Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D01244)
Name
Methylnaltrexone bromide
Synonyms    Click to Show/Hide the Synonyms of This API
Methylnaltrexone bromide; 73232-52-7; Naltrexone methobromide; Methylnaltrexone (Bromide); Relistor; MRZ-2663BR; MNTX; MRZ 2663BR; MOA-728; NALTREXONE METHYLBROMIDE; Relistor (TN); (4R,4aS,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-3-methyl-7-oxo-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-3-ium bromide; N-Methylnaltrexone Bromide; C21H26NO4.Br; N-Cyclopropylmethyl-noroxymorphone Methobromide; MNTX-302; SCHEMBL2798188; CHEMBL1201770; DTXSID30868236; ONO-3849; 3844AH; Methylnaltrexone bromide (JAN/USAN); AKOS015896214; CS-0762; AC-32482; HY-75766; Methylnaltrexone bromide, >=97% (HPLC); D06618; W-5330; Methylnaltrexone bromide, United States Pharmacopeia (USP) Reference Standard; (4R,4aS,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-3-methyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-3-ium-7-one,bromide
Clinical Status
Approved
PubChem CID
5361917
Formula
C21H26BrNO4
Canonical SMILES
C[N+]1(CC[C@]23[C@@H]4C(=O)CC[C@]2([C@H]1CC5=C3C(=C(C=C5)O)O4)O)CC6CC6.[Br-]
InChI
1S/C21H25NO4.BrH/c1-22(11-12-2-3-12)9-8-20-17-13-4-5-14(23)18(17)26-19(20)15(24)6-7-21(20,25)16(22)10-13;/h4-5,12,16,19,25H,2-3,6-11H2,1H3;1H/t16-,19+,20+,21-,22?;/m1./s1
InChIKey
IFGIYSGOEZJNBE-KNLJMPJLSA-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=5361917"></iframe>
3D MOL is unavailable 2D MOL
Physicochemical Properties Molecular Weight 436.3 Topological Polar Surface Area 66.8
XlogP N.A. Complexity 664
Heavy Atom Count 27 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 5
Full List of Drug Formulations (DFMs) Containing This API
          Methylnaltrexone Bromide 150mg 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
Silicified Microcrystalline Cellulose; Microcrystalline Cellulose; Sodium Lauryl Sulfate; Croscarmellose Sodium; Crospovidone; Poloxamer 407; Stearic Acid (Vegetable Source); Colloidal Silicon Dioxide; Edetate Calcium Disodium; Polyvinyl Alcohol; Titanium Dioxide; Polyethylene Glycol; Talc
                   Dosage Form Tablet
                   Company Salix Pharms
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [1]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Poloxamer 407 DIG Info Albendazole monooxygenase (EC50 = 32.8 uM) [3]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [3]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Polyethylene glycol 4000 DIG Info Albendazole monooxygenase (Inhibition ratio < 40 %) [5]
          Methylnaltrexone Bromide 8mg/0.4ml solution 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
Sodium Chloride; Edetate Calcium Disodium; Glycine Hydrochloride
                   Dosage Form Solution
                   Company Salix Pharms
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Glycine hydrochloride DIG Info Glycine receptor alpha-1 (EC50 = 94000 nM) [6]
          Methylnaltrexone Bromide 12mg/0.6ml solution 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
Sodium Chloride; Edetate Calcium Disodium; Glycine Hydrochloride
                   Dosage Form Solution
                   Company Salix Pharms
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Glycine hydrochloride DIG Info Glycine receptor alpha-1 (EC50 = 94000 nM) [6]
References
1 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
2 Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):16009-16018.
3 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
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 Pharmacological characteristics and binding modes of caracurine V analogues and related compounds at the neuronal alpha7 nicotinic acetylcholine receptor. J Med Chem. 2007 Sep 20; 50(19):4616-29.

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