Propiltiouracil

Iz Wikipedije, slobodne enciklopedije
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[1][2] 657298
DrugBank DB00550
ChemSpider[3] 571424
UNII 721M9407IY YesY
KEGG[4] D00562 YesY
ChEBI CHEBI:8502 YesY
ChEMBL[5] CHEMBL1518 YesY
Hemijski podaci
Formula C7H10N2OS 
Mol. masa 170,233 g/mol
SMILES eMolekuli & PubHem
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[uredi - уреди | uredi izvor]

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

Propylthiouracil rxn.png

Reference[uredi - уреди | uredi izvor]

  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. PMID 20970519. doi:10.1016/j.drudis.2010.10.003.  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. PMID 20331846. doi:10.1186/1758-2946-2-3.  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. PMID 21948594. doi:10.1093/nar/gkr777.  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".
  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. PMID 17389704. doi:10.1210/jc.2006-2135. 
  8. "Propylthiouracil (PTU)-Induced Liver Failure". FDA. http://www.fda.gov/Drugs/DrugSafety/PostmarketDrugSafetyInformationforPatientsandProviders/DrugSafetyInformationforHeathcareProfessionals/ucm162701.htm. pristupljeno 3. 5. 2009.. 
  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. PMID 19583480. doi:10.1089/thy.2009.0169. 
  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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