Duloxetine

Duloxetine, sold under the brand name Cymbalta among others, is a medication used to treat major depressive disorder, generalized anxiety disorder, obsessive-compulsive disorder, fibromyalgia, neuropathic pain and central sensitization. It is taken by mouth.

Duloxetine
Clinical data
Trade namesCymbalta, Ariclaim, Yentreve, others
AHFS/Drugs.comMonograph
MedlinePlusa604030
License data
Pregnancy
category
  • AU: B3
Routes of
administration
By mouth
Drug classSerotonin–norepinephrine reuptake inhibitor
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C1 (Other controlled substances)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: WARNINGRx-only
  • EU: Rx-only
Pharmacokinetic data
Bioavailability~ 50% (32% to 80%)
Protein binding~ 95%
MetabolismLiver, two P450 isozymes, CYP2D6 and CYP1A2
Elimination half-life12 hours
Excretion70% in urine, 20% in feces
Identifiers
  • (+)-(S)-N-Methyl-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propan-1-amine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.116.825
Chemical and physical data
FormulaC18H19NOS
Molar mass297.42 g·mol−1
3D model (JSmol)
SMILES
  • CNCC[C@@H](C1=CC=CS1)OC2=CC=CC3=CC=CC=C32
  • InChI=1S/C18H19NOS/c1-19-12-11-17(18-10-5-13-21-18)20-16-9-4-7-14-6-2-3-8-15(14)16/h2-10,13,17,19H,11-12H2,1H3/t17-/m0/s1 Y
  • Key:ZEUITGRIYCTCEM-KRWDZBQOSA-N Y
 NY (what is this?)  (verify)

Duloxetine is a serotonin–norepinephrine reuptake inhibitor (SNRI). Similarly to SSRIs and other SNRIs, the precise mechanism for its antidepressant and anxiolytic effects is not known.

Common side effects include dry mouth, nausea, feeling tired, dizziness, agitation, sexual problems, and increased sweating. Severe side effects include an increased risk of suicide, serotonin syndrome, mania, and liver problems. Antidepressant withdrawal syndrome may occur if stopped. There are concerns that use during the later part of pregnancy can harm the developing fetus.

Duloxetine was approved for medical use in the United States and in the European Union in 2004. It is available as a generic medication. In 2021, it was the 27th most commonly prescribed medication in the United States, with more than 20 million prescriptions.

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