Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00453)
Name
Naldemedine
Synonyms    Click to Show/Hide the Synonyms of This API
NALDEMEDINE; UNII-03KSI6WLXH; 916072-89-4; Symproic; S-297995; 03KSI6WLXH; S-297,995; (4R,4aS,7aR,12bS)-3-(cyclopropylmethyl)-4a,7,9-trihydroxy-N-[2-(3-phenyl-1,2,4-oxadiazol-5-yl)propan-2-yl]-1,2,4,5,7a,13-hexahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-6-carboxamide; Naldemedine [USAN:INN]; Naldemedine (USAN/INN); S 297995; GTPL9150; SCHEMBL9880572; CHEMBL2105755; BDBM50503604; DB11691; compound 9k [PMID: 30446313]; HY-19627; Morphinan-7-carboxamide, 17-(cyclopropylmethyl)-6,7-didehydro-4,5-epoxy-3,6,14- trihydroxy-N-(1-methyl-1-(3-phenyl-1,2,4-oxadiazol-5-yl)ethyl)-,(5alpha)-; CS-0016072; J3.573.009E; D10188; Q6960846
Clinical Status
Approved
Disease Indication Irritable bowel syndrome ICD-11: DD91 [1]
PubChem CID
54732242
Formula
C32H34N4O6
Canonical SMILES
CC(C)(C1=NC(=NO1)C2=CC=CC=C2)NC(=O)C3=C([C@H]4[C@@]56CCN([C@@H]([C@@]5(C3)O)CC7=C6C(=C(C=C7)O)O4)CC8CC8)O
InChI
1S/C32H34N4O6/c1-30(2,29-33-27(35-42-29)18-6-4-3-5-7-18)34-28(39)20-15-32(40)22-14-19-10-11-21(37)25-23(19)31(32,26(41-25)24(20)38)12-13-36(22)16-17-8-9-17/h3-7,10-11,17,22,26,37-38,40H,8-9,12-16H2,1-2H3,(H,34,39)/t22-,26+,31+,32-/m1/s1
InChIKey
AXQACEQYCPKDMV-RZAWKFBISA-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=54732242"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 570.6 Topological Polar Surface Area 141
XlogP 3.2 Complexity 1140
Heavy Atom Count 42 Rotatable Bond Count 6
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 9
Full List of Drug Formulations (DFMs) Containing This API
          Naldemedine 0.2 mg tablet 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
Magnesium stearate; Mannitol; Ferric oxide yellow; Talc; Croscarmellose sodium; Hypromellose, unspecified
                   Dosage Form Oral Tablet
                   Company Purdue Pharma
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [3]
          Naldemedine Tosylate 0.2mg tablet 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
D-Mannitol; Croscarmellose Sodium; Magnesium Stearate; Hypromellose; Talc; Yellow Ferric Oxide
                   Dosage Form Tablet
                   Company Biodelivery Sciences International
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [2]
Hypromellose DIG Info Cytochrome P450 3A5 (IC50 = 19.4 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [3]
References
1 FDA label for approved naldemedine from the official website of the U.S. Food and Drug Administration.
2 Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective. Bioorg Med Chem Lett. 2017 Jun 1; 27(11):2239-2258.
3 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
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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