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Namespace Prefixes

PrefixIRI
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Statements

Subject Item
n2:DB00360
rdf:type
n5:Drug
n5:description
Tetrahydrobiopterin or BH4 is a cofactor in the synthesis of nitric oxide. It is also essential in the conversion of phenylalanine to tyrosine by the enzyme phenylalanine-4-hydroxylase; the conversion of tyrosine to L-dopa by the enzyme tyrosine hydroxylase; and conversion of tryptophan to 5-hydroxytryptophan via tryptophan hydroxylase. [Wikipedia]
n5:dosage
n27:271B5F84-363D-11E5-9242-09173F13E4C5 n27:271B5F85-363D-11E5-9242-09173F13E4C5
n5:generalReferences
# Thony B, Auerbach G, Blau N: Tetrahydrobiopterin biosynthesis, regeneration and functions. Biochem J. 2000 Apr 1;347 Pt 1:1-16. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/10727395
n5:group
approved investigational
n5:indication
For the treatment of tetrahydrobiopterin (BH4) deficiency.
n5:manufacturer
n22:271B5F82-363D-11E5-9242-09173F13E4C5
owl:sameAs
n8:DB00360 n15:DB00360
dcterms:title
Tetrahydrobiopterin
adms:identifier
n4:1093 n9:DB00360 n10:15372 n11:THB n12:1125 n13:C00272 n14:68135-300-01 n16:46508597 n25:PA161990676 n26:Tetrahydrobiopterin
n5:mechanismOfAction
Tetrahydrobiopterin (BH4) is a natural co-factor or co-enzyme for phenylalanine-4-hydroxylase (PAH),Tetrahydrobiopterine, and tryptophan-5-hydroxylase. Tetrahydrobiopterin is also a natural co-factor for nitrate oxide synthase. Therefore BH4 is required for the conversion of phenylalanine to tyrosine, for the production of epinephrine (adrenaline) and the synthesis of the monoamine neuro-transmitters, serotonin, dopamine, and norepinephrine (noradrenaline). It is also involved in apoptosis and other cellular events mediated by nitric oxide production. As a coenzyme, BH4 reacts with molecular oxygen to form an active oxygen intermediate that can hydroxylate substrates. In the hydroxylation process, the co-enzyme loses two electrons and is regenerated in vivo in an NADH-dependent reaction. As a co-factor for PAH, tetrahydrobiopterin allows the conversion of phenylalanine to tyrosine and reduces the level of phenylalanine in the bloodstream, thereby reducing the toxic effects of of this amino acid. Normal serum concentrations of phenylalanine are 100 micomolar, while elevated (toxic) levels are typically >1200 micromolar. Individuals with a deficiency in tetrahydrobiopterin are not able to efficiently convert phenylalanine to tyrosine. The excess levels provided by tetrahydrobiopterin supplementation help improve enzyme efficiency. As a co-factor for tyrosine hydroxylase, BH4 facilitates the conversion of tyrosine to L-dopa while as a co-factor for tryptophan hydroxylase, BH4 allows the conversion of tryptophan to 5-hydroxytryptophan, which is then converted to serotonin.
n5:packager
n22:271B5F81-363D-11E5-9242-09173F13E4C5 n22:271B5F80-363D-11E5-9242-09173F13E4C5
n5:patent
n17:2545968 n17:7566462 n17:7566714
n5:synonym
sapropterin 5,6,7,8-Tetrahydrobiopterin 5,6,7,8 Tetrahydrobiopterin (6R)-2-Amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydropteridin-4(1H)-one Tetrahydrobiopterin 2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydoro-4(1H)-pteridinone BH4
n5:synthesisReference
Steven S. Gross, "Blocking utilization of tetrahydrobiopterin to block induction of nitric oxide synthesis." U.S. Patent US5502050, issued October, 1984.
n19:hasConcept
n20:M0044450
n5:IUPAC-Name
n6:271B5F8A-363D-11E5-9242-09173F13E4C5
n5:InChI
n6:271B5F90-363D-11E5-9242-09173F13E4C5
n5:Molecular-Formula
n6:271B5F8F-363D-11E5-9242-09173F13E4C5
n5:Molecular-Weight
n6:271B5F8C-363D-11E5-9242-09173F13E4C5
n5:Monoisotopic-Weight
n6:271B5F8D-363D-11E5-9242-09173F13E4C5
n5:SMILES
n6:271B5F8E-363D-11E5-9242-09173F13E4C5
n5:Water-Solubility
n6:271B5F88-363D-11E5-9242-09173F13E4C5 n6:271B5FA0-363D-11E5-9242-09173F13E4C5
n5:logP
n6:271B5F89-363D-11E5-9242-09173F13E4C5 n6:271B5FA2-363D-11E5-9242-09173F13E4C5 n6:271B5F86-363D-11E5-9242-09173F13E4C5
n5:logS
n6:271B5F87-363D-11E5-9242-09173F13E4C5
n23:hasATCCode
n24:A16AX07
n5:H-Bond-Acceptor-Count
n6:271B5F96-363D-11E5-9242-09173F13E4C5
n5:H-Bond-Donor-Count
n6:271B5F97-363D-11E5-9242-09173F13E4C5
n5:InChIKey
n6:271B5F91-363D-11E5-9242-09173F13E4C5
n5:Polar-Surface-Area--PSA-
n6:271B5F92-363D-11E5-9242-09173F13E4C5
n5:Polarizability
n6:271B5F94-363D-11E5-9242-09173F13E4C5
n5:Refractivity
n6:271B5F93-363D-11E5-9242-09173F13E4C5
n5:Rotatable-Bond-Count
n6:271B5F95-363D-11E5-9242-09173F13E4C5
n5:affectedOrganism
Humans and other mammals
n5:casRegistryNumber
17528-72-2
n5:category
n5:containedIn
n18:271B5F83-363D-11E5-9242-09173F13E4C5
n5:Bioavailability
n6:271B5F9C-363D-11E5-9242-09173F13E4C5
n5:Ghose-Filter
n6:271B5F9E-363D-11E5-9242-09173F13E4C5
n5:MDDR-Like-Rule
n6:271B5F9F-363D-11E5-9242-09173F13E4C5
n5:Melting-Point
n6:271B5FA1-363D-11E5-9242-09173F13E4C5
n5:Number-of-Rings
n6:271B5F9B-363D-11E5-9242-09173F13E4C5
n5:Physiological-Charge
n6:271B5F9A-363D-11E5-9242-09173F13E4C5
n5:Rule-of-Five
n6:271B5F9D-363D-11E5-9242-09173F13E4C5
n5:Traditional-IUPAC-Name
n6:271B5F8B-363D-11E5-9242-09173F13E4C5
n5:pKa--strongest-acidic-
n6:271B5F98-363D-11E5-9242-09173F13E4C5
n5:pKa--strongest-basic-
n6:271B5F99-363D-11E5-9242-09173F13E4C5