Details
Stereochemistry | ACHIRAL |
Molecular Formula | C19H29N5O2.ClH |
Molecular Weight | 395.927 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CC1(C)CC(=O)N(CCCCN2CCN(CC2)C3=NC=CC=N3)C(=O)C1
InChI
InChIKey=DGOCVISYYYQFEP-UHFFFAOYSA-N
InChI=1S/C19H29N5O2.ClH/c1-19(2)14-16(25)24(17(26)15-19)9-4-3-8-22-10-12-23(13-11-22)18-20-6-5-7-21-18;/h5-7H,3-4,8-15H2,1-2H3;1H
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C19H29N5O2 |
Molecular Weight | 359.4659 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Gepirone (brand name Travivo) is an investigational azapirone antidepressant and anxiolytic drug in development for the treatment of major depressive disorder but has yet to be marketed. Like other azapirones, it acts as a selective partial agonist of the 5-HT1A receptor. Gepirone has been under development in the U.S. in an extended release form (referred to as Gepirone ER). It has been rejected multiple times by the FDA during the drug approval process and Phase III studies evaluating its use in the treatment of MDD were prematurely terminated. These were the initial Phase III studies of gepirone ER in MDD, and the effective dose range had not been determined. In March 2016, the FDA reversed its decision and gave gepirone ER a positive review, clearing the way for the drug to finally gain market approval in the U.S. In addition to its antidepressant and anxiolytic properties, gepirone has been found to improve symptoms of sexual dysfunction in men and women, similarly to the marketed 5-HT1A receptor agonist flibanserin. The pro-sexual effects appear to be independent of its antidepressant and anxiolytic effects. Mechanism of action studies have demonstrated that gepirone possesses a much greater selectivity for 5-HT1A receptors over dopamine D2 receptors. Long-term studies have shown that gepirone has a differential action at presynaptic (agonist) and post-synaptic (partial agonist) 5-HT1A receptors. Treatment with gepirone ER
desensitizes presynaptic 5-HT1A receptors, which decreases serotonin autoregulatory inhibition and enhances activation of postsynaptic 5-HT1A receptors. As a partial agonist gepirone ER acts as an agonist when endogenous serotonin is not present and as an antagonist when endogenous serotonin is present. Overall, gepirone ER increases serotonin production when insufficient amounts are present, and decreases serotonin production when excess amounts are present. Gepirone has been tested in Phase II clinical trial as antidepressant medication for pharmacotherapy for cocaine dependent subjects.
Originator
Sources: http://www.theinfolist.com/php/SummaryGet.php?FindGo=Gepirone | https://www.ncbi.nlm.nih.gov/pubmed/11892924
Curator's Comment: Gepirone was originally developed by Bristol-Myers Squibb in 1986, but was out-licensed to Fabre-Kramer in 1993. # Bristol-Myers Squibb
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P08908 Gene ID: 3350.0 Gene Symbol: HTR1A Target Organism: Homo sapiens (Human) |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Secondary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Strychnine seizure potentiation by azaspirodecanedione anxiolytics in rats. | 1988 Oct 18 |
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Effects of 5-HT1A agonists and 5-HT2 antagonists on haloperidol-induced dyskinesias in squirrel monkeys: no evidence for reciprocal 5-HT-dopamine interaction. | 1989 |
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Prenatal exposure to cocaine: effects on aggression in Sprague-Dawley rats. | 1994 May |
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Involvement of 5-hydroxytryptamine(1A) receptors in nicotine-induced tail tremor in rats. | 2000 Nov 10 |
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Effects of serotonergic compounds on aqueous humor dynamics in monkeys. | 2001 Aug |
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Rigid analogues of buspirone and gepirone, 5-HT1A receptors partial agonists. | 2002 Nov |
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Differential effects of the 5-HT1A agonist gepirone on food intake in rats may depend on their motivation to eat. | 2003 Nov |
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Pharmacokinetic evaluation of gepirone immediate-release capsules and gepirone extended-release tablets in healthy volunteers. | 2003 Sep |
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Cellular consequences of stress and depression. | 2004 Jun |
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Sustained efficacy of gepirone-IR in major depressive disorder: a double-blind placebo substitution trial. | 2004 May-Jun |
Sample Use Guides
Gepirone ER (20 mg to 80 mg) was administered once per day in the morning for 8 weeks (56 days). Patients with moderate to severe depression initiated treatment by taking a 20 mg tablet once daily in the morning with food, followed by an increase to 40 mg daily between days 4 and 7. The dose could be increased to 60 mg daily after day 7, and to 80 mg daily after 14 days.
Route of Administration:
Oral
Substance Class |
Chemical
Created
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admin
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Record UNII |
80C9L8EP6V
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Validated (UNII)
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C28197
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C47794
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