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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
Structure of OXITRIPTAN

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

HIDE SMILES / InChI

Description

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.

CNS Activity

Originator

Approval Year

TargetsConditions
PubMed

PubMed

TitleDatePubMed
Biochemical properties and kinetic parameters of dihydroxyphenylalanine--5-hydroxytryptophan decarboxylase in brain, liver, and adrenals of cat.
1979 Jul
Development of a scleroderma-like illness during therapy with L-5-hydroxytryptophan and carbidopa.
1980 Oct 2
Plasma accumulation of metabolism of orally administered single dose L-5-hydroxytryptophan in man.
1981 Sep
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
Serotonin precursors in chronic primary headache. A double-blind cross-over study with L-5-hydroxytryptophan vs. placebo.
1985 Jul-Sep
Double-blind study of 5-hydroxytryptophan versus placebo in the treatment of primary fibromyalgia syndrome.
1990 May-Jun
Levorotatory form of 5-hydroxytryptophan in Friedreich's ataxia. Results of a double-blind drug-placebo cooperative study.
1995 May
5-Hydroxytryptophan: a clinically-effective serotonin precursor.
1998 Aug
[Study on tetrahydrobiopterin deficiency in Northern Chinese population].
2006 Jun
Familial paragangliomas.
2006 Oct 15
Central serotonergic hypofunction in autism: results of the 5-hydroxy-tryptophan challenge test.
2007 Aug
Nuclear imaging of neuroendocrine tumours.
2007 Mar
Receptor mediation of exaggerated responses to serotonin-enhancing drugs in serotonin transporter (SERT)-deficient mice.
2007 Oct
Antidepressant-like effect of Cordyceps sinensis in the mouse tail suspension test.
2007 Sep
Effects of increased endogenous serotonin on the in vivo binding of [11C]DASB to serotonin transporters in conscious monkey brain.
2007 Sep
Neurochemical, behavioral, and physiological effects of pharmacologically enhanced serotonin levels in serotonin transporter (SERT)-deficient mice.
2008 Dec
Modifications of tryptophan oxidation by phenolic-rich plant materials.
2008 Dec 10
Role of a serotonin precursor in development of gut microvilli.
2008 Feb
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
Biotransformation of indole derivatives by mycelial cultures.
2008 Jan-Feb
Characterization of serotonin-toxicity syndrome (toxidrome) elicited by 5-hydroxy-l-tryptophan in clorgyline-pretreated rats.
2008 Jul 7
Augmented brain 5-HT crosses the blood-brain barrier through the 5-HT transporter in rat.
2008 May
The Parallel Worm Tracker: a platform for measuring average speed and drug-induced paralysis in nematodes.
2008 May 21
Production and Peripheral Roles of 5-HTP, a Precursor of Serotonin.
2009
99mTc-DTPA-amino acids conjugate as specific SPECT pharmaceuticals for tumor imaging.
2009 Aug
Amantadine reduces glucagon and enhances insulin secretion throughout the oral glucose tolerance test: central plus peripheral nervous system mechanisms.
2009 Dec 2
Examination of a pre-exercise, high energy supplement on exercise performance.
2009 Jan 6
Direct and decarboxylation-dependent effects of neurotransmitter precursors on firing of isolated monoaminergic neurons.
2009 Jun
Enhancement of L-tryptophan 5-hydroxylation activity by structure-based modification of L-phenylalanine 4-hydroxylase from Chromobacterium violaceum.
2009 Sep
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
Serum levels of tryptophan, 5-hydroxytryptophan and serotonin in patients affected with different forms of amenorrhea.
2010
Animal violence demystified.
2010
Dimorphic expression of tryptophan hydroxylase in the brain of XX and XY Nile tilapia during early development.
2010 Apr 1
5-hydroxy-L-tryptophan Suppressed Food Intake in Rats Despite an Increase in the Arcuate NPY Expression.
2010 Dec
Enhanced tolerability of the 5-hydroxytryptophane challenge test combined with granisetron.
2010 Jan
Melatonin and structurally-related compounds protect synaptosomal membranes from free radical damage.
2010 Jan 21
5-Hydroxy-L-tryptophan alters gaboxadol pharmacokinetics in rats: involvement of PAT1 and rOat1 in gaboxadol absorption and elimination.
2010 Jan 31
Native serotonin membrane receptors recognize 5-hydroxytryptophan-functionalized substrates: enabling small-molecule recognition.
2010 Jul 21
Effects of amantadine on circulating neurotransmitters in healthy subjects.
2010 Mar
Delta-aminolevulinic acid is a substrate for the amino acid transporter SLC36A1 (hPAT1).
2010 Mar
Chronic melatonin treatment and its precursor L-tryptophan improve the monoaminergic neurotransmission and related behavior in the aged rat brain.
2010 Mar
[The effect of serotonin precursor 5-hydroxytryptophan and neurotoxic analogue 5,7-dihydroxytryptamine on defensive conditioning in a snail].
2010 Mar-Apr
Comparison of the consumption of antidepressants in the immigrant and native populations in a Spanish health region: an observational study.
2010 May 17
The proton-coupled amino acid transporter, SLC36A1 (hPAT1), transports Gly-Gly, Gly-Sar and other Gly-Gly mimetics.
2010 Oct
Involvement of 5-HT2A receptors in the serotonin (5-HT) syndrome caused by excessive 5-HT efflux in rat brain.
2010 Oct
Griffonia simplicifolia negatively affects sexual behavior in female rats.
2010 Oct
Serotonin, but not N-methyltryptamines, activates the serotonin 2A receptor via a ß-arrestin2/Src/Akt signaling complex in vivo.
2010 Oct 6
Non-coplanar polychlorinated biphenyl (PCB)-induced immunotoxicity is coincident with alterations in the serotonergic system.
2010 Oct-Dec
Liquid chromatography on a monolithic column microfluidic chip coupled with "three-T" sample injection mode and amperometric detection.
2010 Sep
Amino acid derivatives are substrates or non-transported inhibitors of the amino acid transporter PAT2 (slc36a2).
2011 Jan
Patents

