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[CAS NO. 768-94-5] Amantadine

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Catalog:	HY-B0402
Brand:	MCE
CAS:	768-94-5

Overview

MDL	-
Molecular Weight	151.25
Molecular Formula	C10H17N
SMILES	NC12C[C@H]3C[C@@H](C2)C[C@@H](C1)C3

For research use only. We do not sell to patients.

2 Publications Citing Use of MCE

[1]Signal Transduct Target Ther. 2021 Mar 27;6(1):134.
[2]Int J Nanomedicine. 2019 Nov 27;14:9217-9234.

Summary

Amantadine (1-Adamantanamine) is an orally avtive and potent antiviral agent with activity against influenza A viruses. Amantadine inhibits several ion channels such as NMDA and M2 , and also inhibits Coronavirus ion channels. Amantadine also has anti- orthopoxvirus and anticancer activity. Amantadine can be used for Parkinson's disease, postoperative cognitive dysfunction (POCD) and COVID-19 research ^[1] ^[2] ^[3] ^[4] ^[5] ^[6] .

IC50 & Target

CDK2

Bcl-2

Bax

In Vitro

Amantadine (0-500 µM, 26 h) inhibits SARS-CoV-2 replication, with IC ₅₀ concentrations between 83 and 119 µM ^[4] .
Amantadine (0-100 µg/mL, 24-72 h) markedly inhibits the proliferation of HepG2 and SMMC‑7721 cells ^[6] .
Amantadine (0-75 µg/mL, 48 h) arrests the cell cycle at the G0/G1 phase and induces apoptosis ^[6] .
Amantadine (0-75 µg/mL, 48 h) reduces the levels of the cell cycle‑related genes and proteins (cyclin D1, cyclin E and CDK2), reduces Bcl-2 and increases the Bax protein and mRNA levels ^[6] .

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Cell Viability Assay ^[4]

Cell Line:	Vero E6 cells
Concentration:	500 µM, 100 µM, 20 µM, 4 µM, and 8 nM
Incubation Time:	26 h
Result:	Caused a concentration-dependent reduction (IC ₅₀ =83 µM) of viral nucleic acids in the supernatant 26 h after infection at 10-500 µM. Caused a concentration-dependent reduction (IC ₅₀ =119 µM) of viral nucleic acids in the cytosol 26 h after infection.

Cell Proliferation Assay ^[6]

Cell Line:	Human HCC cell lines (HepG2 and SMMC-7721) and normal hepatocellular cells (L02 cells)
Concentration:	0, 1, 2, 5, 10, 25, 50 and 100 µg/mL
Incubation Time:	24, 48 and 72 h
Result:	Inhibited cellular proliferation in a time- and dose-dependent manner in HepG2 and SMMC-7721 cells.

Cell Cycle Analysis ^[6]

Cell Line:	HepG2 and SMMC-7721 cells
Concentration:	0, 10, 25, 50 and 75 µg/mL
Incubation Time:	48 h
Result:	Significantly increased the population of HepG2 and SMMC-7721 cells in the G0/G1 phase in a dose-dependent manner, and significantly decreased the number of HepG2 cells in the S phase.

Apoptosis Analysis ^[6]

Cell Line:	HepG2 and SMMC-7721 cells
Concentration:	0, 10, 25, 50 and 75 µg/mL
Incubation Time:	48 h
Result:	Markedly increased the percentage of apoptotic HepG2 and SMMC-7721 cells (early- and late-stage apoptosis) in a dose-dependent manner.

Western Blot Analysis ^[6]

Cell Line:	HepG2 and SMMC-7721 cells
Concentration:	0, 10, 25, 50 and 75 µg/mL
Incubation Time:	48 h
Result:	Showed downregulation of cyclin D1, cyclin E and CDK2, and showed a decrease in Bcl-2 levels and an increase of Bax levels in HepG2 and SMMC-7721 cells.

RT-PCR ^[6]

Cell Line:	HepG2 and SMMC-7721 cells
Concentration:	0, 10, 25, 50 and 75 µg/mL
Incubation Time:	48 h
Result:	Revealed an increase in Bax and decrease in Bcl-2 genes.

In Vivo

Amantadine (25 mg/kg, IP, once daily for 3 days) inhibits surgery induced neuroinflammation and learning and memory impairment ^[5] .

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:	Fischer 344 rats (Four-month old, male, 290-330 g, 15 rats each group) ^[5]
Dosage:	25 mg/kg
Administration:	IP, once daily for 3 days (the first dose at 15 min before surgery)
Result:	Inhibited surgery induced neuroinflammation and learning and memory impairment, increased GDNF (glial cell line-derived neurotrophic factor) that was co-localized with glial fibrillary acidic protein (an astrocytic marker) in the hippocampus.

