Daptomicin

Daptomicin
Klinički podaci
Drugs.com	Monografija
Način primene	Intravenozno
Farmakokinetički podaci
Poluvreme eliminacije	7 dana
Izlučivanje	Renalno
Identifikatori
CAS broj	103060-53-3
ATC kod	J01XX09 (WHO)
PubChem	CID 16129629
DrugBank	DB00080
ChemSpider	10482098
KEGG	C12013
ChEMBL	CHEMBL508162
Hemijski podaci
	InChI InChI=1S/C72H101N17O26/c1-5-6-7-8-9-10-11-22-53(93)81-44(25-38-31-76-42-20-15-13-17-39(38)42)66(108)84-45(27-52(75)92)67(109)86-48(30-59(102)103)68(110)89-61-37(4)115-72(114)49(26-51(91)40-18-12-14-19-41(40)74)87-71(113)60(35(2)24-56(96)97)88-69(111)50(34-90)82-55(95)32-77-63(105)46(28-57(98)99)83-62(104)36(3)79-65(107)47(29-58(100)101)85-64(106)43(21-16-23-73)80-54(94)33-78-70(61)112/h12-15,17-20,31,35-37,43-50,60-61,76,90H,5-11,16,21-30,32-34,73-74H2,1-4H3,(H2,75,92)(H,77,105)(H,78,112)(H,79,107)(H,80,94)(H,81,93)(H,82,95)(H,83,104)(H,84,108)(H,85,106)(H,86,109)(H,87,113)(H,88,111)(H,89,110)(H,96,97)(H,98,99)(H,100,101)(H,102,103)/t35-,36-,37-,43+,44+,45+,46+,47+,48+,49+,50-,60+,61+/m1/s1 ; Key:DOAKLVKFURWEDJ-RWDRXURGSA-N ;

Daptomicinje lipopeptidni antibiotik koji deluje na podložne Gram pozitivne bacterije remećenjem njihovog membranskog potencijala. On se javlja u prirodi u zemljišnim bakterijama vrste Streptomyces roseosporus. Daptomicin je odobren za upotrebu septembera 2003 za lečenje komplikovanih infekcija kože i mekih tkiva. Njegovov bezbednosni prifil je sličan drugim agensima u širokoj upotrebi protiv Gram-pozitivnih infekcija.^[1]^[2]^[3]^[4]^[5]^[6]^[7]

Osobine

Osobina	Vrednost
Broj akceptora vodonika	42
Broj donora vodonika	23
Broj rotacionih veza	35
Particioni koeficijent^[8] (ALogP)	1,7
Rastvorljivost^[9] (logS, log(mol/L))	-15,5
Polarna površina^[10] (PSA, Å²)	748,4

Reference

^ Woodworth JR, Nyhart EH Jr, Brier GL, Wolny JD, Black HR: Single-dose pharmacokinetics and antibacterial activity of daptomycin, a new lipopeptide antibiotic, in healthy volunteers. Antimicrob Agents Chemother. 1992 Feb;36(2):318-25. PMID 1318678
^ Tally FP, DeBruin MF: Development of daptomycin for gram-positive infections. J Antimicrob Chemother. 2000 Oct;46(4):523-6. PMID 11020247
^ Charles PG, Grayson ML: The dearth of new antibiotic development: why we should be worried and what we can do about it. Med J Aust. 2004 Nov 15;181(10):549-53. PMID 15540967
^ Fowler VG Jr, Boucher HW, Corey GR, Abrutyn E, Karchmer AW, Rupp ME, Levine DP, Chambers HF, Tally FP, Vigliani GA, Cabell CH, Link AS, DeMeyer I, Filler SG, Zervos M, Cook P, Parsonnet J, Bernstein JM, Price CS, Forrest GN, Fatkenheuer G, Gareca M, Rehm SJ, Brodt HR, Tice A, Cosgrove SE: Daptomycin versus standard therapy for bacteremia and endocarditis caused by Staphylococcus aureus. N Engl J Med. 2006 Aug 17;355(7):653-65. PMID 16914701
^ Lee SY, Fan HW, Kuti JL, Nicolau DP: Update on daptomycin: the first approved lipopeptide antibiotic. Expert Opin Pharmacother. 2006 Jul;7(10):1381-97. PMID 16805723
^ 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. уреди
^ 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. уреди
^ 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. уреди
^ 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. уреди

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

Daptomycin

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

[1] Woodworth JR, Nyhart EH Jr, Brier GL, Wolny JD, Black HR: Single-dose pharmacokinetics and antibacterial activity of daptomycin, a new lipopeptide antibiotic, in healthy volunteers. Antimicrob Agents Chemother. 1992 Feb;36(2):318-25. PMID 1318678

[2] Tally FP, DeBruin MF: Development of daptomycin for gram-positive infections. J Antimicrob Chemother. 2000 Oct;46(4):523-6. PMID 11020247

[3] Charles PG, Grayson ML: The dearth of new antibiotic development: why we should be worried and what we can do about it. Med J Aust. 2004 Nov 15;181(10):549-53. PMID 15540967

[4] Fowler VG Jr, Boucher HW, Corey GR, Abrutyn E, Karchmer AW, Rupp ME, Levine DP, Chambers HF, Tally FP, Vigliani GA, Cabell CH, Link AS, DeMeyer I, Filler SG, Zervos M, Cook P, Parsonnet J, Bernstein JM, Price CS, Forrest GN, Fatkenheuer G, Gareca M, Rehm SJ, Brodt HR, Tice A, Cosgrove SE: Daptomycin versus standard therapy for bacteremia and endocarditis caused by Staphylococcus aureus. N Engl J Med. 2006 Aug 17;355(7):653-65. PMID 16914701

[5] Lee SY, Fan HW, Kuti JL, Nicolau DP: Update on daptomycin: the first approved lipopeptide antibiotic. Expert Opin Pharmacother. 2006 Jul;7(10):1381-97. PMID 16805723

[6] 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. уреди

[7] 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. уреди

[8] 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.

[9] 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. уреди

[10] 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. уреди

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