Bacitracin

Bacitracin
Klinički podaci
Prodajno ime	Baciguent, Baciim, Bacitracin Bacillus licheniformis
Drugs.com	Monografija
Način primene	Topikalno, intramaskularno
Farmakokinetički podaci
Izlučivanje	Renalno
Identifikatori
CAS broj	1405-87-4
ATC kod	D06AX05 (WHO), J01XX10
PubChem	CID 439542
DrugBank	DB00626
ChemSpider	10481985
KEGG	C01667
ChEBI	CHEBI:28669
ChEMBL	CHEMBL1200558
Hemijski podaci
Formula	C66H103N17O16S
Molarna masa	1422,693
	SMILES CC[C@H](C)[C@H](N)C1=N[C@@H](CS1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H]1CCCCNC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](CC(O)=O)NC(=O)[C@H](CC2=CNC=N2)NC(=O)[C@@H](CC2=CC=CC=C2)NC(=O)[C@@H](NC(=O)[C@@H](CCCN)NC1=O)[C@@H](C)CC; ;
	InChI InChI=1S/C66H103N17O16S/c1-9-35(6)52(69)66-81-48(32-100-66)63(97)76-43(26-34(4)5)59(93)74-42(22-23-50(85)86)58(92)83-53(36(7)10-2)64(98)75-40-20-15-16-25-71-55(89)46(29-49(68)84)78-62(96)47(30-51(87)88)79-61(95)45(28-39-31-70-33-72-39)77-60(94)44(27-38-18-13-12-14-19-38)80-65(99)54(37(8)11-3)82-57(91)41(21-17-24-67)73-56(40)90/h12-14,18-19,31,33-37,40-48,52-54H,9-11,15-17,20-30,32,67,69H2,1-8H3,(H2,68,84)(H,70,72)(H,71,89)(H,73,90)(H,74,93)(H,75,98)(H,76,97)(H,77,94)(H,78,96)(H,79,95)(H,80,99)(H,82,91)(H,83,92)(H,85,86)(H,87,88)/t35-,36-,37-,40-,41+,42+,43-,44+,45-,46-,47+,48-,52-,53-,54-/m0/s1 ; Key:CLKOFPXJLQSYAH-ABRJDSQDSA-N ;
Fizički podaci
Tačka topljenja	221—225 °C (430—437 °F)

Bacitracin je organsko jedinjenje, koje sadrži 66 atoma ugljenika i ima molekulsku masu od 1422,693 Da.^[1]^[2]^[3]^[4]

Osobine

Osobina	Vrednost
Broj akceptora vodonika	21
Broj donora vodonika	17
Broj rotacionih veza	31
Particioni koeficijent^[5] (ALogP)	-6,0
Rastvorljivost^[6] (logS, log(mol/L))	-13,0
Polarna površina^[7] (PSA, Å²)	556,2

Reference

^ Tay WM, Epperson JD, da Silva GF, Ming LJ: 1H NMR, mechanism, and mononuclear oxidative activity of the antibiotic metallopeptide bacitracin: the role of D-Glu-4, interaction with pyrophosphate moiety, DNA binding and cleavage, and bioactivity. J Am Chem Soc. 2010 Apr 28;132(16):5652-61. PMID 20359222
^ Karala AR, Ruddock LW: Bacitracin is not a specific inhibitor of protein disulfide isomerase. FEBS J. 2010 Jun;277(11):2454-62. Epub 2010 Apr 30. PMID 20477872
^ 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

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

Bacitracin

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

[1] Tay WM, Epperson JD, da Silva GF, Ming LJ: 1H NMR, mechanism, and mononuclear oxidative activity of the antibiotic metallopeptide bacitracin: the role of D-Glu-4, interaction with pyrophosphate moiety, DNA binding and cleavage, and bioactivity. J Am Chem Soc. 2010 Apr 28;132(16):5652-61. PMID 20359222

[2] Karala AR, Ruddock LW: Bacitracin is not a specific inhibitor of protein disulfide isomerase. FEBS J. 2010 Jun;277(11):2454-62. Epub 2010 Apr 30. PMID 20477872

[3] 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.

[4] 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.

[5] 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.

[6] 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.

[7] 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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