Protriptyline

Protriptyline

Clinical data
Trade names	Vivactil
AHFS/Drugs.com	Monograph
MedlinePlus	a604025
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	Oral
ATC code	N06AA11 (WHO)
Legal status
Legal status	℞ (Prescription only)
Pharmacokinetic data
Metabolism	Hepatic
Biological half-life	54-92 hours
Excretion	Urine
Identifiers
IUPAC name 3-(5H-dibenzo[a,d][7]annulen-5-yl)-N-methylpropan-1-amine
CAS Number	438-60-8 Y
PubChem (CID)	4976
IUPHAR/BPS	7285
DrugBank	DB00344 Y
ChemSpider	4805 Y
UNII	4NDU154T12 Y
ChEBI	CHEBI:8597 Y
ChEMBL	CHEMBL668 Y
ECHA InfoCard	100.006.474
Chemical and physical data
Formula	C19H21N
Molar mass	263.377 g/mol
3D model (Jmol)	Interactive image
SMILES c3cc2c(\C=C/c1c(cccc1)C2CCCNC)cc3
InChI InChI=1S/C19H21N/c1-20-14-6-11-19-17-9-4-2-7-15(17)12-13-16-8-3-5-10-18(16)19/h2-5,7-10,12-13,19-20H,6,11,14H2,1H3 Y Key:BWPIARFWQZKAIA-UHFFFAOYSA-N Y

Protriptyline (Vivactil) is a tricyclic antidepressant (TCA), specifically a secondary amine, indicated for the treatment of depression and ADHD. Unique among the TCAs, protriptyline tends to be energizing instead of sedating, and is sometimes used for narcolepsy to achieve a wakefulness-promoting effect.

TCAs including protriptyline are also used to reduce the incidence of recurring headaches such as migraine, and for other types of chronic pain. This drug can also be used for sleep apnea treatment along with a carbonic anhydrase inhibitor.

Its sale was discontinued in the UK, Australia, and Republic of Ireland in 2000.

Protriptyline is used primarily to treat depression and to treat the combination of symptoms of anxiety and depression. Like most antidepressants of this chemical and pharmacological class, protriptyline has also been used in limited numbers of patients to treat panic disorder, obsessive-compulsive disorder, attention-deficit/hyperactivity disorder, enuresis, eating disorders such as bulimia nervosa, cocaine dependency, and the depressive phase of bipolar disorder (manic-depressive) disorder. It has also been used to support smoking cessation programs.

Protriptyline hydrochloride, a dibenzocycloheptene derivative, has a molecular weight of 299.84 g/mol. It is a white to yellowish powder that is freely soluble in water and soluble in dilute HCl. Protriptyline hydrochloride is supplied as 5 mg or 10 mg tablets. Inactive ingredients are anhydrous lactose, colloidal silicon dioxide, magnesium stearate, and microcrystalline cellulose.