Oxitriptan

Identification

Summary

Oxitriptan is a naturally occurring amino acid that is used to manage post-hypoxic myoclonus.

Generic Name
Oxitriptan
DrugBank Accession Number
DB02959
Background

5-Hydroxytryptophan (5-HTP), also known as oxitriptan (INN), is a naturally occurring amino acid and metabolic intermediate in the synthesis of serotonin and melatonin. 5-HTP is sold over-the-counter in the United Kingdom, United States and Canada as a dietary supplement for use as an antidepressant, appetite suppressant, and sleep aid, and is also marketed in many European countries for the indication of major depression under trade names like Cincofarm, Levothym, Levotonine, Oxyfan, Telesol, Tript-OH, and Triptum. Several double-blind placebo-controlled clinical trials have demonstrated the effectiveness of 5-HTP in the treatment of depression, though a lack of high quality studies has been noted. More study is needed to determine efficacy in treating depression.

Type
Small Molecule
Groups
Approved, Investigational, Nutraceutical
Structure
Weight
Average: 220.2246
Monoisotopic: 220.08479226
Chemical Formula
C11H12N2O3
Synonyms
  • 5-hydroxy-L-tryptophan
  • 5-hydroxytryptophan L-form
  • L-5 Hydroxytrytophan
  • L-5-HTP
  • L-5-hydroxytryptophan
  • Oxitriptan
  • Oxitriptano
  • Oxitriptanum

Pharmacology

Indication

For use as an antidepressant, appetite suppressant, and sleep aid.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofPost-anoxic myoclonus••••••••••••••••••••••••• •••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

The psychoactive action of 5-HTP is thought to be due to increased serotonin production in central nervous system tissue.

Mechanism of action
TargetActionsOrganism
UTryptophan--tRNA ligase 2Not AvailableDeinococcus radiodurans (strain ATCC 13939 / DSM 20539 / JCM 16871 / LMG 4051 / NBRC 15346 / NCIMB 9279 / R1 / VKM B-1422)
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

5-Hydroxytryptophan is decarboxylated to serotonin (5-hydroxytryptamine or 5-HT) by the enzyme aromatic-L-amino-acid decarboxylase via a vitamin B6 dependent reaction in nervous tissue and in the liver.

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
PathwayCategory
Tryptophan MetabolismMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Oxitriptan is combined with 1,2-Benzodiazepine.
AcenocoumarolThe risk or severity of adverse effects can be increased when Oxitriptan is combined with Acenocoumarol.
AcetazolamideThe risk or severity of CNS depression can be increased when Acetazolamide is combined with Oxitriptan.
AcetophenazineThe risk or severity of CNS depression can be increased when Acetophenazine is combined with Oxitriptan.
AgomelatineThe risk or severity of CNS depression can be increased when Oxitriptan is combined with Agomelatine.
Food Interactions
No interactions found.

Products

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International/Other Brands
Cincofarm / Levothym (Lundbeck) / Quietim (Nativelle) / Tript-OH

Categories

ATC Codes
N06AX01 — Oxitriptan
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as serotonins. These are compounds containing a serotonin moiety, which consists of an indole that bears an aminoethyl a position 2 and a hydroxyl group at position 5.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Tryptamines and derivatives
Direct Parent
Serotonins
Alternative Parents
Indolyl carboxylic acids and derivatives / 3-alkylindoles / L-alpha-amino acids / Hydroxyindoles / 1-hydroxy-2-unsubstituted benzenoids / Aralkylamines / Substituted pyrroles / Heteroaromatic compounds / Amino acids / Monocarboxylic acids and derivatives
show 7 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / 3-alkylindole / Alpha-amino acid / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle
show 22 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
non-proteinogenic L-alpha-amino acid, 5-hydroxytryptophan, hydroxy-L-tryptophan (CHEBI:17780)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
C1LJO185Q9
CAS number
4350-09-8
InChI Key
LDCYZAJDBXYCGN-VIFPVBQESA-N
InChI
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
IUPAC Name
(2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
SMILES
N[C@@H](CC1=CNC2=C1C=C(O)C=C2)C(O)=O

References

Synthesis Reference

British Patent 845,034.

