Tetrahydrobiopterin

Tetrahydrobiopterin
INN: sapropterin
Clinical data
Trade names	Kuvan, Biopten
Other names	Sapropterin hydrochloride (JAN JP), Sapropterin dihydrochloride (USAN US)
AHFS/Drugs.com	Monograph
MedlinePlus	a608020
License data	EU EMA: by INN; US DailyMed: Sapropterin; US FDA: Sapropterin;
Pregnancy; category	AU: B1; ;
Routes of; administration	By mouth
ATC code	A16AX07 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; US: ℞-only; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Elimination half-life	4 hours (healthy adults); 6–7 hours (PKU patients)
Identifiers
	IUPAC name (6R)-2-Amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydropteridin-4(1H)-one;
CAS Number	62989-33-7 ; as salt: 69056-38-8;
PubChem CID	135398654;
IUPHAR/BPS	5276;
DrugBank	DB00360 ; as salt: DBSALT001133;
ChemSpider	40270 ; as salt: 552166;
UNII	EGX657432I;
KEGG	D08505; as salt: D01798;
ChEBI	CHEBI:59560 ; as salt: CHEBI:32120;
ChEMBL	ChEMBL1201774 ; as salt: ChEMBL1201775;
PDB ligand	H4B (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID1041138 ;
ECHA InfoCard	100.164.121
Chemical and physical data
Formula	C9H15N5O3
Molar mass	241.251 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C(C1CNC2=C(N1)C(=O)N=C(N2)N)O)O;
	InChI InChI=1S/C9H15N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,6,12,15-16H,2H2,1H3,(H4,10,11,13,14,17)/t3-,4+,6-/m0/s1 ; Key:FNKQXYHWGSIFBK-RPDRRWSUSA-N ;
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Tetrahydrobiopterin (BH₄, THB), also known as sapropterin (INN),^[5]^[6] is a cofactor of the three aromatic amino acid hydroxylase enzymes,^[7] used in the degradation 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.^[8]^[9] Chemically, its structure is that of a (dihydropteridine reductase) reduced pteridine derivative (quinonoid dihydrobiopterin).^[10]^{[citation needed]}

^ "Sapropterin (Kuvan) Use During Pregnancy". Drugs.com. 17 May 2019. Retrieved 4 March 2020.
^ Cite error: The named reference Kuvan CA Product information was invoked but never defined (see the help page).
^ Cite error: The named reference Kuvan FDA label was invoked but never defined (see the help page).
^ Cite error: The named reference Kuvan EPAR was invoked but never defined (see the help page).
^ "Sapropterin". Drugs.com. 28 February 2020. Retrieved 4 March 2020.
^ "International Non-proprietary Names for Pharmaceutical Substances (INN)". Fimea. Retrieved 4 March 2020.
^ Kappock TJ, Caradonna JP (November 1996). "Pterin-Dependent Amino Acid Hydroxylases". Chemical Reviews. 96 (7): 2659–2756. doi:10.1021/CR9402034. PMID 11848840.
^ Cavaleri et al. Blood concentrations of neopterin and biopterin in subjects with depression: A systematic review and meta-analysis Progress in Neuro-Psychopharmacology and Biological Psychiatry 2023. 120:110633. http://dx.doi.org/10.1016/j.pnpbp.2022.110633
^ Całka J (2006). "The role of nitric oxide in the hypothalamic control of LHRH and oxytocin release, sexual behavior and aging of the LHRH and oxytocin neurons". Folia Histochemica et Cytobiologica. 44 (1): 3–12. PMID 16584085.
^ Bhagavan NV (2015). Essentials of Medical Biochemistry With Clinical Cases, 2nd Edition. USA: Elsevier. p. 256. ISBN 978-0-12-416687-5.