Details of the Drug

General Information of Drug (ID: DMS3YE9)

Drug Name
Amantadine
Synonyms
Adamantamine; Adamantanamine; Adamantylamine; Amant; Amantadina; Amantadinum; Amantidine; Aminoadamantane; Endantadine; Mantadine; Symadine; Wiregyt; Amantadine Base; BIA4304; OR14310; Amantadina [INN-Spanish]; Amantadine (INN); Amantadine [INN:BAN]; Amantadinum [INN-Latin]; Gen-Amantadine; Pk-merz; Symmetrel (TN); TCMDC-125869; ADAMANTANE,1-AMINO; Adamantan-1-amine; Adamantan-1-ylamine; Tricyclo[3.3.1.1^3,7]decan-1-amine; Tricyclo(3.3.1.13,7)decan-1-amine; Tricyclo[3.3.1.1(3,7)]decan-1-amine; Tricyclo[3.3.1.1(3,7)]decan-1-ylamine; Tricyclo[3.3.1.1(3,7)]decane-1-amine; Tricyclo[3.3.1.1(sup3,7)]decan-1-amine; Tricyclo(3.3.1.1(sup 3,7))decan-1-amine; Tricyclo(3.3.1.1(sup 3.7))decan-1-amine; Tricyclo[3.3.1.1~3,7~]decan-1-amine; Tricyclo(3.3.1.1(3,7))-decan-1-amine; 1-Adamantamine; 1-Adamantanamine; 1-Adamantanamine (8CI); 1-Adamantylamine; 1-Aminoadamantane; 1-Aminotricyclo(3.3.1.1(sup 3,7))decane
Indication
Disease Entry ICD 11 Status REF
Influenza A virus infection 1E30 Approved [1], [2]
Therapeutic Class
Antiviral Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 151.25
Topological Polar Surface Area (xlogp) 2.4
Rotatable Bond Count (rotbonds) 0
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 1
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [3]
Bioavailability
90% of drug becomes completely available to its intended biological destination(s) [4]
Clearance
The drug present in the plasma can be removed from the body at the rate of 4.8 mL/min/kg [5]
Elimination
85% 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 16 hours [5]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 37.78 micromolar/kg/day [6]
Unbound Fraction
The unbound fraction of drug in plasma is 0.33% [5]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 6.6 L/kg [5]
Water Solubility
The ability of drug to dissolve in water is measured as 50 mg/mL [3]
Chemical Identifiers
Formula
C10H17N
IUPAC Name
adamantan-1-amine
Canonical SMILES
C1C2CC3CC1CC(C2)(C3)N
InChI
InChI=1S/C10H17N/c11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9H,1-6,11H2
InChIKey
DKNWSYNQZKUICI-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
2130
ChEBI ID
CHEBI:2618
CAS Number
768-94-5
DrugBank ID
DB00915
TTD ID
D02KRS
VARIDT ID
DR00040
INTEDE ID
DR2259
ACDINA ID
D00027

