Niaprazine

Niaprazine

Systematic (IUPAC) name
N-{4-[4-(4-fluorophenyl)piperazin- 1-yl]butan- 2-yl}pyridine- 3-carboxamide
Clinical data
AHFS/Drugs.com	International Drug Names
Legal status	℞ (Prescription only)
Routes of administration	Oral
Pharmacokinetic data
Biological half-life	~4.5 hours
Identifiers
CAS Number	27367-90-4
ATC code	N05CM16 (WHO)
PubChem	CID: 71919
ChemSpider	64930
UNII	R2H3YN6E3L Y
KEGG	D07333
Chemical data
Formula	C20H25FN4O
Molecular mass	356.437 g/mol
SMILES Fc3ccc(N2CCN(CCC(NC(=O)c1cccnc1)C)CC2)cc3

Niaprazine (Nopron) is a sedative-hypnotic drug of the phenylpiperazine class. It has been used in the treatment of sleep disturbances since the early 1970s in several European countries, including France, Italy, and Luxembourg. It is commonly used with children and adolescents on account of its favorable safety and tolerability profile and lack of abuse potential.

Originally believed to act as an antihistamine and anticholinergic, niaprazine was later discovered to have no significant binding affinity for either the H₁ or the mACh receptors (K_i = > 1 μM), and was instead found to act as a potent and selective 5-HT_2A and α₁-adrenergic receptor antagonist (K_i = 75 nM and 86 nM, respectively). It is virtually inactive at 5-HT_1A, 5-HT_2B, D₂, and β-adrenergic, as well as at SERT and VMAT (K_i = all > 1 μM), but it does have some weak affinity for the α₂-adrenergic receptor (K_i = 730 nM), likely acting as an antagonist there as well.

Niaprazine has been shown to metabolize to the compound pFPP in a similar manner to how trazodone and nefazodone metabolize to mCPP. It is unclear what role, if any, pFPP plays in the clinical effects of niaprazine. However, from animal studies it is known that pFPP, unlike niaprazine, does not produce sedative effects, and instead exerts a behavioral profile indicative of serotonergic activation.

See also

• Phenylpiperazine