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Statements

Subject Item
n2:DB02959
rdf:type
n3:Drug
n3:description
5-Hydroxytryptophan (5-HTP), also known as oxitriptan (INN), is a naturally occurring amino acid and chemical precursor as well as a metabolic intermediate in the biosynthesis of the neurotransmitters serotonin and melatonin from tryptophan. 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 and larger studies are needed to determine if 5-HTP is truly effective in treating depression.
n3:generalReferences
# 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. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/15893130 # Shaw K, Turner J, Del Mar C: Tryptophan and 5-hydroxytryptophan for depression. Cochrane Database Syst Rev. 2002;(1):CD003198. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/11869656 # 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. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/6983619 # 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. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/18445233 # 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. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/39668 # 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. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/1088369 # 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. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/6175178 # Birdsall TC: 5-Hydroxytryptophan: a clinically-effective serotonin precursor. Altern Med Rev. 1998 Aug;3(4):271-80. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/9727088 # 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. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/6997735 # 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. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/2193835 # 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. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/7733839 # Birdsall TC: 5-Hydroxytryptophan: a clinically-effective serotonin precursor. Altern Med Rev. 1998 Aug;3(4):271-80. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/9727088 # 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. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/3913752
n3:group
approved nutraceutical
n3:indication
For use as an antidepressant, appetite suppressant, and sleep aid.
owl:sameAs
n6:DB02959 n7:DB02959
dcterms:title
Oxitriptan
adms:identifier
n10:17780 n13:D07339 n14:HRP n15:DB02959 n16:C00643 n19:5-Hydroxytryptophan
n3:synonym
5-Hydroxy-L-Tryptophan Levothym Oxitriptan L-5-Hydroxytryptophan 5-Hydroxytryptophan L-form Tript-OH Cincofarm Hydroxy-5 L-tryptophane
n3:synthesisReference
British Patent 845,034.
n17:hasConcept
n18:M0010787
n3:IUPAC-Name
n4:271B41F6-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B41FC-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B41FB-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B41F8-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B41F9-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B41FA-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B41F4-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B41F2-363D-11E5-9242-09173F13E4C5 n4:271B41F5-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B41F3-363D-11E5-9242-09173F13E4C5
n11:hasATCCode
n12:N06AX01
n3:H-Bond-Acceptor-Count
n4:271B4202-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B4203-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B41FD-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B41FE-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B4200-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B41FF-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B4201-363D-11E5-9242-09173F13E4C5
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
4350-09-8
n3:category
n3:Bioavailability
n4:271B4208-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B420A-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B420B-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n4:271B420C-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B4207-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B4206-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B4209-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B41F7-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n4:271B4204-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B4205-363D-11E5-9242-09173F13E4C5