n-2,10-dion(1:1)

Names

[ Name ]:
n-2,10-dion(1:1)

[Synonym ]:
decane-2,10-dione (1:1)
Erythrocin lactobionate
(2R,3R,4R,5R)-2,3,5,6-Tetrahydroxy-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}hexanoic acid - (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione (1:1) (non-preferred name)
ERYTHROMYCIN LACTOBIONATE USP(CRM STANDARD)
lactobionic acid,compd. with erythromycin
Azithromycin lactobionate
(2R,3R,4R,5R)-2,3,5,6-Tetrahydroxy-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}hexanoic acid - (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione (1:1)
Erythromycin,lactobionate (1:1) (salt)
4-O-b-D-Galactopyranosyl-D-gluconic Acid compd. with Erythromycin (1:1)
Erythomycin lactobionate
lactobionicacid,compd.witherythromycin(1:1)
tradécane-2,10-dione (1:1)
decane-2,10-dione (1:1) (non-preferred name)
Erythromycin,compd. with lactobionic acid (7CI)
acide (2R,3R,4R,5R)-2,3,5,6-tétrahydroxy-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxyméthyl)tétrahydro-2H-pyran-2-yl]oxy}hexanoïque - (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(diméthylamino)-3-hydroxy-6-méthyltétrahydro-2H-pyran-2-yl]oxy}-14-éthyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-méthoxy-4,6-diméthyltétrahydro-2H-pyran-2-yl]oxy}-3,5,7,9,11,13-hexaméthyloxacyclotétradécane-2,10-dione (1:1)
n-2,10-dion(1:1)
erythromycin lactobionate
(2R,3R,4R,5R)-2,3,5,6-Tetrahydroxy-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}hexansäure--(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-3,5,7,9,11,13-hexamethyloxacyclotetradecan-2,10-dion(1:1)

Biological Activity

[Description]:

Erythromycin lactobionate is a macrolide antibiotic produced by actinomycete Streptomyces erythreus with a broad spectrum of antimicrobial activity. Erythromycin lactobionate binds to bacterial 50S ribosomal subunits and inhibits RNA-dependent protein synthesis by blockage of transpeptidation and/or translocation reactions, without affecting synthesis of nucleic acid[1][2]. Erythromycin lactobionate also exhibits antitumor and neuroprotective effect in different fields of research[3][4].

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Infection

Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis

Signaling Pathways >> Anti-infection >> Bacterial

[Target]

Bacterial; RNA-dependent protein synthesis[1]

[In Vitro]

Erythromycin lactobionate inhibits growth of P. falciparum with IC50 and IC90 values of 58.2 μM and 104.0 μM, respectively[1]. Erythromycin lactobionate (10 μM, 100 μM; 24 h, 72 h) shows antioxidant and anti-inflammatory effects and suppresses the accumulation of 4-HNE (p<0.01) and 8-OHdG (p<0.01), reduces Iba-1 (p<0.01) and TNF-α (p<0.01) expression significantly[4]. Cell Viability Assay[4] Cell Line: Embryos primary cortical neuron (from the cerebral cortices of 17-day-old Sprague-Dawley rat) Concentration: 10, 100 μM Incubation Time: 24, 72 hours Result: Improved the viability of cultured neuronal cells in vitro after 3 hours oxygen-glucose deprivation (OGD).

[In Vivo]

Erythromycin lactobionate (gastric intubation; 0.1-50 mg/kg; 30-120 days) decreases tumor growth and prolong the survival time of mice from dose of 5 mg/kg in mice[3]. Erythromycin lactobionate (gastric intubation; 5 mg/kg) protects mice alive even at 120 days after inoculation, but shortens mean survival time in tumor-bearing mice by 4-5 days with dose of 50 mg/kg[3]. Erythromycin lactobionate (i.h.; single injection; 50 mg/kg) has a protective effect on the rat model with cerebral ischemia reperfusion-injury[4]. Animal Model: Female ddY mice (6 week-old) with EAC cells or CDF mice (6 week-old) with P388 cells[3] Dosage: 0.1 mg/kg; 0.5 mg/kg; 10 mg/kg; 30 mg/kg; 50 mg/kg Administration: Gastric intubation; 30-120 days Result: Decreased tumor growth and prolonged the mean survival time of mice from the dose of 5 mg/kg, however, the 50 mg/kg dosage shortened the MST in tumorbearing mice. Animal Model: Male Sprague-Dawley rats (8-week-old, 250-300 g)[4] Dosage: 50 mg/kg Administration: Subcutaneous single injection Result: Reduced infarct volume and edema volume, improved neurological deficit.

[References]

[1]. Gribble MJ, et al. Erythromycin. Med Clin North Am. 1982 Jan;66(1):79-89.

[2]. Nakornchai S, et al. Activity of azithromycin or erythromycin in combination with antimalarial drugs against multidrug-resistant Plasmodium falciparum in vitro. Acta Trop. 2006 Dec;100(3):185-91. Epub 2006 Nov 28.

[3]. Hamada K, et al. Antitumor effect of erythromycin in mice. Chemotherapy. 1995 Jan-Feb. 41(1):59-69.

[4]. Katayama Y, et al. Neuroprotective effects of erythromycin on cerebral ischemia reperfusion-injury and cell viability after oxygen-glucose deprivation in cultured neuronal cells. Brain Res. 2014 Nov 7. 1588:159-67.

Chemical & Physical Properties

[ Density]:
0.9083 (rough estimate)

[ Boiling Point ]:
818.4ºC at 760mmHg

[ Melting Point ]:
145-150°

[ Molecular Formula ]:
C₄₉H₈₉NO₂₅

[ Molecular Weight ]:
1092.223

[ Flash Point ]:
448.8ºC

[ Exact Mass ]:
1091.572388

[ PSA ]:
411.51000

[ Index of Refraction ]:
1.5300 (estimate)

[ Storage condition ]:
20°C

[ Water Solubility ]:
Soluble in water, freely soluble in anhydrous ethanol and in methanol, very slightly soluble in acetone and in methylene chloride.

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: OD7320000

CAS REGISTRY NUMBER :: 3847-29-8

LAST UPDATED :: 199712

DATA ITEMS CITED :: 7

MOLECULAR FORMULA :: C37-H67-N-O13.C12-H22-O12

MOLECULAR WEIGHT :: 1092.39

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 61 mg/kg/1D-I

TOXIC EFFECTS :: Sense Organs and Special Senses (Ear) - tinnitus Sense Organs and Special Senses (Ear) - changes in vestibular functions

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 60 mg/kg/1D-I

TOXIC EFFECTS :: Cardiac - EKG changes not diagnostic of specified effects Cardiac - pulse rate increase, without fall in BP

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 240 mg/kg/4D-I

TOXIC EFFECTS :: Sense Organs and Special Senses (Ear) - change in acuity

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 735 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 50 gm/kg/6W-I

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

MUTATION DATA

TYPE OF TEST :: Gene conversion and mitotic recombination

TEST SYSTEM :: Yeast - Saccharomyces cerevisiae

DOSE/DURATION :: 1 gm/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 12,357,1971 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3884 No. of Facilities: 98 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 3317 (estimated) No. of Female Employees: 1523 (estimated)

n-2,10-dion(1:1)

Names

Biological Activity

Chemical & Physical Properties

Toxicological Information

CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

Safety Information

Synthetic Route

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Precursor & DownStream

Precursor

DownStream

Related Compounds