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]
Parkinsonian disorder N.A. Approved [2]
Postencephalitic Parkinson disease N.A. Approved [2]
Therapeutic Class
Antiviral Agents
ATC Code
N04BB01: Amantadine
N04BB: Adamantane derivatives
N04B: DOPAMINERGIC AGENTS
N04: ANTI-PARKINSON DRUGS
N: NERVOUS SYSTEM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 151.25
Logarithm of the Partition Coefficient (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
CHEMBL660
CAS Number
768-94-5
UNII
PJY633525U
DrugBank ID
DB03627
TTD ID
D02KRS
VARIDT ID
DR00040
INTEDE ID
DR2259
ACDINA ID
D00027
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

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]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Organic cation transporter 2 (SLC22A2) DT9IDPW S22A2_HUMAN Substrate [8]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
2'-5'-oligoadenylate synthase 2 (OAS2) OT64CCTM OAS2_HUMAN Gene/Protein Processing [9]
Interferon alpha-inducible protein 27, mitochondrial (IFI27) OTI2XGIT IFI27_HUMAN Gene/Protein Processing [9]
Interferon alpha-inducible protein 6 (IFI6) OTWOOAM4 IFI6_HUMAN Gene/Protein Processing [9]
Microtubule-associated protein 2 (MAP2) OT6UYT3X MTAP2_HUMAN Gene/Protein Processing [10]
Tyrosine-protein kinase JAK1 (JAK1) OT0X3D17 JAK1_HUMAN Gene/Protein Processing [9]
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] [11]
Phenyltoloxamine DMKAEQW Moderate Additive anticholinergic effects by the combination of Amantadine and Phenyltoloxamine. Allergic/hypersensitivity disorder [4A80-4A8Z] [11]
Desipramine DMT2FDC Moderate Additive anticholinergic effects by the combination of Amantadine and Desipramine. Attention deficit hyperactivity disorder [6A05] [11]
Cariprazine DMJYDVK Moderate Additive anticholinergic effects by the combination of Amantadine and Cariprazine. Bipolar disorder [6A60] [11]
Cyclobenzaprine DM1YBRM Moderate Additive anticholinergic effects by the combination of Amantadine and Cyclobenzaprine. Depression [6A70-6A7Z] [11]
OPC-34712 DMHG57U Moderate Additive anticholinergic effects by the combination of Amantadine and OPC-34712. Depression [6A70-6A7Z] [11]
Clomipramine DMINRKW Moderate Additive anticholinergic effects by the combination of Amantadine and Clomipramine. Depression [6A70-6A7Z] [11]
Doxepin DMPI98T Moderate Additive anticholinergic effects by the combination of Amantadine and Doxepin. Depression [6A70-6A7Z] [11]
Maprotiline DMPWB7T Moderate Additive anticholinergic effects by the combination of Amantadine and Maprotiline. Depression [6A70-6A7Z] [11]
Esketamine DMVU687 Moderate Additive CNS depression effects by the combination of Amantadine and Esketamine. Depression [6A70-6A7Z] [12]
Mepenzolate DM8YU2F Moderate Additive anticholinergic effects by the combination of Amantadine and Mepenzolate. Digestive system disease [DE2Z] [11]
Oxybutynine DMJPBAX Moderate Additive anticholinergic effects by the combination of Amantadine and Oxybutynine. Discovery agent [N.A.] [11]
Solifenacin DMG592Q Moderate Additive anticholinergic effects by the combination of Amantadine and Solifenacin. Functional bladder disorder [GC50] [11]
Tolterodine DMSHPW8 Moderate Additive anticholinergic effects by the combination of Amantadine and Tolterodine. Functional bladder disorder [GC50] [11]
Belladonna DM2RBWK Moderate Additive anticholinergic effects by the combination of Amantadine and Belladonna. Infectious gastroenteritis/colitis [1A40] [11]
ITI-007 DMUQ1DO Moderate Additive anticholinergic effects by the combination of Amantadine and ITI-007. Insomnia [7A00-7A0Z] [11]
Polyethylene glycol DM4I1JP Moderate Increased risk of lowers seizure threshold by the combination of Amantadine and Polyethylene glycol. Irritable bowel syndrome [DD91] [13]
Flibanserin DM70DTN Moderate Additive CNS depression effects by the combination of Amantadine and Flibanserin. Mood disorder [6A60-6E23] [14]
Phenindamine DMDTC7R Moderate Additive anticholinergic effects by the combination of Amantadine and Phenindamine. Nasopharyngitis [CA00] [11]
Dimenhydrinate DM264B3 Moderate Additive anticholinergic effects by the combination of Amantadine and Dimenhydrinate. Nausea/vomiting [MD90] [11]
Promethazine DM6I5GR Moderate Additive anticholinergic effects by the combination of Amantadine and Promethazine. Nausea/vomiting [MD90] [11]
