Sepiapterin

Sepiapterin, also known as 2-amino-6-[(2S)-2-hydroxypropanoyl]-7,8-dihydro-1H-pteridin-4-one, is a member of the pteridine class of organic chemicals.

l-Sepiapterin

Names
IUPAC name 2-amino-6-[(2S)-2-hydroxypropanoyl]-7,8-dihydro-1H-pteridin-4-one
Identifiers
CAS Number	17094-01-8
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1255653
ChemSpider	58746
KEGG	C00835
PubChem CID	65253
UNII	CJQ26KO7HP
InChI InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3,15H,2H2,1H3,(H4,10,11,13,14,17)/t3-/m0/s1 Key: VPVOXUSPXFPWBN-VKHMYHEASA-N InChI=1/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3,15H,2H2,1H3,(H4,10,11,13,14,17)/t3-/m0/s1 Key: VPVOXUSPXFPWBN-VKHMYHEABT
SMILES O=C1\N=C(/NC=2NCC(=N/C1=2)\C(=O)[C@@H](O)C)N
Properties
Chemical formula	C9H11N5O3
Molar mass	237.22 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Sepiapterin can be metabolized into tetrahydrobiopterin via a salvage pathway. Tetrahydrobiopterin is an essential cofactor in humans for breakdown of phenylalanine and a catalyst of the metabolism of phenylalanine, tyrosine, and tryptophan to precursors of the neurotransmitters dopamine and serotonin.

Deficiency of tetrahydrobiopterin can cause toxic buildup of phenylalanine (phenylketonuria) as well as deficiencies of dopamine, norepinephrine, and epinephrine, leading to dystonia and other neurological illnesses. This has led to clinical study of sepiapterin in humans to treat tetrahydrobiopterin deficiency.[1]

Since atherosclerosis and other circulatory diseases associated with diabetes are also associated with tetrahydrobiopterin deficiency, animal studies of the value of sepiaterin in these vascular diseases have been done. These studies show that relaxation of the blood vessels studied was impaired after animals were given sepiapterin, even though their levels of tetrahydrobiopterin were replenished.[2]

See also

• Dihydrobiopterin
• Tetrahydrobiopterin
• Dystonia
• Phenylketonuria
• Salvage pathway

References

1. Smith, Neil; Longo, Nicola; Levert, Keith; Hyland, Keith; Blau, Nenad (1 April 2019). "Phase I clinical evaluation of CNSA-001 (sepiapterin), a novel pharmacological treatment for phenylketonuria and tetrahydrobiopterin deficiencies, in healthy volunteers". Molecular Genetics and Metabolism. 126 (4): 406–412. doi:10.1016/j.ymgme.2019.02.001. ISSN 1096-7192. PMID 30922814.
2. Vasquez-Vivar, Jeannette; Duquiane, Damon; Whitsett, Jennifer; Kalyanaraman, B.; Rajagopalan, Sanjay (1 October 2002). "Altered Tetrahydrobiopterin Metabolism in Atherosclerosis". Arteriosclerosis, Thrombosis, and Vascular Biology. 22 (10): 1655–1661. doi:10.1161/01.ATV.0000029122.79665.D9. PMID 12377745.