Sample Use Guides

In Vivo Use Guide
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
Oxitriptan showed high hydroxyl radical scavenging effects with a 50% inhibition concentration (IC50) of 1.8 uM.
Name Type Language
OXITRIPTAN
INN   MART.   WHO-DD  
INN  
Official Name English
OXITRIPTAN [WHO-DD]
Common Name English
HYDROXYTRYPTOPHAN
INCI   VANDF  
INCI  
Official Name English
5-HYDROXYTRYPTOPHAN
Systematic Name English
OXYFAN
Brand Name English
OXITRIPTAN [MART.]
Common Name English
(S)-5-HYDROXYTRYPTOPHAN
Systematic Name English
TELESOL
Brand Name English
CINCOFARM
Brand Name English
PRETONINE
Brand Name English
HYDROXYTRYPTOPHAN [INCI]
Common Name English
5-HYDROXY-L-TRYPTOPHAN
USP-RS  
Systematic Name English
L-5-HYDROXYTRYPTOPHAN
Common Name English
5-HYDROXYTRYPTOPHAN L-FORM
MI  
Common Name English
HYDROXYTRYPTOPHAN [VANDF]
Common Name English
LEVOTHYM
Brand Name English
LEVOTININE
Brand Name English
QUIETIM
Brand Name English
SEROTONYL
Brand Name English
5-HYDROXY-L-TRYPTOPHAN [USP-RS]
Common Name English
L-5-HTP
Common Name English
OXITRIPTAN [INN]
Common Name English
L-TRYPTOPHAN, 5-HYDROXY-
Systematic Name English
TRIPTENE
Brand Name English
5-HYDROXYTRYPTOPHAN L-FORM [MI]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 118298
Created by admin on Tue Oct 22 00:30:55 UTC 2019 , Edited by admin on Tue Oct 22 00:30:55 UTC 2019
WHO-VATC QN06AX01
Created by admin on Tue Oct 22 00:30:55 UTC 2019 , Edited by admin on Tue Oct 22 00:30:55 UTC 2019
NCI_THESAURUS C73539
Created by admin on Tue Oct 22 00:30:55 UTC 2019 , Edited by admin on Tue Oct 22 00:30:55 UTC 2019
WHO-ATC N06AX01
Created by admin on Tue Oct 22 00:30:55 UTC 2019 , Edited by admin on Tue Oct 22 00:30:55 UTC 2019
FDA ORPHAN DRUG 3984
Created by admin on Tue Oct 22 00:30:55 UTC 2019 , Edited by admin on Tue Oct 22 00:30:55 UTC 2019
Code System Code Type Description
ChEMBL
CHEMBL350221
Created by admin on Tue Oct 22 00:30:55 UTC 2019 , Edited by admin on Tue Oct 22 00:30:55 UTC 2019
PRIMARY
RXCUI
94
Created by admin on Tue Oct 22 00:30:55 UTC 2019 , Edited by admin on Tue Oct 22 00:30:55 UTC 2019
PRIMARY RxNorm
MERCK INDEX
M6156
Created by admin on Tue Oct 22 00:30:55 UTC 2019 , Edited by admin on Tue Oct 22 00:30:55 UTC 2019
PRIMARY Merck Index
NCI_THESAURUS
C52181
Created by admin on Tue Oct 22 00:30:55 UTC 2019 , Edited by admin on Tue Oct 22 00:30:55 UTC 2019
PRIMARY
WIKIPEDIA
5-HYDROXYTRYPTOPHAN
Created by admin on Tue Oct 22 00:30:55 UTC 2019 , Edited by admin on Tue Oct 22 00:30:55 UTC 2019
PRIMARY
EPA CompTox
4350-09-8
Created by admin on Tue Oct 22 00:30:55 UTC 2019 , Edited by admin on Tue Oct 22 00:30:55 UTC 2019
PRIMARY
EVMPD
SUB09541MIG
Created by admin on Tue Oct 22 00:30:55 UTC 2019 , Edited by admin on Tue Oct 22 00:30:55 UTC 2019
PRIMARY
ECHA (EC/EINECS)
224-411-1
Created by admin on Tue Oct 22 00:30:55 UTC 2019 , Edited by admin on Tue Oct 22 00:30:55 UTC 2019
PRIMARY
CAS
4350-09-8
Created by admin on Tue Oct 22 00:30:55 UTC 2019 , Edited by admin on Tue Oct 22 00:30:55 UTC 2019
PRIMARY
MESH
D006916
Created by admin on Tue Oct 22 00:30:55 UTC 2019 , Edited by admin on Tue Oct 22 00:30:55 UTC 2019
PRIMARY
DRUG BANK
DB02959
Created by admin on Tue Oct 22 00:30:55 UTC 2019 , Edited by admin on Tue Oct 22 00:30:55 UTC 2019
PRIMARY
INN
4407
Created by admin on Tue Oct 22 00:30:55 UTC 2019 , Edited by admin on Tue Oct 22 00:30:55 UTC 2019
PRIMARY