CAS: 55297-95-5; Tiamulin

该化合物是一种属于苯甲胺类的合成抗生素,主要用于兽医治疗牲畜,特别是猪和家禽的细菌感染,它展示了针对各种抗淋病细菌和某些抗淋病细菌的广泛活动,使其对呼吸道和肠道感染有效;提阿穆林通过禁止细菌蛋白合成,具体针对50S 肋骨类子单位;该物质通常通过口服或注射方式施用,其药理和基因学表明动物组织中吸收和分布良好;蒂阿穆林以对动物的毒性低而著称,但必须注意其在生产食物的动物中的使用,因为肉类产品中可能存在残留物;监管机构制定了使用该物质的准则,以确保食品安全;此外,抗亚穆林可以发展,需要谨慎地使用兽医方法来保持其效力;

英文名称Tiamulin
中文名称硫姆林
IUPAC名称(3aS,4R,5S,6S,8R,9S,9aR,10R)-2-[[2-(Diethylamino)ethyl]thio]acetic Acid 6-Ethenyldecahydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-3a,9-propano-3aH-cyclopentacycloocten-8-yl Ester
其它别名(1S,2R,3S,4S,6R,7S,14R)-6-[(2-Diethylaminoethylthio)acetoxy]-3-hydroxy-2,4,7,14-tetramethyl-4-vinyltricyclo[5,4,3,01.8]tetradecan-9-one
CAS编号55297-95-5
MFCD编号:MFCD00864839
EINECS号:259-580-0
分子式:C28H47NO4S
分子量:493.74
产品CID: 2512212
同类组份化合物CAS55297-95-5 (free base)55297-96-6 9 (furmarate)
产品分类分析化学 → 标准品 → 生命科学标准品

相似结构搜索
InChIKey: UURAUHCOJAIIRQ-QGLSALSOSA-N
InChI=1S/C28H47NO4S/c1-8-26(6)17-22(33-23(31)18-34-16-15-29(9-2)10-3)27(7)19(4)11-13-28(20(5)25(26)32)14-12-21(30)24(27)28/h8,19-20,22,24-25…
计算化学: 氢键受体数6.0氢键供体数1.0可旋转键数10.0

物理性质

熔点147.5°C
沸点563.0±50.0 °C(预测)
闪点294.3 °C
密度1.0160 (粗估)
pKa:14.65±0.70(预测)
PSA:92.14
LogP:4.9679
折射率1.6550 (估算)
蒸汽压4.2X10-14 mm Hg at 25 °C (est)
溶解性Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
外观形态无色油状物
储存条件-20°C 冷藏
产品应用该化合物是一种百花素抗生素药物,主要用于兽药,特别是猪和家禽. TIAMULIN是一种二极节抗微生物药物,其胸膜化学结构类似于VALNEMULIN.

