Imipramine

Imipramine
Clinical data
Trade names	Tofranil, Tofranil-PM, others
Other names	Melipramine; G-22355
AHFS/Drugs.com	Monograph
MedlinePlus	a682389
License data	US DailyMed: Imipramine;
Pregnancy; category	AU: C;
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); CA: ℞-only; UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	94–96%
Protein binding	86%
Metabolism	Liver (CYP1A2, CYP2C19, CYP2D6)
Metabolites	Desipramine
Elimination half-life	20 hours
Excretion	Kidney (80%), fecal (20%)
Identifiers
	IUPAC name 3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine;
CAS Number	50-49-7 ;
PubChem CID	3696;
IUPHAR/BPS	357;
DrugBank	DB00458 ;
ChemSpider	3568 ;
UNII	OGG85SX4E4;
KEGG	D08070 ; as HCl: D00815 ;
ChEBI	CHEBI:47499 ;
ChEMBL	ChEMBL11 ;
PDB ligand	IXX (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID1043881 ;
ECHA InfoCard	100.000.039
Chemical and physical data
Formula	C19H24N2
Molar mass	280.415 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 ; Key:BCGWQEUPMDMJNV-UHFFFAOYSA-N ;
	(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 TCAs other than amitriptyline (which, at least in the U.K., is prescribed comparatively as frequently as SSRIs) have decreased in prescription frequency with the rise of SSRIs—which have fewer inherent side effects and are far safer in overdose. Regardless of its caveats, imipramine retains importance in psychopharmacology and pediatrics (e.g., with childhood enuresis).^[5]^[6]

^ "Imipramine Use During Pregnancy". Drugs.com. 28 August 2019. Retrieved 7 February 2020.
^ 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.
^ 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.
^ ^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.
^ Michelson LK, Marchione K (February 1991). "Behavioral, cognitive, and pharmacological treatments of panic disorder with agoraphobia: critique and synthesis". Journal of Consulting and Clinical Psychology. 59 (1): 100–14. doi:10.1037/0022-006x.59.1.100. PMID 2002125.
^ Schwartz TL, Nihalani N, Simionescu M, Hopkins G (2005). "History repeats itself: pharmacodynamic trends in the treatment of anxiety disorders". Current Pharmaceutical Design. 11 (2): 255–63. doi:10.2174/1381612053382214. PMID 15638761.

[Drugs.com_pregnancy-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.

[Pharm-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.

[Tolerade-4] "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.

[pmid2002125-5] Michelson LK, Marchione K (February 1991). "Behavioral, cognitive, and pharmacological treatments of panic disorder with agoraphobia: critique and synthesis". Journal of Consulting and Clinical Psychology. 59 (1): 100–14. doi:10.1037/0022-006x.59.1.100. PMID 2002125.

[pmid15638761-6] Schwartz TL, Nihalani N, Simionescu M, Hopkins G (2005). "History repeats itself: pharmacodynamic trends in the treatment of anxiety disorders". Current Pharmaceutical Design. 11 (2): 255–63. doi:10.2174/1381612053382214. PMID 15638761.

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