Drug Information
Drug General Information | Top | |||
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Drug ID |
D02KRS
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Former ID |
DAP000781
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Drug Name |
Amantadine
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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
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Drug Type |
Small molecular drug
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Indication | Influenza A virus infection [ICD-11: 1E30] | Approved | [1], [2] | |
Therapeutic Class |
Antiviral Agents
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Structure |
Download2D MOL |
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Formula |
C10H17N
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Canonical SMILES |
C1C2CC3CC1CC(C2)(C3)N
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InChI |
1S/C10H17N/c11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9H,1-6,11H2
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InChIKey |
DKNWSYNQZKUICI-UHFFFAOYSA-N
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CAS Number |
CAS 768-94-5
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PubChem Compound ID | ||||
PubChem Substance ID |
9036, 461565, 588114, 597379, 3136147, 5106490, 7978680, 8147192, 8151445, 10535392, 11110715, 11335990, 11361229, 11362804, 11365366, 11367928, 11371422, 11373687, 11376090, 11448576, 11462201, 11466435, 11467555, 11483738, 11486009, 11487897, 11490107, 11491949, 11493844, 15170902, 15219251, 16666659, 24848359, 26755640, 26755641, 29221309, 30400536, 38395099, 46168239, 46507081, 47216816, 47216817, 47440544, 47515356, 47589230, 47736526, 47959791, 48035167, 48035168, 48259495
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ChEBI ID |
CHEBI:2618
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ADReCS Drug ID | BADD_D00097 | |||
SuperDrug ATC ID |
N04BB01
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SuperDrug CAS ID |
cas=000768945
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Interaction between the Drug and Microbe | Top | |||
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The Metabolism of Drug Affected by Studied Microbe(s) | ||||
The Order in the Taxonomic Hierarchy of the following Microbe(s): Bacteroidales | ||||
Studied Microbe: Bacteroides fragilis str. DS-208
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[3] | |||
Hierarchy | ||||
Experimental Method | High-throughput screening | |||
Description | Amantadine can be metabolized by Bacteroides fragilis str. DS-208 (log2FC = -0.325; p = 0.013). | |||
Studied Microbe: Bacteroides thetaiotaomicron 7330
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[3] | |||
Hierarchy | ||||
Experimental Method | High-throughput screening | |||
Description | Amantadine can be metabolized by Bacteroides thetaiotaomicron 7330 (log2FC = -0.347; p = 0.013). | |||
Studied Microbe: Bacteroides uniformis ATCC 8492
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[3] | |||
Hierarchy | ||||
Experimental Method | High-throughput screening | |||
Description | Amantadine can be metabolized by Bacteroides uniformis ATCC 8492 (log2FC = -0.378; p = 0.017). | |||
The Order in the Taxonomic Hierarchy of the following Microbe(s): Bifidobacteriales | ||||
Studied Microbe: Bifidobacterium ruminantium
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[3] | |||
Hierarchy | ||||
Experimental Method | High-throughput screening | |||
Description | Amantadine can be metabolized by Bifidobacterium ruminantium (log2FC = -0.422; p = 0.006). |
Drug Resistance Mutation (DRM) | Top | |||
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DRM | DRM Info |
Target and Pathway | Top | |||
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Target(s) | Influenza M2 protein (Influ M) | Target Info | Inhibitor | [4], [5], [6], [7] |
WikiPathways | Influenza Life Cycle |
References | Top | |||
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REF 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). | |||
REF 2 | Emerging treatments for traumatic brain injury. Expert Opin Emerg Drugs. 2009 Mar;14(1):67-84. | |||
REF 3 | Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467. | |||
REF 4 | 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. | |||
REF 5 | Current and future antiviral therapy of severe seasonal and avian influenza. Antiviral Res. 2008 Apr;78(1):91-102. | |||
REF 6 | 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. | |||
REF 7 | 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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