Tetrahidrobiopterin

Tetrahidrobiopterin
(IUPAC) ime
	(6R)-2-Amino-6-[(1R,2S)-1,2-dihidroksipropil]-5,6,7,8-tetrahidropteridin-4(1H)-on
Klinički podaci
Identifikatori
CAS broj	17528-72-2
ATC kod	A16AX07
PubChem	44257
DrugBank	DB00360
ChemSpider	40270
ChEBI	CHEBI:59560
ChEMBL	CHEMBL1201774
Hemijski podaci
Formula	C9H15N5O3
Mol. masa	241,25 g/mol
SMILES	eMolekuli & PubHem
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
Farmakokinetički podaci
Poluvreme eliminacije	4 sata (zdrave odrasle osobe); 6–7 sati (PKU pacijenti)
Farmakoinformacioni podaci
Licenca	US FDA:link
Trudnoća	C(US)
Pravni status	℞-only (SAD)
Način primene	Oralno

Tetrahydrobiopterin (BH₄, THB, Kuvan, sapropterin) je prirodni esencijalni kofaktor tri hidroksilazna enzima aromatičnih aminokiselina. On se koristi u degradaciji aminokiseline fenilalanina, u biosintezi neurotransmitera serotonina (5-hidroksitriptamina, 5-HT), melatonina, dopamina, norepinefrina (noradrenalina), epinefrina (adrenalina), i deluje kao kofaktor u produkciji azotsuboksida (NO) sintazom azot oksida.^[5]

Istorija

Utvrđeno je da tetrahidrobiopterin deluje kao enzimski kofaktor. Prvi enzim za koji je ustanovljeno da koristi tetrahidrobiopterin je fenilalaninska hidroksilaza (PAH).^[6]

Biosinteza

Tetrahydrobiopterin se biosintetiše iz guanozin trifosfata (GTP) putem tri hemijske reakcije posredovane enzimima GTP ciklohidrolaza I (GTPCH), 6-piruvoiltetrahidropterin sinthaza (PTPS), i sepijapterin reduktaza (SR).^[7]

Reference

↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit
↑ 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; Author: Jarosław Całka; Department of Functional Morphology, Division of Animal Anatomy, University of Warmia and Mazury, Olsztyn, Poland; 2005; page 4^{[mrtav link]}
↑ Kaufman, S (1958-01-02). „A New Cofactor Required for the Enzymatic Conversion of Phenylalanine to Tyrosine.”. J. Biol. Chem. 230 (2): 931–939. PMID 13525410. Arhivirano iz originala na datum 2008-10-06. Pristupljeno 2014-04-05.
↑ Thony B, Auerbach G, Blau N (2000). „Tetrahydrobiopterin biosynthesis, regeneration and functions”. Biochem J 347 (1): 1–16. DOI:10.1042/0264-6021:3470001. PMC 1220924. PMID 10727395.

Povezano

Spoljašnje veze

	Portal Medicina
	Portal Hemija

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit

[2] Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.

[3] Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit

[4] Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit

[5] 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; Author: Jarosław Całka; Department of Functional Morphology, Division of Animal Anatomy, University of Warmia and Mazury, Olsztyn, Poland; 2005; page 4^{[mrtav link]}

[6] Kaufman, S (1958-01-02). „A New Cofactor Required for the Enzymatic Conversion of Phenylalanine to Tyrosine.”. J. Biol. Chem. 230 (2): 931–939. PMID 13525410. Arhivirano iz originala na datum 2008-10-06. Pristupljeno 2014-04-05.

[pmid10727395-7] Thony B, Auerbach G, Blau N (2000). „Tetrahydrobiopterin biosynthesis, regeneration and functions”. Biochem J 347 (1): 1–16. DOI:10.1042/0264-6021:3470001. PMC 1220924. PMID 10727395.

[1]

[2]

[3]

[4]

[5]

[6]

[7]