OXITRIPTAN

Possibly Marketed Outside US

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 Search

SMILES

N[C@@H](CC1=CNC2=CC=C(O)C=C12)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

Description
Sources: https://www.cancer.gov/publications/dictionaries/cancer-drug?cdrid=459776 | https://druginfo.nlm.nih.gov/drugportal/rn/4350-09-8 | https://www.ncbi.nlm.nih.gov/pubmed/2178909 | http://www.angelini.pt/wps/wcm/connect/pt/home/produtos/medicamentos-venda-livre/cincofarm

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

Targets

Primary Target	Pharmacology	Condition	Potency
Aromatic-L-amino-acid decarboxylase 5 Target ID: P14173 Gene ID: 24311.0 Gene Symbol: Ddc Target Organism: Rattus norvegicus (Rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/6983619	Substrate 661
Serotonin (5-HT) receptor 34 Target ID: CHEMBL2096904 Sources: https://www.cancer.gov/publications/dictionaries/cancer-drug?cdrid=459776	Agonist 2752

Conditions

Condition	Modality	Highest Phase	Product
Migraine 107 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3536521 https://www.ncbi.nlm.nih.gov/pubmed/10721054	Preventing	Approved 8583	Cincofarm Approved Use Oxitriptan is indicated in the prophylactic treatment of migraine. Launch Date 2014
Post-anoxic myoclonus 1 Sources: https://www.codifa.it/farmaci/t/tript-oh-oxitriptano-antidepressivi https://www.ncbi.nlm.nih.gov/pubmed/8836591	Primary	Approved 8583	Tript-Oh Approved Use Oxitriptan is indicated in the treatment of post-anoxic myoclonus Launch Date 2005
Major depressive disorder 179 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3298325 https://clinicaltrials.gov/ct2/show/NCT02922725	Primary	Approved 8583	Triptosan Approved Use Oxitriptan is used to treat episodes of mild depression. Launch Date 2011

C_max

Value	Dose	Co-administered	Analyte	Population
1.47 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6187038/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: CARBIDOPA	CARBIDOPA	OXITRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
9.2 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6187038/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: CARBIDOPA	CARBIDOPA	OXITRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
4.34 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6187038/	10 mg single, intravenous dose: 10 mg route of administration: Intravenous experiment type: SINGLE co-administered: CARBIDOPA	CARBIDOPA	OXITRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
4.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6187038/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: CARBIDOPA	CARBIDOPA	OXITRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
81% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6182005/			OXITRIPTAN serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

Doses

Dose	Population	Adverse events
300 mg single, oral Highest studied dose Dose: 300 mg Route: oral Route: single Dose: 300 mg Sources: https://pubmed.ncbi.nlm.nih.gov/18308795/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/18308795/	Disc. AE: Nausea, Vomiting... AEs leading to discontinuation/dose reduction: Nausea (45.4%) Vomiting (45.4%) Sources: https://pubmed.ncbi.nlm.nih.gov/18308795/

AEs

AE	Significance	Dose	Population
Nausea	45.4% Disc. AE	300 mg single, oral Highest studied dose Dose: 300 mg Route: oral Route: single Dose: 300 mg Sources: https://pubmed.ncbi.nlm.nih.gov/18308795/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/18308795/
Vomiting	45.4% Disc. AE	300 mg single, oral Highest studied dose Dose: 300 mg Route: oral Route: single Dose: 300 mg Sources: https://pubmed.ncbi.nlm.nih.gov/18308795/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/18308795/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1741	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP3A4 2633	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMzUwMjIxIn19	inconclusive [IC50 19.9526 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11207028/	no [Ki >500 uM]
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/36605716/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/144#section=BioAssay-Results Page: 10 \| 14	no

