Propiltiouracil

Propiltiouracil
(IUPAC) ime
	6-propil-2-sulfanilpirimidin-4-on
Klinički podaci
AHFS/Drugs.com	Monografija
MedlinePlus	a682465
Identifikatori
CAS broj	51-52-5
ATC kod	H03BA02
PubChem	657298
DrugBank	DB00550
ChemSpider	571424
UNII	721M9407IY
KEGG	D00562
ChEBI	CHEBI:8502
ChEMBL	CHEMBL1518
Hemijski podaci
Formula	C7H10N2OS
Mol. masa	170,233 g/mol
SMILES	eMolekuli & PubHem
InChI
	InChI=1S/C7H10N2OS/c1-2-3-5-4-6(10)9-7(11)8-5/h4H,2-3H2,1H3,(H2,8,9,10,11) ; Key: KNAHARQHSZJURB-UHFFFAOYSA-N
Farmakokinetički podaci
Bioraspoloživost	80%-95%
Poluvreme eliminacije	2 sata
Farmakoinformacioni podaci
Trudnoća	?
Pravni status
Način primene	Oralno

Propiltiouracil (PTU, 6-n-propiltiouracil,^[6] PROP) je lek izveden iz tiouracila koji se koristio za tretiranje hipertiroidizma (uključujući Gravesovu bolest). On deluje tako što umanjuje količinu tiroidnog hormona koji proizvodi štitasta žlezda.^[7] Njegove nuspojave obuhvataju rizik od agranulocitoze.

FDA je 2009. objavila upozorenje kojim je informisala zdravstvene radnike o riziku od ozbiljnog oštećenja jetre, uključujući zatajenje jetre i smrt, pri upotrebu propiltiouracila.^[8] Posledica toga je da propiltiouracil nije više preporučen kao lek prvog izbora.^[9]

Hemijska sinteza

Propiltiouracil se može pripremiti iz etil 3-oksoheksanoata i tioureje.^[10]

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
↑ Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.
↑ 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 letter "n" should be a lower case letter, as it describes the nature of the propyl substituent as normal, rather than its position on one of the ring nitrogens. Thereby, the position already is marked by the "6".
↑ Nakamura H, Noh JY, Itoh K, Fukata S, Miyauchi A, Hamada N (June 2007). „Comparison of methimazole and propylthiouracil in patients with hyperthyroidism caused by Graves' disease”. The Journal of Clinical Endocrinology and Metabolism 92 (6): 2157–62. DOI:10.1210/jc.2006-2135. PMID 17389704. Arhivirano iz originala na datum 2020-05-18. Pristupljeno 2013-04-19.
↑ „Propylthiouracil (PTU)-Induced Liver Failure”. FDA. Pristupljeno 3. 5. 2009.
↑ Bahn RS, Burch HS, Cooper DS, et al. (July 2009). „The Role of Propylthiouracil in the Management of Graves' Disease in Adults: report of a meeting jointly sponsored by the American Thyroid Association and the Food and Drug Administration”. Thyroid 19 (7): 673–4. DOI:10.1089/thy.2009.0169. PMID 19583480.
↑ Anderson, George W.; Halverstadt, I. F.; Miller, Wilbur H.; Roblin, Richard O. (1945). „Studies in Chemotherapy. X. Antithyroid Compounds. Synthesis of 5- and 6- Substituted 2-Thiouracils from β-Oxoesters and Thiourea”. Journal of the American Chemical Society 67 (12): 2197. DOI:10.1021/ja01228a042.

Povezano

Spoljašnje veze

„Clinical Pharmacology Online Database”. Arhivirano iz originala na datum 2007-12-16.

[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] Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.

[5] 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

[6] The letter "n" should be a lower case letter, as it describes the nature of the propyl substituent as normal, rather than its position on one of the ring nitrogens. Thereby, the position already is marked by the "6".

[pmid17389704-7] Nakamura H, Noh JY, Itoh K, Fukata S, Miyauchi A, Hamada N (June 2007). „Comparison of methimazole and propylthiouracil in patients with hyperthyroidism caused by Graves' disease”. The Journal of Clinical Endocrinology and Metabolism 92 (6): 2157–62. DOI:10.1210/jc.2006-2135. PMID 17389704. Arhivirano iz originala na datum 2020-05-18. Pristupljeno 2013-04-19.

[8] „Propylthiouracil (PTU)-Induced Liver Failure”. FDA. Pristupljeno 3. 5. 2009.

[FDA_PTU_Guidelines-9] Bahn RS, Burch HS, Cooper DS, et al. (July 2009). „The Role of Propylthiouracil in the Management of Graves' Disease in Adults: report of a meeting jointly sponsored by the American Thyroid Association and the Food and Drug Administration”. Thyroid 19 (7): 673–4. DOI:10.1089/thy.2009.0169. PMID 19583480.

[10] Anderson, George W.; Halverstadt, I. F.; Miller, Wilbur H.; Roblin, Richard O. (1945). „Studies in Chemotherapy. X. Antithyroid Compounds. Synthesis of 5- and 6- Substituted 2-Thiouracils from β-Oxoesters and Thiourea”. Journal of the American Chemical Society 67 (12): 2197. DOI:10.1021/ja01228a042.

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