Aclarubicin

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Aclarubicin
Aclarubicin.svg
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration
IV
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • (1S,2S,4R)-Methyl 4-(((2S,5R,6R)-4-(dimethylamino)-5-(((1S,3R,4S)-3-hydroxy-5-methyl-4-(((2S,6R)-6-methyl-5-oxotetrahydro-2H-pyran-2-yl)oxy)cyclohexyl)oxy)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.055.277 Edit this at Wikidata
Chemical and physical data
FormulaC42H53NO15
Molar mass811.878 g·mol−1
3D model (JSmol)
Melting point151 to 153 °C (304 to 307 °F) (decomposes)
  • CCC1(CC(C2=C(C1C(=O)OC)C=C3C(=C2O)C(=O)C4=C(C3=O)C=CC=C4O)OC5CC(C(C(O5)C)OC6CC(C(C(O6)C)OC7CCC(=O)C(O7)C)O)N(C)C)O
  • InChI=1S/C42H53NO15/c1-8-42(51)17-28(33-22(35(42)41(50)52-7)14-23-34(38(33)49)37(48)32-21(36(23)47)10-9-11-26(32)45)56-30-15-24(43(5)6)39(19(3)54-30)58-31-16-27(46)40(20(4)55-31)57-29-13-12-25(44)18(2)53-29/h9-11,14,18-20,24,27-31,35,39-40,45-46,49,51H,8,12-13,15-17H2,1-7H3 checkY
  • Key:USZYSDMBJDPRIF-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Aclarubicin (INN) or aclacinomycin A[1] is an anthracycline drug[2] that is used in the treatment of cancer. Soil bacteria Streptomyces galilaeus can produce aclarubicin. It can induce histone eviction from chromatin upon intercalation.[3][4]

References

  1. ^ CID 451415 from PubChem
  2. ^ Jensen PB, Jensen PS, Demant EJ, et al. (October 1991). "Antagonistic effect of aclarubicin on daunorubicin-induced cytotoxicity in human small cell lung cancer cells: relationship to DNA integrity and topoisomerase II". Cancer Res. 51 (19): 5093–9. PMID 1655244.
  3. ^ Pang B, Qiao X, Janssen L, Velds A, Groothuis T, Kerkhoven R, Nieuwland M, Ovaa H, Rottenberg S, van Tellingen O, Janssen J, Huijgens P, Zwart W, Neefjes J (2013). "Drug-induced histone eviction from open chromatin contributes to the chemotherapeutic effects of doxorubicin". Nature Communications. 4: 1908. doi:10.1038/ncomms2921. PMC 3674280. PMID 23715267.
  4. ^ Pang B, de Jong J, Qiao X, Wessels LF, Neefjes J (2015). "Chemical profiling of the genome with anti-cancer drugs defines target specificities". Nature Chemical Biology. 11 (7): 472–480. doi:10.1038/nchembio.1811. PMID 25961671.