Clinical Trial

NCT Number	Sponsor	Condition	Start Date	Phase
NCT01099059	Tehran University of Medical Sciences	Attention Deficit Hyperactivity Disorder	April 2010	Phase 2
NCT04260581	Seoul National University Hospital	Parkinson Disease	March 1, 2020	Not Applicable
NCT00627250	Wake Forest University Health Sciences\|U.S. Department of Education	Irritable Mood\|Aggression\|Traumatic Brain Injury	March 2003	Not Applicable
NCT00127114	Johns Hopkins University	Dementia	September 2005	Phase 4
NCT00950196	Sheba Medical Center	Ataxia\|Chorea\|Dystonia\|Parkinsonism\|Fatigue	November 2008	Phase 4
NCT02566720	Hamilton Health Sciences Corporation	Acquired Brain Injury\|Coma\|Persistent Vegetative State\|Minimally Conscious State\|Traumatic Brain Injury	January 2016	Not Applicable
NCT00830323	Hospices Civils de Lyon	Influenza A Infection	January 2009	Phase 2
NCT04936126	All India Institute of Medical Sciences, Bhubaneswar\|Indian Council of Medical Research	Treatment Resistant Depression	August 7, 2021	Phase 4
NCT01789047	Rush University Medical Center\|Michael J. Fox Foundation for Parkinson´s Research	Idiopathic Parkinson´s Disease\|Drug Induced Dyskinesia	March 2013	Phase 2
NCT01071395	Rush University Medical Center\|Michael J. Fox Foundation for Parkinson´s Research	Parkinson´s Disease	January 2010	Phase 4
NCT00127777	University Hospital, Saarland\|Hoffmann-La Roche	Hepatitis C, Chronic	July 2002	Phase 4
NCT00600093	Rabin Medical Center	Parkinson Disease\|Perioperative Care	January 2008	Phase 2
NCT00416962	Novartis\|Hoffmann-La Roche	Healthy	August 2006	Phase 1
NCT00188383	University Health Network, Toronto\|Canadian Institutes of Health Research (CIHR)	Hyperalgesia\|Pain\|Prostate Cancer	January 2004	Phase 1\|Phase 2
NCT00000301	University of California, Los Angeles\|National Institute on Drug Abuse (NIDA)	Cocaine-Related Disorders	March 1996	Phase 2
NCT03612921	Assiut University	Intubation, Intratracheal	August 15, 2018	Phase 2
NCT00970944	JFK Medical Center\|U.S. Department of Education	Traumatic Brain Injury	February 2003	Phase 2\|Phase 3
NCT03172234	Ghada Mohammed AboelFadl\|Assiut University	Effect of Laryngoscopy and Tracheal Intubation	June 15, 2017	Phase 2\|Phase 3
NCT05479032	University Hospital Tuebingen	Disorder of Consciousness	September 2022	Phase 2
NCT00800514	Wake Forest University Health Sciences	Traumatic Brain Injury	January 2009	Not Applicable
NCT02486211	Jon Rittenberger, MD\|American Heart Association\|University of Pittsburgh	Coma\|Heart Arrest\|Anoxia	September 2015	Phase 2
NCT00999505	Hospital de Clinicas de Porto Alegre	Schizophrenia	May 2010	Phase 3
NCT04244058	Weill Medical College of Cornell University	Disorder of Consciousness\|Traumatic Brain Injury	September 23, 2020	Early Phase 1
NCT05140148	University of Pennsylvania	Stroke, Ischemic\|Stroke Hemorrhagic	February 1, 2022	Phase 2
NCT00287352	University of North Carolina, Chapel Hill\|Eli Lilly and Company	Psychotic Disorder\|Schizophreniform Disorder\|Schizophrenia\|Schizoaffective Disorder\|Mood Disorders With Psychotic Features	May 2005	Phase 1
NCT01467258	University of Manitoba\|St. Boniface Hospital	Healthy Metabolism	November 2011	Not Applicable
NCT00779324	Wake Forest University Health Sciences\|Indiana University\|University of Washington\|The Institute for Rehabilitaion and Research Foundation\|Spaulding Rehabilitation Hospital\|Ohio State University\|Icahn School of Medicine at Mount Sinai	Brain Injury\|Aggression	August 2009	Not Applicable
NCT02277938	University of Manitoba\|BioMark Technologies Inc.\|St. Boniface Hospital	Cancer	August 2013
NCT04854759	Independent Public Clinical Hospital No. 4 in Lublin	COVID-19\|SARS-CoV-2	March 15, 2021	Phase 3
NCT04530006	CancerCare Manitoba\|University of Manitoba\|The Metabolomics Innovation Centre\|BioMark Diagnostics Inc.\|Canadian Institutes of Health Research (CIHR)	Glioblastoma Multiforme	December 2, 2020	Not Applicable
NCT02321761	Loewenstein Hospital	Traumatic Brain Injury	June 2014	Phase 4
NCT01441986	Profil Institut für Stoffwechselforschung GmbH\|Heinrich-Heine University, Duesseldorf	Type 2 Diabetes Mellitus	September 2011	Phase 2
NCT00401973	Eli Lilly and Company	Schizophrenia\|Schizoaffective Disorders	November 2006	Phase 3
NCT00299923	University of Hamburg-Eppendorf\|Universitätsklinikum Hamburg-Eppendorf\|Hoffmann-La Roche	Hepatitis C, Chronic\|Relapse	November 2005	Phase 3
NCT00146016	UMC Utrecht	Chronic Hepatitis C	February 2000	Phase 3
