General Information of Drug (ID: DMS3YE9)

Drug Name
Amantadine Drug Info
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 Approved [2]
Postencephalitic Parkinson disease Approved [2]
Therapeutic Class
Antiviral Agents
Cross-matching ID
PubChem CID
2130
ChEBI ID
CHEMBL660
CAS Number
CAS 768-94-5
TTD Drug ID
DMS3YE9
VARIDT Drug ID
DR00040
INTEDE Drug ID
DR2259
ACDINA Drug ID
D00027

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DTP
DOT
Drug Status:
Approved Drug(s)
Clinical Trial Drug(s)
Investigative Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Rimantadine DM5DWMU Influenza A virus infection 1E30 Approved [7]
TCN-032 DM9PVNJ Influenza virus infection 1E30-1E32 Phase 2 [8]
B-Octylglucoside DMMO75G Discovery agent N.A. Investigative [9]
Spiro[piperidine-2,2-adamantane] DMWU9PV Discovery agent N.A. Investigative [10]
2-(1-adamantyl) piperidine DM05OJD Discovery agent N.A. Investigative [10]
Rimantadine isomer 2 DM3BEF7 Discovery agent N.A. Investigative [10]
2-(1-adamantyl) pyrrolidine DMMSFEU Discovery agent N.A. Investigative [10]
3-(2-adamantyl) pyrrolidine DMS98WA Discovery agent N.A. Investigative [10]
Spiro[pyrrolidine-2,2-adamantane] DMW48JD Discovery agent N.A. Investigative [10]
2-(1-adamantyl)-2-methyl-pyrrolidine DMIGRMV Discovery agent N.A. Investigative [10]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Dinoprostone DMTYOPD Medical abortion JA00.1Z Approved [11]
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [12]
Oxaliplatin DMQNWRD Adenocarcinoma 2D40 Approved [13]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [14]
Dopamine DMPGUCF Acromegaly 5A60.0 Approved [15]
Propranolol DM79NTF Angina pectoris BA40 Approved [16]
Ergotidine DM78IME Osteoarthritis FA00-FA05 Approved [17]
Metformin DM89QE1 Colorectal carcinoma Approved [18]
Clonidine DM6RZ9Q Attention deficit hyperactivity disorder 6A05.Z Approved [16]
Ranitidine DM0GUSX Gastric ulcer DA60 Approved [19]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [20]
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [21]
Gefitinib DM15F0X Colon adenocarcinoma Approved [22]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [23]
Selenium DM25CGV N. A. N. A. Approved [24]
Methotrexate DM2TEOL Anterior urethra cancer Approved [25]
Quercetin DM3NC4M Obesity 5B81 Approved [26]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [27]
Methylprednisolone DM4BDON Acute adrenal insufficiency Approved [25]
Hydroquinone DM6AVR4 Melasma ED60.1 Approved [28]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [29]
Colchicine DM2POTE Acute gout flare FA25.0 Approved [6]
Methotrexate DM2TEOL Anterior urethra cancer Approved [30]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [31]
Panobinostat DM58WKG Chronic graft versus host disease Approved [32]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [27]
Leflunomide DMR8ONJ Arthritis FA20 Approved [33]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [34]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [35]
Ivermectin DMDBX5F Intestinal strongyloidiasis due to nematode parasite 1F6B Approved [36]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [37]
Quercetin DM3NC4M Obesity 5B81 Approved [26]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [38]
Isotretinoin DM4QTBN Acne vulgaris ED80 Approved [39]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [40]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [41]
Tofacitinib DMBS370 Rheumatoid arthritis FA20 Approved [42]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [43]
Clozapine DMFC71L Schizophrenia 6A20 Approved [44]
Zoledronate DMIXC7G Adenocarcinoma 2D40 Approved [45]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Tretinoin DM49DUI Acne vulgaris ED80 Approved [46]
Hydroquinone DM6AVR4 Melasma ED60.1 Approved [28]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [47]
Testosterone enanthate DMB6871 N. A. N. A. Approved [48]
Tofacitinib DMBS370 Rheumatoid arthritis FA20 Approved [49]
Temozolomide DMKECZD Adenocarcinoma 2D40 Approved [50]
