Olanzapine

Olanzapine (sold under the trade name Zyprexa among others) is an atypical antipsychotic primarily used to treat schizophrenia and bipolar disorder. For schizophrenia, it can be used for both new-onset disease and long-term maintenance. It is taken by mouth or by injection into a muscle.

Olanzapine
Clinical data
Trade namesZyprexa, Zypine, others
AHFS/Drugs.comMonograph
MedlinePlusa601213
License data
Pregnancy
category
  • AU: C
Routes of
administration
By mouth, intramuscular injection
Drug classAtypical antipsychotic
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C1 (Other controlled substances)
  • CA: ℞-only
  • NZ: Prescription only
  • UK: POM (Prescription only)
  • US: WARNINGRx-only
  • EU: Rx-only
Pharmacokinetic data
Bioavailability60-65%
Protein binding93%
MetabolismLiver (direct glucuronidation and CYP1A2 mediated oxidation)
Elimination half-life33 hours, 51.8 hours (elderly)
ExcretionUrine (57%; 7% as unchanged drug), faeces (30%)
Identifiers
  • 2-Methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5]benzodiazepine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.125.320
Chemical and physical data
FormulaC17H20N4S
Molar mass312.44 g·mol−1
3D model (JSmol)
Melting point195 °C (383 °F)
Solubility in waterPractically insoluble in water mg/mL (20 °C)
  • CN1CCN(CC1)C/2=N/c4ccccc4Nc3sc(C)cc\23
  • InChI=1S/C17H20N4S/c1-12-11-13-16(21-9-7-20(2)8-10-21)18-14-5-3-4-6-15(14)19-17(13)22-12/h3-6,11,19H,7-10H2,1-2H3 Y
  • Key:KVWDHTXUZHCGIO-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Common side effects include weight gain, movement disorders, dizziness, feeling tired, constipation, and dry mouth. Other side effects include low blood pressure with standing, allergic reactions, neuroleptic malignant syndrome, high blood sugar, seizures, and tardive dyskinesia. In older people with dementia, its use increases the risk of death. Use in the later part of pregnancy may result in a movement disorder in the baby for some time after birth. Although how it works is not entirely clear, it blocks dopamine and serotonin receptors.

Olanzapine was patented in 1991 and approved for medical use in the United States in 1996. It is available as a generic medication. In 2020, it was the 164th most commonly prescribed medication in the United States, with more than 3 million prescriptions. Eli Lilly also markets olanzapine in a fixed-dose combination with fluoxetine as olanzapine/fluoxetine (Symbyax). It is on the World Health Organization's List of Essential Medicines.

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