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Substance Name: Aclarubicin [USAN:INN:BAN]
RN: 57576-44-0
UNII: 74KXF8I502
InChIKey: USZYSDMBJDPRIF-SVEJIMAYSA-N

Note

  • An anthracycline produced by Streptomyces galilaeus. It has potent antineoplastic activity.

Molecular Formula

  • C42-H53-N-O15

Molecular Weight

  • 811.8727
 

Classification Codes

  • Antibiotics, Antineoplastic
  • Antineoplastic
  • Antineoplastic Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Mutation Data
  • Natural Product
  • Reproductive Effect
  • Skin / Eye Irritant
  • Topoisomerase II Inhibitors
  • Topoisomerase Inhibitors
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Names and Synonyms

Name of Substance

  • Aclacinomycin A
  • Aclarubicin
  • Aclarubicin [USAN:INN:BAN]

MeSH Heading

  • Aclarubicin

Synonyms

  • 1-Naphthacenecarboxylic acid, 2-ethyl-1,2,3,4,6,11-hexahydro-2,5,7-trihydroxy-6,11-dioxo-4-((2,3,6-trideoxy-4-O-(2,6-dideoxy-4-O-((2R-trans)-tetrahydro-6-methyl-5-oxo-2H-pyran-2-yl)-alpha-L-lyxo-hexopyranosyl)-3-(dimethylamino)-alpha-L-lyxo-hexopyranosyl)oxy)-, methyl ester, (1R-(1alpha,2beta,4beta))-
  • Aclacinomycin A
  • Aclacur
  • Aclarubicin
  • Aclarubicine
  • Aclarubicine [INN-French]
  • Aclarubicino
  • Aclarubicino [INN-Spanish]
  • Aclarubicinum
  • Aclarubicinum [INN-Latin]
  • Aclucinomycin A
  • Antibiotic MA 144A
  • Antibiotic MA 144A1
  • CCRIS 2262
  • EINECS 260-824-3
  • MA 144-A1
  • Methyl (1R,2R,4S)-2-ethyl-1,2,3,4,6,11-hexahydro-2,5,7-trihydroxy-6,11-dioxo-4-((2,3,6-trideoxy-4-O-(2,6-dideoxy-4-O-((2R,6S)-tetrahydro-6-methyl-5-oxo-2H-pyran-2-yl)-alpha-L-lyxo-hexopyranosyl)-3-(dimethylamino)-alpha-L-lyxo-hexopyranosyl)oxy)-1-naphthacenecarboxylate
  • NSC 208734
  • NSC-208734
  • UNII-74KXF8I502

Systematic Names

  • 1-Naphthacenecarboxylic acid, 2-ethyl-1,2,3,4,6,11-hexahydro-2,5,7-trihydroxy-6,11-dioxo-4-((2,3,6-trideoxy-4-O-(2,6-dideoxy-4-O-((2R-trans)-tetrahydro-6-methyl-5-oxo-2H-pyran-2-yl)-alpha-L-lyxo-hexopyranosyl)-3-(dimethylamino)-alpha-L-lyxo-hexopyranosyl)oxy)-, methyl ester, (1R-(1alpha,2beta,4beta))-
  • 1-Naphthacenecarboxylic acid,(2-ethyl-1,2,3,4,6,11-hexahydro-2,5,7-trihydroxy-6,11-dioxo-4-((2,3,6-trideoxy-4-O-(2,6-dideoxy-4-O-((2R-trans)-tetrahydro-6-methyl-5-oxo-2H-pyran-2-yl)-alpha-L-lyxo-hexopyranosyl)-3-(dimethylamino)-alpha-L-lyxo-hexopyranosyl)-3-(dimethylamino)-alpha-L-Lyxo-hexopyranosyl)oxy)-, methyl ester, (1R-(1alpha,2beta,4beta))-
  • Aclacinomycin A
  • Aclarubicin

Registry Numbers

CAS Registry Number

  • 57576-44-0

FDA UNII

  • 74KXF8I502

Other Registry Number

  • 72711-48-9

System Generated Number

  • 0057576440

Structure Descriptors

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/t18-,19-,20-,24-,27-,28-,29-,30-,31-,35-,39+,40+,42+/m0/s1

InChIKey

USZYSDMBJDPRIF-SVEJIMAYSA-N

Smiles

CC[C@@]1(O)C[C@H](O[C@H]2C[C@@H]([C@H](O[C@H]3C[C@H](O)[C@H](O[C@H]4CCC(=O)[C@H](C)O4)[C@H](C)O3)[C@H](C)O2)N(C)C)c5c(O)c6C(=O)c7c(O)cccc7C(=O)c6cc5[C@H]1C(=O)OC

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 5mg/kg (5mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: FOOD INTAKE (ANIMAL)
Japanese Journal of Antibiotics. Vol. 33, Pg. 138, 1980.
mammal (species unspecified) LD50 intraperitoneal 25mg/kg (25mg/kg)   Antibiotiki. Vol. 29, Pg. 748, 1984.
mouse LD50 intraperitoneal 16100ug/kg (16.1mg/kg)   Antibiotiki i Meditsinskaya Biotekhnologiya. Antibiotics and Medical Biotechnology. Vol. 30, Pg. 918, 1985.
mouse LD50 intravenous 16500ug/kg (16.5mg/kg)   Antibiotiki i Meditsinskaya Biotekhnologiya. Antibiotics and Medical Biotechnology. Vol. 30, Pg. 918, 1985.
mouse LD50 oral 30100ug/kg (30.1mg/kg)   Antibiotiki i Meditsinskaya Biotekhnologiya. Antibiotics and Medical Biotechnology. Vol. 30, Pg. 918, 1985.
mouse LD50 subcutaneous 22100ug/kg (22.1mg/kg)   Antibiotiki i Meditsinskaya Biotekhnologiya. Antibiotics and Medical Biotechnology. Vol. 30, Pg. 918, 1985.
rat LD50 intraperitoneal 17400ug/kg (17.4mg/kg) BLOOD: CHANGES IN CELL COUNT (UNSPECIFIED)

BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE
Antibiotiki i Meditsinskaya Biotekhnologiya. Antibiotics and Medical Biotechnology. Vol. 32, Pg. 915, 1987.
rat LD50 intravenous 25710ug/kg (25.71mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: FOOD INTAKE (ANIMAL)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Japanese Journal of Antibiotics. Vol. 33, Pg. 138, 1980.
rat LD50 oral 58560ug/kg (58.56mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: FOOD INTAKE (ANIMAL)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Japanese Journal of Antibiotics. Vol. 33, Pg. 138, 1980.
rat LD50 subcutaneous 20mg/kg (20mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: FOOD INTAKE (ANIMAL)
Japanese Journal of Antibiotics. Vol. 33, Pg. 138, 1980.