Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C11H12N2O3 |
Molecular Weight | 220.225 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
c1cc2c(cc1O)c(C[C@@]([H])(C(=O)O)N)c[nH]2
InChI
InChIKey=LDCYZAJDBXYCGN-VIFPVBQESA-N
InChI=1S/C11H12N2O3/c12-9(11(15)16)3-6-5-13-10-2-1-7(14)4-8(6)10/h1-2,4-5,9,13-14H,3,12H2,(H,15,16)/t9-/m0/s1
Molecular Formula | C11H12N2O3 |
Molecular Weight | 220.225 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Oxitriptan is an aromatic amino acid with antidepressant activity. In vivo, oxitriptan is converted into 5-hydroxytryptamine (serotonin) as well as other neurotransmitters. Oxitriptan may exert its antidepressant activity via conversion to serotonin or directly by binding to serotonin receptors within the central nervous system. It is used as an antiepileptic and antidepressant. Oxitriptan is a worthwhile addition to the limited treatments available for obsessive-compulsive disorder and panic disorder, two psychiatric disorders which have previously been difficult to manage pharmacologically. Possible gastrointestinal side effects are: nausea, vomiting, abdominal pain, constipation or flatulence, which tend to disappear with continued treatment or, in any case, dose reduction. Other undesirable effects such as anorexia, xerostomia, tachycardia, extrasystoles, dizziness, headache, lightheadedness, tremor or myalgia may occur.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P14173 Gene ID: 24311.0 Gene Symbol: Ddc Target Organism: Rattus norvegicus (Rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/6983619 |
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Target ID: CHEMBL2096904 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Preventing | Cincofarm Approved UseOxitriptan is indicated in the prophylactic treatment of migraine. Launch Date1.39743357E12 |
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Primary | Tript-Oh Approved UseOxitriptan is indicated in the treatment of post-anoxic myoclonus Launch Date1.11715195E12 |
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Primary | Triptosan Approved UseOxitriptan is used to treat episodes of mild depression. Launch Date1.29513606E12 |
PubMed
Title | Date | PubMed |
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Biochemical properties and kinetic parameters of dihydroxyphenylalanine--5-hydroxytryptophan decarboxylase in brain, liver, and adrenals of cat. | 1979 Jul |
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Development of a scleroderma-like illness during therapy with L-5-hydroxytryptophan and carbidopa. | 1980 Oct 2 |
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Plasma accumulation of metabolism of orally administered single dose L-5-hydroxytryptophan in man. | 1981 Sep |
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Effect of pyridoxal phosphate deficiency on aromatic L-amino acid decarboxylase activity with L-DOPA and L-5-hydroxytryptophan as substrates in rats. | 1982 Oct |
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Serotonin precursors in chronic primary headache. A double-blind cross-over study with L-5-hydroxytryptophan vs. placebo. | 1985 Jul-Sep |
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Double-blind study of 5-hydroxytryptophan versus placebo in the treatment of primary fibromyalgia syndrome. | 1990 May-Jun |
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Levorotatory form of 5-hydroxytryptophan in Friedreich's ataxia. Results of a double-blind drug-placebo cooperative study. | 1995 May |
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5-Hydroxytryptophan: a clinically-effective serotonin precursor. | 1998 Aug |
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Familial paragangliomas. | 2006 Oct 15 |
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Central serotonergic hypofunction in autism: results of the 5-hydroxy-tryptophan challenge test. | 2007 Aug |
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Tyrosine hydroxylase (TH)- and aromatic-L-amino acid decarboxylase (AADC)-immunoreactive neurons of the common marmoset (Callithrix jacchus) brain: an immunohistochemical analysis. | 2007 Jul 3 |
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Nuclear imaging of neuroendocrine tumours. | 2007 Mar |
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Receptor mediation of exaggerated responses to serotonin-enhancing drugs in serotonin transporter (SERT)-deficient mice. | 2007 Oct |
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Antidepressant-like effect of Cordyceps sinensis in the mouse tail suspension test. | 2007 Sep |
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Effects of increased endogenous serotonin on the in vivo binding of [11C]DASB to serotonin transporters in conscious monkey brain. | 2007 Sep |
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Neurochemical, behavioral, and physiological effects of pharmacologically enhanced serotonin levels in serotonin transporter (SERT)-deficient mice. | 2008 Dec |
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Modifications of tryptophan oxidation by phenolic-rich plant materials. | 2008 Dec 10 |
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Role of a serotonin precursor in development of gut microvilli. | 2008 Feb |
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Delta 9-tetrahydrocannabinol-induced catalepsy-like immobilization is mediated by decreased 5-HT neurotransmission in the nucleus accumbens due to the action of glutamate-containing neurons. | 2008 Jan 24 |
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Biotransformation of indole derivatives by mycelial cultures. | 2008 Jan-Feb |
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Characterization of serotonin-toxicity syndrome (toxidrome) elicited by 5-hydroxy-l-tryptophan in clorgyline-pretreated rats. | 2008 Jul 7 |
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Augmented brain 5-HT crosses the blood-brain barrier through the 5-HT transporter in rat. | 2008 May |
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The Parallel Worm Tracker: a platform for measuring average speed and drug-induced paralysis in nematodes. | 2008 May 21 |
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Production and Peripheral Roles of 5-HTP, a Precursor of Serotonin. | 2009 |
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99mTc-DTPA-amino acids conjugate as specific SPECT pharmaceuticals for tumor imaging. | 2009 Aug |
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Amantadine reduces glucagon and enhances insulin secretion throughout the oral glucose tolerance test: central plus peripheral nervous system mechanisms. | 2009 Dec 2 |
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Examination of a pre-exercise, high energy supplement on exercise performance. | 2009 Jan 6 |
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Direct and decarboxylation-dependent effects of neurotransmitter precursors on firing of isolated monoaminergic neurons. | 2009 Jun |
