Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C11H12N2O3 |
Molecular Weight | 220.2246 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
N[C@@H](CC1=CNC2=C1C=C(O)C=C2)C(O)=O
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 | 220.2246 |
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 |
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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 Date2014 |
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Primary | Tript-Oh Approved UseOxitriptan is indicated in the treatment of post-anoxic myoclonus Launch Date2005 |
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Primary | Triptosan Approved UseOxitriptan is used to treat episodes of mild depression. Launch Date2011 |
PubMed
Title | Date | PubMed |
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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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Pharmacological studies of geissoschizine methyl ether, isolated from Uncaria sinensis Oliv., in the central nervous system. | 2001 Aug 17 |
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[Changes of plasma serotonin precursor metabolite concentrations in postmenopausal women with hot flushes]. | 2002 Dec |
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Efficient biosynthetic incorporation of tryptophan and indole analogs in an integral membrane protein. | 2003 Sep |
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Systemic 5-hydroxy-L-tryptophan down-regulates the arcuate CART mRNA level in rats. | 2003 Sep 15 |
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Chemistry and antioxidative activity of hot water extract of Japanese radish (daikon). | 2004 |
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Depletion and restoration of endogenous monoamines affects beta-CIT binding to serotonin but not dopamine transporters in non-human primates. | 2004 |
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Effect of orally administered L-tryptophan on serotonin, melatonin, and the innate immune response in the rat. | 2004 Dec |
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L -5-Hydroxytryptophan treatment of sleep terrors in children. | 2004 Jul |
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[Determination of the antioxidant activity of potential scavengers of nitric oxide]. | 2004 Nov |
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Separation and determination of L-tryptophan and its metabolites by capillary micellar electrokinetic chromatography with amperometric detection. | 2005 Feb |
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Effect of toluene and cresols on Na+,K+-ATPase, and serotonin in rat brain. | 2005 Feb |
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Evidence-based medicine in migraine prevention. | 2005 May |
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Antidepressant-like effect of Cordyceps sinensis in the mouse tail suspension test. | 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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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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Characterization of serotonin-toxicity syndrome (toxidrome) elicited by 5-hydroxy-l-tryptophan in clorgyline-pretreated rats. | 2008 Jul 7 |
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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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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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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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Dimorphic expression of tryptophan hydroxylase in the brain of XX and XY Nile tilapia during early development. | 2010 Apr 1 |
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Enhanced tolerability of the 5-hydroxytryptophane challenge test combined with granisetron. | 2010 Jan |
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Delta-aminolevulinic acid is a substrate for the amino acid transporter SLC36A1 (hPAT1). | 2010 Mar |
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The proton-coupled amino acid transporter, SLC36A1 (hPAT1), transports Gly-Gly, Gly-Sar and other Gly-Gly mimetics. | 2010 Oct |
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
Fri Dec 15 15:00:28 GMT 2023
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on
Fri Dec 15 15:00:28 GMT 2023
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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)
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FDA ORPHAN DRUG |
118298
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LOINC |
74768-3
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WHO-VATC |
QN06AX01
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NCI_THESAURUS |
C73539
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WHO-ATC |
N06AX01
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FDA ORPHAN DRUG |
3984
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28171
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CHEMBL350221
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C1LJO185Q9
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100000083049
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94
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m6156
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C52181
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5-HYDROXYTRYPTOPHAN
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DTXSID1025437
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SUB09541MIG
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224-411-1
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17780
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4006
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58266
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D006916
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DB02959
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4407
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TARGET -> AGONIST | |||
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LABELED -> NON-LABELED |
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PARENT -> METABOLITE |
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PARENT -> IMPURITY |
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |