Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00454)
Name
Naloxegol
Synonyms    Click to Show/Hide the Synonyms of This API
Naloxegol; NKTR-118; Movantik; 854601-70-0; NKTR118; UNII-44T7335BKE; NKTR 118; AZ13337019; CHEBI:82975; 44T7335BKE; AZ-13337019; moventig; Naloxegol [USAN:INN]; Naloxegol (USAN/INN); GTPL7539; CHEMBL2219418; SCHEMBL19433066; HSDB 8338; DTXSID80234684; (4R,4aS,7S,7aR,12bS)-7-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]-3-prop-2-enyl-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,9-diol; HY-A0118; NSC787509; ZINC95564694; CS-4987; DB09049; NSC-787509; NCGC00509863-01; D10479; Q15708351; (5alpha,6alpha)-17-Allyl-6-[(20-hydroxy-3,6,9,12,15,18-hexaoxaicos-1-yl)oxy]-4,5-epoxymorphinan-3,14-diol; Morphinan-3,14-diol, 4,5-epoxy-6-(3,6,9,12,15,18,21-heptaoxadocos-1-yloxy)- 17-(2-propenyl)-, (5alpha,6alpha)-
Clinical Status
Approved
Disease Indication Irritable bowel syndrome ICD-11: DD91 [1]
PubChem CID
56959087
Formula
C34H53NO11
Canonical SMILES
COCCOCCOCCOCCOCCOCCOCCO[C@H]1CC[C@]2([C@H]3CC4=C5[C@]2([C@H]1OC5=C(C=C4)O)CCN3CC=C)O
InChI
1S/C34H53NO11/c1-3-9-35-10-8-33-30-26-4-5-27(36)31(30)46-32(33)28(6-7-34(33,37)29(35)25-26)45-24-23-44-22-21-43-20-19-42-18-17-41-16-15-40-14-13-39-12-11-38-2/h3-5,28-29,32,36-37H,1,6-25H2,2H3/t28-,29+,32-,33-,34+/m0/s1
InChIKey
XNKCCCKFOQNXKV-ZRSCBOBOSA-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=56959087"></iframe>
3D MOL is unavailable 2D MOL
Physicochemical Properties Molecular Weight 651.8 Topological Polar Surface Area 127
XlogP -1 Complexity 899
Heavy Atom Count 46 Rotatable Bond Count 24
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 12
Full List of Drug Formulations (DFMs) Containing This API
          Naloxegol 12.5 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; Propyl gallate; Ferric oxide red; Ferrosoferric oxide; Titanium dioxide; Water; Croscarmellose sodium; Polyethylene glycol 400; Cellulose, microcrystalline; Hypromelloses
                   Dosage Form Oral Tablet
                   Company AstraZeneca
                   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]
Propyl gallate DIG Info Arachidonate 5-lipoxygenase (Ki = 0.43 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
Polyethylene glycol 400 DIG Info Albendazole monooxygenase (IC50 = 10.77 mg.mL-1) [5]
          Naloxegol 25 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; Propyl gallate; Ferric oxide red; Ferrosoferric oxide; Titanium dioxide; Water; Croscarmellose sodium; Polyethylene glycol 400; Cellulose, microcrystalline; Hypromelloses
                   Dosage Form Oral Tablet
                   Company AstraZeneca; Avera McKennan Hospital; Lake Eire Medical & Surgical Supply DBA Quality Care Products
                   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]
Propyl gallate DIG Info Arachidonate 5-lipoxygenase (Ki = 0.43 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
Polyethylene glycol 400 DIG Info Albendazole monooxygenase (IC50 = 10.77 mg.mL-1) [5]
          Naloxegol Oxalate eq 12.5mg base 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
Mannitol; Cellulose Microcrystalline; Croscarmellose Sodium; Magnesium Stearate; Propyl Gallate; Hypromellose; Titanium Dioxide; Polyethylene Glycol; Iron Oxide Red; Iron Oxide Black
                   Dosage Form Tablet
                   Company Redhill
                   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]
Propyl gallate DIG Info Arachidonate 5-lipoxygenase (Ki = 0.43 uM) [3]
Hypromellose DIG Info Cytochrome P450 3A5 (IC50 = 19.4 uM) [6]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
Polyethylene glycol 4000 DIG Info Albendazole monooxygenase (Inhibition ratio < 40 %) [5]
          Naloxegol Oxalate eq 25mg base 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
Mannitol; Cellulose Microcrystalline; Croscarmellose Sodium; Magnesium Stearate; Propyl Gallate; Hypromellose; Titanium Dioxide; Polyethylene Glycol; Iron Oxide Red; Iron Oxide Black
                   Dosage Form Tablet
                   Company Redhill
                   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]
Propyl gallate DIG Info Arachidonate 5-lipoxygenase (Ki = 0.43 uM) [3]
Hypromellose DIG Info Cytochrome P450 3A5 (IC50 = 19.4 uM) [6]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
Polyethylene glycol 4000 DIG Info Albendazole monooxygenase (Inhibition ratio < 40 %) [5]
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 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
4 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
5 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.
6 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.

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