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Aclarubicin

Basic information Safety Supplier Related

Aclarubicin Basic information

Product Name:
Aclarubicin
Synonyms:
  • 1-naphthacenecarboxylicacid,2-ethyl-1,2,3,4,6,11-hexahydro-2,5,7-trihydroxy-6
  • aclacur
  • aclarubicinfreebase
  • antibiotic3082a
  • ACLARUBLCIN
  • ACLARUNBICIN
  • 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]-α-L-lyxo-hexopyranosyl]-3-(dimethylamino)-α-L-lyxo-hexopyranosyl]oxy]-, methyl ester, [1R-(1α,2β,4β)]-
  • Jaclacin
CAS:
57576-44-0
MF:
C42H53NO15
MW:
811.87
EINECS:
260-824-3
Product Categories:
  • Interferes with DNA Synthesis
  • Antibiotics
  • Antibiotics A to
  • Antibiotics A-FAntibiotics
  • Antibiotics by Application
  • Antineoplastic and Immunosuppressive AntibioticsAntibiotics
  • Mechanism of Action
  • Antitumour
  • ProteasomeInhibitors
Mol File:
57576-44-0.mol
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Aclarubicin Chemical Properties

Melting point:
151-153° (dec)
alpha 
D24 -11.5° (c = 1 in methylene chloride)
Boiling point:
756.05°C (rough estimate)
Density 
1.2261 (rough estimate)
refractive index 
1.6220 (estimate)
storage temp. 
2-8°C
pka
6.41±0.70(Predicted)
form 
Yellow powder with orange cast.
color 
Yellow powder
CAS DataBase Reference
57576-44-0(CAS DataBase Reference)
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Safety Information

Hazard Codes 
T
Risk Statements 
25
Safety Statements 
36/37/39-45
RIDADR 
3249
RTECS 
QI9279300
HazardClass 
6.1(a)
PackingGroup 
II
Toxicity
LD50 in mice (mg/kg): 22.6 i.p., 33.7 i.v. (Oki)
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Aclarubicin Usage And Synthesis

Originator

Aclacinon ,Yamanouchi ,Japan ,1981

Uses

Antineoplastic.

Definition

ChEBI: An anthracycline antibiotic that is produced by Streptomyces galilaeus and also has potent antineoplastic activity.

Manufacturing Process

100 ml of this medium was sterilized at 120°C for 15 min in a 500 ml Sakaguchi-shaking flask which was inoculated from an agar slant culture of Streptomyces galilaeus MA144-M1 by platinum loop. Incubation proceeded for 48 hr at 28°C on a reciprocal shaker. 10 L of the previously sterilized medium in a 20 L stainless steel jar fermenter were aseptically inoculated with 200 ml of the above seed cultures. Fermentation was carried out at 28°C for 32 hours with agitation (240 rpm) and aeration (5 L/min). The cultured broth obtained was adjusted to pH 4.5, mixed with an adsorbent siliceous earth material and filtered from the mycelium. The filtrate and cake obtained thereby were extracted separately. The cake was suspended in acetone (3 L/kg wet cake), stirred for 2 hr and filtered, and the cake was further extracted with acetone once again. The extracts thus obtained were evaporated to one-tenth volume in vacuum. The culture filtrate was adjusted to pH 6.8 and extracted twice with one-third volume of ethyl acetate, and the ethyl acetate extracts were concentrated to one-tenth volume in vacuum.
Twenty grams of the resulting oily substances were mixed with 20 grams of silicic acid (Mallinckrodt Chemical Co.), applied to a column 40 cm in length and 4.5 cm in diameter filled with silicic acid, and eluted with a benzeneacetone- methanol mixture. The initial eluate which eluted with a 1:1:0 mixture was discarded and the active fractions eluted with 1:3:0 and 1:3:0.3 mixtures were collected and concentrated to dryness in vacuum. 11.5 g of this crude substance was then dissolved in a small amount of ethyl acetate and applied to the same silicic acid column as above. After discarding the initial eluates by the 1:1 and 2:1 benzene-acetone mixtures, aclacinomycin B fractions were first eluted with the above mixtures of 1:3 and 1:5 ratio, and aclacinomycin A fractions were then eluted with the 1:5:0.5 and 1:5:1 benzene-acetone-methanol mixtures. The eluates were dried over anhydrous sodium sulfate and concentrated to dryness in vacuum. 4.8 g of crude aclacinomycin A and 3.5 g of aclacinomycin B were obtained as yellow powder. 2.0 g of crude aclacinomycin A obtained as above were dissolved in a small amount of chloroform, applied to a column 20 cm in length and 20 cm in diameter filled with 30 g of silicic acid. After eluting off the pigments containing aglycone and aclacinomycin B and other impurities with chloroform and 1.5% methanol-containing chloroform, aclacinomycin A fractions were eluted with 2% methanol-containing chloroform, and concentrated to dryness in vacuum. 53 mg of yellow powder of aclacinomycin A was obtained. Its melting point was 129°C to 135°C.

Therapeutic Function

Antitumor, Antibiotic

Safety Profile

Poison by ingestion,intraperitoneal, subcutaneous, and intravenous routes. Anexperimental teratogen. Other experimental reproductiveeffects. Mutation data reported. An eye and subcutaneousirritant. When heated to decomposition it emits toxicfumes of

Enzyme inhibitor

This non-peptidic aclacinomycin antibiotic (FW = 811.88 g/mol; CAS CAS 57576-44-0; Source: strain of Streptomyces galilaeus), also known as aclarubicin, induces DNA strand scission. Target(s): nitric oxide synthase; RNA biosynthesis; DNA polymerase I; RNA polymerase, Escherichia coli; reverse transcriptase, avian myeloblastosis virus; Na+/K+-exchanging ATPase; Ca2+-transporting ATPase; cyclicnucleotide phosphodiesterase; electron transport and oxidative phosphorylation, mitochondrial; DNA helicase; DNA topoisomerase II; 20S proteasome, chymotrypsin-like activity; DNA topoisomerase I; 3'-5' DNA helicase, Plasmodium falciparum.

Aclarubicin Preparation Products And Raw materials

Raw materials

AclarubicinSupplier

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