo duodenal alkaline secretion in Sprague-Dawley rats, and lowers the mean arterial blood pressure in anesthetized, spontaneously hypertensive rats. In a mouse model of atherosclerosis, plaque size and stability were improved in ApoE‐/‐ mice treated with M24. Treatment with M24 resulted in decrease in scar size and reduction in markers of inflammation in a rat model of myocardial infaction.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Angiotensin II type 2 (AT-2) receptor 9 Target ID: CHEMBL4607 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15537354	Agonist 2678		0.4 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Hypertension 567 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15537354	Primary	Preclinical	Unknown Approved Use Unknown
Atherosclerosis 74 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25560767	Preventing	Preclinical	Unknown Approved Use Unknown
Myocardial infarction 121 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19029468	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Design, synthesis, and biological evaluation of the first selective nonpeptide AT2 receptor agonist.	2004 Nov 18	15537354
Angiotensin II type 2 receptor stimulation: a novel option of therapeutic interference with the renin-angiotensin system in myocardial infarction?	2008 Dec 9	19029468
Compound 21, a selective agonist of angiotensin AT2 receptors, prevents endothelial inflammation and leukocyte adhesion in vitro and in vivo.	2016 Feb	25560767

Patents

Sample Use Guides

In Vivo Use Guide

The in vivo experiments were performed on anaesthetized nonfasted male Sprague-Dawley rats and spontaneously hypertensive rats (SHR). Compound M24 was administered intravenously at 0.003-0.3 mg/kg h. Oral PK study on rats have demonstrated absolute bioavailability of 20-30%. In the model of miocardial infarction rats were treated with M24 intraperitoneally at 0.01-0.3 mg/kg.

Route of Administration: Other

In Vitro Use Guide

Affinity towards AT2 receptor was evaluated in a radioligand binding assays by displacement of [125I]Ang II from AT2 receptors in pig uterus membranes. Compound M24 binds to AT2 receptor with Ki of 0.4 nM.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 13:28:40 GMT 2023` Edited by `admin` on `Sat Dec 16 13:28:40 GMT 2023`
Record UNII	RC2V4W0EYC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Buloxibutid

Official Name

English

C-21

Code

English

M-24

Code

English

buloxibutid [INN]

Common Name

English

C21

Code

English

Carbamic acid, [[3-[4-(1H-imidazol-1-ylmethyl)phenyl]-5-(2-methylpropyl)-2-thienyl]sulfonyl]-, butyl ester

Systematic Name

English

butyl [3-{4-[(1H-imidazol-1-yl)methyl]phenyl}-5-(2-methylpropyl)thiophene-2-sulfonyl]carbamate

Systematic Name

English

T2 AGONIST COMPOUND 21

Common Name

English

COMPOUND 21

Common Name

English

Butyl [3-[4-[(1H-imidazol-1-yl)methyl]phenyl]-5-isobutylthiophen-2-yl]sulfonylcarbamate

Systematic Name

English

C 21 [WHO-DD]

Common Name

English

Code System Code Type Description

PUBCHEM

9804984