SETMELANOTIDE HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C49H68N18O9S2.ClH
Molecular Weight	1153.77
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of SETMELANOTIDE HYDROCHLORIDE

Structure Search

SMILES

Cl.C[C@H]1NC(=O)[C@H](CSSC[C@H](NC(=O)[C@H](CC2=CNC3=CC=CC=C23)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](CC4=CC=CC=C4)NC(=O)[C@H](CC5=CN=CN5)NC1=O)C(N)=O)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O

InChI

InChIKey=MANLVWQYYRHWLE-GZRAWZNHSA-N

InChI=1S/C49H68N18O9S2.ClH/c1-26-41(70)63-37(20-30-22-55-25-59-30)46(75)64-35(18-28-10-4-3-5-11-28)44(73)62-34(15-9-17-57-49(53)54)43(72)65-36(19-29-21-58-32-13-7-6-12-31(29)32)45(74)66-38(40(50)69)23-77-78-24-39(47(76)60-26)67-42(71)33(61-27(2)68)14-8-16-56-48(51)52;/h3-7,10-13,21-22,25-26,33-39,58H,8-9,14-20,23-24H2,1-2H3,(H2,50,69)(H,55,59)(H,60,76)(H,61,68)(H,62,73)(H,63,70)(H,64,75)(H,65,72)(H,66,74)(H,67,71)(H4,51,52,56)(H4,53,54,57);1H/t26-,33+,34+,35-,36+,37+,38+,39+;/m1./s1

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

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

Molecular Formula	C49H68N18O9S2
Molecular Weight	1117.309
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.rhythmtx.com/pipeline/product-pipeline/ | https://www.ncbi.nlm.nih.gov/pubmed/29031731

Setmelanotide (RM-493), is an investigational, first-in-class melanocortin-4 receptor (MC4R) agonist in development for the treatment of rare genetic disorders of obesity. Setmelanotide is thought to activate the MC4R, part of a key biological pathway in humans that regulates weight by increasing energy expenditure and reducing appetite. Variants in genes within the MC4 pathway are associated with unrelenting hunger, known as hyperphagia, and severe, early-onset obesity. Setmelanotide is a potential replacement therapy that may restore lost activity in the MC4 pathway, reestablishing weight and appetite control in patients with these rare genetic disorders.

Originator

Approval Year

PubMed

Title	Date	PubMed
Chronic treatment with a melanocortin-4 receptor agonist causes weight loss, reduces insulin resistance, and improves cardiovascular function in diet-induced obese rhesus macaques.	2013 Feb	23048186
Insights into the Allosteric Mechanism of Setmelanotide (RM-493) as a Potent and First-in-Class Melanocortin-4 Receptor (MC4R) Agonist To Treat Rare Genetic Disorders of Obesity through an in Silico Approach.	2019 Mar 20	30048591

Sample Use Guides

In Vivo Use Guide

Bardet-Biedl Syndrome (BBS) and Alström Syndrome (AS) patients with moderate to severe obesity: Subcutaneous injection, 3 mg, daily

Route of Administration: Other

In Vitro Use Guide

Setmelanotide (RM-493) binds human MC4R with Ki value of 0.71 nM in radioligand binding assay and activated MC4R with EC50 value of 1.5 nM in intracellular cAMP production assay.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 16:08:21 GMT 2023` Edited by `admin` on `Sat Dec 16 16:08:21 GMT 2023`
Record UNII	9L64H0UE5Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SETMELANOTIDE HYDROCHLORIDE

Official Name

English

SETMELANOTIDE HYDROCHLORIDE [USAN]

Common Name

English

L-CYSTEINAMIDE, N2-ACETYL-L-ARGINYL-L-CYSTEINYL-D-ALANYL-L-HISTIDYL-D-PHENYLALANYL-L-ARGINYL-L-TRYPTOPHYL-, CYCLIC (2->8)-DISULFIDE, HYDROCHLORIDE

Systematic Name

English

N2-ACETYL-L-ARGINYL-L-CYSTEINYL-D-ALANYL-L-HISTIDYL-D-PHENYLALANYL-L-ARGINYL-L-TRYPTOPHYL-L-CYSTEINAMIDE, CYCLIC (2-8)-DISULFIDE, HYDROCHLORIDE

Systematic Name

English

Code System Code Type Description

USAN

HI-90