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Influenza M2 protein (Influ M) TTXT3PU M2_I34A1 Inhibitor [7], [8], [9], [10]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Organic cation transporter 2 (SLC22A2) DT9IDPW S22A2_HUMAN Substrate [11]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Amantadine (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Mepyramine DMB4SFH Moderate Additive anticholinergic effects by the combination of Amantadine and Mepyramine. Allergic/hypersensitivity disorder [4A80-4A8Z] [25]
Phenyltoloxamine DMKAEQW Moderate Additive anticholinergic effects by the combination of Amantadine and Phenyltoloxamine. Allergic/hypersensitivity disorder [4A80-4A8Z] [25]
Desipramine DMT2FDC Moderate Additive anticholinergic effects by the combination of Amantadine and Desipramine. Attention deficit hyperactivity disorder [6A05] [25]
Cariprazine DMJYDVK Moderate Additive anticholinergic effects by the combination of Amantadine and Cariprazine. Bipolar disorder [6A60] [25]
Cyclobenzaprine DM1YBRM Moderate Additive anticholinergic effects by the combination of Amantadine and Cyclobenzaprine. Depression [6A70-6A7Z] [25]
OPC-34712 DMHG57U Moderate Additive anticholinergic effects by the combination of Amantadine and OPC-34712. Depression [6A70-6A7Z] [25]
Clomipramine DMINRKW Moderate Additive anticholinergic effects by the combination of Amantadine and Clomipramine. Depression [6A70-6A7Z] [25]
Doxepin DMPI98T Moderate Additive anticholinergic effects by the combination of Amantadine and Doxepin. Depression [6A70-6A7Z] [25]
Maprotiline DMPWB7T Moderate Additive anticholinergic effects by the combination of Amantadine and Maprotiline. Depression [6A70-6A7Z] [25]
Esketamine DMVU687 Moderate Additive CNS depression effects by the combination of Amantadine and Esketamine. Depression [6A70-6A7Z] [26]
Mepenzolate DM8YU2F Moderate Additive anticholinergic effects by the combination of Amantadine and Mepenzolate. Digestive system disease [DE2Z] [25]
Oxybutynine DMJPBAX Moderate Additive anticholinergic effects by the combination of Amantadine and Oxybutynine. Discovery agent [N.A.] [25]
Solifenacin DMG592Q Moderate Additive anticholinergic effects by the combination of Amantadine and Solifenacin. Functional bladder disorder [GC50] [25]
Tolterodine DMSHPW8 Moderate Additive anticholinergic effects by the combination of Amantadine and Tolterodine. Functional bladder disorder [GC50] [25]
Belladonna DM2RBWK Moderate Additive anticholinergic effects by the combination of Amantadine and Belladonna. Infectious gastroenteritis/colitis [1A40] [25]
ITI-007 DMUQ1DO Moderate Additive anticholinergic effects by the combination of Amantadine and ITI-007. Insomnia [7A00-7A0Z] [25]
Polyethylene glycol DM4I1JP Moderate Increased risk of lowers seizure threshold by the combination of Amantadine and Polyethylene glycol. Irritable bowel syndrome [DD91] [27]
Flibanserin DM70DTN Moderate Additive CNS depression effects by the combination of Amantadine and Flibanserin. Mood disorder [6A60-6E23] [28]
Phenindamine DMDTC7R Moderate Additive anticholinergic effects by the combination of Amantadine and Phenindamine. Nasopharyngitis [CA00] [25]
Dimenhydrinate DM264B3 Moderate Additive anticholinergic effects by the combination of Amantadine and Dimenhydrinate. Nausea/vomiting [MD90] [25]
Promethazine DM6I5GR Moderate Additive anticholinergic effects by the combination of Amantadine and Promethazine. Nausea/vomiting [MD90] [25]
Cyclizine DM9G7BS Moderate Additive anticholinergic effects by the combination of Amantadine and Cyclizine. Nausea/vomiting [MD90] [25]
Metoclopramide DMFA5MY Moderate Antagonize the effect of Amantadine when combined with Metoclopramide. Nausea/vomiting [MD90] [29]
Apraclonidine DMO4PVE Moderate Additive CNS depression effects by the combination of Amantadine and Apraclonidine. Optic nerve disorder [9C40] [30]
Flavoxate DMKV4NL Moderate Additive anticholinergic effects by the combination of Amantadine and Flavoxate. Pain [MG30-MG3Z] [25]
Orphenadrine DMW542E Moderate Additive anticholinergic effects by the combination of Amantadine and Orphenadrine. Parkinsonism [8A00] [25]
Methylscopolamine DM5VWOB Moderate Additive anticholinergic effects by the combination of Amantadine and Methylscopolamine. Peptic ulcer [DA61] [25]
Levomepromazine DMIKFEL Moderate Additive anticholinergic effects by the combination of Amantadine and Levomepromazine. Psychotic disorder [6A20-6A25] [25]
Quetiapine DM1N62C Moderate Additive anticholinergic effects by the combination of Amantadine and Quetiapine. Schizophrenia [6A20] [25]
Mesoridazine DM2ZGAN Moderate Additive anticholinergic effects by the combination of Amantadine and Mesoridazine. Schizophrenia [6A20] [25]
Aripiprazole DM3NUMH Moderate Additive anticholinergic effects by the combination of Amantadine and Aripiprazole. Schizophrenia [6A20] [25]
Iloperidone DM6AUFY Moderate Additive anticholinergic effects by the combination of Amantadine and Iloperidone. Schizophrenia [6A20] [25]
Paliperidone DM7NPJS Moderate Additive anticholinergic effects by the combination of Amantadine and Paliperidone. Schizophrenia [6A20] [25]
Molindone DMAH70G Moderate Additive anticholinergic effects by the combination of Amantadine and Molindone. Schizophrenia [6A20] [25]
Thiothixene DMDINC4 Moderate Additive anticholinergic effects by the combination of Amantadine and Thiothixene. Schizophrenia [6A20] [25]
Asenapine DMSQZE2 Moderate Additive anticholinergic effects by the combination of Amantadine and Asenapine. Schizophrenia [6A20] [25]
Pimozide DMW83TP Moderate Additive anticholinergic effects by the combination of Amantadine and Pimozide. Schizophrenia [6A20] [25]
Chlorpheniramine DM5URA2 Moderate Additive anticholinergic effects by the combination of Amantadine and Chlorpheniramine. Vasomotor/allergic rhinitis [CA08] [25]
Trimeprazine DMEMV9D Moderate Additive anticholinergic effects by the combination of Amantadine and Trimeprazine. Vasomotor/allergic rhinitis [CA08] [25]
Acrivastine DMTIGA0 Moderate Additive anticholinergic effects by the combination of Amantadine and Acrivastine. Vasomotor/allergic rhinitis [CA08] [25]
⏷ Show the Full List of 40 DDI Information of This Drug

