U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

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

Sources: DOI: 10.1021/ja01651a001

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P14173
Gene ID: 24311.0
Gene Symbol: Ddc
Target Organism: Rattus norvegicus (Rat)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Cincofarm

Approved Use

Oxitriptan is indicated in the prophylactic treatment of migraine.

Launch Date

2014
Primary
Tript-Oh

Approved Use

Oxitriptan is indicated in the treatment of post-anoxic myoclonus

Launch Date

2005
Primary
Triptosan

Approved Use

Oxitriptan is used to treat episodes of mild depression.

Launch Date

2011
PubMed

PubMed

TitleDatePubMed
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
Pharmacological studies of geissoschizine methyl ether, isolated from Uncaria sinensis Oliv., in the central nervous system.
2001 Aug 17
[Changes of plasma serotonin precursor metabolite concentrations in postmenopausal women with hot flushes].
2002 Dec
Efficient biosynthetic incorporation of tryptophan and indole analogs in an integral membrane protein.
2003 Sep
Systemic 5-hydroxy-L-tryptophan down-regulates the arcuate CART mRNA level in rats.
2003 Sep 15
Chemistry and antioxidative activity of hot water extract of Japanese radish (daikon).
2004
Depletion and restoration of endogenous monoamines affects beta-CIT binding to serotonin but not dopamine transporters in non-human primates.
2004
Effect of orally administered L-tryptophan on serotonin, melatonin, and the innate immune response in the rat.
2004 Dec
L -5-Hydroxytryptophan treatment of sleep terrors in children.
2004 Jul
[Determination of the antioxidant activity of potential scavengers of nitric oxide].
2004 Nov
Separation and determination of L-tryptophan and its metabolites by capillary micellar electrokinetic chromatography with amperometric detection.
2005 Feb
Effect of toluene and cresols on Na+,K+-ATPase, and serotonin in rat brain.
2005 Feb
Evidence-based medicine in migraine prevention.
2005 May
Antidepressant-like effect of Cordyceps sinensis in the mouse tail suspension test.
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
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
Characterization of serotonin-toxicity syndrome (toxidrome) elicited by 5-hydroxy-l-tryptophan in clorgyline-pretreated rats.
2008 Jul 7
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
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
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
Dimorphic expression of tryptophan hydroxylase in the brain of XX and XY Nile tilapia during early development.
2010 Apr 1
Enhanced tolerability of the 5-hydroxytryptophane challenge test combined with granisetron.
2010 Jan
Delta-aminolevulinic acid is a substrate for the amino acid transporter SLC36A1 (hPAT1).
2010 Mar
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
Oxitriptan showed high hydroxyl radical scavenging effects with a 50% inhibition concentration (IC50) of 1.8 uM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:00:28 GMT 2023
Edited
by admin
on Fri Dec 15 15:00:28 GMT 2023
Record UNII
C1LJO185Q9
Record Status Validated (UNII)
Record Version
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Name Type Language
OXITRIPTAN
INN   MART.   WHO-DD  
INN  
Official Name English
HYDROXYTRYPTOPHAN
INCI   VANDF  
INCI  
Official Name English
5-HYDROXYTRYPTOPHAN
Systematic Name English
OXYFAN
Brand Name English
OXITRIPTAN [MART.]
Common Name English
(2S)-2-AMINO-3-(5-HYDROXY-1H-INDOL-3-YL)PROPANOIC ACID
Systematic Name English
(S)-5-HYDROXYTRYPTOPHAN
Systematic Name English
N-ACETYLTRYPTOPHAN IMPURITY D [EP IMPURITY]
Common 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
Oxitriptan [WHO-DD]
Common Name English
TRYPTOPHAN IMPURITY D [EP IMPURITY]
Common Name English
TRIPTENE
Brand Name English
5-HYDROXYTRYPTOPHAN L-FORM [MI]
Common Name English
Classification Tree Code System Code
DSLD 305 (Number of products:540)
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
FDA ORPHAN DRUG 118298
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
LOINC 74768-3
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
WHO-VATC QN06AX01
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
NCI_THESAURUS C73539
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
WHO-ATC N06AX01
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
FDA ORPHAN DRUG 3984
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
Code System Code Type Description
CHEBI
28171
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
ChEMBL
CHEMBL350221
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
DAILYMED
C1LJO185Q9
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
SMS_ID
100000083049
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
RXCUI
94
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY RxNorm
MERCK INDEX
m6156
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C52181
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
WIKIPEDIA
5-HYDROXYTRYPTOPHAN
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
EPA CompTox
DTXSID1025437
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
EVMPD
SUB09541MIG
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
ECHA (EC/EINECS)
224-411-1
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
CHEBI
17780
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
FDA UNII
C1LJO185Q9
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
PUBCHEM
439280
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
CAS
4350-09-8
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
RS_ITEM_NUM
1329913
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
DRUG CENTRAL
4006
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
CHEBI
58266
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
MESH
D006916
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
DRUG BANK
DB02959
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
INN
4407
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
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