PubMed

Title	Date	PubMed
Amino acid derivatives are substrates or non-transported inhibitors of the amino acid transporter PAT2 (slc36a2).	2011-01	20691150
5-hydroxy-L-tryptophan Suppressed Food Intake in Rats Despite an Increase in the Arcuate NPY Expression.	2010-12	22110352
Serotonin, but not N-methyltryptamines, activates the serotonin 2A receptor via a ß-arrestin2/Src/Akt signaling complex in vivo.	2010-10-06	20926677
The proton-coupled amino acid transporter, SLC36A1 (hPAT1), transports Gly-Gly, Gly-Sar and other Gly-Gly mimetics.	2010-10	20880398
Involvement of 5-HT2A receptors in the serotonin (5-HT) syndrome caused by excessive 5-HT efflux in rat brain.	2010-10	20456331
Griffonia simplicifolia negatively affects sexual behavior in female rats.	2010-10	20359873
Non-coplanar polychlorinated biphenyl (PCB)-induced immunotoxicity is coincident with alterations in the serotonergic system.	2010-09-17	20843273
Liquid chromatography on a monolithic column microfluidic chip coupled with "three-T" sample injection mode and amperometric detection.	2010-09	20658493
Native serotonin membrane receptors recognize 5-hydroxytryptophan-functionalized substrates: enabling small-molecule recognition.	2010-07-21	22778841
[The effect of serotonin precursor 5-hydroxytryptophan and neurotoxic analogue 5,7-dihydroxytryptamine on defensive conditioning in a snail].	2010-05-18	20469595
Comparison of the consumption of antidepressants in the immigrant and native populations in a Spanish health region: an observational study.	2010-05-17	20478063
Dimorphic expression of tryptophan hydroxylase in the brain of XX and XY Nile tilapia during early development.	2010-04-01	19925800
Effects of amantadine on circulating neurotransmitters in healthy subjects.	2010-03	20131070
Delta-aminolevulinic acid is a substrate for the amino acid transporter SLC36A1 (hPAT1).	2010-03	20128809
Chronic melatonin treatment and its precursor L-tryptophan improve the monoaminergic neurotransmission and related behavior in the aged rat brain.	2010-03	20082664
5-Hydroxy-L-tryptophan alters gaboxadol pharmacokinetics in rats: involvement of PAT1 and rOat1 in gaboxadol absorption and elimination.	2010-01-31	19900542
Melatonin and structurally-related compounds protect synaptosomal membranes from free radical damage.	2010-01-21	20162018
Enhanced tolerability of the 5-hydroxytryptophane challenge test combined with granisetron.	2010-01	18719048
Serum levels of tryptophan, 5-hydroxytryptophan and serotonin in patients affected with different forms of amenorrhea.	2010	22084589
Animal violence demystified.	2010	20407576
Amantadine reduces glucagon and enhances insulin secretion throughout the oral glucose tolerance test: central plus peripheral nervous system mechanisms.	2009-12-02	21437134
Enhancement of L-tryptophan 5-hydroxylation activity by structure-based modification of L-phenylalanine 4-hydroxylase from Chromobacterium violaceum.	2009-09	19664549
Tramadol and another atypical opioid meperidine have exaggerated serotonin syndrome behavioural effects, but decreased analgesic effects, in genetically deficient serotonin transporter (SERT) mice.	2009-09	19275775
99mTc-DTPA-amino acids conjugate as specific SPECT pharmaceuticals for tumor imaging.	2009-08	19614681
Direct and decarboxylation-dependent effects of neurotransmitter precursors on firing of isolated monoaminergic neurons.	2009-06	19274466
Examination of a pre-exercise, high energy supplement on exercise performance.	2009-01-06	19126213
Production and Peripheral Roles of 5-HTP, a Precursor of Serotonin.	2009	22084581
Modifications of tryptophan oxidation by phenolic-rich plant materials.	2008-12-10	19007128
Neurochemical, behavioral, and physiological effects of pharmacologically enhanced serotonin levels in serotonin transporter (SERT)-deficient mice.	2008-12	18712364
Characterization of serotonin-toxicity syndrome (toxidrome) elicited by 5-hydroxy-l-tryptophan in clorgyline-pretreated rats.	2008-07-07	18499101
The Parallel Worm Tracker: a platform for measuring average speed and drug-induced paralysis in nematodes.	2008-05-21	18493300
Augmented brain 5-HT crosses the blood-brain barrier through the 5-HT transporter in rat.	2008-05	18445233
Biotransformation of indole derivatives by mycelial cultures.	2008-04-05	18386493
Role of a serotonin precursor in development of gut microvilli.	2008-02	18202184
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.	2008-01-24	18083311
Receptor mediation of exaggerated responses to serotonin-enhancing drugs in serotonin transporter (SERT)-deficient mice.	2007-10	17765930
Antidepressant-like effect of Cordyceps sinensis in the mouse tail suspension test.	2007-09	17827735
Effects of increased endogenous serotonin on the in vivo binding of [11C]DASB to serotonin transporters in conscious monkey brain.	2007-09	17559093
Central serotonergic hypofunction in autism: results of the 5-hydroxy-tryptophan challenge test.	2007-08	17693983
Tyrosine hydroxylase (TH)- and aromatic-L-amino acid decarboxylase (AADC)-immunoreactive neurons of the common marmoset (Callithrix jacchus) brain: an immunohistochemical analysis.	2007-07-03	17653300
Nuclear imaging of neuroendocrine tumours.	2007-03	17382266
Familial paragangliomas.	2006-10-15	20223020
5-Hydroxytryptophan: a clinically-effective serotonin precursor.	1998-08	9727088
Levorotatory form of 5-hydroxytryptophan in Friedreich's ataxia. Results of a double-blind drug-placebo cooperative study.	1995-05	7733839
Double-blind study of 5-hydroxytryptophan versus placebo in the treatment of primary fibromyalgia syndrome.	1990-05-01	2193835
Serotonin precursors in chronic primary headache. A double-blind cross-over study with L-5-hydroxytryptophan vs. placebo.	1985-07-01	3913752
Effect of pyridoxal phosphate deficiency on aromatic L-amino acid decarboxylase activity with L-DOPA and L-5-hydroxytryptophan as substrates in rats.	1982-10	6983619
Plasma accumulation of metabolism of orally administered single dose L-5-hydroxytryptophan in man.	1981-09	6175178
Development of a scleroderma-like illness during therapy with L-5-hydroxytryptophan and carbidopa.	1980-10-02	6997735
Biochemical properties and kinetic parameters of dihydroxyphenylalanine--5-hydroxytryptophan decarboxylase in brain, liver, and adrenals of cat.	1979-07	39668

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:34:57 GMT 2025` Edited by `admin` on `Mon Mar 31 17:34:57 GMT 2025`
Record UNII	C1LJO185Q9
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

HYDROXYTRYPTOPHAN

Preferred Name

English

OXITRIPTAN

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

5-HYDROXY-L-TRYPTOPHAN

Systematic Name

English

L-5-HYDROXYTRYPTOPHAN

Common Name

English

5-HYDROXYTRYPTOPHAN L-FORM

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)