Cyclizine DM9G7BS Moderate Additive anticholinergic effects by the combination of Amantadine and Cyclizine. Nausea/vomiting [MD90] [11]
Metoclopramide DMFA5MY Moderate Antagonize the effect of Amantadine when combined with Metoclopramide. Nausea/vomiting [MD90] [15]
Apraclonidine DMO4PVE Moderate Additive CNS depression effects by the combination of Amantadine and Apraclonidine. Optic nerve disorder [9C40] [16]
Flavoxate DMKV4NL Moderate Additive anticholinergic effects by the combination of Amantadine and Flavoxate. Pain [MG30-MG3Z] [11]
Orphenadrine DMW542E Moderate Additive anticholinergic effects by the combination of Amantadine and Orphenadrine. Parkinsonism [8A00] [11]
Methylscopolamine DM5VWOB Moderate Additive anticholinergic effects by the combination of Amantadine and Methylscopolamine. Peptic ulcer [DA61] [11]
Levomepromazine DMIKFEL Moderate Additive anticholinergic effects by the combination of Amantadine and Levomepromazine. Psychotic disorder [6A20-6A25] [11]
Quetiapine DM1N62C Moderate Additive anticholinergic effects by the combination of Amantadine and Quetiapine. Schizophrenia [6A20] [11]
Mesoridazine DM2ZGAN Moderate Additive anticholinergic effects by the combination of Amantadine and Mesoridazine. Schizophrenia [6A20] [11]
Aripiprazole DM3NUMH Moderate Additive anticholinergic effects by the combination of Amantadine and Aripiprazole. Schizophrenia [6A20] [11]
Iloperidone DM6AUFY Moderate Additive anticholinergic effects by the combination of Amantadine and Iloperidone. Schizophrenia [6A20] [11]
Paliperidone DM7NPJS Moderate Additive anticholinergic effects by the combination of Amantadine and Paliperidone. Schizophrenia [6A20] [11]
Molindone DMAH70G Moderate Additive anticholinergic effects by the combination of Amantadine and Molindone. Schizophrenia [6A20] [11]
Thiothixene DMDINC4 Moderate Additive anticholinergic effects by the combination of Amantadine and Thiothixene. Schizophrenia [6A20] [11]
Asenapine DMSQZE2 Moderate Additive anticholinergic effects by the combination of Amantadine and Asenapine. Schizophrenia [6A20] [11]
Pimozide DMW83TP Moderate Additive anticholinergic effects by the combination of Amantadine and Pimozide. Schizophrenia [6A20] [11]
Chlorpheniramine DM5URA2 Moderate Additive anticholinergic effects by the combination of Amantadine and Chlorpheniramine. Vasomotor/allergic rhinitis [CA08] [11]
Trimeprazine DMEMV9D Moderate Additive anticholinergic effects by the combination of Amantadine and Trimeprazine. Vasomotor/allergic rhinitis [CA08] [11]
Acrivastine DMTIGA0 Moderate Additive anticholinergic effects by the combination of Amantadine and Acrivastine. Vasomotor/allergic rhinitis [CA08] [11]
⏷ 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

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: 4128).
2 Amantadine FDA Label
3 BDDCS applied to over 900 drugs
4 Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
5 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
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 Discovery of spiro-piperidine inhibitors and their modulation of the dynamics of the M2 proton channel from influenza A virus. J Am Chem Soc. 2009 Jun 17;131(23):8066-76.
8 Human neurons express the polyspecific cation transporter hOCT2, which translocates monoamine neurotransmitters, amantadine, and memantine. Mol Pharmacol. 1998 Aug;54(2):342-52.
9 Interferon signal transduction of biphenyl dimethyl dicarboxylate/amantadine and anti-HBV activity in HepG2 2.2.15. Arch Pharm Res. 2006 May;29(5):405-11. doi: 10.1007/BF02968591.
10 Establishment of a 13 genes-based molecular prediction score model to discriminate the neurotoxic potential of food relevant-chemicals. Toxicol Lett. 2022 Feb 1;355:1-18. doi: 10.1016/j.toxlet.2021.10.013. Epub 2021 Nov 5.
11 Postma JU, van Tilburg W "Visual hallucinations and delirium during treatment with amantadine (Symmetrel)." J Am Geriatr Soc 23 (1975): 212-5. [PMID: 123540]
12 Cerner Multum, Inc. "Australian Product Information.".
13 Product Information. Suprep Bowel Prep Kit (magnesium/potassium/sodium sulfates). Braintree Laboratories, Braintree, MA.
14 Product Information. Addyi (flibanserin). Sprout Pharmaceuticals, Raleigh, NC.
15 Product Information. Reglan (metoclopramide). Wyeth-Ayerst Laboratories, Philadelphia, PA.
16 Product Information. Alphagan (brimonidine ophthalmic). Allergan Inc, Irvine, CA.