Setmelanotide acetateProduct ingredient for Setmelanotide

Name

Setmelanotide acetate

Drug Entry

Setmelanotide

Setmelanotide is the first available treatment for patients with pro-opiomelanocortin, proprotein subilisin/kexin type 1, or leptin deficiencies.⁶ It is an agonist of the melanocortin 4 receptor.¹ Earlier attempts at agonizing MC4R (such as LY2112688) lead to successful weight loss, but also an increase in blood pressure and heart rate.¹ Other earlier treatments for these patients included gastric bypass surgery.¹ Patients taking setmelanotide experienced an average weight loss of 0.6 kg/week.¹

Imcivree was granted EMA orphan designation on November 19, 2018 ⁷ and FDA approval on November 25, 2020.⁵ On May 4, 2023, it was approved by Health Canada.¹¹

See full entry for Setmelanotide

Accession Number

DBSALT003489

Structure

Similar Structures

Synonyms

RM-493 acetate

UNII

224I1W20I7

CAS Number

1504602-49-6

Weight

Average: 1297.48
Monoisotopic: 1296.549196296

Chemical Formula

C₅₅H₈₀N₁₈O₁₅S₂

InChI Key

PILXXDANZBQUJH-PUHLIQIQSA-N

InChI

InChI=1S/C49H68N18O9S2.3C2H4O2/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;3*1-2(3)4/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);3*1H3,(H,3,4)/t26-,33+,34?,35-,36+,37?,38+,39?;;;/m1.../s1

IUPAC Name

(4R,7S,10S,13R,16S,19R,22R)-13-benzyl-22-[(2S)-5-[(diaminomethylidene)amino]-2-acetamidopentanamido]-10-{3-[(diaminomethylidene)amino]propyl}-16-[(1H-imidazol-5-yl)methyl]-7-[(1H-indol-3-yl)methyl]-19-methyl-6,9,12,15,18,21-hexaoxo-1,2-dithia-5,8,11,14,17,20-hexaazacyclotricosane-4-carboxamide; tris(acetic acid)

SMILES

CC(O)=O.CC(O)=O.CC(O)=O.C[C@H]1NC(=O)[C@H](CSSC[C@H](NC(=O)[C@H](CC2=CNC3=CC=CC=C23)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](CC2=CC=CC=C2)NC(=O)[C@H](CC2=CN=CN2)NC1=O)C(N)=O)NC(=O)[C@H](CCCN=C(N)N)NC(C)=O

External Links

Wikipedia: Setmelanotide

Predicted Properties

Property	Value	Source
logP	-5.3	Chemaxon
pKa (Strongest Acidic)	11.64	Chemaxon
pKa (Strongest Basic)	11.04	Chemaxon
Physiological Charge	2	Chemaxon
Hydrogen Acceptor Count	16	Chemaxon
Hydrogen Donor Count	15	Chemaxon
Polar Surface Area	449.16 Å²	Chemaxon
Rotatable Bond Count	18	Chemaxon
Refractivity	290.87 m³·mol^-1	Chemaxon
Polarizability	114.63 Å³	Chemaxon
Number of Rings	5	Chemaxon
Bioavailability	0	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Setmelanotide acetateProduct ingredient for Setmelanotide

Structure for Setmelanotide acetate (DBSALT003489)