General References
  1. Turner EH, Blackwell AD: 5-Hydroxytryptophan plus SSRIs for interferon-induced depression: synergistic mechanisms for normalizing synaptic serotonin. Med Hypotheses. 2005;65(1):138-44. [Article]
  2. Shaw K, Turner J, Del Mar C: Tryptophan and 5-hydroxytryptophan for depression. Cochrane Database Syst Rev. 2002;(1):CD003198. [Article]
  3. Rahman MK, Nagatsu T, Sakurai T, Hori S, Abe M, Matsuda M: Effect of pyridoxal phosphate deficiency on aromatic L-amino acid decarboxylase activity with L-DOPA and L-5-hydroxytryptophan as substrates in rats. Jpn J Pharmacol. 1982 Oct;32(5):803-11. [Article]
  4. Nakatani Y, Sato-Suzuki I, Tsujino N, Nakasato A, Seki Y, Fumoto M, Arita H: Augmented brain 5-HT crosses the blood-brain barrier through the 5-HT transporter in rat. Eur J Neurosci. 2008 May;27(9):2466-72. doi: 10.1111/j.1460-9568.2008.06201.x. [Article]
  5. Bouchard S, Roberge AG: Biochemical properties and kinetic parameters of dihydroxyphenylalanine--5-hydroxytryptophan decarboxylase in brain, liver, and adrenals of cat. Can J Biochem. 1979 Jul;57(7):1014-8. [Article]
  6. Amamoto T, Sarai K: On the tryptophan-serotonin metabolism in manic-depressive disorders. Changes in plasma 5-HT and 5-HIAA levels and urinary 5-HIAA excretion following oral loading of L-5HTP in patients with depression. Hiroshima J Med Sci. 1976 Sep;25(2-3):135-40. [Article]
  7. Magnussen I, Jensen TS, Rand JH, Van Woert MH: Plasma accumulation of metabolism of orally administered single dose L-5-hydroxytryptophan in man. Acta Pharmacol Toxicol (Copenh). 1981 Sep;49(3):184-9. [Article]
  8. Birdsall TC: 5-Hydroxytryptophan: a clinically-effective serotonin precursor. Altern Med Rev. 1998 Aug;3(4):271-80. [Article]
  9. Sternberg EM, Van Woert MH, Young SN, Magnussen I, Baker H, Gauthier S, Osterland CK: Development of a scleroderma-like illness during therapy with L-5-hydroxytryptophan and carbidopa. N Engl J Med. 1980 Oct 2;303(14):782-7. [Article]
  10. Caruso I, Sarzi Puttini P, Cazzola M, Azzolini V: Double-blind study of 5-hydroxytryptophan versus placebo in the treatment of primary fibromyalgia syndrome. J Int Med Res. 1990 May-Jun;18(3):201-9. [Article]
  11. Trouillas P, Serratrice G, Laplane D, Rascol A, Augustin P, Barroche G, Clanet M, Degos CF, Desnuelle C, Dumas R, et al.: Levorotatory form of 5-hydroxytryptophan in Friedreich's ataxia. Results of a double-blind drug-placebo cooperative study. Arch Neurol. 1995 May;52(5):456-60. [Article]
  12. De Benedittis G, Massei R: Serotonin precursors in chronic primary headache. A double-blind cross-over study with L-5-hydroxytryptophan vs. placebo. J Neurosurg Sci. 1985 Jul-Sep;29(3):239-48. [Article]
Human Metabolome Database
HMDB0000472
KEGG Drug
D07339
KEGG Compound
C00643
PubChem Compound
439280
PubChem Substance
46505826
ChemSpider
388413
BindingDB
50403163
RxNav
94
ChEBI
58266
ChEMBL
CHEMBL350221
ZINC
ZINC000000895330
PDBe Ligand
4PQ
Wikipedia
5-Hydroxytryptophan
PDB Entries
5kpy / 7ofv
MSDS
Download (1.4 MB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
Not AvailableCompletedBasic ScienceIrritable Bowel Syndrome (IBS)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral
CapsuleOral
Granule, for solutionOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)295-297British Patent 845,034.
Predicted Properties
PropertyValueSource
Water Solubility3.63 mg/mLALOGPS
logP-1.6ALOGPS
logP-1.4Chemaxon
logS-1.8ALOGPS
pKa (Strongest Acidic)2.15Chemaxon
pKa (Strongest Basic)9.18Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area99.34 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity58.18 m3·mol-1Chemaxon
Polarizability22.03 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9891
Blood Brain Barrier+0.8916
Caco-2 permeable-0.7442
P-glycoprotein substrateNon-substrate0.5159
P-glycoprotein inhibitor INon-inhibitor0.9971
P-glycoprotein inhibitor IINon-inhibitor0.9838
Renal organic cation transporterNon-inhibitor0.8689
CYP450 2C9 substrateNon-substrate0.8399
CYP450 2D6 substrateNon-substrate0.7445
CYP450 3A4 substrateNon-substrate0.7324
