Stereochemistry | ACHIRAL |
Molecular Formula | C19H21N |
Molecular Weight | 263.3767 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CNCCCC1C2=C(C=CC=C2)C=CC3=C1C=CC=C3
InChI
InChIKey=BWPIARFWQZKAIA-UHFFFAOYSA-N
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
Molecular Formula | C19H21N |
Molecular Weight | 263.3767 |
Charge | 0 |
Count |
MOL RATIO
1 MOL RATIO (average) |
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Protriptyline (trade name Vivactil) is a tricyclic antidepressant, indicated for the treatment of depression. Protriptyline acts by decreasing the reuptake of norepinephrine and to a lesser extent serotonin (5-HT) in the brain. Tricyclic antidepressants act to change the balance of naturally occurring chemicals in the brain that regulate the transmission of nerve impulses between cells. Protriptyline increases the concentration of norepinephrine and serotonin (both chemicals that stimulate nerve cells) and, to a lesser extent, blocks the action of another brain chemical, acetylcholine. The therapeutic effects of protriptyline, like other antidepressants, appear slowly. Maximum benefit is often not evident for at least two weeks after starting the drug. 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. Like all tricyclic antidepressants, protriptyline should be used cautiously and with close physician supervision. This is especially so in the elderly, or people who have benign prostatic hypertrophy (enlarged prostate gland), or urinary retention, or glaucoma, especially angle-closure glaucoma (the most severe form). Before starting treatment, people should discuss the relative risks and benefits of treatment with their doctors to help determine if protriptyline is the right antidepressant for them. A common problem with tricyclic antidepressants is sedation (drowsiness, lack of physical and mental alertness), but protriptyline is considered the least sedating agent among this class of agents. Its side effects are especially noticeable early in therapy. In most people, early tricyclic side-effects decrease or disappear entirely with time, but, until then, patients taking protriptyline should take care to assess which side-effects occur in them and should not perform hazardous activities requiring mental acuity or coordination. The side-effects are increased when protriptyline is taken with central nervous system depressants, such as alcoholic beverages, sleeping medications, other sedatives, or antihistamines, as well as with other antidepressants including SSRIs, SNRIs or monoamine oxidase Inhibitors.
CNS Activity
Originator
Approval Year
Doses
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Tox targets
Sourcing
PubMed
Sample Use Guides
Usual Adult Dosage
Fifteen to 40 mg a day divided into 3 or 4 doses. If necessary, dosage may be increased to 60 mg a day. Dosages
above this amount are not recommended. Increases should be made in the morning dose.
Route of Administration:
Oral
The standard reaction mixture with calf thymus DNA contained (unless otherwise specified) 0.2 μM HRP, 13 μM per bp calf thymus DNA (∼10 ng/μL), 500 μM Protriptyline, and 500 μM H2O2 in Sorenson buffer (pH 7.0) containing 67 mM dibasic sodium phosphate and 67 mM monobasic potassium phosphate.
The standard reaction mixture with pBR322 plasmid contained 0.2 μM HRP, 3 ng/μL (∼5 μM per bp) plasmid, 500 μM Protriptyline, and 500 μMH2O2 in 67 mM Sorenson buffer (pH 7.0). The volume of the reaction mixtures prepared for the 15-well gels was 10 μL; the volume of the reactions prepared for 8-well gels was 20 μL. The components were added in the order listed. All reaction mixtures were incubated at 37 C for 1 h in a water bath.