U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C49H68N18O9S2
Molecular Weight 1117.309
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SETMELANOTIDE

SMILES

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=HDHDTKMUACZDAA-PHNIDTBTSA-N
InChI=1S/C49H68N18O9S2/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)/t26-,33+,34+,35-,36+,37+,38+,39+/m1/s1

HIDE SMILES / InChI

Molecular Formula C49H68N18O9S2
Molecular Weight 1117.309
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 1
Optical Activity UNSPECIFIED

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
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

Sample Use Guides

Bardet-Biedl Syndrome (BBS) and Alström Syndrome (AS) patients with moderate to severe obesity: Subcutaneous injection, 3 mg, daily
Route of Administration: Other
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 Thu Jul 06 13:53:28 UTC 2023
Edited
by admin
on Thu Jul 06 13:53:28 UTC 2023
Record UNII
N7T15V1FUY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SETMELANOTIDE
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
L-CYSTEINAMIDE, N2-ACETYL-L-ARGINYL-L-CYSTEINYL-D-ALANYL-L-HISTIDYL-D-PHENYLALANYL-L-ARGINYL-L-TRYPTOPHYL-, CYCLIC (2->8)-DISULFIDE
Systematic Name English
Setmelanotide [WHO-DD]
Common Name English
BIM-22493
Code English
setmelanotide [INN]
Common Name English
SETMELANOTIDE [USAN]
Common Name English
RM-493
Code English
Classification Tree Code System Code
FDA ORPHAN DRUG 700719
Created by admin on Thu Jul 06 13:53:28 UTC 2023 , Edited by admin on Thu Jul 06 13:53:28 UTC 2023
FDA ORPHAN DRUG 613717
Created by admin on Thu Jul 06 13:53:28 UTC 2023 , Edited by admin on Thu Jul 06 13:53:28 UTC 2023
FDA ORPHAN DRUG 480615
Created by admin on Thu Jul 06 13:53:28 UTC 2023 , Edited by admin on Thu Jul 06 13:53:28 UTC 2023
EU-Orphan Drug EU/3/18/2101
Created by admin on Thu Jul 06 13:53:28 UTC 2023 , Edited by admin on Thu Jul 06 13:53:28 UTC 2023
FDA ORPHAN DRUG 726419
Created by admin on Thu Jul 06 13:53:28 UTC 2023 , Edited by admin on Thu Jul 06 13:53:28 UTC 2023
FDA ORPHAN DRUG 514815
Created by admin on Thu Jul 06 13:53:28 UTC 2023 , Edited by admin on Thu Jul 06 13:53:28 UTC 2023
NCI_THESAURUS C29711
Created by admin on Thu Jul 06 13:53:28 UTC 2023 , Edited by admin on Thu Jul 06 13:53:28 UTC 2023
Code System Code Type Description
SMS_ID
100000177229
Created by admin on Thu Jul 06 13:53:28 UTC 2023 , Edited by admin on Thu Jul 06 13:53:28 UTC 2023
PRIMARY
RXCUI
2469247
Created by admin on Thu Jul 06 13:53:28 UTC 2023 , Edited by admin on Thu Jul 06 13:53:28 UTC 2023
PRIMARY
WIKIPEDIA
Setmelanotide
Created by admin on Thu Jul 06 13:53:28 UTC 2023 , Edited by admin on Thu Jul 06 13:53:28 UTC 2023
PRIMARY
CAS
920014-72-8
Created by admin on Thu Jul 06 13:53:28 UTC 2023 , Edited by admin on Thu Jul 06 13:53:28 UTC 2023
PRIMARY
DAILYMED
N7T15V1FUY
Created by admin on Thu Jul 06 13:53:28 UTC 2023 , Edited by admin on Thu Jul 06 13:53:28 UTC 2023
PRIMARY
FDA UNII
N7T15V1FUY
Created by admin on Thu Jul 06 13:53:28 UTC 2023 , Edited by admin on Thu Jul 06 13:53:28 UTC 2023
PRIMARY
DRUG BANK
DB11700
Created by admin on Thu Jul 06 13:53:28 UTC 2023 , Edited by admin on Thu Jul 06 13:53:28 UTC 2023
PRIMARY
INN
10011
Created by admin on Thu Jul 06 13:53:28 UTC 2023 , Edited by admin on Thu Jul 06 13:53:28 UTC 2023
PRIMARY
EPA CompTox
DTXSID501032320
Created by admin on Thu Jul 06 13:53:28 UTC 2023 , Edited by admin on Thu Jul 06 13:53:28 UTC 2023
PRIMARY
ChEMBL
CHEMBL3301624
Created by admin on Thu Jul 06 13:53:28 UTC 2023 , Edited by admin on Thu Jul 06 13:53:28 UTC 2023
PRIMARY
NCI_THESAURUS
C152349
Created by admin on Thu Jul 06 13:53:28 UTC 2023 , Edited by admin on Thu Jul 06 13:53:28 UTC 2023
PRIMARY
USAN
BC-38
Created by admin on Thu Jul 06 13:53:28 UTC 2023 , Edited by admin on Thu Jul 06 13:53:28 UTC 2023
PRIMARY
PUBCHEM
11993702
Created by admin on Thu Jul 06 13:53:28 UTC 2023 , Edited by admin on Thu Jul 06 13:53:28 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
EXCRETED UNCHANGED
Approximately 39% of the administered setmelanotide dose was excreted unchanged in urine during the 24-hour dosing interval following subcutaneous administration of 3 mg once daily.
URINE
BINDER->LIGAND
BINDING
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC ONCE DAILY

SUBCUTANEOUS INJECTION

Tmax PHARMACOKINETIC SUBCUTANEOUS INJECTION