Fenspiride

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Fenspiride
Fenspiride.svg
Fenspiride ball-and-stick animation.gif
Systematic (IUPAC) name
8-(2-phenylethyl)-1-oxa-3,8-diazaspiro[4.5]decan-2-one
Clinical data
Trade names Eurespal, Pneumorel
AHFS/Drugs.com International Drug Names
  • (Prescription only)
Oral
Pharmacokinetic data
Bioavailability 90%[1]
Half-life 14–16 hours
Excretion Urine (90%), feces (~10%)
Identifiers
5053-06-5 YesY
R03BX01 R03DX03
PubChem CID 68626
DrugBank DB08979 N
UNII S983QC7HKM N
KEGG D07949 YesY
ChEMBL CHEMBL576127 N
Chemical data
Formula C15H20N2O2
260.331 g/mol
 N (what is this?)  (verify)

Fenspiride (INN, brand names Eurespal, Pneumorel and others) is an oxazolidinone spiro compound used as a drug in the treatment of certain respiratory diseases.[2] The pharmacotherapeutic classification is antitussives. In Russia it is approved for the treatment of acute and chronic inflammatory diseases of ENT organs (ear, nose, throat) and the respiratory tract (like rhinopharyngitis, laryngitis, tracheobronchitis, otitis and sinusitis), as well as for maintenance treatment of asthma.[3]

Synthesis[edit]

The cyanohydrin of N-benzyl-4-piperidone is reduced with hydride to the aminoalcohol. This forms a cyclic carbamate on heating with diethyl carbonate. Hydrogenolysis of the N-benzyl group and alkylation of the liberated amino group with phenethyl chloride gives fenspiride.[4]

References[edit]

  1. ^ Montes, B; Catalan, M; Roces, A; Jeanniot, JP; Honorato, JM (1993). "Single dose pharmacokinetics of fenspiride hydrochloride: phase I clinical trial.". European journal of clinical pharmacology 45 (2): 169–72. doi:10.1007/bf00315501. PMID 7901024. 
  2. ^ Płusa T, Nawacka D (Dec 1998). "Efficacy and tolerance of fenspiride in adult patients with acute respiratory tract infections". Pol Merkur Lekarski 5 (30): 368–71. PMID 10101527. 
  3. ^ "Эреспал® (Eurespal®) Prescribing Information. VIDAL Drug Compendium" (in Russian). Retrieved 6 February 2014. 
  4. ^ NL 6504602