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Rimantadine information


Rimantadine
Clinical data
Trade namesFlumadine
AHFS/Drugs.comMonograph
MedlinePlusa698029
Pregnancy
category
  • C (United States)
Routes of
administration
Oral
ATC code
  • J05AC02 (WHO)
Legal status
Legal status
  • US: ℞-only
Pharmacokinetic data
Bioavailabilitywell absorbed
Protein binding40%
MetabolismHepatic hydroxylation and glucuronidation
Elimination half-life25.4 ± 6.3 hours
ExcretionRenal
Identifiers
IUPAC name
  • 1-(adamantanyl)ethanamine
CAS Number
  • 13392-28-4 checkY
PubChem CID
  • 5071
DrugBank
  • DB00478 checkY
ChemSpider
  • 4893 checkY
UNII
  • 0T2EF4JQTU
KEGG
  • D08483 checkY
ChEMBL
  • ChEMBL959 checkY
PDB ligand
  • RIM (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID2023561 Edit this at Wikidata
Chemical and physical data
FormulaC12H21N
Molar mass179.307 g·mol−1
3D model (JSmol)
  • Interactive image
ChiralityRacemic mixture
SMILES
  • NC(C)C13CC2CC(CC(C1)C2)C3
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 checkY
  • Key:UBCHPRBFMUDMNC-UHFFFAOYSA-N checkY
  (verify)

Rimantadine (INN, sold under the trade name Flumadine) is an orally administered antiviral drug[1] 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.[2] 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.[3] Rimantadine was approved by the Food and Drug Administration (FDA) in 1994.

Rimantadine was approved for medical use in 1993.[4] 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.[5]

  1. ^ 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.
  2. ^ 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.
  3. ^ 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.
  4. ^ Long SS, Pickering LK, Prober CG (2012). Principles and Practice of Pediatric Infectious Disease. Elsevier Health Sciences. p. 1502. ISBN 978-1437727029.
  5. ^ Antiviral Agents for the Treatment and Chemoprophylaxis of Influenza: Recommendations of the Advisory Committee on Immunization Practices (ACIP)

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