A derivative of amantadine with antiviral activity
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Rimantadine (hydrochloride)

Item No. 23838

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
α-methyl-tricyclo[3.3.1.13,7]decane-1-methanamine, monohydrochloride
CAS Number
1501-84-4
Synonyms
  • 1-(1-Adamantyl)ethylamine Hydrochloride
  • NSC 206764
Molecular Formula
C12H21N • HCl
Formula Weight
215.8
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 2 mg/mlDMSO: 50 mg/mlEthanol: 5 mg/mlPBS (pH 7.2): 5 mg/ml
λmax
202 nm
SMILES
NC(C)C12C[C@@H]3C[C@@H](C[C@@H](C3)C2)C1.Cl
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/t8?,9-,10+,11-,12?;
InChi Key
OZBDFBJXRJWNAV-LHRDWUBSSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 mg

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    Product Description

    Rimantadine is a derivative of amantadine (Item No. 21364) with antiviral activity.1 It 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).2,3 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).4 It increases the survival rate of mice infected with the influenza A strain A2/Jap/305 from 20 to 90% when administered at a dose of 24 mg/kg two hours post-infection, with the survival rate decreasing when rimantadine is administered at longer timepoints following infection.5 It also has trypanocidal activity against bloodstream forms of T. brucei in vitro (IC50 = 1.26 µg/ml).6 Formulations containing rimantadine have been used in the prophylaxis and treatment of influenza A.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bean, B. Antiviral therapy: Current concepts and practices. Clin. Microbiol. Rev. 5(2), 146-182 (1992).

    2. Wang, J., Ma, C., Wang, J., et al. Discovery of novel dual inhibitors of the wild-type and the most prevalent drug-resistant mutant, S31N, of the M2 proton channel from influenza A virus. J. Med. Chem. 56(7), 2804-2812 (2013).

    3. Breitinger, U., Farag, N.S., Ali, N.K.M., et al. Patch-clamp study of hepatitis C p7 channels reveals genotype-specific sensitivity to inhibitors. Biophys J. 110(11), 2419-2429 (2016).

    4. Rey-Carrizo, M., Torres, E., Ma, C., et al. 3-Azatetracyclo[5.2.1.15,8.01,5]undecane derivatives: From wild-type inhibitors of the M2 ion channel of influenza A virus to derivatives with potent activity against the V27A mutant. J. Med. Chem. 56(22), 9265-9274 (2013).

    5. Rabinovich, S. Rimantadine therapy of influenza A infection in mice. Antimicrob. Agents Chemother. 1(5), 408-411 (1972).

    6. Kelly, J.M., Miles, M.A., and Skinner, A.C. The anti-influenza virus drug rimantadine has trypanocidal activity. Antimicrob. Agents Chemother. 43(4), 985-987 (1999).