Decitabine DMQL8XJ Acute myelogenous leukaemia 2A41 Approved [51]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [52]
Fluorouracil DMUM7HZ Adenocarcinoma 2D40 Approved [53]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [54]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [55]
Methotrexate DM2TEOL Anterior urethra cancer Approved [25]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [56]
Methylprednisolone DM4BDON Acute adrenal insufficiency Approved [25]
Testosterone DM7HUNW Hot flushes GA30 Approved [57]
Calcitriol DM8ZVJ7 Congenital alopecia LC30 Approved [58]
Testosterone enanthate DMB6871 N. A. N. A. Approved [48]
Tofacitinib DMBS370 Rheumatoid arthritis FA20 Approved [49]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [43]
Demecolcine DMCZQGK Solid tumour/cancer 2A00-2F9Z Approved [59]
⏷ Show the Full List of 10 Drug(s)

Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas

Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Influenza M2 protein (Influ M) TTXT3PU M2_I34A1 Inhibitor [3]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Organic cation transporter 2 (SLC22A2) DT9IDPW S22A2_HUMAN Substrate [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
2'-5'-oligoadenylate synthase 2 (OAS2) OT64CCTM OAS2_HUMAN Gene/Protein Processing [5]
Interferon alpha-inducible protein 27, mitochondrial (IFI27) OTI2XGIT IFI27_HUMAN Gene/Protein Processing [5]
Interferon alpha-inducible protein 6 (IFI6) OTWOOAM4 IFI6_HUMAN Gene/Protein Processing [5]
Microtubule-associated protein 2 (MAP2) OT6UYT3X MTAP2_HUMAN Gene/Protein Processing [6]
Tyrosine-protein kinase JAK1 (JAK1) OT0X3D17 JAK1_HUMAN Gene/Protein Processing [5]

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 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.
4 Human neurons express the polyspecific cation transporter hOCT2, which translocates monoamine neurotransmitters, amantadine, and memantine. Mol Pharmacol. 1998 Aug;54(2):342-52.
5 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.
6 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.
7 Antiviral resistance of influenza A (H3N2) strains isolated in northern Greece between 2004 and 2007. Euro Surveill. 2009 Jan 29;14(4). pii: 19104.
8 Human antibodies reveal a protective epitope that is highly conserved among human and nonhuman influenza A viruses. Proc Natl Acad Sci U S A. 2010 July 13; 107(28): 12658-12663.
9 How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
10 Antiviral agents active against influenza A viruses. Nat Rev Drug Discov. 2006 Dec;5(12):1015-25.
11 Are organic cation transporters capable of transporting prostaglandins? Naunyn Schmiedebergs Arch Pharmacol. 2005 Aug;372(2):125-30.
12 Cisplatin nephrotoxicity is critically mediated via the human organic cation transporter 2. Am J Pathol. 2005 Dec;167(6):1477-84.
13 Relevance of copper transporter 1 and organic cation transporters 1-3 for oxaliplatin uptake and drug resistance in colorectal cancer cells. Metallomics. 2018 Mar 1;10(3):414-425.
14 Cloning and characterization of two human polyspecific organic cation transporters. DNA Cell Biol. 1997 Jul;16(7):871-81.
15 Differential pharmacological in vitro properties of organic cation transporters and regional distribution in rat brain. Neuropharmacology. 2006 Jun;50(8):941-52.
16 Influx Transport of Cationic Drug at the Blood-Retinal Barrier: Impact on the Retinal Delivery of Neuroprotectants. Biol Pharm Bull. 2017;40(8):1139-1145.
17 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.
18 Metformin is a superior substrate for renal organic cation transporter OCT2 rather than hepatic OCT1. Drug Metab Pharmacokinet. 2005 Oct;20(5):379-86.
19 A species difference in the transport activities of H2 receptor antagonists by rat and human renal organic anion and cation transporters. J Pharmacol Exp Ther. 2005 Oct;315(1):337-45.
20 Cannabidiol Modulates the Immunophenotype and Inhibits the Activation of the Inflammasome in Human Gingival Mesenchymal Stem Cells. Front Physiol. 2016 Nov 24;7:559. doi: 10.3389/fphys.2016.00559. eCollection 2016.
