Desipramine

Desipramine
Clinical data
Trade names	Norpramin, Pertofrane, others
Other names	Desmethylimipramine; Norimipramine; EX-4355; G-35020; JB-8181; NSC-114901
AHFS/Drugs.com	Monograph
MedlinePlus	a682387
Routes of; administration	Oral, intramuscular injection
ATC code	N06AA01 (WHO) ;
Legal status
Legal status	BR: Class C1 (Other controlled substances); US: WARNINGRx-only;
Pharmacokinetic data
Bioavailability	60–70%
Protein binding	91%
Metabolism	Liver (CYP2D6)
Elimination half-life	12–30 hours
Excretion	Urine (70%), feces
Identifiers
	IUPAC name 3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N-methylpropan-1-amine;
CAS Number	50-47-5 ; 58-28-6 (hydrochloride); 62265-06-9 (dibudinate);
PubChem CID	2995;
IUPHAR/BPS	2399;
DrugBank	DB01151 ;
ChemSpider	2888 ;
UNII	TG537D343B;
KEGG	D07791 ;
ChEBI	CHEBI:47781 ;
ChEMBL	ChEMBL72 ;
CompTox Dashboard (EPA)	DTXSID6022896 ;
ECHA InfoCard	100.000.037
Chemical and physical data
Formula	C18H22N2
Molar mass	266.388 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c1cc3c(cc1)CCc2c(cccc2)N3CCCNC;
	InChI InChI=1S/C18H22N2/c1-19-13-6-14-20-17-9-4-2-7-15(17)11-12-16-8-3-5-10-18(16)20/h2-5,7-10,19H,6,11-14H2,1H3 ; Key:HCYAFALTSJYZDH-UHFFFAOYSA-N ;
	(verify)

Desipramine, sold under the brand name Norpramin among others, is a tricyclic antidepressant (TCA) used in the treatment of depression.^[8] It acts as a relatively selective norepinephrine reuptake inhibitor, though it does also have other activities such as weak serotonin reuptake inhibitory, α₁-blocking, antihistamine, and anticholinergic effects. The drug is not considered a first-line treatment for depression since the introduction of selective serotonin reuptake inhibitor (SSRI) antidepressants, which have fewer side effects and are safer in overdose.

^ Cite error: The named reference Elks2014 was invoked but never defined (see the help page).
^ Cite error: The named reference IndexNominum2000 was invoked but never defined (see the help page).
^ Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
^ "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 Oct 2023.
^ 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.
^ ^a ^b ^c ^d Lemke TL, Williams DA (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 588–. ISBN 978-1-60913-345-0.
^ Sallee FR, Pollock BG (May 1990). "Clinical pharmacokinetics of imipramine and desipramine". Clinical Pharmacokinetics. 18 (5): 346–364. doi:10.2165/00003088-199018050-00002. PMID 2185906. S2CID 37529573.
^ Brunton L, Chabner B, Knollman B (2010). Goodman and Gilman's The Pharmacological Basis of Therapeutics (12th ed.). New York: McGraw-Hill Professional. ISBN 978-0-07-162442-8.