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MedKoo Cat#: 318665 | Name: Rimantadine Hydrochloride
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Rimantadine is an orally administered antiviral drug used to treat, and in rare cases prevent, influenza A infection. Rimantadine is a derivate of adamantane.

Chemical Structure

Rimantadine Hydrochloride
Rimantadine Hydrochloride
CAS#1501-84-4

Theoretical Analysis

MedKoo Cat#: 318665

Name: Rimantadine Hydrochloride

CAS#: 1501-84-4

Chemical Formula: C12H22ClN

Exact Mass: 0.0000

Molecular Weight: 215.77

Elemental Analysis: C, 66.80; H, 10.28; Cl, 16.43; N, 6.49

Price and Availability

Size Price Availability Quantity
5g USD 350.00 2 Weeks
25g USD 550.00 2 Weeks
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Related CAS #
1501-84-4 (HCl) 13392-28-4 (free)
Synonym
Rimantadine, Flumadine, Remantadine, Riamantadine, Rimantadine Hydrochloride, Rimantadine HCl
IUPAC/Chemical Name
1-(adamantan-1-yl)ethanamine hydrochloride
InChi Key
OZBDFBJXRJWNAV-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H21N.ClH/c1-8(13)12-5-9-2-10(6-12)4-11(3-9)7-12;/h8-11H,2-7,13H2,1H3;1H
SMILES Code
CC(N)C12CC3CC(C2)CC(C3)C1.[H]Cl
Appearance
White to off-white crystalline powder.
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, DMF, and ethanol
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO, DMF, and ethanol
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Rimantadine inhibits recombinant influenza A matrix protein 2 (M2) expressed in X. laevis oocytes (IC50 = 10.8 µM) and recombinant hepatitis C virus (HCV) p7 protein expressed in HEK293 cells (IC50s = 0.7, 24, 1.6, and 3.0 nM for HCV genotypes 1a, 2a, 3a, and 4a, respectively). Rimantadine inhibits cytotoxicity induced by the influenza A strains A/PR/8/34 (H1N1) and A/HK/7/87 (H3N2), but not the influenza B strain B/HK/72, in MDCK cells (EC50s = 18, 0.62, and >500 µM, respectively). It also has trypanocidal activity against bloodstream forms of T. brucei in vitro (IC50 = 1.26 µg/ml).
In vitro activity:
Of the compounds tested, (rimantadine, memantine, and amantadine), rimantadine showed the most promise for treatment of SARS-CoV-2. In VeroE6 cells, rimantadine was a potent ion-channel inhibitor. Similar results were observed in human hepatoma Huh7.5 and lung carcinoma A549-hACE2 cells. Reference: Viruses. 2021 Oct 15;13(10):2082. https://pubmed.ncbi.nlm.nih.gov/34696509/
In vivo activity:
In children, rimantadine was effective in the abatement of influenza A related fever on day three of treatment. AMT showed a prophylactic effect against influenza A infection. There is a proven benefit of rimantadine, but further research is needed. Reference: Cochrane Database Syst Rev. 2008 Jan 23;(1):CD002745. https://pubmed.ncbi.nlm.nih.gov/18254006/
Solvent mg/mL mM
Solubility
DMF 2.0 9.27
DMSO 50.0 231.73
Ethanol 5.0 23.17
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 215.77 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Santos IA, Pereira AKDS, Guevara-Vega M, de Paiva REF, Sabino-Silva R, Bergamini FRG, Corbi PP, Jardim ACG. Repurposing potential of rimantadine hydrochloride and development of a promising platinum(II)-rimantadine metallodrug for the treatment of Chikungunya virus infection. Acta Trop. 2022 Mar;227:106300. doi: 10.1016/j.actatropica.2021.106300. Epub 2021 Dec 31. PMID: 34979144. 2. Simeonova L, Gegova G, Galabov AS. Prophylactic and therapeutic combination effects of rimantadine and oseltamivir against influenza virus A (H3N2) infection in mice. Antiviral Res. 2012 Aug;95(2):172-81. doi: 10.1016/j.antiviral.2012.05.004. Epub 2012 May 19. PMID: 22617756. 3. Atiee G, Lasseter K, Baughman S, McCullough A, Collis P, Hollister A, Hernandez J. Absence of pharmacokinetic interaction between intravenous peramivir and oral oseltamivir or rimantadine in humans. J Clin Pharmacol. 2012 Sep;52(9):1410-9. doi: 10.1177/0091270011414574. Epub 2011 Sep 29. PMID: 21960669. 4. Alves Galvão MG, Rocha Crispino Santos MA, Alves da Cunha AJ. Amantadine and rimantadine for influenza A in children and the elderly. Cochrane Database Syst Rev. 2008 Jan 23;(1):CD002745. doi: 10.1002/14651858.CD002745.pub2. Update in: Cochrane Database Syst Rev. 2012;1:CD002745. PMID: 18254006