21 Analysis of estrogen agonism and antagonism of tamoxifen, raloxifene, and ICI182780 in endometrial cancer cells: a putative role for the epidermal growth factor receptor ligand amphiregulin. J Soc Gynecol Investig. 2005 Oct;12(7):e55-67.
22 Identification of genes linked to gefitinib treatment in prostate cancer cell lines with or without resistance to androgen: a clue to application of gefitinib to hormone-resistant prostate cancer. Oncol Rep. 2006 Jun;15(6):1453-60.
23 MS4A3-HSP27 target pathway reveals potential for haematopoietic disorder treatment in alimentary toxic aleukia. Cell Biol Toxicol. 2023 Feb;39(1):201-216. doi: 10.1007/s10565-021-09639-4. Epub 2021 Sep 28.
24 Selenium and vitamin E: cell type- and intervention-specific tissue effects in prostate cancer. J Natl Cancer Inst. 2009 Mar 4;101(5):306-20.
25 Antirheumatic drug response signatures in human chondrocytes: potential molecular targets to stimulate cartilage regeneration. Arthritis Res Ther. 2009;11(1):R15.
26 Comparison of phenotypic and transcriptomic effects of false-positive genotoxins, true genotoxins and non-genotoxins using HepG2 cells. Mutagenesis. 2011 Sep;26(5):593-604.
27 Systems analysis of transcriptome and proteome in retinoic acid/arsenic trioxide-induced cell differentiation/apoptosis of promyelocytic leukemia. Proc Natl Acad Sci U S A. 2005 May 24;102(21):7653-8.
28 Keratinocyte-derived IL-36gama plays a role in hydroquinone-induced chemical leukoderma through inhibition of melanogenesis in human epidermal melanocytes. Arch Toxicol. 2019 Aug;93(8):2307-2320.
29 Minimal peroxide exposure of neuronal cells induces multifaceted adaptive responses. PLoS One. 2010 Dec 17;5(12):e14352. doi: 10.1371/journal.pone.0014352.
30 Global molecular effects of tocilizumab therapy in rheumatoid arthritis synovium. Arthritis Rheumatol. 2014 Jan;66(1):15-23.
31 Development of a neural teratogenicity test based on human embryonic stem cells: response to retinoic acid exposure. Toxicol Sci. 2011 Dec;124(2):370-7.
32 A transcriptome-based classifier to identify developmental toxicants by stem cell testing: design, validation and optimization for histone deacetylase inhibitors. Arch Toxicol. 2015 Sep;89(9):1599-618.
33 Endoplasmic reticulum stress and MAPK signaling pathway activation underlie leflunomide-induced toxicity in HepG2 Cells. Toxicology. 2017 Dec 1;392:11-21.
34 Comparison of HepG2 and HepaRG by whole-genome gene expression analysis for the purpose of chemical hazard identification. Toxicol Sci. 2010 May;115(1):66-79.
35 Neuronal and cardiac toxicity of pharmacological compounds identified through transcriptomic analysis of human pluripotent stem cell-derived embryoid bodies. Toxicol Appl Pharmacol. 2021 Dec 15;433:115792. doi: 10.1016/j.taap.2021.115792. Epub 2021 Nov 3.
36 Quantitative proteomics reveals a broad-spectrum antiviral property of ivermectin, benefiting for COVID-19 treatment. J Cell Physiol. 2021 Apr;236(4):2959-2975. doi: 10.1002/jcp.30055. Epub 2020 Sep 22.
37 Oxidative stress modulates theophylline effects on steroid responsiveness. Biochem Biophys Res Commun. 2008 Dec 19;377(3):797-802.
38 Differential modulation of PI3-kinase/Akt pathway during all-trans retinoic acid- and Am80-induced HL-60 cell differentiation revealed by DNA microarray analysis. Biochem Pharmacol. 2004 Dec 1;68(11):2177-86.
39 Temporal changes in gene expression in the skin of patients treated with isotretinoin provide insight into its mechanism of action. Dermatoendocrinol. 2009 May;1(3):177-87.
40 Arsenic trioxide induces differentiation of cancer stem cells in hepatocellular carcinoma through inhibition of LIF/JAK1/STAT3 and NF-kB signaling pathways synergistically. Clin Transl Med. 2021 Feb;11(2):e335. doi: 10.1002/ctm2.335.
