Butokonazol

Butokonazol
IUPAC ime
	1-[4-(4-hlorofenil)-2-(2,6-dihlorofenil)sulfanilbutil]imidazol
Klinički podaci
Prodajno ime	Femstat, Femstat 3, Gynazole-1, Mycelex-3
Drugs.com	Monografija
Način primene	Intravaginalno
Identifikatori
CAS broj	64872-77-1
ATC kod	G01AF15 (WHO)
PubChem	CID 47472
DrugBank	DB00639
ChemSpider	43192
KEGG	C08066
ChEMBL	CHEMBL1295
Hemijski podaci
Formula	C19H17Cl3N2S
Molarna masa	411,776
	SMILES ClC1=CC=C(CCC(CN2C=CN=C2)SC2=C(Cl)C=CC=C2Cl)C=C1; ;
	InChI InChI=1S/C19H17Cl3N2S/c20-15-7-4-14(5-8-15)6-9-16(12-24-11-10-23-13-24)25-19-17(21)2-1-3-18(19)22/h1-5,7-8,10-11,13,16H,6,9,12H2 ; Key:SWLMUYACZKCSHZ-UHFFFAOYSA-N ;
Fizički podaci
Tačka topljenja	159 °C (318 °F)

Butokonazol (prodajni nazivi Gynazole-1, Mycelex-3) je imidazolni antifungalni lek koji se koristi u ginekologij. On se administerira kao vaginalna krema.^[1]^[2]

Sinteza уреди

Sinteza butokonazola:^[3] Keith A. M. Walker U.S. Patent 4.078.071 (1978 to Syntex)

Reakcija epihlorohidrina sa 4-hlorofenilbenzil magnezijum hloridom proizvodi 1-hloro-4-(4-hlorofenil)butan-2-ol (3). Zamena sa natrijum imidazolom, konverzija sekundarnog alkohola do hlorida (SOCl₂), i zamenom sa 2,6-dihlorobenzentiolom završava se sinteza antifungalnog leka butokonazola.

Osobine уреди

Butokonazol je organsko jedinjenje, koje sadrži 19 atoma ugljenika i ima molekulsku masu od 411,776 Da.^[4]^[5]

Osobina	Vrednost
Broj akceptora vodonika	2
Broj donora vodonika	0
Broj rotacionih veza	7
Particioni koeficijent^[6] (ALogP)	6,5
Rastvorljivost^[7] (logS, log(mol/L))	-9,0
Polarna površina^[8] (PSA, Å²)	43,1

Reference уреди

^ Seidman, L. S.; Skokos, C. K. (2005). „An evaluation of butoconazole nitrate 2% site release vaginal cream (Gynazole-1) compared to fluconazole 150 mg tablets (Diflucan) in the time to relief of symptoms in patients with vulvovaginal candidiasis”. Infectious diseases in obstetrics and gynecology. 13 (4): 197—206. PMC 1784583  . PMID 16338779. doi:10.1080/10647440500240615.
^ Butoconazole Монографија
^ Walker, Keith A. M.; Braemer, Allen C.; Hitt, Sharon; Jones, Richard E.; Matthews, Thomas R. (1978). „1-[4-(4-Chlorophenyl)-2-(2,6-dichlorophenylthio)-n-butyl]-1H-imidazole nitrate, a new potent antifungal agent”. Journal of Medicinal Chemistry. 21 (8): 840. PMID 357722. doi:10.1021/jm00206a028.
^ 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 AC, Wishart DS (2011). „DrugBank 3.0: a comprehensive resource for omics research on drugs”. Nucleic Acids Res. 39 (Database issue): D1035—41. PMC 3013709  . PMID 21059682. doi:10.1093/nar/gkq1126.
^ David S. Wishart; Craig Knox; An Chi Guo; Dean Cheng; Savita Shrivastava; Dan Tzur; Bijaya Gautam; Murtaza Hassanali (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, A.K.; Viswanadhan V.N. & Wendoloski, J.J. (1998). „Prediction of Hydrophobic (Lipophilic) Properties of Small Organic Molecules Using Fragment Methods: An Analysis of AlogP and CLogP Methods”. J. Phys. Chem. A. 102: 3762—3772. doi:10.1021/jp980230o.
^ Tetko IV, Tanchuk VY, Kasheva TN, Villa AE (2001). „Estimation of Aqueous Solubility of Chemical Compounds Using E-State Indices”. Chem Inf. Comput. Sci. 41: 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”. J. Med. Chem. 43: 3714—3717. PMID 11020286. doi:10.1021/jm000942e.

Literatura уреди

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 уреди

Butoconazole

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

[1] Seidman, L. S.; Skokos, C. K. (2005). „An evaluation of butoconazole nitrate 2% site release vaginal cream (Gynazole-1) compared to fluconazole 150 mg tablets (Diflucan) in the time to relief of symptoms in patients with vulvovaginal candidiasis”. Infectious diseases in obstetrics and gynecology. 13 (4): 197—206. PMC 1784583  . PMID 16338779. doi:10.1080/10647440500240615.

[2] Butoconazole Монографија

[3] Walker, Keith A. M.; Braemer, Allen C.; Hitt, Sharon; Jones, Richard E.; Matthews, Thomas R. (1978). „1-[4-(4-Chlorophenyl)-2-(2,6-dichlorophenylthio)-n-butyl]-1H-imidazole nitrate, a new potent antifungal agent”. Journal of Medicinal Chemistry. 21 (8): 840. PMID 357722. doi:10.1021/jm00206a028.

[4] 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 AC, Wishart DS (2011). „DrugBank 3.0: a comprehensive resource for omics research on drugs”. Nucleic Acids Res. 39 (Database issue): D1035—41. PMC 3013709  . PMID 21059682. doi:10.1093/nar/gkq1126.

[5] David S. Wishart; Craig Knox; An Chi Guo; Dean Cheng; Savita Shrivastava; Dan Tzur; Bijaya Gautam; Murtaza Hassanali (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.

[6] Ghose, A.K.; Viswanadhan V.N. & Wendoloski, J.J. (1998). „Prediction of Hydrophobic (Lipophilic) Properties of Small Organic Molecules Using Fragment Methods: An Analysis of AlogP and CLogP Methods”. J. Phys. Chem. A. 102: 3762—3772. doi:10.1021/jp980230o.

[7] Tetko IV, Tanchuk VY, Kasheva TN, Villa AE (2001). „Estimation of Aqueous Solubility of Chemical Compounds Using E-State Indices”. Chem Inf. Comput. Sci. 41: 1488—1493. PMID 11749573. doi:10.1021/ci000392t.

[8] 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”. J. Med. Chem. 43: 3714—3717. PMID 11020286. doi:10.1021/jm000942e.

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