NCT03988010	TC Erciyes University	Postoperative Cognitive Dysfunction	May 1, 2019	Phase 4
NCT03430817	Ain Shams University	Intensive Care Unit	December 7, 2017	Phase 4
NCT05504057	Consorci Sanitari de Terrassa\|Institut Català de la Salut	COVID-19	March 1, 2020
NCT01313819	Seoul National University Hospital	Parkinson´s Disease\|Freezing of Gait	April 2011	Phase 4
NCT04273737	Columbia University	Cerebral Palsy	February 28, 2020	Phase 4
NCT02025439	Edward Hines Jr. VA Hospital	Traumatic Brain Injury	February 2014	Not Applicable
NCT00158132	University of Pennsylvania\|National Institute on Drug Abuse (NIDA)	Cocaine-Related Disorders	September 1999	Phase 2
NCT01652534	Northwestern University	Parkinson´s Disease	June 2011	Phase 3
NCT02153645	Adamas Pharmaceuticals, Inc.	Parkinson´s Disease\|Levodopa Induced Dyskinesias (LID)	August 18, 2014	Phase 3
NCT00693121	Methodist Rehabilitation Center\|U.S. Department of Education	Traumatic Brain Injury\|Posttraumatic Confusional State\|Delirium	April 2003	Phase 4
NCT04894617	Copenhagen University Hospital, Hvidovre\|University of Copenhagen	Covid19	June 1, 2021	Phase 3
NCT00755898	University of Manitoba\|Canadian Institutes of Health Research (CIHR)\|BioMark Technologies Inc.	Cancer	December 2003	Phase 2
NCT04527289	Damanhour University	Trauma, Brain	September 30, 2020	Phase 4
NCT01313845	Jee-Young Lee\|Seoul National University Boramae Hospital\|Samsung Medical Center\|Seoul National University Bundang Hospital\|Hanyang University\|Seoul National University Hospital	Parkinson´s Disease	February 2011	Phase 4
NCT00538811	Aga Khan University	Hepatitis C\|Genotype 3\|Non-responders\|Relapsers		Phase 2\|Phase 3
NCT03185065	Johns Hopkins University\|Patient-Centered Outcomes Research Institute	Fatigue in Multiple Sclerosis	October 4, 2017	Phase 3
NCT04427241	Konkuk University Medical Center\|Ever Neuro Pharma GmbH	Brain Injuries, Traumatic\|Disorder of Consciousness	August 1, 2022	Phase 4
NCT03527134	Zhiyi Zuo\|Sun Yat-Sen Memorial Hospital of Sun Yat-Sen University\|Sun Yat-sen University	Postoperative Cognitive Dysfunction	April 30, 2019	Not Applicable
NCT01538329	University Hospital, Toulouse	Parkinson Disease	March 4, 2012	Phase 2
NCT00221624	University Hospital, Bordeaux\|Hoffmann-La Roche	HCV Infection\|Hepatitis C, Chronic	November 2001	Phase 3
NCT02153632	Adamas Pharmaceuticals, Inc.	Parkinson´s Disease\|Levodopa Induced Dyskinesia (LID)	July 30, 2014	Phase 3
NCT03178708	Assiut University	Spinal Curvatures	August 1, 2017	Phase 2\|Phase 3
NCT00122629	French National Agency for Research on AIDS and Viral Hepatitis\|Schering-Plough	Hepatitis C, Chronic	October 2000	Phase 3
NCT03443037	Dokuz Eylul University	Coma; Prolonged\|Amantadine	March 1, 2016
NCT00001930	National Institute of Neurological Disorders and Stroke (NINDS)\|National Institutes of Health Clinical Center (CC)	Chorea\|Huntington´s Disease	April 1999	Phase 2
NCT00975611	David C. Henderson, MD\|Ortho-McNeil Janssen Scientific Affairs, LLC\|North Suffolk Mental Health Association	Schizophrenia\|Schizoaffective Disorder	October 2009	Phase 4
NCT04173832	Xinhua Hospital, Shanghai Jiao Tong University School of Medicine\|Shanghai University of Traditional Chinese Medicine\|Shanghai Municipal Hospital of Traditional Chinese Medicine\|Wenzhou Central Hospital\|The Affiliated Hospital of Qingdao University\|Nanjing Hospital of Chinese Medicine affiliated to Nanjing University of Chinese Medicine\|The Affiliated Hospital of Xuzhou Medical University	L-DOPA-Induced Dyskinesia	January 1, 2020	Not Applicable
NCT00015249	National Institute on Drug Abuse (NIDA)\|New York MDRU	Cocaine-Related Disorders\|Substance-Related Disorders	February 1997	Phase 1
NCT00794313	Oregon Health and Science University	Parkinson´s Disease	September 2009	Not Applicable
NCT00015236	National Institute on Drug Abuse (NIDA)\|New York MDRU	Cocaine-Related Disorders\|Substance-Related Disorders	March 1997	Phase 4
NCT04952519	Noblewell\|Medical Research Agency, Poland\|Leszek Giec Upper-Silesian Medical Centre of the Silesian Medical University in Katowice, Poland	Patients With Moderate or Severe COVID-19	March 30, 2021	Phase 3
NCT01190553	Rabin Medical Center	Parkinson Disease	November 2010	Not Applicable
NCT00000281	Yale University\|National Institute on Drug Abuse (NIDA)\|VA Connecticut Healthcare System	Cocaine-Related Disorders\|Substance-Related Disorders\|Shcizophrenia	September 1994	Phase 2

