1-Adamantanamine sulfate (2:1)

Modify Date: 2024-01-23 17:00:50

1-Adamantanamine sulfate (2:1) Structure
1-Adamantanamine sulfate (2:1) structure
 Common Name 1-Adamantanamine sulfate (2:1)
CAS Number 31377-23-8 Molecular Weight 400.576
Density 1.066g/cm3 Boiling Point 225.7ºC at 760 mmHg
Molecular Formula C20H36N2O4S Melting Point 300 °C
MSDS N/A Flash Point 96ºC

 Use of 1-Adamantanamine sulfate (2:1)


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].

 Names

Name amantadine sulfate
Synonym More Synonyms

 1-Adamantanamine sulfate (2:1) Biological Activity

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].
Related Catalog
Target

CDK2

Bcl-2

Bax
In Vitro Amantadine sulfate (0-500 µM, 26 h) inhibits SARS-CoV-2 replication, with IC50 concentrations between 83 and 119 µM[4]. Amantadine sulfate (0-100 µg/mL, 24-72 h) markedly inhibits the proliferation of HepG2 and SMMC‑7721 cells[6]. Amantadine sulfate (0-75 µg/mL, 48 h) arrests the cell cycle at the G0/G1 phase and induces apoptosis[6]. Amantadine sulfate (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]. 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 (IC50=83 µM) of viral nucleic acids in the supernatant 26 h after infection at 10-500 µM. Caused a concentration-dependent reduction (IC50=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 sulfate (25 mg/kg, IP, once daily for 3 days) inhibits surgery induced neuroinflammation and learning and memory impairment[5]. 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.
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.

 Chemical & Physical Properties

Density 1.066g/cm3
Boiling Point 225.7ºC at 760 mmHg
Melting Point 300 °C
Molecular Formula C20H36N2O4S
Molecular Weight 400.576
Flash Point 96ºC
Exact Mass 400.239563
PSA 135.02000
LogP 5.65640
Storage condition 2-8°C

 Safety Information

Safety Phrases S24/25
HS Code 2921300090

 Customs

HS Code 2921300090
Summary 2921300090 other cyclanic, cyclenic or cyclotherpenic mono- or polyamines, and their derivatives; salts thereof。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%

 Synonyms

1-AMINOADAMANTANE SULFATE
1-Adamantanaminesulfate
1-AMINOADAMANTANE SULPHATE
1-Adamantanamine sulfate (2:1)
1-Adamantanamine sulfate
1-Adamantylamine sulfate
ADAMANTYLAMINE SULFATE
AMANTADINE SULFATE
Tricyclo[3.3.1.1]decan-1-amine, sulfate (2:1)
1-AMINOADAMANTANSULFATE
MFCD00077251
EINECS 250-604-5
Adamantan-1-amine sulfate
1-ADAMANTANAMINE SULPHATE
AMANTADINE SULPHATE
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