CAS 31377-23-8|1-Adamantanamine sulfate (2:1)
Introduction：Basic information about CAS 31377-23-8|1-Adamantanamine sulfate (2:1), including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| 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 | / | Flash Point | 96ºC |
Names
| Name | amantadine sulfate |
|---|---|
| Synonym | More Synonyms |
1-Adamantanamine sulfate (2:1) BiologicalActivity
| 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]. |
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| Related Catalog | Signaling Pathways >>Apoptosis >>Bcl-2 FamilySignaling Pathways >>Anti-infection >>Influenza VirusSignaling Pathways >>Apoptosis >>ApoptosisResearch Areas >>CancerResearch Areas >>InfectionSignaling Pathways >>Anti-infection >>SARS-CoVSignaling Pathways >>Cell Cycle/DNA Damage >>CDKResearch Areas >>Neurological Disease |
| 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 |
| InChIKey | MYWTWSQFJLXGGQ-UHFFFAOYSA-N |
| SMILES | NC12CC3CC(CC(C3)C1)C2.NC12CC3CC(CC(C3)C1)C2.O=S(=O)(O)O |
| 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 |