Appearance

Solid

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

4°C, protect from light

* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

Solvent & Solubility

In Vitro:

DMSO : 1 mg/mL ( 6.61 mM ; ultrasonic and warming and heat to 60°C)

Preparing
Stock Solutions

Concentration Solvent Mass	1 mg	5 mg	10 mg

1 mM	6.6116 mL	33.0578 mL	66.1157 mL
5 mM	1.3223 mL	6.6116 mL	13.2231 mL
10 mM	---	---	---

* Please refer to the solubility information to select the appropriate solvent.

In Vivo:

1.

Add each solvent one by one: 10% DMSO >> 40% PEG300 >> 5% Tween-80 >> 45% saline

Solubility: ≥ 0.5 mg/mL (3.31 mM); Clear solution
2.

Add each solvent one by one: 10% DMSO >> 90% (20% SBE-β-CD in saline)

Solubility: ≥ 0.5 mg/mL (3.31 mM); Clear solution
3.

Add each solvent one by one: 10% DMSO >> 90% corn oil

Solubility: ≥ 0.5 mg/mL (3.31 mM); Clear solution

* All of the co-solvents are available by MCE.

References

[1] Suzuki H, et al. Emergence of amantadine-resistant influenza A viruses: epidemiological study. J Infect Chemother. 2003;9(3):195-200.
[2] Hubsher G, et al. Amantadine: the journey from fighting flu to treating Parkinson disease. Neurology. 2012;78(14):1096-1099.
[3] Donald F Smee, et al. A review of compounds exhibiting anti-orthopoxvirus activity in animal models. Antiviral Res. 2003 Jan;57(1-2):41-52.
[4] Fink K, et al. Amantadine Inhibits SARS-CoV-2 In Vitro. Viruses. 2021 Mar 24;13(4):539.
[5] Zhang J, et al. Amantadine alleviates postoperative cognitive dysfunction possibly by increasing glial cell line-derived neurotrophic factor in rats. Anesthesiology. 2014 Oct;121(4):773-85.
[6] Lan Z, et al. Amantadine inhibits cellular proliferation and induces the apoptosis of hepatocellular cancer cells in vitro. Int J Mol Med. 2015;36(3):904-910.

Synonyms

Tricyclo[3.3.1.1^3,7]decan-1-amine

1-Adamantanamine

Amantadine

1-Aminoadamantane

1-Adamantamine

Adamantylamine

1-Adamantylamine

1-Amantadine

Adamantamine

Adamantanamine

NSC 341865

Tricyclo[3.3.1.1^3,7]decane-1-amine

(Adamantan-1-yl)amine

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