Details of the Drug

General Information of Drug (ID: DMO381I)

• Drug Name: Acamprosate
• Synonyms: AOTA; Acamprosato; Acamprosatum; Acamprostate; Aotal; Campral; Calcium acetyl homotaurinate; Calcium acetylhomotaurinate; Calcium acetylhomotaurine; Sodium acetylhomotaurine; Acamprosate 6473; Acamprosate (Campral); Acamprosate (INN); Acamprosate [INN:BAN]; Acamprosato [INN-Spanish]; Acamprosatum [INN-Latin]; Aotal (TN); Campral (TN); N-Acetylhomotaurine; 3-(Acetylamino)propanesulphonic acid; 3-Acetamido-1-propanesulfonic acid; 3-acetamidopropane-1-sulfonic acid

Indication

Disease Entry	ICD 11	Status	REF
Alcohol dependence	6C40.2	Approved	[1]

• Therapeutic Class: Alcohol Deterrents
• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 181.21
  Logarithm of the Partition Coefficient (xlogp); -1.2
  Rotatable Bond Count (rotbonds); 4
  Hydrogen Bond Donor Count (hbonddonor); 2
  Hydrogen Bond Acceptor Count (hbondacc); 4
• ADMET Property:
  Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 0.94 mg/L [2]
  Absorption Tmax: The time to maximum plasma concentration (Tmax) is 0.81 h [2]
  BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [3]
  Bioavailability: The bioavailability of drug is 70-80% [2]
  Clearance: The clearance of drug is 30-50 mL/min [4]
  Elimination: 50% of drug is excreted from urine in the unchanged form [3]
  Half-life: The concentration or amount of drug in body reduced by one-half in 20 - 33 hours [5]
  Metabolism: The drug is not metabolised [5]
  MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 71.272 micromolar/kg/day [6]
  Unbound Fraction: The unbound fraction of drug in plasma is 1% [7]
  Vd: The volume of distribution (Vd) of drug is 20 L [5]
• Chemical Identifiers:
  Formula: C5H11NO4S
  IUPAC Name: 3-acetamidopropane-1-sulfonic acid
  Canonical SMILES: CC(=O)NCCCS(=O)(=O)O
  InChI: 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
• Cross-matching ID:
  PubChem CID: 71158
  ChEBI ID: CHEBI:51041
  CAS Number: 77337-76-9
  DrugBank ID: DB00659
  TTD ID: D0GC2M
  ACDINA ID: D00006

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Glutamate receptor AMPA (GRIA)	TTAN6JD	NOUNIPROTAC	Agonist	[8]

Molecular Expression Atlas of This Drug

• The Studied Disease: Alcohol dependence
• ICD Disease Classification: 6C40.2

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Glutamate receptor AMPA (GRIA)	DTT	NO-GeName	1.79E-04	-0.69	-0.58

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Ammonia	E00007	222	Alkalizing agent
Crospovidone	E00626	Not Available	Disintegrant
Ferrosoferric oxide	E00231	14789	Colorant
Glyceryl dibehenate	E00537	22477175	Binding agent; Coating agent; Flavoring agent; Modified-release agent; Viscosity-controlling agent; lubricant
Magnesium silicate	E00596	72941442	Anticaking agent; Glidant; Lubricant
Magnesium stearate	E00208	11177	lubricant
Magnesium trisilicate	E00477	5311266	Glidant
Polyethylene glycol 400	E00653	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Propylene glycol	E00040	1030	Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Sodium bicarbonate	E00424	516892	Alkalizing agent; Diluent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Vinylpyrrolidone	E00668	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Acamprosate 333 mg tablet	333 mg	Delayed Release Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

• [1] URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7106).
• [2] Pharmacokinetics of ciprofloxacin after oral and intravenous administration in healthy volunteers. Eur J Clin Microbiol. 1984 Aug;3(4):355-9.
• [3] BDDCS applied to over 900 drugs
• [4] FDA Approved Drug Products: CAMPRAL (acamprosate calcium) delayed-release tablets
• [5] Clinical pharmacokinetics of acamprosate. Clin Pharmacokinet. 1998 Nov;35(5):331-45. doi: 10.2165/00003088-199835050-00001.
• [6] Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
• [7] Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
• [8] Predicting the effect of naltrexone and acamprosate in alcohol-dependent patients using genetic indicators. Addict Biol. 2009 Jul;14(3):328-37.