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643-22-1

643-22-1 structure
643-22-1 structure
  • Name: Erythromycin stearate
  • Chemical Name: Erythromycin Stearate
  • CAS Number: 643-22-1
  • Molecular Formula: C55H103NO15
  • Molecular Weight: 1004.377
  • Catalog: API Antibiotics Macrolide drug
  • Create Date: 2018-05-26 08:00:00
  • Modify Date: 2024-01-08 10:49:47
  • Erythromycin stearate is a macrolide antibiotic produced by actinomycete Streptomyces erythreus with a broad spectrum of antimicrobial activity. Erythromycin stearate 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 stearate also exhibits antitumor and neuroprotective effect in different fields of research[3][4].
Name Erythromycin Stearate
Synonyms EINECS 211-396-1
MFCD00084690
Heptadecanoic 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 stearate
Description Erythromycin stearate is a macrolide antibiotic produced by actinomycete Streptomyces erythreus with a broad spectrum of antimicrobial activity. Erythromycin stearate 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 stearate also exhibits antitumor and neuroprotective effect in different fields of research[3][4].
Related Catalog
Target

Bacterial; RNA-dependent protein synthesis[1]

In Vitro Erythromycin stearate inhibits growth of P. falciparum with IC50 and IC90 values of 58.2 μM and 104.0 μM, respectively[1]. Erythromycin stearate (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 stearate (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 stearate (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 stearate (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]. K Hamada, et al. Antitumor Effect of Erythromycin in Mice. Chemotherapy

[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.

Density 1.112g/cm3
Melting Point 77-79ºC
Molecular Formula C55H103NO15
Molecular Weight 1004.377
Flash Point 523.101ºC
Exact Mass 1003.717102
PSA 231.21000
LogP 8.11810
Index of Refraction 1.518
Storage condition 2-8°C
Stability Stable. Combustible. Incompatible with acids, strong oxidizing agents.
Water Solubility ethanol: soluble50mg/mL, clear to very slightly hazy, colorless

CHEMICAL IDENTIFICATION

RTECS NUMBER :
KF5785000
CHEMICAL NAME :
Erythromycin, stearate (salt)
CAS REGISTRY NUMBER :
643-22-1
LAST UPDATED :
199612
DATA ITEMS CITED :
9
MOLECULAR FORMULA :
C37-H67-N-O13.C18-H36-O2
MOLECULAR WEIGHT :
1018.59
WISWESSER LINE NOTATION :
T-14-VO GVTJ C2 DQ D EQ F H JQ J L N KO- BT6OTJ CQ DN1&1 F& MO- FT6OTJ B CQ DO1 D &622

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
60 mg/kg
TOXIC EFFECTS :
Gastrointestinal - changes in structure or function of endocrine pancreas Gastrointestinal - nausea or vomiting Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - other Enzymes
REFERENCE :
JTCTDW Journal of Toxicology, Clinical Toxicology. (Marcel Dekker, 270 Madison Ave., New York, NY 10016) V.19- 1982- Volume(issue)/page/year: 34,93,1996
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
3112 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,211,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>2500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,211,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
413 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,211,1990 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
13037 mg/kg/14D-C
TOXIC EFFECTS :
Behavioral - food intake (animal) Gastrointestinal - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
NTPTR* National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No.206- Volume(issue)/page/year: NTP-TR-338,1988
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
71 gm/kg/14D-C
TOXIC EFFECTS :
Behavioral - food intake (animal) Gastrointestinal - other changes Related to Chronic Data - death
REFERENCE :
NTPTR* National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No.206- Volume(issue)/page/year: NTP-TR-338,1988 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - M0726 No. of Facilities: 592 (estimated) No. of Industries: 2 No. of Occupations: 2 No. of Employees: 1977 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - M0726 No. of Facilities: 78 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 1108 (estimated) No. of Female Employees: 615 (estimated)
Symbol GHS08
GHS08
Signal Word Danger
Hazard Statements H317-H334
Precautionary Statements P261-P280-P284-P304 + P340-P342 + P311
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Faceshields;Gloves
Hazard Codes Xn:Harmful;
Risk Phrases R42/43
Safety Phrases S36
RIDADR NONH for all modes of transport
WGK Germany 2
RTECS KF5785000
HS Code 2942000000
HS Code 2942000000

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