Structure via PubChem · Public domain (PubChem)
setmelanotide
Sign in to saveAlso known as BIM-22493, RM-493
Setmelanotide, sold under the brand name Imcivree, is a medication used for the treatment of genetic obesity caused by a rare single-gene mutation.
Chemical data
- Formula
- C49H68N18O9S2
- Molecular weight
- 1117.3 g/mol
- IUPAC name
- (4R,7S,10S,13R,16S,19R,22R)-22-[[(2S)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-13-benzyl-10-[3-(diaminomethylideneamino)propyl]-16-(1H-imidazol-5-ylmethyl)-7-(1H-indol-3-ylmethyl)-19-methyl-6,9,12,15,18,21-hexaoxo-1,2-dithia-5,8,11,14,17,20-hexazacyclotricosane-4-carboxamide
- SMILES
- C[C@@H]1C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSC[C@@H](C(=O)N1)NC(=O)[C@H](CCCN=C(N)N)NC(=O)C)C(=O)N)CC2=CNC3=CC=CC=C32)CCCN=C(N)N)CC4=CC=CC=C4)CC5=CN=CN5
- InChIKey
- HDHDTKMUACZDAA-PHNIDTBTSA-N
- XLogP
- -2.5
- Polar surface area
- 500 Ų
- H-bond donors
- 15
- H-bond acceptors
- 14
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Protein
- First approval
- 2020
- Admin. routes
- parenteral
- Indications
- obesity, morbid obesity, Renal insufficiency, Prader-Willi syndrome
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 1116.485808
Show 4 more facts
- chemical formula
- C₄₉H₆₈N₁₈O₉S₂
- canonical SMILES
- CC1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(CSSCC(C(=O)N1)NC(=O)C(CCCN=C(N)N)NC(=O)C)C(=O)N)CC2=CNC3=CC=CC=C32)CCCN=C(N)N)CC4=CC=CC=C4)CC5=CN=CN5
- isomeric SMILES
- C[C@@H]1C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSC[C@@H](C(=O)N1)NC(=O)[C@H](CCCN=C(N)N)NC(=O)C)C(=O)N)CC2=CNC3=CC=CC=C32)CCCN=C(N)N)CC4=CC=CC=C4)CC5=CN=CN5
- physically interacts with
- Melanocortin 4 receptor
Sources (2)
via Wikidata · CC0
~5 min read
Encyclopedic overview
9 sectionsContents
- Medical uses
- Pharmacology
- History
- Society and culture
- Economics
- Legal status
- Research
- References
- External links
Setmelanotide, sold under the brand name Imcivree, is a medication used for the treatment of genetic obesity caused by a rare single-gene mutation.
The most common side effects include injection site reactions, skin hyperpigmentation (skin patches that are darker than surrounding skin), headache and gastrointestinal side effects (such as nausea, diarrhea, and abdominal pain), among others. Spontaneous penile erections in males and adverse sexual reactions in females have occurred with treatment. Depression and suicidal ideation have also occurred with setmelanotide.
Excerpted from Wikipedia’s “setmelanotide” article, available under the CC BY-SA 4.0 licence.