Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00006)
Name
Acamprosate
Synonyms    Click to Show/Hide the Synonyms of This API
Acamprosate; 77337-76-9; N-Acetylhomotaurine; 3-acetamidopropane-1-sulfonic acid; Campral; Acamprosatum; Acamprosato; 3-Acetamido-1-propanesulfonic acid; 3-(Acetylamino)propanesulphonic acid; UNII-N4K14YGM3J; 1-Propanesulfonic acid,3-(acetylamino)-; N4K14YGM3J; CHEBI:51041; calcium 3-acetamidopropane-1-sulfonate; Acamprosate [INN:BAN]; Acamprosatum [INN-Latin]; Acamprosato [INN-Spanish]; Acamprosate (INN); Aotal (TN); HSDB 7358; EINECS 278-667-4; 3-(acetylamino)propanesulphonicacid; N-acetyl homotaurine; 1-Propanesulfonic acid, 3-(acetylamino)-; SCHEMBL41983; GTPL7106; 3-Acetamido-1-propansulfonsaure; CHEMBL1201293; DTXSID3044259; HMS3743O03; N-(3-sulfopropyl)ethanimidic acid; ZINC1554588; AKOS006272019; DB00659; AS-64312; DB-117008; D07058; A840197; Q337668; SR-01000944872; SR-01000944872-1
Clinical Status
Approved
Disease Indication Alcohol dependence ICD-11: 6C40 [1]
PubChem CID
71158
Formula
C5H11NO4S
Canonical SMILES
CC(=O)NCCCS(=O)(=O)O
InChI
1S/C5H11NO4S/c1-5(7)6-3-2-4-11(8,9)10/h2-4H2,1H3,(H,6,7)(H,8,9,10)
InChIKey
AFCGFAGUEYAMAO-UHFFFAOYSA-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=71158"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 181.21 Topological Polar Surface Area 91.8
XlogP -1.2 Complexity 215
Heavy Atom Count 11 Rotatable Bond Count 4
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Full List of Drug Formulations (DFMs) Containing This API
          Acamprosate 333 mg tablet Click to Show/Hide the Full List of Formulation(s):          9 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 lauryl sulfate; Magnesium stearate; Sodium bicarbonate; Talc; Silicon dioxide; Cellulose, microcrystalline; Methacrylic acid; Polyethylene glycol 8000; Povidone k90; Sodium starch glycolate type a potato
                   Dosage Form Delayed Release Oral Tablet
                   Company Cadila Healthcare; Zydus Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
             Drug Formulation 2 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; Magnesium silicate; Propylene glycol; Talc; Crospovidone; Povidone k30; Silicon dioxide; Cellulose, microcrystalline; Methacrylic acid - ethyl acrylate copolymer (1:1) type a; Sodium starch glycolate type a potato
                   Dosage Form Delayed Release Oral Tablet
                   Company Marlex Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
             Drug Formulation 3 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; Magnesium silicate; Propylene glycol; Talc; Crospovidone; Povidone k30; Silicon dioxide; Cellulose, microcrystalline; Methacrylic acid - ethyl acrylate copolymer (1:1) type a; Sodium starch glycolate type a potato
                   Dosage Form Delayed Release Oral Tablet
                   Company American Health Packaging
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
             Drug Formulation 4 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; Magnesium silicate; Propylene glycol; Talc; Crospovidone; Silicon dioxide; Cellulose, microcrystalline; Methacrylic acid - ethyl acrylate copolymer (1:1) type a; Sodium starch glycolate type a potato
                   Dosage Form Delayed Release Oral Tablet
                   Company Carilion Materials Management; Forest Laboratories
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
             Drug Formulation 5 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; Magnesium trisilicate; Propylene glycol; Talc; Polyethylene glycol 400; Silicon dioxide; Cellulose, microcrystalline; Crospovidone (12 mpa.s at 5%); Hypromellose 2910 (5 mpa.s); Hypromellose 2910 (6 mpa.s); Methacrylic acid - ethyl acrylate copolymer (1:1) type a; Polyethylene glycol 8000; Sodium starch glycolate type a potato
                   Dosage Form Delayed Release Oral Tablet
                   Company AvKARE
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Polyethylene glycol 400 DIG Info Albendazole monooxygenase (IC50 = 10.77 mg.mL-1) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
             Drug Formulation 6 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; Magnesium trisilicate; Propylene glycol; Talc; Polyethylene glycol 400; Silicon dioxide; Cellulose, microcrystalline; Crospovidone (15 mpa.s at 5%); Hypromellose 2910 (5 mpa.s); Hypromellose 2910 (6 mpa.s); Methacrylic acid - ethyl acrylate copolymer (1:1) type a; Polyethylene glycol 8000; Sodium starch glycolate type a potato
                   Dosage Form Delayed Release Oral Tablet
                   Company Teva Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Polyethylene glycol 400 DIG Info Albendazole monooxygenase (IC50 = 10.77 mg.mL-1) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
             Drug Formulation 7 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; Magnesium silicate; Propylene glycol; Talc; Crospovidone; Silicon dioxide; Cellulose, microcrystalline; Methacrylic acid - ethyl acrylate copolymer (1:1) type a; Povidone k29/32; Sodium starch glycolate type a potato
                   Dosage Form Delayed Release Oral Tablet
                   Company Avera McKennan Hospital; Glenmark Pharmaceutials
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
             Drug Formulation 8 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
Glyceryl dibehenate; Magnesium stearate; Ammonia; Ferrosoferric oxide; Propylene glycol; Talc; Silicon dioxide; Hypromellose, unspecified; Methacrylic acid - methyl methacrylate copolymer (1:1); Microcrystalline cellulose; Shellac
                   Dosage Form Delayed Release Oral Tablet
                   Company Mylan Pharamceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
             Drug Formulation 9 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
Glyceryl dibehenate; Magnesium stearate; Ammonia; Ferrosoferric oxide; Propylene glycol; Talc; Silicon dioxide; Cellulose, microcrystalline; Hypromelloses; Methacrylic acid - methyl methacrylate copolymer (1:1); Shellac
                   Dosage Form Delayed Release Oral Tablet
                   Company Mylan Pharamceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
References
1 FDA label for approved acamprosate from the official website of the U.S. Food and Drug Administration.
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 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
4 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.

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