41 Integrating multiple omics to unravel mechanisms of Cyclosporin A induced hepatotoxicity in vitro. Toxicol In Vitro. 2015 Apr;29(3):489-501.
42 JAK inhibitors: treatment efficacy and safety profile in patients with psoriasis. J Immunol Res. 2014;2014:283617. doi: 10.1155/2014/283617. Epub 2014 May 5.
43 Integrative omics data analyses of repeated dose toxicity of valproic acid in vitro reveal new mechanisms of steatosis induction. Toxicology. 2018 Jan 15;393:160-170.
44 Toxicoproteomics reveals an effect of clozapine on autophagy in human liver spheroids. Toxicol Mech Methods. 2023 Jun;33(5):401-410. doi: 10.1080/15376516.2022.2156005. Epub 2022 Dec 19.
45 Interleukin-19 as a translational indicator of renal injury. Arch Toxicol. 2015 Jan;89(1):101-6.
46 Retinoic acid exerts dual regulatory actions on the expression and nuclear localization of interferon regulatory factor-1. Exp Biol Med (Maywood). 2006 May;231(5):619-31. doi: 10.1177/153537020623100517.
47 Cyclosporine A--induced oxidative stress in human renal mesangial cells: a role for ERK 1/2 MAPK signaling. Toxicol Sci. 2012 Mar;126(1):101-13.
48 Transcriptional profiling of testosterone-regulated genes in the skeletal muscle of human immunodeficiency virus-infected men experiencing weight loss. J Clin Endocrinol Metab. 2007 Jul;92(7):2793-802. doi: 10.1210/jc.2006-2722. Epub 2007 Apr 17.
49 White-to-brown metabolic conversion of human adipocytes by JAK inhibition. Nat Cell Biol. 2015 Jan;17(1):57-67. doi: 10.1038/ncb3075. Epub 2014 Dec 8.
50 Temozolomide induces activation of Wnt/-catenin signaling in glioma cells via PI3K/Akt pathway: implications in glioma therapy. Cell Biol Toxicol. 2020 Jun;36(3):273-278. doi: 10.1007/s10565-019-09502-7. Epub 2019 Nov 22.
51 Characterization of DOK1, a candidate tumor suppressor gene, in epithelial ovarian cancer. Mol Oncol. 2011 Oct;5(5):438-53. doi: 10.1016/j.molonc.2011.07.003. Epub 2011 Jul 26.
52 Multiple microRNAs function as self-protective modules in acetaminophen-induced hepatotoxicity in humans. Arch Toxicol. 2018 Feb;92(2):845-858.
53 Transcriptional profiling of MCF7 breast cancer cells in response to 5-Fluorouracil: relationship with cell cycle changes and apoptosis, and identification of novel targets of p53. Int J Cancer. 2006 Sep 1;119(5):1164-75.
54 Long-term estrogen exposure promotes carcinogen bioactivation, induces persistent changes in gene expression, and enhances the tumorigenicity of MCF-7 human breast cancer cells. Toxicol Appl Pharmacol. 2009 Nov 1;240(3):355-66.
55 Global gene expression analysis reveals differences in cellular responses to hydroxyl- and superoxide anion radical-induced oxidative stress in caco-2 cells. Toxicol Sci. 2010 Apr;114(2):193-203. doi: 10.1093/toxsci/kfp309. Epub 2009 Dec 31.
56 Transcriptional and Metabolic Dissection of ATRA-Induced Granulocytic Differentiation in NB4 Acute Promyelocytic Leukemia Cells. Cells. 2020 Nov 5;9(11):2423. doi: 10.3390/cells9112423.
57 The exosome-like vesicles derived from androgen exposed-prostate stromal cells promote epithelial cells proliferation and epithelial-mesenchymal transition. Toxicol Appl Pharmacol. 2021 Jan 15;411:115384. doi: 10.1016/j.taap.2020.115384. Epub 2020 Dec 25.
58 Identification of vitamin D3 target genes in human breast cancer tissue. J Steroid Biochem Mol Biol. 2016 Nov;164:90-97.
59 Characterization of formaldehyde's genotoxic mode of action by gene expression analysis in TK6 cells. Arch Toxicol. 2013 Nov;87(11):1999-2012.