Aclarubicin

Aclarubicin

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	IV
ATC code	L01DB04 (WHO)
Legal status
Legal status	℞ (Prescription only)
Identifiers
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
CAS Number	57576-44-0
PubChem (CID)	42474
ChemSpider	1931
UNII	74KXF8I502
KEGG	D02756
ChEBI	CHEBI:74619
ChEMBL	CHEMBL502620
Chemical and physical data
Formula	C42H53NO15
Molar mass	811.86 g/mol
3D model (Jmol)	Interactive image
Melting point	151 to 153 °C (304 to 307 °F) (decomposes)
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.