Fenacetin

Fenacetin
Klinički podaci
Prodajno ime	Achrocidin, Codempiral, Commotional, Contradol
Drugs.com	Monografija
Identifikatori
CAS broj	62-44-2
ATC kod	N02BE03 (WHO)
PubChem	CID 4754
DrugBank	DB03783
ChemSpider	4590
KEGG	C07591
ChEBI	CHEBI:8050
ChEMBL	CHEMBL16073
Hemijski podaci
Formula	C10H13NO2
Molarna masa	179,216
	SMILES CCOC1=CC=C(NC(C)=O)C=C1; ;
	InChI InChI=1S/C10H13NO2/c1-3-13-10-6-4-9(5-7-10)11-8(2)12/h4-7H,3H2,1-2H3,(H,11,12) ; Key:CPJSUEIXXCENMM-UHFFFAOYSA-N ;
Fizički podaci
Tačka topljenja	1.375 °C (2.507 °F)

Fenacetin je organsko jedinjenje, koje sadrži 10 atoma ugljenika i ima molekulsku masu od 179,216 Da.^[1]^[2]^[3]^[4]^[5]^[6]

Osobine

Osobina	Vrednost
Broj akceptora vodonika	2
Broj donora vodonika	1
Broj rotacionih veza	3
Particioni koeficijent^[7] (ALogP)	1,3
Rastvorljivost^[8] (logS, log(mol/L))	-2,3
Polarna površina^[9] (PSA, Å²)	38,3

Reference

^ Dubach UC, Rosner B, Sturmer T: An epidemiologic study of abuse of analgesic drugs. Effects of phenacetin and salicylate on mortality and cardiovascular morbidity (1968 to 1987) N Engl J Med. Dubach, U. C.; Rosner, B.; Stürmer, T. (јануар 1991). „An epidemiologic study of abuse of analgesic drugs. Effects of phenacetin and salicylate on mortality and cardiovascular morbidity (1968 to 1987)”. The New England Journal of Medicine. 324 (3): 155—60. PMID 1984193. doi:10.1056/NEJM199101173240304.
^ Cochran AJ, Lawson DH, Linton AL: Renal papillary necrosis following phenacetin excess. Scott Med J. Cochran, A. J.; Lawson, D. H.; Linton, A. L. (јул 1967). „Renal papillary necrosis following phenacetin excess”. Scottish Medical Journal. 12 (7): 246—50. PMID 6036245. doi:10.1177/003693306701200702.
^ TAN GH, RABBINO MD, HOPPER J Jr: IS PHENACETIN A NEPHROTOXIN?A REPORT ON TWENTY-THREE USERS OF THE DRUG. Calif Med. ;101:73-7. TAN GH; RABBINO MD; HOPPER J Jr (1964 Aug). „Is Phenacetin a Nephrotoxin?A Report on Twenty-Three Users of the Drug”. California Medicine. 101 (2): 73—77. PMC 1515485 . PMID 14180501. Проверите вредност парамет(а)ра за датум: |date= (помоћ)
^ Brix AE: Renal papillary necrosis. Toxicol Pathol. ;Brix, A. E. (2002 Nov-Dec). „Renal papillary necrosis”. Toxicologic Pathology. 30 (6): 672—4. PMID 12512867. doi:10.1080/01926230290166760. Проверите вредност парамет(а)ра за датум: |date= (помоћ)
^ Knox, C.; Law, V.; Jewison, T.; Liu, P.; Ly, S.; Frolkis, A.; Pon, A.; Banco, K.; Mak, C.; Neveu, V.; Djoumbou, Y.; Eisner, R.; Guo, A. C.; Wishart, D. S. (2011). „DrugBank 3.0: A comprehensive resource for 'omics' research on drugs”. Nucleic Acids Research. 39 (Database issue): D1035—41. PMC 3013709 . PMID 21059682. doi:10.1093/nar/gkq1126.
^ Wishart, D. S.; Knox, C.; Guo, A. C.; Cheng, D.; Shrivastava, S.; Tzur, D.; Gautam, B.; Hassanali, M. (2008). „DrugBank: A knowledgebase for drugs, drug actions and drug targets”. Nucleic Acids Research. 36 (Database issue): D901—6. PMC 2238889 . PMID 18048412. doi:10.1093/nar/gkm958.
^ Ghose, Arup K.; Viswanadhan, Vellarkad N.; Wendoloski, John J. (1998). „Prediction of Hydrophobic (Lipophilic) Properties of Small Organic Molecules Using Fragmental Methods: An Analysis of ALOGP and CLOGP Methods”. The Journal of Physical Chemistry A. 102 (21): 3762—3772. Bibcode:1998JPCA..102.3762G. doi:10.1021/jp980230o.
^ Tetko, I. V.; Tanchuk, V. Y.; Kasheva, T. N.; Villa, A. E. (2001). „Estimation of aqueous solubility of chemical compounds using E-state indices”. Journal of Chemical Information and Computer Sciences. 41 (6): 1488—1493. PMID 11749573. doi:10.1021/ci000392t.
^ Ertl, P.; Rohde, B.; Selzer, P. (2000). „Fast calculation of molecular polar surface area as a sum of fragment-based contributions and its application to the prediction of drug transport properties”. Journal of Medicinal Chemistry. 43 (20): 3714—3717. PMID 11020286. doi:10.1021/jm000942e.