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Enhancement of L-tryptophan 5-hydroxylation activity by structure-based modification of L-phenylalanine 4-hydroxylase from Chromobacterium violaceum. | 2009 Sep |
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Tramadol and another atypical opioid meperidine have exaggerated serotonin syndrome behavioural effects, but decreased analgesic effects, in genetically deficient serotonin transporter (SERT) mice. | 2009 Sep |
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Serum levels of tryptophan, 5-hydroxytryptophan and serotonin in patients affected with different forms of amenorrhea. | 2010 |
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Animal violence demystified. | 2010 |
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Dimorphic expression of tryptophan hydroxylase in the brain of XX and XY Nile tilapia during early development. | 2010 Apr 1 |
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5-hydroxy-L-tryptophan Suppressed Food Intake in Rats Despite an Increase in the Arcuate NPY Expression. | 2010 Dec |
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Enhanced tolerability of the 5-hydroxytryptophane challenge test combined with granisetron. | 2010 Jan |
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Melatonin and structurally-related compounds protect synaptosomal membranes from free radical damage. | 2010 Jan 21 |
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5-Hydroxy-L-tryptophan alters gaboxadol pharmacokinetics in rats: involvement of PAT1 and rOat1 in gaboxadol absorption and elimination. | 2010 Jan 31 |
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Native serotonin membrane receptors recognize 5-hydroxytryptophan-functionalized substrates: enabling small-molecule recognition. | 2010 Jul 21 |
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Effects of amantadine on circulating neurotransmitters in healthy subjects. | 2010 Mar |
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Delta-aminolevulinic acid is a substrate for the amino acid transporter SLC36A1 (hPAT1). | 2010 Mar |
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Chronic melatonin treatment and its precursor L-tryptophan improve the monoaminergic neurotransmission and related behavior in the aged rat brain. | 2010 Mar |
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[The effect of serotonin precursor 5-hydroxytryptophan and neurotoxic analogue 5,7-dihydroxytryptamine on defensive conditioning in a snail]. | 2010 Mar-Apr |
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Comparison of the consumption of antidepressants in the immigrant and native populations in a Spanish health region: an observational study. | 2010 May 17 |
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The proton-coupled amino acid transporter, SLC36A1 (hPAT1), transports Gly-Gly, Gly-Sar and other Gly-Gly mimetics. | 2010 Oct |
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Involvement of 5-HT2A receptors in the serotonin (5-HT) syndrome caused by excessive 5-HT efflux in rat brain. | 2010 Oct |
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Griffonia simplicifolia negatively affects sexual behavior in female rats. | 2010 Oct |
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Serotonin, but not N-methyltryptamines, activates the serotonin 2A receptor via a ß-arrestin2/Src/Akt signaling complex in vivo. | 2010 Oct 6 |
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Non-coplanar polychlorinated biphenyl (PCB)-induced immunotoxicity is coincident with alterations in the serotonergic system. | 2010 Oct-Dec |
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Liquid chromatography on a monolithic column microfluidic chip coupled with "three-T" sample injection mode and amperometric detection. | 2010 Sep |
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Amino acid derivatives are substrates or non-transported inhibitors of the amino acid transporter PAT2 (slc36a2). | 2011 Jan |
Patents
Sample Use Guides
The recommended mean dose for adults is 3 capsules per day (300 mg daily) divided into 3 divided doses. The maintenance dose: between 300 and 600 mg per day.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15617538
Oxitriptan showed high hydroxyl radical scavenging effects with a 50% inhibition concentration (IC50) of 1.8 uM.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 09:06:18 UTC 2021
by
admin
on
Sat Jun 26 09:06:18 UTC 2021
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Record UNII |
C1LJO185Q9
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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DSLD |
305 (Number of products:540)
Created by
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FDA ORPHAN DRUG |
118298
Created by
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LOINC |
74768-3
Created by
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WHO-VATC |
QN06AX01
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NCI_THESAURUS |
C73539
Created by
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WHO-ATC |
N06AX01
Created by
admin on Sat Jun 26 09:06:18 UTC 2021 , Edited by admin on Sat Jun 26 09:06:18 UTC 2021
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FDA ORPHAN DRUG |
3984
Created by
admin on Sat Jun 26 09:06:18 UTC 2021 , Edited by admin on Sat Jun 26 09:06:18 UTC 2021
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Code System | Code | Type | Description | ||
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CHEMBL350221
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PRIMARY | |||
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94
Created by
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PRIMARY | RxNorm | ||
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M6156
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PRIMARY | Merck Index | ||
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C52181
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PRIMARY | |||
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5-HYDROXYTRYPTOPHAN
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4350-09-8
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SUB09541MIG
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224-411-1
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1329913
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PRIMARY | USP-RS | ||
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C1LJO185Q9
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439280
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4350-09-8
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4006
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D006916
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DB02959
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4407
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Related Record | Type | Details | ||
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TARGET -> AGONIST |
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PARENT -> METABOLITE |
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PARENT -> IMPURITY |
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ACTIVE MOIETY |