Rimantadine

Rimantadine
Clinical data
Trade namesFlumadine
AHFS/Drugs.comMonograph
MedlinePlusa698029
Pregnancy
category
  • C (United States)
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailabilitywell absorbed
Protein binding40%
MetabolismHepatic hydroxylation and glucuronidation
Elimination half-life25.4 ± 6.3 hours
ExcretionRenal
Identifiers
  • 1-(adamantanyl)ethanamine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H21N
Molar mass179.307 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • NC(C)C13CC2CC(CC(C1)C2)C3
  • 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 checkY
  • Key:UBCHPRBFMUDMNC-UHFFFAOYSA-N checkY
  (verify)

Rimantadine (INN, sold under the trade name Flumadine[1]) is an orally administered antiviral drug[2] used to treat, and in rare cases prevent, influenzavirus A infection. When taken within one to two days of developing symptoms, rimantadine can shorten the duration and moderate the severity of influenza. Rimantadine can mitigate symptoms, including fever.[3] Both rimantadine and the similar drug amantadine are derivates of adamantane. Rimantadine is found to be more effective than amantadine because when used the patient displays fewer symptoms.[4] Rimantadine was approved by the Food and Drug Administration (FDA) in 1994.

Rimantadine was approved for medical use in 1993.[5] Seasonal H3N2 and 2009 pandemic flu samples tested have shown resistance to rimantadine, and it is no longer recommended to prescribe for treatment of the flu.[6]

  1. ^ "Flumadine (Rimantadine): Side Effects, Uses, Dosage, Interactions, Warnings".
  2. ^ Govorkova EA, Fang HB, Tan M, Webster RG (December 2004). "Neuraminidase inhibitor-rimantadine combinations exert additive and synergistic anti-influenza virus effects in MDCK cells". Antimicrobial Agents and Chemotherapy. 48 (12): 4855–63. doi:10.1128/AAC.48.12.4855-4863.2004. PMC 529183. PMID 15561867.
  3. ^ Zimmerman RK (March 2007). "Rationing of influenza vaccine during a pandemic: ethical analyses". Vaccine. 25 (11): 2019–26. doi:10.1016/j.vaccine.2006.11.045. PMID 17258359.
  4. ^ Jefferson T, Demicheli V, Di Pietrantonj C, Rivetti D, et al. (Cochrane Acute Respiratory Infections Group) (April 2006). "Amantadine and rimantadine for influenza A in adults". The Cochrane Database of Systematic Reviews. 2006 (2): CD001169. doi:10.1002/14651858.CD001169.pub3. PMC 7068158. PMID 16625539.
  5. ^ Long SS, Pickering LK, Prober CG (2012). Principles and Practice of Pediatric Infectious Disease. Elsevier Health Sciences. p. 1502. ISBN 978-1437727029.
  6. ^ Antiviral Agents for the Treatment and Chemoprophylaxis of Influenza: Recommendations of the Advisory Committee on Immunization Practices (ACIP)