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

DIG
DIG Name DIG ID PubChem CID Functional Classification
Allura red AC dye E00338 33258 Colorant
FD&C blue no. 1 E00263 19700 Colorant
Isopropyl alcohol E00070 3776 Antimicrobial preservative; Solvent
Mannitol E00103 6251 Diluent; Flavoring agent; Lyophilization aid; Plasticizing agent; Tonicity agent
methylparaben E00149 7456 Antimicrobial preservative
Propyl 4-hydroxybenzoate E00141 7175 Antimicrobial preservative
Quinoline yellow WS E00309 24671 Colorant
Sodium lauryl sulfate E00464 3423265 Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Sunset yellow FCF E00255 17730 Colorant
Ammonia E00007 222 Alkalizing agent
Butyl alcohol E00011 263 Flavoring agent; Solvent
Carmellose sodium E00625 Not Available Disintegrant
Ferric hydroxide oxide yellow E00539 23320441 Colorant
Ferrosoferric oxide E00231 14789 Colorant
Glycerin E00026 753 Antimicrobial preservative; Emollient; Flavoring agent; Humectant; Lubricant; Plasticizing agent; Solvent; Suppository base; Tonicity agent; Viscosity-controlling agent
Hexahydric alcohol E00083 5780 Diluent; Flavoring agent; Humectant; Plasticizing agent
Magnesium stearate E00208 11177 lubricant
Potassium hydroxide E00233 14797 Alkalizing agent
Povidone E00667 Not Available Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Propylene glycol E00040 1030 Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Silicon dioxide E00670 Not Available Anticaking agent; Opacifying agent; Viscosity-controlling agent
Soybean lecithin E00637 Not Available Other agent
Titanium dioxide E00322 26042 Coating agent; Colorant; Opacifying agent
Vinylpyrrolidone E00668 Not Available Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Water E00035 962 Solvent
⏷ Show the Full List of 25 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Amantadine 100 mg capsule 100 mg Oral Capsule Oral
Amantadine 100 mg tablet 100 mg Oral Tablet Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

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3 BDDCS applied to over 900 drugs
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9 Proton conduction through the M2 protein of the influenza A virus; a quantitative, mechanistic analysis of experimental data. FEBS Lett. 2003 Sep 18;552(1):17-22.
10 pH-dependent tetramerization and amantadine binding of the transmembrane helix of M2 from the influenza A virus. Biochemistry. 2000 Nov 21;39(46):14160-70.
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18 The organic cation transporters (OCT1, OCT2, EMT) and the plasma membrane monoamine transporter (PMAT) show differential distribution and cyclic expression pattern in human endometrium and early pregnancy decidua. Mol Reprod Dev. 2007 Oct;74(10):1303-11.
19 Metformin is a superior substrate for renal organic cation transporter OCT2 rather than hepatic OCT1. Drug Metab Pharmacokinet. 2005 Oct;20(5):379-86.
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