Compound: Sapropterin
SMILES: O=c1nc([nH]c2c1N[C@@H]([C@@H](O)[C@@H](O)C)CN2)N
InChIKey: FNKQXYHWGSIFBK-RPDRRWSUSA-N
Synonyms: Sapropterin, 62989-33-7, R-THBP, Dapropterin, Sapropterina, Sapropterinum, 6R-BH4, (6R)-L-erythro-tetrahydrobiopterin, 6R-5,6,7,8-Tetrahydrobiopterin, 6R-L-5,6,7,8-Tetrahydrobiopterin, sapropterine, EGX657432I, (6R)-L-erythro-5,6,7,8-Tetrahydrobiopterin, (-)-(6R)-2-Amino-6-((1R,2S)-1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(3H)-pteridinone, (6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydropteridin-4(3H)-one, CHEBI:59560, (6R)-2-Amino-6-((1R,2S)-1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(1H)-pteridinone, (6R)-2-Amino-6-((1R,2S)-1,2-dihydroxypropyl)-5,6,7,8-tetrahydropteridin-4(1H)-one, (6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-1H-pteridin-4-one, 4(1H)-Pteridinone, (6R)-2-amino-6-((1R,2S)-1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-, (6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-3,4,5,6,7,8-hexahydropteridin-4-one, (6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydropteridin-4(1H)-one, (6R)-2-amino-6-((1R,2S)-1,2-dihydroxypropyl)-3,4,5,6,7,8-hexahydropteridin-4-one, (6R)-2-amino-6-((1R,2S)-1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-1H-pteridin-4-one, (6R)-2-amino-6-((1R,2S)-1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-3H-pteridin-4-one, (6R)-2-amino-6-((1R,2S)-1,2-dihydroxypropyl)-5,6,7,8-tetrahydropteridin-4(3H)-one, (6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-3H-pteridin-4-one, RefChem:56674, A16AX07, Sapropterin [INN], Sapropterin [MI], Sapropterin [VANDF], Sapropterin (INN), Sapropterin free base, tetrahydro-l-biopterin, L-erythro-tetrahydrobiopterin, BH4, tetra-H-biopterin, tetra-hydro-biopterin, 5,6,7,8-tetra-H-biopterin, (R)-2-amino-6-((1R,2S)-1,2-dihydroxypropyl)-5,6,7,8-tetrahydropteridin-4(1H)-one, Sapropterin [EMA EPAR], Sapropterinum [INN-Latin], Sapropterina [INN-Spanish], Tetrahydrobiopterin [WHO-DD], UNII-EGX657432I, (1R,2S)-(2-Amino-3,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl)-1,2-propandiol, L-erythro-2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(3H)-pteridinon, 5,6,7,8-erythro-tetrahydrobiopterin, (6R)-Tetrahydrobiopterin, GlyTouCan:G94261RF, tetrahydrobiopterin (THB), bmse000911, SAPROPTERIN [WHO-DD], THB, SCHEMBL258544, SCHEMBL260185, GTPL5276, orb1705105, CHEMBL1201774, DTXSID1041138, BCBcMAP01_000204, EX-A2877, G94261RF, HY-A0124, BDBM50373697, EBC-26283, AKOS030231420, DB00360, SMP1_000285, NCGC00485328-01, DA-67406, (6r)-erythro-5,6,7,8-tet-rahydrobiopterin, CS-0014264, NS00010506, C00272, C16118, D08505, EN300-262982, BRD-K36859431-300-02-3, BRD-K36859431-300-03-1, 69081654-1FB6-4B89-B9B9-823C9887EE36, 2-amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(1H)-pteridinone, 2-Amino-6R-(1R,2S-dihydroxypropyl)-5,6,7,8-tetrahydro-4(1H)-pteridinone, 2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydoro-4(1H)-5,6,7,8-Tetrahydro-2-amino-6-(1,2-dihydroxypropyl)-4(1H)-pteridinone, 27070-47-9
Theoretical properties:
molecular_formula: C9H15N5O3
molecular_weight: 241.25 g/mol
exact_mass: 241.11748936 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 6
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 2
heavy_atom_count: 17
topological_polar_surface_area: 132 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 250-255 °C (hydrochloride salt)
solubility: >20 mg/mL (dichloride salt)
Descriptions:
pubchem: Sapropterin is a tetrahydropterin that is 2-amino-5,6,7,8-tetrahydropteridin-4(3H)-one in which a hydrogen at position 6 is substituted by a 1,2-dihydroxypropyl group (6R,1'R,2'S-enantiomer). It has a role as a coenzyme, a cofactor, a diagnostic agent and a human metabolite.
chebi: A tetrahydropterin that is 2-amino-5,6,7,8-tetrahydropteridin-4(3<em>H</em>)-one in which a hydrogen at position 6 is substituted by a 1,2-dihydroxypropyl group (6<i>R</i>,1'<i>R</i>,2'<i>S</i>-enantiomer).
chembl: SAPROPTERIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Tetrahydrobiopterin (BH4, THB), also known as sapropterin (INN), is a cofactor of the three aromatic amino acid hydroxylase enzymes, used in the metabolism of amino acid phenylalanine and in the biosynthesis of the neurotransmitters serotonin (5-hydroxytryptamine, 5-HT), melatonin, dopamine, norepinephrine (noradrenaline), epinephrine (adrenaline), and is a cofactor for the production of nitric oxide (NO) by the nitric oxide synthases. Chemically, its structure is that of a (dihydropteridine reductase) reduced pteridine derivative (quinonoid dihydrobiopterin).
Tetrahydrobiopterin is available as a tablet for oral administration in the form of sapropterin dihydrochloride (BH4*2HCL). It was approved for use in the United States as a tablet in December 2007 and as a powder in December 2013. It was approved for use in the European Union in December 2008, Canada in April 2010, and Japan in July 2008.  It is sold under the brand names Kuvan and Biopten. The typical cost of treating a patient with Kuvan is US$100,000 per year. BioMarin holds the patent for Kuvan until at least 2024, but Par Pharmaceutical has a right to produce a generic version by 2020.