Zolpidem

Zolpidem
Clinical data


Trade names	originally Ambien, many names worldwide
AHFS/Drugs.com	Monograph
MedlinePlus	a693025
Pregnancy category	AU: B3 US: C (Risk not ruled out)
Dependence liability	High
Routes of administration	Oral (tablet), sublingual, oromucosal (spray), rectal
ATC code	N05CF02 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: Schedule IV DE: Anlage III (Prescription only) UK: Class C US: Schedule IV ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	70% (oral)
Protein binding	92%
Metabolism	Liver through CYP3A4
Biological half-life	2–3 hours
Duration of action	3 hours
Excretion	Kidney (56%) fecal (34%)
Identifiers
IUPAC name N,N-dimethyl-2-[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetamide
CAS Number	82626-48-0^Y
PubChem (CID)	5732
IUPHAR/BPS	4362
DrugBank	DB00425^N
ChemSpider	5530^Y
UNII	7K383OQI23^Y
KEGG	D08690^Y
ChEBI	CHEBI:10125^N
ChEMBL	CHEMBL911^Y
ECHA InfoCard	100.115.604
Chemical and physical data
Formula	C₁₉H₂₁N₃O
Molar mass	307.395 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(CC1=C(C2=CC=C(C)C=C2)N=C3C=CC(C)=CN13)N(C)C
InChI InChI=1S/C19H21N3O/c1-13-5-8-15(9-6-13)19-16(11-18(23)21(3)4)22-12-14(2)7-10-17(22)20-19/h5-10,12H,11H2,1-4H3^Y Key:ZAFYATHCZYHLPB-UHFFFAOYSA-N^Y
^NY (what is this?)

Zolpidem (originally marketed as Ambien and available worldwide under many brand names) is a sedative primarily used for the treatment of insomnia. It works quickly, usually within 15 minutes, and has a short half-life of two to three hours. Zolpidem has not adequately demonstrated effectiveness in maintaining sleep, unless delivered in a controlled-release (CR) form. However, it is effective in initiating sleep. Its hypnotic effects are similar to those of the benzodiazepine class of drugs.

In 2013, the Food and Drug Administration required manufacturers to decrease the recommended dose for women by half, after studies showed that the medicines can leave people drowsy in the morning and at risk for motor vehicle collisions. The FDA recommended that manufacturers extend the new dosage cuts to men as well, who process the drug at a faster rate; however, the reasons men and women metabolize the drugs at different rates are still unknown. In May 2013, the FDA approved label changes specifying new dosage recommendations for zolpidem products because of concerns regarding next-morning impairment. The underlying mechanism involves GABA.

It is a short-acting nonbenzodiazepine compound of the imidazopyridine class that increases the activity of GABA, an inhibitory neurotransmitter, by binding to GABA_A receptors at the same location as benzodiazepines. It is molecularly distinct from the classical benzodiazepine molecule and is classified as an imidazopyridine. Flumazenil, a benzodiazepine receptor antagonist, which is used for benzodiazepine overdose, can also reverse zolpidem's sedative/hypnotic and memory-impairing effects.

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Wikipedia