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
Structure for Oxitriptan (DB02959)
- Weight
- Average: 220.2246
Monoisotopic: 220.08479226 - Chemical Formula
- C11H12N2O3
- Synonyms
- 5-hydroxy-L-tryptophan
- 5-hydroxytryptophan L-form
- 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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- Contraindications & Blackbox Warnings
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The psychoactive action of 5-HTP is thought to be due to increased serotonin production in central nervous system tissue.
- Mechanism of action
Target Actions Organism UTryptophan--tRNA ligase 2 Not Available Deinococcus 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
Pathway Category Tryptophan Metabolism Metabolic - 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when Oxitriptan is combined with 1,2-Benzodiazepine. Acenocoumarol The risk or severity of adverse effects can be increased when Oxitriptan is combined with Acenocoumarol. Acetazolamide The risk or severity of adverse effects can be increased when Acetazolamide is combined with Oxitriptan. Acetophenazine The risk or severity of adverse effects can be increased when Acetophenazine is combined with Oxitriptan. Agomelatine The risk or severity of adverse effects can be increased when Oxitriptan is combined with Agomelatine. Alfentanil The risk or severity of adverse effects can be increased when Alfentanil is combined with Oxitriptan. Alimemazine The risk or severity of adverse effects can be increased when Alimemazine is combined with Oxitriptan. Almotriptan The risk or severity of adverse effects can be increased when Almotriptan is combined with Oxitriptan. Alosetron The risk or severity of adverse effects can be increased when Alosetron is combined with Oxitriptan. Alprazolam The risk or severity of adverse effects can be increased when Alprazolam is combined with Oxitriptan. 
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- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- 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
- 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]
- Shaw K, Turner J, Del Mar C: Tryptophan and 5-hydroxytryptophan for depression. Cochrane Database Syst Rev. 2002;(1):CD003198. [Article]
- 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]
- 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]
- 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]
- 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]
- 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]
- Birdsall TC: 5-Hydroxytryptophan: a clinically-effective serotonin precursor. Altern Med Rev. 1998 Aug;3(4):271-80. [Article]
- 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]
- 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]
- 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]
- 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]
- External Links
- Human Metabolome Database
- HMDB0000472
- KEGG Drug
- D07339
- KEGG Compound
- C00643
- PubChem Compound
- 439280
- PubChem Substance
- 46505826
- ChemSpider
- 388413
- BindingDB
- 50403163
- 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
Phase Status Purpose Conditions Count Not Available Completed Basic Science Irritable Bowel Syndrome (IBS) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral Capsule Oral Granule, for solution Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 295-297 British Patent 845,034. - Predicted Properties
Property Value Source Water Solubility 3.63 mg/mL ALOGPS logP -1.6 ALOGPS logP -1.4 Chemaxon logS -1.8 ALOGPS pKa (Strongest Acidic) 2.15 Chemaxon pKa (Strongest Basic) 9.18 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 99.34 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 58.18 m3·mol-1 Chemaxon Polarizability 22.03 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9891 Blood Brain Barrier + 0.8916 Caco-2 permeable - 0.7442 P-glycoprotein substrate Non-substrate 0.5159 P-glycoprotein inhibitor I Non-inhibitor 0.9971 P-glycoprotein inhibitor II Non-inhibitor 0.9838 Renal organic cation transporter Non-inhibitor 0.8689 CYP450 2C9 substrate Non-substrate 0.8399 CYP450 2D6 substrate Non-substrate 0.7445 CYP450 3A4 substrate Non-substrate 0.7324 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9072 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.9642 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8947 Ames test Non AMES toxic 0.9133 Carcinogenicity Non-carcinogens 0.9519 Biodegradation Not ready biodegradable 0.7897 Rat acute toxicity 2.9260 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9784 hERG inhibition (predictor II) Non-inhibitor 0.9299
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
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
- 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]
- 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 June 08, 2021 11:32