Literatura

Hardman JG, Limbird LE, Gilman AG (2001). Goodman & Gilman's The Pharmacological Basis of Therapeutics (10. изд.). New York: McGraw-Hill. ISBN 0071354697. doi:10.1036/0071422803.
Thomas L. Lemke; David A. Williams, ур. (2007). Foye's Principles of Medicinal Chemistry (6. изд.). Baltimore: Lippincott Willams & Wilkins. ISBN 0781768799.

Spoljašnje veze

Phenacetin

Molimo Vas, obratite pažnju na važno upozorenje
u vezi sa temama iz oblasti medicine (zdravlja).

[1] Dubach UC, Rosner B, Sturmer T: An epidemiologic study of abuse of analgesic drugs. Effects of phenacetin and salicylate on mortality and cardiovascular morbidity (1968 to 1987) N Engl J Med. Dubach, U. C.; Rosner, B.; Stürmer, T. (јануар 1991). „An epidemiologic study of abuse of analgesic drugs. Effects of phenacetin and salicylate on mortality and cardiovascular morbidity (1968 to 1987)”. The New England Journal of Medicine. 324 (3): 155—60. PMID 1984193. doi:10.1056/NEJM199101173240304.

[2] Cochran AJ, Lawson DH, Linton AL: Renal papillary necrosis following phenacetin excess. Scott Med J. Cochran, A. J.; Lawson, D. H.; Linton, A. L. (јул 1967). „Renal papillary necrosis following phenacetin excess”. Scottish Medical Journal. 12 (7): 246—50. PMID 6036245. doi:10.1177/003693306701200702.

[3] TAN GH, RABBINO MD, HOPPER J Jr: IS PHENACETIN A NEPHROTOXIN?A REPORT ON TWENTY-THREE USERS OF THE DRUG. Calif Med. ;101:73-7. TAN GH; RABBINO MD; HOPPER J Jr (1964 Aug). „Is Phenacetin a Nephrotoxin?A Report on Twenty-Three Users of the Drug”. California Medicine. 101 (2): 73—77. PMC 1515485 . PMID 14180501. Проверите вредност парамет(а)ра за датум: |date= (помоћ)

[4] Brix AE: Renal papillary necrosis. Toxicol Pathol. ;Brix, A. E. (2002 Nov-Dec). „Renal papillary necrosis”. Toxicologic Pathology. 30 (6): 672—4. PMID 12512867. doi:10.1080/01926230290166760. Проверите вредност парамет(а)ра за датум: |date= (помоћ)

[5] Knox, C.; Law, V.; Jewison, T.; Liu, P.; Ly, S.; Frolkis, A.; Pon, A.; Banco, K.; Mak, C.; Neveu, V.; Djoumbou, Y.; Eisner, R.; Guo, A. C.; Wishart, D. S. (2011). „DrugBank 3.0: A comprehensive resource for 'omics' research on drugs”. Nucleic Acids Research. 39 (Database issue): D1035—41. PMC 3013709 . PMID 21059682. doi:10.1093/nar/gkq1126.

[6] Wishart, D. S.; Knox, C.; Guo, A. C.; Cheng, D.; Shrivastava, S.; Tzur, D.; Gautam, B.; Hassanali, M. (2008). „DrugBank: A knowledgebase for drugs, drug actions and drug targets”. Nucleic Acids Research. 36 (Database issue): D901—6. PMC 2238889 . PMID 18048412. doi:10.1093/nar/gkm958.

[7] Ghose, Arup K.; Viswanadhan, Vellarkad N.; Wendoloski, John J. (1998). „Prediction of Hydrophobic (Lipophilic) Properties of Small Organic Molecules Using Fragmental Methods: An Analysis of ALOGP and CLOGP Methods”. The Journal of Physical Chemistry A. 102 (21): 3762—3772. Bibcode:1998JPCA..102.3762G. doi:10.1021/jp980230o.

[8] Tetko, I. V.; Tanchuk, V. Y.; Kasheva, T. N.; Villa, A. E. (2001). „Estimation of aqueous solubility of chemical compounds using E-state indices”. Journal of Chemical Information and Computer Sciences. 41 (6): 1488—1493. PMID 11749573. doi:10.1021/ci000392t.

[9] Ertl, P.; Rohde, B.; Selzer, P. (2000). „Fast calculation of molecular polar surface area as a sum of fragment-based contributions and its application to the prediction of drug transport properties”. Journal of Medicinal Chemistry. 43 (20): 3714—3717. PMID 11020286. doi:10.1021/jm000942e.

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