Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D01425)
Name
Setmelanotide
Synonyms    Click to Show/Hide the Synonyms of This API
Setmelanotide; UNII-N7T15V1FUY; BIM-22493; RM-493; N7T15V1FUY; Imcivree; 920014-72-8; Setmelanotide [USAN:INN]; GTPL9272; CHEMBL3301624; SCHEMBL21840385; CS-6399; DB11700; IRC-022493; HY-19870; Q21098917; RM-493; BIM-22493; IRC-022493; (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; (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; L-Cysteinamide, N2-acetyl-L-arginyl-L-cysteinyl-D-alanyl-L-histidyl-D-phenylalanyl-L-arginyl-L-tryptophyl-, cyclic (2->8)-disulfide; N2-acetyl-L-arginyl-L-cysteinyl-D-alanyl-L-histidyl-D-phenylalanyl-L-arginyl-L-tryptophyl-L-cysteinamide, cyclic (2-8)-disulfide
Clinical Status
Approved
PubChem CID
11993702
Formula
C49H68N18O9S2
Canonical 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
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
InChIKey
HDHDTKMUACZDAA-PHNIDTBTSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=11993702"></iframe>
3D MOL is unavailable 2D MOL
Physicochemical Properties Molecular Weight 1117.3 Topological Polar Surface Area 500
XlogP -2.5 Complexity 2130
Heavy Atom Count 78 Rotatable Bond Count 18
Hydrogen Bond Donor Count 15 Hydrogen Bond Acceptor Count 14
Full List of Drug Formulations (DFMs) Containing This API
          Setmelanotide 10 mg/ml Injection Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
N-(Carbonyl-Methoxypolyethylene Glycol 2000)-1; 2-Distearoyl- Glycero-3- Phosphoethanolamine Sodium Salt; Carboxymethylcellulose Sodium (Average Mwt 90, 500); Mannitol; Phenol; Benzyl Alcohol; Edetate Disodium Dihydrate; Water For Injection
                   Dosage Form Injection
                   Company Rhythm Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Benzyl alcohol DIG Info Indoleamine 2,3-dioxygenase 1 (IC50 = 1400 nM) [1]
Phenol DIG Info Carbonic anhydrase III (Ki = 2700 nM) [2]
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Carboxymethylcellulose sodium DIG Info Albendazole monooxygenase (EC50 = 12.6 uM) [4]
References
1 O-alkylhydroxylamines as rationally-designed mechanism-based inhibitors of indoleamine 2,3-dioxygenase-1. Eur J Med Chem. 2016 Jan 27; 108:564-576.
2 Synthesis of C-cinnamoyl glycosides and their inhibitory activity against mammalian carbonic anhydrases. Bioorg Med Chem. 2013 Mar 15; 21(6):1489-94.
3 Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective. Bioorg Med Chem Lett. 2017 Jun 1; 27(11):2239-2258.
4 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.

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