Estazolam

Estazolam

Clinical data
Trade names	ProSom
AHFS/Drugs.com	Monograph
MedlinePlus	a691003
Pregnancy category	US: X (Contraindicated)
Routes of administration	Oral
ATC code	N05CD04 (WHO)
Legal status
Legal status	CA: Schedule IV DE: Anlage III (Prescription only) UK: Class C US: Schedule IV
Pharmacokinetic data
Bioavailability	93%
Metabolism	Hepatic
Biological half-life	10–24 hours
Excretion	Renal
Identifiers
IUPAC name 8-chloro-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine
CAS Number	29975-16-4 Y
PubChem (CID)	3261
IUPHAR/BPS	7550
DrugBank	DB01215 Y
ChemSpider	3146 Y
UNII	36S3EQV54C Y
KEGG	D00311 Y
ChEBI	CHEBI:4858 Y
ChEMBL	CHEMBL285674 Y
ECHA InfoCard	100.045.424
Chemical and physical data
Formula	C16H11ClN4
Molar mass	294.7
3D model (Jmol)	Interactive image
SMILES ClC1=CC2=C(C=C1)N3C=NN=C3CN=C2C4=CC=CC=C4
InChI InChI=1S/C16H11ClN4/c17-12-6-7-14-13(8-12)16(11-4-2-1-3-5-11)18-9-15-20-19-10-21(14)15/h1-8,10H,9H2 Y Key:CDCHDCWJMGXXRH-UHFFFAOYSA-N Y

Estazolam (desmethylalprazolam, marketed under the brand names ProSom, Eurodin) is a benzodiazepine derivative drug developed by Upjohn in the 1970s. It possesses anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. Estazolam is an intermediate-acting oral benzodiazepine.

It is commonly prescribed for short-term treatment of insomnia.

Estazolam is prescribed for the short-term treatment of certain sleep disorders. It is an effective hypnotic drug showing efficacy in increasing the time spent asleep as well as reducing awakenings during the night. Combination with non-pharmacological options for sleep management results in long-term improvements in sleep quality after discontinuation of short-term estazolam therapy. Estazolam is also sometimes used as a preoperative sleep aid. It was found to be superior to triazolam in side effect profile in preoperative patients in a trial. Estazolam also has anxiolytic properties and due to its long half life can be an effective short-term treatment for insomnia associated with anxiety.

A hang-over effect commonly occurs with next day impairments of mental and physical performance. Other side effects of estazolam include somnolence, dizziness, hypokinesia, and abnormal coordination.

The main safety concern of benzodiazepines such as estazolam is a benzodiazepine dependence and the subsequent benzodiazepine withdrawal syndrome which can occur upon discontinuation of the estazolam. A review of the literature found that long-term use of benzodiazepines such as estazolam is associated with drug tolerance, drug dependence, rebound insomnia and CNS related adverse effects. Estazolam should only be used short term and at the lowest effective dose to avoid complications related to long-term use. Non-pharmacological treatment options however, were found to have sustained improvements in sleep quality. The short-term benefits of benzodiazepines on sleep begin to reduce after a few days due to tolerance to the hypnotic effects of benzodiazepines in the elderly.