Aclarubicin

Aclarubicin

Systematic (IUPAC) name
(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
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	IV
Legal status	℞ (Prescription only)
Identifiers
CAS Number	57576-44-0
ATC code	L01DB04 (WHO)
PubChem	CID 42474
ChemSpider	1931
UNII	74KXF8I502
KEGG	D02756
ChEBI	CHEBI:74619
ChEMBL	CHEMBL502620
Chemical data
Formula	C42H53NO15
Molar mass	811.86 g/mol
SMILES 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 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 Key:USZYSDMBJDPRIF-UHFFFAOYSA-N
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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. 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. doi:10.1038/nchembio.1811. PMID 25961671.