Aclarubicin

Aclarubicin
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	IV
ATC code	L01DB04 (WHO) ;
Legal status
Legal status	In general: ℞ (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 ;
CompTox Dashboard (EPA)	DTXSID1022554 ;
ECHA InfoCard	100.055.277
Chemical and physical data
Formula	C42H53NO15
Molar mass	811.878 g·mol−1
3D model (JSmol)	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 in China. It was previously approved for use in Europe but was discontinued in 2004 due to being rarely prescribed and unprofitable.

However, it has subsequently been reevaluated^[3] due to possible advantages over other chemotherapeutic drugs in the treatment of certain cancers such as acute myeloid leukemia.^[4]^[5]

Soil bacteria Streptomyces galilaeus can produce aclarubicin.

It can induce histone eviction from chromatin upon intercalation.^[6]^[7]

References

^ CID 451415 from PubChem
^ Jensen PB, Jensen PS, Demant EJ, Friche E, Sørensen BS, Sehested M, 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 Research. 51 (19): 5093–5099. PMID 1655244.
^ Amsen E (27 July 2024). "One man's mission to revive a forgotten, life-saving cancer drug". The Guardian.
^ Wei G, Ni W, Chiao JW, Cai Z, Huang H, Liu D (November 2011). "A meta-analysis of CAG (cytarabine, aclarubicin, G-CSF) regimen for the treatment of 1029 patients with acute myeloid leukemia and myelodysplastic syndrome". Journal of Hematology & Oncology. 4: 46. doi:10.1186/1756-8722-4-46. PMC 3230125. PMID 22082134.
^ Murzyn A, Orzeł J, Obajtek N, Mróz A, Miodowska D, Bojdo P, et al. (July 2024). "Aclarubicin: contemporary insights into its mechanism of action, toxicity, pharmacokinetics, and clinical standing". Cancer Chemotherapy and Pharmacology. 94 (2): 123–139. doi:10.1007/s00280-024-04693-1. PMC 11390774. PMID 38965080.
^ Pang B, Qiao X, Janssen L, Velds A, Groothuis T, Kerkhoven R, et al. (2013). "Drug-induced histone eviction from open chromatin contributes to the chemotherapeutic effects of doxorubicin". Nature Communications. 4: 1908. Bibcode:2013NatCo...4.1908P. doi:10.1038/ncomms2921. PMC 3674280. PMID 23715267.
^ Pang B, de Jong J, Qiao X, Wessels LF, Neefjes J (July 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.

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[pubchem-1] CID 451415 from PubChem

[pmid1655244-2] Jensen PB, Jensen PS, Demant EJ, Friche E, Sørensen BS, Sehested M, 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 Research. 51 (19): 5093–5099. PMID 1655244.

[3] Amsen E (27 July 2024). "One man's mission to revive a forgotten, life-saving cancer drug". The Guardian.

[4] Wei G, Ni W, Chiao JW, Cai Z, Huang H, Liu D (November 2011). "A meta-analysis of CAG (cytarabine, aclarubicin, G-CSF) regimen for the treatment of 1029 patients with acute myeloid leukemia and myelodysplastic syndrome". Journal of Hematology & Oncology. 4: 46. doi:10.1186/1756-8722-4-46. PMC 3230125. PMID 22082134.

[5] Murzyn A, Orzeł J, Obajtek N, Mróz A, Miodowska D, Bojdo P, et al. (July 2024). "Aclarubicin: contemporary insights into its mechanism of action, toxicity, pharmacokinetics, and clinical standing". Cancer Chemotherapy and Pharmacology. 94 (2): 123–139. doi:10.1007/s00280-024-04693-1. PMC 11390774. PMID 38965080.

[Pang-6] Pang B, Qiao X, Janssen L, Velds A, Groothuis T, Kerkhoven R, et al. (2013). "Drug-induced histone eviction from open chromatin contributes to the chemotherapeutic effects of doxorubicin". Nature Communications. 4: 1908. Bibcode:2013NatCo...4.1908P. doi:10.1038/ncomms2921. PMC 3674280. PMID 23715267.

[pang-7] Pang B, de Jong J, Qiao X, Wessels LF, Neefjes J (July 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.

[1]