3847-29-8

• 常用中文名：乳糖酸阿奇霉素
• 常用英文名：n-2,10-dion(1:1)
• CAS号：3847-29-8
• 分子式：C₄₉H₈₉NO₂₅
• 分子量：1092.223
• 相关类别： 原料药 抗生素类药物 大环内酯类药
• 发布时间：2018-07-22 15:45:40
• 更新时间：2024-01-02 13:38:25
• 乳酸红霉素是一种由放线菌红霉素链霉菌产生的大环内酯类抗生素,具有广谱抗菌活性。乳糖酸红霉素结合细菌50S核糖体亚基,通过阻断转肽和/或易位反应抑制RNA依赖性蛋白质合成,而不影响核酸的合成[1][2]。乳糖酸红霉素在不同的研究领域也表现出抗肿瘤和神经保护作用[3][4]。

名称

• 中文名: 乳糖酸红霉素
• 英文名: erythromycin lactobionate (200 mg)
• 中文别名: 糖酸罗红霉素; 红霉素乳糖醛酸
• 英文别名: 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)

物化性质

• 密度: 0.9083 (rough estimate)
• 沸点: 818.4ºC at 760mmHg
• 熔点: 145-150°
• 分子式: C₄₉H₈₉NO₂₅
• 分子量: 1092.223
• 闪点: 448.8ºC
• 精确质量: 1091.572388
• PSA: 411.51000
• 外观性状: 白色至米白色固体
• 折射率: 1.5300 (estimate)
• 储存条件: 20°C
• 水溶解性: Soluble in water, freely soluble in anhydrous ethanol and in methanol, very slightly soluble in acetone and in methylene chloride.

生物活性

• 描述: 乳酸红霉素是一种由放线菌红霉素链霉菌产生的大环内酯类抗生素,具有广谱抗菌活性。乳糖酸红霉素结合细菌50S核糖体亚基,通过阻断转肽和/或易位反应抑制RNA依赖性蛋白质合成,而不影响核酸的合成[1][2]。乳糖酸红霉素在不同的研究领域也表现出抗肿瘤和神经保护作用[3][4]。
• 相关类别:
  研究领域 >> 癌症
  研究领域 >> 感染
  信号通路 >> 细胞周期/DNA损伤 >> DNA/RNA合成
  信号通路 >> 抗感染 >> 细菌
• 靶点:

  Bacterial; RNA-dependent protein synthesis[1]

• 体外研究: 乳糖酸红霉素抑制恶性疟原虫的生长,IC50和IC90值分别为58.2μM和104.0μM[1]。乳糖酸红霉素(10μM,100μM；24小时,72小时)具有抗氧化和抗炎作用,抑制4-HNE(p<0.01)和8-OHdG(p<1.01)的积累,显著降低Iba-1(p<2.01)及TNF-α(p<3.01)表达[4]。细胞存活率测定[4]细胞系：胚胎原代皮质神经元(来自17日龄Sprague-Dawley大鼠的大脑皮质)浓度：10,100μM孵育时间：24,72小时结果：在3小时缺氧-葡萄糖剥夺(OGD)后,提高了体外培养的神经元细胞的存活率。
• 体内研究: 乳糖酸红霉素(胃插管；0.1-50 mg/kg；30-120天)可降低肿瘤生长,并延长小鼠的存活时间,剂量为5 mg/kg[3]。乳糖酸红霉素(胃插管；5 mg/kg)即使在接种后120天也能保护小鼠的存活,但50 mg/kg剂量可将荷瘤小鼠的平均存活时间缩短4-5天[3]。乳糖酸红霉素(i.h.单次注射；50 mg/kg)对大鼠脑缺血再灌注损伤模型具有保护作用[4]。动物模型：具有EAC细胞的雌性ddY小鼠(6周龄)或具有P388细胞的CDF小鼠(6周龄)[3]剂量：0.1mg/kg；0.5mg/kg；10mg/kg；30mg/kg；50mg/kg给药：胃插管；30-120天结果：从5mg/kg剂量开始,降低肿瘤生长并延长小鼠的平均生存时间,然而,50mg/kg剂量缩短了荷瘤小鼠的MST。动物模型：雄性Sprague-Dawley大鼠(8周龄,250-300 g)[4]剂量：50 mg/kg给药：
• 参考文献:

  [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.

毒性和生态

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)

安全

• 危险品运输编码: NONH for all modes of transport

合成路线

114-07-8 96-82-2 ~98% 3847-29-8

文献：Liu, Li Patent: EP2301945 A1, 2011 ; Location in patent: Page/Page column 9-10 ;

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