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9072
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9642
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8947
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9519
BiodegradationNot ready biodegradable0.7897
Rat acute toxicity2.9260 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9784
hERG inhibition (predictor II)Non-inhibitor0.9299
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (4 TMS)GC-MSsplash10-0006-0390000000-d4e36a90b7591787e67b
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-0006-1390000000-b0af49def87c0211653c
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-014i-0390000000-8b7f6cc8f51c032dd86d
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-00bd-4920000000-c1f07beecfc6ada179c1
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-0390000000-88191cf8140abf0f3205
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0006-0290000000-a30ea02ff8d4d14ba7a4
GC-MS Spectrum - GC-MSGC-MSsplash10-0006-0390000000-d4e36a90b7591787e67b
GC-MS Spectrum - GC-MSGC-MSsplash10-0006-1390000000-b0af49def87c0211653c
GC-MS Spectrum - GC-MSGC-MSsplash10-014i-0390000000-8b7f6cc8f51c032dd86d
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0790000000-a699ed429ebd1609f995
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03e9-0900000000-bbd302f8ff188f6cf93d
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-053r-0900000000-6cc3ba396b1cfa8db1e6
MS/MS Spectrum - , positiveLC-MS/MSsplash10-053r-2900000000-90a465428eacaced71e2
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fk9-0190000000-e4e04896bfa5dc506015
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-9230000000-78fa4947efeb301ea81d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0kmi-0690000000-a66f0427c00e2a77aa29
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-9510000000-4285d4ab67e9896bc5a8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0bu0-0900000000-c154f464bb7853543a8e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-06dj-1900000000-85517165975f8b0fabf8
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-157.7126671
predicted
DarkChem Lite v0.1.0
[M-H]-153.1871076
predicted
DarkChem Standard v0.1.0
[M-H]-157.7088671
predicted
DarkChem Lite v0.1.0
[M-H]-157.5881671
predicted
DarkChem Lite v0.1.0
[M-H]-147.02977
predicted
DeepCCS 1.0 (2019)
[M+H]+157.9434671
predicted
DarkChem Lite v0.1.0
[M+H]+157.9410671
predicted
DarkChem Lite v0.1.0
[M+H]+157.7341671
predicted
DarkChem Lite v0.1.0
[M+H]+157.5926671
predicted
DarkChem Lite v0.1.0
[M+H]+149.42534
predicted
DeepCCS 1.0 (2019)
[M+Na]+157.3258671
predicted
DarkChem Lite v0.1.0
[M+Na]+155.8550228
predicted
DarkChem Standard v0.1.0
[M+Na]+156.9654671
predicted
DarkChem Lite v0.1.0
[M+Na]+157.0575671
predicted
DarkChem Lite v0.1.0
[M+Na]+155.37772
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Deinococcus radiodurans (strain ATCC 13939 / DSM 20539 / JCM 16871 / LMG 4051 / NBRC 15346 / NCIMB 9279 / R1 / VKM B-1422)
Pharmacological action
Unknown
Curator comments
Tryptophan--tRNA ligase is an active unit within the tryptophanyl-tRNA synthetase.
General Function
Tryptophan-trna ligase activity
Specific Function
Catalyzes the formation of 5'adenyl-Trp and tRNA(Trp) but with 5-fold less activity than TrpRS. Increases the solubility of the nitric oxide synthase oxygenase (nos), as well as its affinity for su...
Gene Name
trpS2
Uniprot ID
Q9RVD6
Uniprot Name
Tryptophan--tRNA ligase 2
Molecular Weight
38179.35 Da
References
  1. Hogue CW, Szabo AG: Characterization of aminoacyl-adenylates in B. subtilis tryptophanyl-tRNA synthetase, by the fluorescence of tryptophan analogs 5-hydroxytryptophan and 7-azatryptophan. Biophys Chem. 1993 Dec;48(2):159-69. doi: 10.1016/0301-4622(93)85007-5. [Article]
  2. Zhang Z, Alfonta L, Tian F, Bursulaya B, Uryu S, King DS, Schultz PG: Selective incorporation of 5-hydroxytryptophan into proteins in mammalian cells. Proc Natl Acad Sci U S A. 2004 Jun 15;101(24):8882-7. doi: 10.1073/pnas.0307029101. Epub 2004 Jun 8. [Article]

Drug created at June 13, 2005 13:24 / Updated at July 18, 2023 22:55