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Erythromycin thiocyanate

(Synonyms: 红霉素硫氰酸盐) 目录号 : GC67842

Erythromycin thiocyanate 是由放线菌产生的大环内酯类抗生素 (Antibiotic),具有广泛的抗菌活性。Erythromycin thiocyanate 通过结合细菌的 50S 核糖体亚基而起作用,并通过阻断转肽和/或易位反应来抑制 RNA 依赖性蛋白 (RNA-dependent protein synthesis) 的合成,而不会影响核酸的合成。Erythromycin thiocyanate 在不同领域的研究中显示出抗肿瘤特性和保护神经的作用。

Erythromycin thiocyanate Chemical Structure

Cas No.:7704-67-8

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产品描述

Erythromycin thiocyanate is a macrolide Antibiotic produced by actinomycete Streptomyces erythreus with a broad spectrum of antimicrobial activity. Erythromycin thiocyanate 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 thiocyanate also exhibits antitumor and neuroprotective effect in different fields of research[3][4].

Erythromycin thiocyanate inhibits growth of P. falciparum with IC50 and IC90 values of 58.2 μM and 104.0 μM, respectively[1].
Erythromycin thiocyanate (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).

Erythromycin thiocyanate (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 thiocyanate (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 thiocyanate (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.

[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 Properties

Cas No. 7704-67-8 SDF Download SDF
别名 红霉素硫氰酸盐
分子式 C38H68N2O13S 分子量 793.02
溶解度 DMSO : 100 mg/mL (126.10 mM; Need ultrasonic) 储存条件 Store at -20°C, away from moisture
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1 mM 1.261 mL 6.305 mL 12.61 mL
5 mM 0.2522 mL 1.261 mL 2.522 mL
10 mM 0.1261 mL 0.6305 mL 1.261 mL
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Research Update

Microbiological bioassay of Erythromycin thiocyanate: optimisation and validation

J Pharm Biomed Anal 1999 Nov;21(2):347-53.PMID:10703990DOI:10.1016/s0731-7085(99)00143-0.

The validation of an analytical method for the quantitative determination of Erythromycin thiocyanate formulated in an antibiotic preparation for veterinary use was carried out. This method is based on the microbiological method described in the European Pharmacopoeia to analyze Erythromycin thiocyanate as a raw material. This Erythromycin thiocyanate preparation is presented as a powder for oral administration after mixing with feed. For that reason, it was planned to validate the method for the quantitative determination of Erythromycin thiocyanate incorporated both in the medicated premix and the mixture with feed. The microbiological method followed a linear model and was not proportional. The number of replicates needed to obtain a valid result was less than four in all cases. The small difference in concentration, expressed in natural logarithm detected by the method, was 0.1.

Chronic toxicity of Erythromycin thiocyanate to Daphnia magna in a flow-through, continuous exposure test system

Bull Environ Contam Toxicol 2011 Dec;87(6):621-5.PMID:21984684DOI:10.1007/s00128-011-0415-8.

Approval of a new animal drug application for AQUAMYCIN 100(®) (Erythromycin thiocyanate; ET) to treat freshwater salmonid species with bacterial kidney disease is being pursued in the US. As part of the approval process, ET's impact on an aquatic environment had to be described in an environmental assessment. The environmental assessment was lacking data to characterize the effect ET would have on a chronically exposed aquatic invertebrate organism. A major step to fulfilling the environmental assessment was completed after conducting a comprehensive study continuously exposing Daphnia magna to ET for 21 days. Results indicated that the no observable effect concentration for ET was 179 μg/L.

Chronic toxicity of diphenhydramine hydrochloride and Erythromycin thiocyanate to daphnia, Daphnia magna, in a continuous exposure test system

Bull Environ Contam Toxicol 2010 Nov;85(5):447-51.PMID:20976439DOI:10.1007/s00128-010-0117-7.

Diphenhydramine hydrochloride (DH; Benadryl™, an over-the-counter antihistamine) and Erythromycin thiocyanate (ET; a commonly used macrolide antibiotic) are pharmaceutical compounds whose chronic toxicity to Daphnia magna had not been characterized. Continuous exposure to DH concentrations about 5 times greater than the maximum reported environmental concentration of 0.023 μg/L for 21 days or to ET concentrations about 40 times the maximum reported environmental concentration of 6 μg/L for 21 days did not significantly impact D. magna survival and production. In this study the no observable effect concentration for DH was 0.12 μg/L and for ET was 248 μg/L.

Procedure to evaluate the stability during processing and storage of a medicated premix and medicated farm feed: Erythromycin thiocyanate

J Agric Food Chem 2001 Aug;49(8):3709-12.PMID:11513652DOI:10.1021/jf010169b.

In this paper, a stability study of a medicated premix and medicated farm feed containing Erythromycin thiocyanate was planned. No drug degradation was detected during the medicated farm feed processing. In the medicated premix stability study, significant drug degradation was detected only at 40 degrees C and 75% relative humidity. Because after 2 years of storage at 25 degrees C and 60% relative humidity no degradation of Erythromycin thiocyanate was detected, this period of time is proposed as the premix shelf life. In the medicated farm feed stability study, drug degradation was detected under accelerated conditions, but it was not detected under long-term storage conditions for 3 months. Therefore, the proposed shelf life of the medicated farm feed is 3 months, as this is time enough to be consumed. The planned stability study-storage conditions, testing frequency, and proposed data evaluation-allowed an easy and reliable evaluation of veterinary medicine stability.

Pharmacokinetics and bioavailability of erythromycin in pigeons (Columba livia)

J Vet Pharmacol Ther 1990 Dec;13(4):356-60.PMID:2287027DOI:10.1111/j.1365-2885.1990.tb00789.x.

Tissue and plasma concentrations were determined after intravenous and oral administration of erythromycin to pigeons to establish the pharmacokinetics and bioavailability of the drug. A short mean half-life of elimination of 0.9 h was found. The relative bioavailability after direct crop administration of Erythromycin thiocyanate or erythromycin ethylsuccinate at a dosage rate of 100 mg/kg was less than 10%. At a drug concentration in drinking water of 1 g/l, erythromycin plasma levels were barely detectable, whilst lung and trachea concentrations reached a maximum of 1.6 micrograms/ml. Even after crop administration of 100-mg/kg Erythromycin thiocyanate, low plasma levels were obtained, whilst lung and trachea concentrations were substantially higher. Prescribed drinking-water regimens seemed unable to yield therapeutic tissue concentrations. Only individual crop administration seemed an appropriate medication method. The use of erythromycin ethylsuccinate did not present any advantage in comparison with Erythromycin thiocyanate.