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Imipramine information


Imipramine
Clinical data
Trade namesTofranil, Tofranil-PM, others
Other namesMelipramine; G-22355
AHFS/Drugs.comMonograph
MedlinePlusa682389
License data
  • US DailyMed: Imipramine
Pregnancy
category
  • AU: C[1]
Routes of
administration
By mouth, intramuscular injection
ATC code
  • N06AA02 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C1 (Other controlled substances)[2]
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: ℞-only
Pharmacokinetic data
Bioavailability94–96%[3]
Protein binding86%[4]
MetabolismLiver (CYP1A2, CYP2C19, CYP2D6)[4]
MetabolitesDesipramine[4]
Elimination half-life20 hours[4]
ExcretionKidney (80%), fecal (20%)[4]
Identifiers
IUPAC name
  • 3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine
CAS Number
  • 50-49-7 checkY
PubChem CID
  • 3696
IUPHAR/BPS
  • 357
DrugBank
  • DB00458 checkY
ChemSpider
  • 3568 checkY
UNII
  • OGG85SX4E4
KEGG
  • D08070 checkY
  • as HCl: D00815 checkY
ChEBI
  • CHEBI:47499 checkY
ChEMBL
  • ChEMBL11 checkY
PDB ligand
  • IXX (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID1043881 Edit this at Wikidata
ECHA InfoCard100.000.039 Edit this at Wikidata
Chemical and physical data
FormulaC19H24N2
Molar mass280.415 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • CN(C)CCCN1c2ccccc2CCc2ccccc21
InChI
  • InChI=1S/C19H24N2/c1-20(2)14-7-15-21-18-10-5-3-8-16(18)12-13-17-9-4-6-11-19(17)21/h3-6,8-11H,7,12-15H2,1-2H3 checkY
  • Key:BCGWQEUPMDMJNV-UHFFFAOYSA-N checkY
  (verify)

Imipramine, sold under the brand name Tofranil, among others, is a tricyclic antidepressant (TCA) mainly used in the treatment of depression. It is also effective in treating anxiety and panic disorder. Imipramine is taken by mouth.

Common side effects of imipramine include dry mouth, drowsiness, dizziness, low blood pressure, rapid heart rate, urinary retention, and electrocardiogram changes. Overdose of the medication can result in death. Imipramine appears to work by increasing levels of serotonin and norepinephrine and by blocking certain serotonin, adrenergic, histamine, and cholinergic receptors.

Imipramine was discovered in 1951 and was introduced for medical use in 1957. It was the first TCA to be marketed. Imipramine and the other TCAs (besides amitriptyline, which, at least in the U.K., remains at least just as commonly-prescribed as SSRIs) have decreased in use in recent decades, due to the introduction of the selective serotonin reuptake inhibitors (SSRIs), which, although generally significantly less potent in terms of clinical efficacy per-se, have fewer inherent side effects and are far safer in overdose. Irrespective of these caveats, however, imipramine has an invaluable place in psychiatry and other fields of medicine (e.g., with childhood enuresis), and is considered the "gold standard" for panic disorder.[5][6]

  1. ^ "Imipramine Use During Pregnancy". Drugs.com. 28 August 2019. Retrieved 7 February 2020.
  2. ^ Anvisa (2023-03-31). "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 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  3. ^ Heck HA, Buttrill SE, Flynn NW, Dyer RL, Anbar M, Cairns T, et al. (June 1979). "Bioavailability of imipramine tablets relative to a stable isotope-labeled internal standard: increasing the power of bioavailability tests". Journal of Pharmacokinetics and Biopharmaceutics. 7 (3): 233–248. doi:10.1007/BF01060015. PMID 480146. S2CID 23232584.
  4. ^ a b c d e "Product Information Tolerade (imipramine hydrochloride)". TGA eBusiness Services. PMIP Pty Ltd. 4 June 2013. Archived from the original on 10 December 2019. Retrieved 16 October 2013.
  5. ^ Michelson, L.K. and Marchione, K., 1991. Behavioral, cognitive, and pharmacological treatments of panic disorder with agoraphobia: critique and synthesis. Journal of Consulting and Clinical Psychology, 59(1), p.100.
  6. ^ Schwartz, T.L., Nihalani, N., Simionescu, M. and Hopkins, G., 2005. History repeats itself: pharmacodynamic trends in the treatment of anxiety disorders. Current pharmaceutical design, 11(2), pp.255-263.

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