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Amantadine (sulfate)

CAT: 0804-HY-B0402BSize: 1 EachDry Ice: NoHazardous: No
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Description
Amantadine (1-Adamantanamine) sulfate is an orally avtive and potent antiviral agent with activity against influenza A viruses. Amantadine sulfate inhibits several ion channels such as NMDA and M2, and also inhibits Coronavirus ion channels. Amantadine sulfate also has anti-orthopoxvirus and anticancer activity. Amantadine sulfate can be used for Parkinson's disease, postoperative cognitive dysfunction (POCD) and COVID-19 research[1][2][3][4][5][6].
CAS Number
31377-23-8
Product Name Alternative
1-Adamantanamine (sulfate) ; 1-Aminoadamantane (sulfate)
UNSPSC
12352211
Hazard Statement
H315-H319
Target
Apoptosis; Bcl-2 Family; CDK; Influenza Virus; Orthopoxvirus; SARS-CoV
Type
Reference compound
Related Pathways
Anti-infection; Apoptosis; Cell Cycle/DNA Damage
Applications
COVID-19-anti-virus
Field of Research
Cancer; Infection; Neurological Disease
Assay Protocol
https://www.medchemexpress.com/amantadine-sulfate.html
Solubility
10 mM in DMSO
Smiles
NC1(C[C@H](C2)C3)C[C@H]3C[C@H]2C1.O=S(O)(O)=O.[1/2]
Molecular Formula
C10H17N.1/2H2O4S
Molecular Weight
200.18
Precautions
P264-P280-P302+P352-P362+P364
References & Citations
[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.
Shipping Conditions
Room temperature
Scientific Category
Reference compound1
Clinical Information
Launched
Isoform
Bax; Bcl-2; CDK2

Chemical Information

Amantadine Sulfate

Amantadine sulfate is an alkylammonium sulfate salt obtained by combining amantadine and sulfuric acid in a 2:1 ratio. Used as an antiviral and antiparkinson drug. It has a role as a non-narcotic analgesic, an antiviral drug, an antiparkinson drug, a dopaminergic agent and a NMDA receptor antagonist. It contains an adamantan-1-aminium.

CAS Number31377-23-8
PubChem CID124108
IUPAC Namebis(adamantan-1-amine);sulfuric acid
Molecular FormulaC20H36N2O4S
Molecular Weight400.6
Topological Polar Surface Area135
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count6
Rotatable Bond Count0
Heavy Atom Count27
Formal Charge0
Complexity225
SMILES
C1C2CC3CC1CC(C2)(C3)N.C1C2CC3CC1CC(C2)(C3)N.OS(=O)(=O)O
InChI
InChI=1S/2C10H17N.H2O4S/c2*11-10-4-7-1-8(5-10)3-9(2-7)6-10;1-5(2,3)4/h2*7-9H,1-6,11H2;(H2,1,2,3,4)
InChIKey
MYWTWSQFJLXGGQ-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Amantadine Sulfate
CAS: 31377-23-8
CID: 124108
Formula: C20H36N2O4S
MW: 400.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight400.6
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count6
Rotatable Bond Count0
Exact Mass400.23957881
Monoisotopic Mass400.23957881
Topological Polar Surface Area135 Ų
Heavy Atom Count27
Formal Charge0
Complexity225
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count3
Compound Is CanonicalizedYes

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