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Duloxetine information



Duloxetine
Clinical data
Trade namesCymbalta, Ariclaim, Yentreve, others[1]
AHFS/Drugs.comMonograph
MedlinePlusa604030
License data
  • US DailyMed: Duloxetine
Pregnancy
category
  • AU: B3
Routes of
administration
By mouth
Drug classSerotonin–norepinephrine reuptake inhibitor
ATC code
  • N06AX21 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C1 (Other controlled substances)[3]
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: WARNING[2]Rx-only[4]
  • EU: Rx-only[5][6]
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
IUPAC name
  • (+)-(S)-N-Methyl-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propan-1-amine
CAS Number
  • 116539-59-4 checkY
  • as HCl: 136434-34-9 checkY
PubChem CID
  • 60835
IUPHAR/BPS
  • 202
DrugBank
  • DB00476 checkY
ChemSpider
  • 54822 checkY
UNII
  • O5TNM5N07U
  • as HCl: 9044SC542W checkY
KEGG
  • D07880 checkY
  • as HCl: D01179 checkY
ChEBI
  • CHEBI:36795 checkY
  • as HCl: CHEBI:31526 checkY
ChEMBL
  • ChEMBL1175 checkY
  • as HCl: ChEMBL1200328 checkY
PDB ligand
  • 29E (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID6048385 Edit this at Wikidata
ECHA InfoCard100.116.825 Edit this at Wikidata
Chemical and physical data
FormulaC18H19NOS
Molar mass297.42 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • CNCC[C@@H](C1=CC=CS1)OC2=CC=CC3=CC=CC=C32
InChI
  • 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 checkY
  • Key:ZEUITGRIYCTCEM-KRWDZBQOSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Duloxetine, sold under the brand name Cymbalta among others,[1] is a medication used to treat major depressive disorder, generalized anxiety disorder, obsessive-compulsive disorder, fibromyalgia, neuropathic pain and central sensitization.[7][8] It is taken by mouth.[7]

Duloxetine is a serotonin–norepinephrine reuptake inhibitor (SNRI).[9] Similarly to SSRIs and other SNRIs, the precise mechanism for its antidepressant and anxiolytic effects is not known.[7]

Common side effects include dry mouth, nausea, feeling tired, dizziness, agitation, sexual problems, and increased sweating.[7] Severe side effects include an increased risk of suicide, serotonin syndrome, mania, and liver problems.[7] Antidepressant withdrawal syndrome may occur if stopped.[7] There are concerns that use during the later part of pregnancy can harm the developing fetus.[7]

Duloxetine was approved for medical use in the United States and in the European Union in 2004.[5][6][7] It is available as a generic medication.[9] In 2021, it was the 27th most commonly prescribed medication in the United States, with more than 20 million prescriptions.[10][11]

  1. ^ a b "Duloxetine". Drugs.com. Archived from the original on 29 September 2018. Retrieved 24 December 2018.
  2. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  3. ^ "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). 31 March 2023. Archived from the original on 3 August 2023. Retrieved 16 August 2023.
  4. ^ Cite error: The named reference Cymbalta FDA label was invoked but never defined (see the help page).
  5. ^ a b "Cymbalta EPAR". European Medicines Agency (EMA). 17 September 2018. Archived from the original on 20 October 2020. Retrieved 30 September 2020.
  6. ^ a b Cite error: The named reference EMA-2018-EPAR was invoked but never defined (see the help page).
  7. ^ a b c d e f g h "Duloxetine". Monograph. The American Society of Health-System Pharmacists. Archived from the original on 26 November 2018. Retrieved 24 December 2018.
  8. ^ "Medications for OCD". International OCD Foundation. Archived from the original on 27 January 2024. Retrieved 25 February 2024.
  9. ^ a b British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 364–365. ISBN 9780857113382.
  10. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  11. ^ "Duloxetine - Drug Usage Statistics". ClinCalc. Archived from the original on 12 April 2020. Retrieved 14 January 2024.

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