In vitro protocol:
1. Santos IA, Pereira AKDS, Guevara-Vega M, de Paiva REF, Sabino-Silva R, Bergamini FRG, Corbi PP, Jardim ACG. Repurposing potential of rimantadine hydrochloride and development of a promising platinum(II)-rimantadine metallodrug for the treatment of Chikungunya virus infection. Acta Trop. 2022 Mar;227:106300. doi: 10.1016/j.actatropica.2021.106300. Epub 2021 Dec 31. PMID: 34979144. 2. Simeonova L, Gegova G, Galabov AS. Prophylactic and therapeutic combination effects of rimantadine and oseltamivir against influenza virus A (H3N2) infection in mice. Antiviral Res. 2012 Aug;95(2):172-81. doi: 10.1016/j.antiviral.2012.05.004. Epub 2012 May 19. PMID: 22617756.
In vivo protocol:
1. Atiee G, Lasseter K, Baughman S, McCullough A, Collis P, Hollister A, Hernandez J. Absence of pharmacokinetic interaction between intravenous peramivir and oral oseltamivir or rimantadine in humans. J Clin Pharmacol. 2012 Sep;52(9):1410-9. doi: 10.1177/0091270011414574. Epub 2011 Sep 29. PMID: 21960669. 2. Alves Galvão MG, Rocha Crispino Santos MA, Alves da Cunha AJ. Amantadine and rimantadine for influenza A in children and the elderly. Cochrane Database Syst Rev. 2008 Jan 23;(1):CD002745. doi: 10.1002/14651858.CD002745.pub2. Update in: Cochrane Database Syst Rev. 2012;1:CD002745. PMID: 18254006
1: Marinho MDS, Zhang YN, Cassani NM, Santos IA, Costa Oliveira AL, Dos Santos Pereira AK, Corbi PP, Zhang B, Jardim ACG. Development and validation of Mayaro virus with luciferase reporter genes as a tool for antiviral assays. Heliyon. 2024 Jul 2;10(13):e33885. doi: 10.1016/j.heliyon.2024.e33885. PMID: 39071632; PMCID: PMC11283106. 2: Santos IA, Pereira AKDS, Guevara-Vega M, de Paiva REF, Sabino-Silva R, Bergamini FRG, Corbi PP, Jardim ACG. Repurposing potential of rimantadine hydrochloride and development of a promising platinum(II)-rimantadine metallodrug for the treatment of Chikungunya virus infection. Acta Trop. 2022 Mar;227:106300. doi: 10.1016/j.actatropica.2021.106300. Epub 2021 Dec 31. PMID: 34979144. 3: Bazyleva A, Paulechka E, Zaitsau DH, Blokhin AV, Kabo GJ. Heat capacity and decomposition of rimantadine hydrochloride. Thermochim Acta. 2020;686:10.1016/j.tca.2020.178538. doi: 10.1016/j.tca.2020.178538. PMID: 34658454; PMCID: PMC8519015. 4: Han J, Takeda R, Sato T, Moriwaki H, Abe H, Izawa K, Soloshonok VA. Optical Resolution of Rimantadine. Molecules. 2019 May 12;24(9):1828. doi: 10.3390/molecules24091828. PMID: 31083636; PMCID: PMC6539882. 5: Wright AK, Batsomboon P, Dai J, Hung I, Zhou HX, Dudley GB, Cross TA. Differential Binding of Rimantadine Enantiomers to Influenza A M2 Proton Channel. J Am Chem Soc. 2016 Feb 10;138(5):1506-9. doi: 10.1021/jacs.5b13129. Epub 2016 Jan 28. PMID: 26804976; PMCID: PMC9328162. 6: Wang GQ, Qin YF, Du LM, Li JF, Jing X, Chang YX, Wu H. Determination of amantadine and rimantadine using a sensitive fluorescent probe. Spectrochim Acta A Mol Biomol Spectrosc. 2012 Dec;98:275-81. doi: 10.1016/j.saa.2012.08.016. Epub 2012 Aug 19. PMID: 22959366. 7: Sobczak A, Muszalska I, Rohowska P, Inerowicz T, Dotka H, Jelińska A. Determination of adamantane derivatives in pharmaceutical formulations by using spectrophotometric UV-Vis method. Drug Dev Ind Pharm. 2013 May;39(5):657-61. doi: 10.3109/03639045.2012.684391. Epub 2012 May 9. PMID: 22568696. 