Rimantadine

• CAT Number: I001300
• CAS Number: 13392-28-4
• Molecular Formula: C12H21N
• Molecular Weight: 179.30
• Purity: ≥95%
• Target: Influenza Virus
• Solubility: DMSO 33 mg/mL; Water 33 mg/mL
• Storage: 3 years -20℃ powder
• IUPAC Name: 1-(1-adamantyl)ethanamine
• InChI: InChI=1S/C12H21N/c1-8(13)12-5-9-2-10(6-12)4-11(3-9)7-12/h8-11H,2-7,13H2,1H3
• InChIKey: UBCHPRBFMUDMNC-UHFFFAOYSA-N
• SMILES: CC(C12CC3CC(C1)CC(C3)C2)N

Rimantadine（Cat No.:I001300）is an antiviral medication used primarily to prevent and treat influenza A infections. As an adamantane derivative, it works by inhibiting the M2 protein in the influenza A virus, blocking viral replication and reducing the severity and duration of flu symptoms. Rimantadine is most effective when administered early in the infection cycle, making it valuable during flu season and in outbreak control. Although it is generally well-tolerated, resistance to rimantadine has limited its use, especially in strains with increased resistance, prompting research into combination therapies and alternative antiviral agents.

Reference

1:Stereoselective synthesis of novel adamantane derivatives with high potency against rimantadine-resistant influenza A virus strains. Kuznetsov NY, Tikhov RM, Godovikov IA, Medvedev MG, Lyssenko KA, Burtseva EI, Kirillova ES, Bubnov YN.Org Biomol Chem. 2017 Apr 11;15(15):3152-3157. doi: 10.1039/c7ob00331e. PMID: 28338150 2:Dispersive micro solid phase extraction of amantadine, rimantadine and memantine in chicken muscle with magnetic cation exchange polymer. Chen D, Miao H, Zhao Y, Wu Y.J Chromatogr B Analyt Technol Biomed Life Sci. 2017 Apr 15;1051:92-96. doi: 10.1016/j.jchromb.2017.03.005. Epub 2017 Mar 10. PMID: 28334651 3:Affinity of Rimantadine Enantiomers against Influenza A/M2 Protein Revisited. Drakopoulos A, Tzitzoglaki C, Ma C, Freudenberger K, Hoffmann A, Hu Y, Gauglitz G, Schmidtke M, Wang J, Kolocouris A.ACS Med Chem Lett. 2017 Jan 27;8(2):145-150. doi: 10.1021/acsmedchemlett.6b00311. eCollection 2017 Feb 9. PMID: 28217261 4:Simultaneous determination of amantadine, rimantadine, and memantine in processed products, chicken tissues, and eggs by liquid chromatography with tandem mass spectrometry. Tsuruoka Y, Nakajima T, Kanda M, Hayashi H, Matsushima Y, Yoshikawa S, Nagata M, Koike H, Nagano C, Sekimura K, Hashimoto T, Takano I, Shindo T.J Chromatogr B Analyt Technol Biomed Life Sci. 2017 Feb 15;1044-1045:142-148. doi: 10.1016/j.jchromb.2017.01.014. Epub 2017 Jan 11. PMID: 28107701 5:Preparation of a monoclonal antibody against amantadine and rimantadine and development of an indirect competitive enzyme-linked immunosorbent assay for detecting the same in chicken muscle and liver. Peng D, Wei W, Pan Y, Wang Y, Chen D, Liu Z, Wang X, Dai M, Yuan Z.J Pharm Biomed Anal. 2017 Jan 30;133:56-63. doi: 10.1016/j.jpba.2016.11.009. Epub 2016 Nov 10. PMID: 27856102 6:Chromatography column comparison and rapid pretreatment for the simultaneous analysis of amantadine, rimantadine, acyclovir, ribavirin, and moroxydine in chicken muscle by ultra high performance liquid chromatography and tandem mass spectrometry. Zhang Q, Xiao C, Wang W, Qian M, Xu J, Yang H.J Sep Sci. 2016 Oct;39(20):3998-4010. doi: 10.1002/jssc.201600490. Epub 2016 Sep 28. PMID: 27568878 7:Intrathecal rimantadine induces motor, proprioceptive, and nociceptive blockades in rats. Tzeng JI, Wang JN, Wang JJ, Chen YW, Hung CH.Neurosci Lett. 2016 Apr 8;618:94-8. doi: 10.1016/j.neulet.2016.02.061. Epub 2016 Mar 3. PMID: 26949181 8:[Determination of amantadine and rimantadine residues in egg and chicken samples by dispersive solid phase extraction purification-ultra high performance liquid chromatography-tandem mass spectrometry]. Lin T, Fan J, Liu X, Chen X, Li Y, Liu H.Se Pu. 2015 Nov;33(11):1169-74. Chinese. PMID: 26939363 9:Differential Binding of Rimantadine Enantiomers to Influenza A M2 Proton Channel. Wright AK, Batsomboon P, Dai J, Hung I, Zhou HX, Dudley GB, Cross TA.J Am Chem Soc. 2016 Feb 10;138(5):1506-9. doi: 10.1021/jacs.5b13129. Epub 2016 Jan 28. PMID: 26804976 10:Investigation of the free energy profiles of amantadine and rimantadine in the AM2 binding pocket. Van Nguyen H, Nguyen HT, Le LT.Eur Biophys J. 2016 Jan;45(1):63-70. doi: 10.1007/s00249-015-1077-y. Epub 2015 Sep 21. PMID: 26391902