Rimantadine

Rimantadine
Clinical data
Trade names	Flumadine
AHFS/Drugs.com	Monograph
MedlinePlus	a698029
Pregnancy; category	C (United States);
Routes of; administration	Oral
ATC code	J05AC02 (WHO) ;
Legal status
Legal status	US: ℞-only;
Pharmacokinetic data
Bioavailability	well absorbed
Protein binding	40%
Metabolism	Hepatic hydroxylation and glucuronidation
Elimination half-life	25.4 ± 6.3 hours
Excretion	Renal
Identifiers
	IUPAC name 1-(adamantanyl)ethanamine;
CAS Number	13392-28-4 ;
PubChem CID	5071;
DrugBank	DB00478 ;
ChemSpider	4893 ;
UNII	0T2EF4JQTU;
KEGG	D08483 ;
ChEMBL	ChEMBL959 ;
PDB ligand	RIM (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID2023561 ;
Chemical and physical data
Formula	C12H21N
Molar mass	179.307 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic 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 ; Key:UBCHPRBFMUDMNC-UHFFFAOYSA-N ;
	(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]

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

[pmid15561867-1] 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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