Daunorubicin

Daunorubicin
(IUPAC) ime
	(8S,10S)-8-acetil-10-[(2S,4S,5S,6S)-; 4-amino-5-hidroksi-6-metil-oksan-; 2-il]oksi-6,8,11-trihidroksi-1-metoksi-; 9,10-dihidro-7H-tetracen-5,12-dion
Klinički podaci
Robne marke	Cerubidin
AHFS/Drugs.com	Monografija
MedlinePlus	a682289
Identifikatori
CAS broj	20830-81-3
ATC kod	L01DB02
PubChem	30323
DrugBank	DB00694
ChemSpider	28163
UNII	ZS7284E0ZP
KEGG	C01907
ChEBI	CHEBI:41977
ChEMBL	CHEMBL178
Hemijski podaci
Formula	C27H29NO10
Mol. masa	527.52 g/mol; 563.99 g/mol (HCl so)
SMILES	eMolekuli & PubHem
InChI
	InChI=1S/C27H29NO10/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3/t10-,14-,16-,17-,22+,27-/m0/s1 ; Key: STQGQHZAVUOBTE-VGBVRHCVSA-N
Farmakokinetički podaci
Metabolizam	Hepatički
Poluvreme eliminacije	26.7 sata (metabolit)
Izlučivanje	putem žuči ili urina
Farmakoinformacioni podaci
Trudnoća	?
Pravni status	℞-only (SAD)
Način primene	Isključiva intravenozno. Uzrokuje jaku nekrozu ako se dozira intramukularno ili supkutano

Daunorubicin ili daunomicin (daunomicin cerubidin) je hemoterapeutik iz famijije antraciklina koji se koristi za tretman pojedinih tipova kancera. On se najčešće koristi za tretiranje specifičnih tipova leukemije (akutna mijelocitna leukemija i akutna limfocitna leukemija). On je inicijalno bio izolovan iz Streptomyces peucetius.^[6]^[7]

Lipozomna formulacija daunorubicina je u prodaji u Sjedinjenim Državama kao DaunoXome.

Način dejstva

Pri vezivanju za DNK, daunomicin se interkalira. Njegov aminski ostatak je usmeren ka manjem žlebu. On ima jaku preferenciju za dva susedna G/C bazna para na čijoj 5' strani je A/T bazni par. Daunomicin se efektivno vezuje za svaka 3 para baza i indukuje ugao odvijanja od 11° i neznatnu distorciju heliksa.^[8]

Reference

↑ 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. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ 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.
↑ 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. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ 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.
↑ 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. DOI:10.1093/nar/gkr777. PMID 21948594. edit
↑ Hardman JG, Limbird LE, Gilman AG. (2001). Goodman & Gilman's The Pharmacological Basis of Therapeutics (10 izd.). New York: McGraw-Hill. DOI:10.1036/0071422803. ISBN 0-07-135469-7.
↑ Pdr Staff (2009). PDR: Physicians Desk Reference 2010 (Physicians' Desk Reference (Pdr)). Rozelle, N.S.W: Thomson Reuters. ISBN 1-56363-748-0.
↑ G J Quigley, A H Wang, G Ughetto, G van der Marel, J H van Boom, and A Rich (December 1980). „Molecular structure of an anticancer drug-DNA complex: daunomycin plus d(CpGpTpApCpG)”. PNAS 77 (12): 7204-7208.

Vanjske veze

Daunomicin Arhivirano 2012-05-15 na Wayback Machine-u
Informacije o leku

[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. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. 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. DOI:10.1186/1758-2946-2-3. PMID 20331846. 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. DOI:10.1093/nar/gkr777. PMID 21948594. edit

[Goodman_Gilman-6] Hardman JG, Limbird LE, Gilman AG. (2001). Goodman & Gilman's The Pharmacological Basis of Therapeutics (10 izd.). New York: McGraw-Hill. DOI:10.1036/0071422803. ISBN 0-07-135469-7.

[PDR-7] Pdr Staff (2009). PDR: Physicians Desk Reference 2010 (Physicians' Desk Reference (Pdr)). Rozelle, N.S.W: Thomson Reuters. ISBN 1-56363-748-0.

[8] G J Quigley, A H Wang, G Ughetto, G van der Marel, J H van Boom, and A Rich (December 1980). „Molecular structure of an anticancer drug-DNA complex: daunomycin plus d(CpGpTpApCpG)”. PNAS 77 (12): 7204-7208.

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