Propiltiouracil

Propiltiouracil
IUPAC ime
	6-propil-2-sulfanilpirimidin-4-on
Klinički podaci
Drugs.com	Monografija
MedlinePlus	a682465
Kategorija trudnoće	D;
Način primene	Oralno
Farmakokinetički podaci
Bioraspoloživost	80%-95%
Poluvreme eliminacije	2 sata
Identifikatori
CAS broj	51-52-5
ATC kod	H03BA02 (WHO)
PubChem	CID 657298
DrugBank	DB00550
ChemSpider	571424
UNII	721M9407IY
KEGG	D00562
ChEBI	CHEBI:8502
ChEMBL	CHEMBL1518
Hemijski podaci
Formula	C7H10N2OS
Molarna masa	170,233 g/mol
	SMILES S=C1N/C(=C\C(=O)N1)CCC; ;
	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 ;

Propiltiouracil (PTU, 6-n-propiltiouracil,^[1] 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.^[2] 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.^[3] Posledica toga je da propiltiouracil nije više preporučen kao lek prvog izbora.^[4]

Hemijska sinteza

Propiltiouracil se može pripremiti iz etil 3-oksoheksanoata i tioureje.^[5]

Reference

^ 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 (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. PMID 17389704. doi:10.1210/jc.2006-2135. Архивирано из оригинала 18. 05. 2020. г. Приступљено 07. 08. 2012.
^ „Propylthiouracil (PTU)-Induced Liver Failure”. FDA. Приступљено 3. 5. 2009.
^ Bahn RS; Burch HS; Cooper DS; et al. (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. PMID 19583480. doi:10.1089/thy.2009.0169.
^ 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.

Vidi još

Spoljašnje veze

„Clinical Pharmacology Online Database”. Архивирано из оригинала 16. 12. 2007. г.

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[1] 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".

[pmid17389704-2] Nakamura H, Noh JY, Itoh K, Fukata S, Miyauchi A, Hamada N (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. PMID 17389704. doi:10.1210/jc.2006-2135. Архивирано из оригинала 18. 05. 2020. г. Приступљено 07. 08. 2012.

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

[FDA_PTU_Guidelines-4] Bahn RS; Burch HS; Cooper DS; et al. (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. PMID 19583480. doi:10.1089/thy.2009.0169.

[5] 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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