Fenspiride

Fenspiride

Clinical data
Trade names	Eurespal, Pneumorel
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	R03BX01 (WHO) R03DX03 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	90%
Elimination half-life	14–16 hours
Excretion	Urine (90%), feces (~10%)
Identifiers
IUPAC name 8-(2-phenylethyl)-1-oxa-3,8-diazaspiro[4.5]decan-2-one
CAS Number	5053-06-5 Y
PubChem CID	68626
DrugBank	DB08979 N
UNII	S983QC7HKM
KEGG	D07949 Y
ChEMBL	ChEMBL576127 N
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C15H20N2O2
Molar mass	260.331 g/mol
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Evidence Based Medicine
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Fenspiride (INN, brand names Eurespal, Pneumorel and others) is an oxazolidinone spiro compound used as a drug in the treatment of certain respiratory diseases. 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.

Synthesis

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.