8: Ji H, Yang Z, Jiang W, Geng C, Gong M, Xiao H, Wang Z, Cheng L. Antiviral activity of nano carbon fullerene lipidosome against influenza virus in vitro. J Huazhong Univ Sci Technolog Med Sci. 2008 Jun;28(3):243-6. doi: 10.1007/s11596-008-0303-6. Epub 2008 Jun 19. PMID: 18563315. 9: Xu M, Ju W, Xia X, Tan H, Chen M, Zhang J, Xiong N, Jiang M, Chen L, Gong L. Determination of rimantadine in rat plasma by liquid chromatography/electrospray mass spectrometry and its application in a pharmacokinetic study. J Chromatogr B Analyt Technol Biomed Life Sci. 2008 Mar 15;864(1-2):123-8. doi: 10.1016/j.jchromb.2008.01.053. Epub 2008 Feb 15. PMID: 18316252. 10: Galabov AS, Simeonova L, Gegova G. Rimantadine and oseltamivir demonstrate synergistic combination effect in an experimental infection with type A (H3N2) influenza virus in mice. Antivir Chem Chemother. 2006;17(5):251-8. doi: 10.1177/095632020601700502. PMID: 17176629. 11: Jefferson T, Demicheli V, Di Pietrantonj C, Rivetti D. Amantadine and rimantadine for influenza A in adults. Cochrane Database Syst Rev. 2006 Apr 19;2006(2):CD001169. doi: 10.1002/14651858.CD001169.pub3. PMID: 16625539; PMCID: PMC7068158. 12: Han J, Fu H. [Determination of rimantadine hydrochloride in compound rimantadine hydrochloride capsules by capillary gas chromatography]. Se Pu. 2005 Nov;23(6):683. Chinese. PMID: 16499008. 13: Higashi Y, Uemori I, Fujii Y. Simultaneous determination of amantadine and rimantadine by HPLC in rat plasma with pre-column derivatization and fluorescence detection for pharmacokinetic studies. Biomed Chromatogr. 2005 Nov;19(9):655-62. doi: 10.1002/bmc.492. PMID: 15803448. 14: Jefferson T, Deeks JJ, Demicheli V, Rivetti D, Rudin M. Amantadine and rimantadine for preventing and treating influenza A in adults. Cochrane Database Syst Rev. 2004;(3):CD001169. doi: 10.1002/14651858.CD001169.pub2. Update in: Cochrane Database Syst Rev. 2006 Apr 19;(2):CD001169. doi: 10.1002/14651858.CD001169.pub3. PMID: 15266442. 15: Pazourek J, Revilla AL, Gajdosová D, Havel J. Validation of a capillary zone electrophoresis method for determination of rimantadine hydrochloride in Rimantadin100 tablets and the method application to dissolution test monitoring. Drug Dev Ind Pharm. 2004 Feb;30(2):125-34. doi: 10.1081/ddc-120028707. PMID: 15089046. 16: Serkedjieva J, Roeva I, Angelova M, Dolashka P, Voelter WG. Combined protective effect of a fungal Cu/Zn-containing superoxide dismutase and rimantadine hydrochloride in experimental murine influenza a virus infection. Acta Virol. 2003;47(1):53-6. PMID: 12828346. 17: Jefferson TO, Demicheli V, Deeks JJ, Rivetti D. Amantadine and rimantadine for preventing and treating influenza A in adults. Cochrane Database Syst Rev. 2002;(3):CD001169. doi: 10.1002/14651858.CD001169. Update in: Cochrane Database Syst Rev. 2004;(3):CD001169. doi: 10.1002/14651858.CD001169.pub2. PMID: 12137620. 18: Jefferson TO, Demicheli V, Deeks JJ, Rivetti D. Amantadine and rimantadine for preventing and treating influenza A in adults. Cochrane Database Syst Rev. 2001;(2):CD001169. doi: 10.1002/14651858.CD001169. Update in: Cochrane Database Syst Rev. 2002;(3):CD001169. doi: 10.1002/14651858.CD001169. PMID: 11405978. 19: Chládek J, Sispera L, Martinková J, Zaludek B, Sova P, Mièuda S, Grim J, Cermanová J, Zaludek B, Sova P, Franc A. Bioequivalence of two rimantadine tablet formulations in healthy male volunteers after single dose administration. Int J Clin Pharmacol Ther. 2001 Apr;39(4):179-84. doi: 10.5414/cpp39179. PMID: 11332875. 20: Keyser LA, Karl M, Nafziger AN, Bertino JS Jr. Comparison of central nervous system adverse effects of amantadine and rimantadine used as sequential prophylaxis of influenza A in elderly nursing home patients. Arch Intern Med. 2000 May 22;160(10):1485-8. doi: 10.1001/archinte.160.10.1485. PMID: 10826462.