MSDS等安全信息

GHS符号GHS07
危险类别特定目标器官毒性 - 单次接触类别3
严重眼刺激类别2
水生慢性毒性类别4
警示词Warning
危险描述H335 |可能引起呼吸道刺激.
H319 |造成严重眼刺激.
H413 |可能对水生生物造成长期有害影响.
防范说明P273-P501
UN编号NONH for all modes of transport
安全声明IDENTIFICATION AND USE: Tiamulin, when administered in the drinking water for five consecutive days, is an effective antibiotic for the treatment of swine dysentery associated with Brachyspira (formerly Serpulina or Treponema) and for treatment of swine pneumonia due to Actinobacillus pleuropneumoniae. As a feed additive, it is used to cause increased weight gain in swine. HUMAN EXPOSURE AND TOXICITY: Topical administration of a 0.05% formulation of tiamulin did not cause skin irritation or sensitization. Another study was carried out in 6 healthy male human volunteers. Three volunteers were given 5 oral doses progressing from 0.125 to 7.2 mg/kg bw with 72 hours between each dose. The remaining volunteers were given a single oral dose in the range of 8.2 to 10.7 mg/kg bw tiamulin. There was no substance-related changes in blood pressure, serum chemistry or electrocardiograms. ANIMAL STUDIES: Overdoses of tiamulin have produced transitory salivation, vomiting and an apparent calming effect on the pig. In a subchronic study, rats were fed diets containing 0.5 or 30 mg tiamulin/kg bw/day for 26 weeks. Further groups of rats received 180 mg/kg bw/day for 10 weeks, followed by 270 mg/kg bw/day for 16 weeks; one group was necropsied at the end of treatment, the remaining rats were maintained on untreated control diets for a further 4 or 8 weeks. There were increases in serum cholesterol and in water intake in the 180 mg/kg bw group. When the dose was increased to 270 mg/kg bw/day, the effects included increased serum alkaline phosphatase, alanine phosphatase, alanine aminotransferase and aspartate aminotransferase. Abdominal distension, dense feces and increased urine specific gravity were also observed. Absolute and relative liver weights were increased in both sexes and fatty infiltration of the liver was observed on histopathological examination. In a chronic study, dogs were given daily oral doses of 0, 3, 10 or 30 mg/kg bw/day of tiamulin for 54 weeks. In the groups given 10 and 30 mg/kg bw/day, occasional emesis was observed, serum potassium concentrations were decreased and electrocardiograms showed prolongation of the QT interval. Serum lactate dehydrogenase (LDH) was significantly increased; there was no increase in the cardiac-related isoenzyme LDH1. Rats were fed diets containing tiamulin at concentrations designed to provide intakes of 0, 2, 8 or 32 mg/kg bw/day of tiamulin for 30 months. There was no significant dose-related trend in the incidence of any tumor type. In another study, mice were fed diets containing the equivalent of 0, 1, 6 or 48 mg/kg bw/day of tiamulin for up to 123 weeks. There was no significant dose-related trend in the incidence of any tumor type. Pregnant female rats were given daily oral doses of 0, 30, 100 or 300 mg/kg bw/day from days 6 to 15 of gestation. At 300 mg/kg bw/day there were minor signs of maternal toxicity. At this dose level, the mean fetal weight was reduced and there was an increased incidence of retarded skeletal development. There was no evidence of teratogenicity. Pregnant female rabbits were given daily oral doses of 0, 30, 55 or 100 mg/kg bw/day from days 6 to 18 of gestation. Doses of 55 mg/kg bw/day and above caused the deaths of some dams and maternal body weight gain was reduced. Litter size and fetal weights were reduced at 55 mg/kg bw/day and above. There was no evidence of teratogenicity at any dose level. Several reproductive studies were performed in pigs. Breeding sows were fed a diet containing 200 mg/kg feed from days 84 to 92 of gestation, another group was maintained on a diet containing 16 mg/kg bw/day from 2 days after mating for 6 weeks, and further groups were given tiamulin in the drinking water at a dose of 8.8 mg/kg bw/day for various periods during gestation and in some cases up to weaning of the offspring. There were no adverse effects on health of the sows, pregnancy, parturition, letter size, growth and survival of the piglets, estrus cycle or subsequent breeding performance. When given to breeding boars, at a diet containing 16 mg/kg bw/day for 14 days, there were no effects on health status, libido or semen quality. Tiamulin did not induce gene mutations in Salmonella typhimurium strains TA98, TA100, TA1535, TA1537 or TA1538. An in vitro assay for gene mutation at the HPRT locus of V79 Chinese hamster cells also gave negative results. In an in vivo micronucleus test in mice tiamulin had no effect on the frequency of micronucleated polychromatic erythrocytes.
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上下游产品

14-Deoxy-14-p-tosyloxyacetoxymutilin 2-(diethylamino)ethanethiol hydr°Chloride(6R,7R)-7-((1R,3S)-1-Methoxy-3-methyl-4-oxo-5-phenylselanyl-3-vinyl-hexyl)-6,7-dimethyl-2,3,4,5,6,7-hexahydro-inden-1-one

合成工艺路线路线简述

截短侧耳素置于氯化亚砜,对甲苯磺酰氯,Sodium Iodide,Sodium Hydroxide体系中,用水,甲苯作为反应溶剂,化学反应 21.5H,反应生成泰妙菌素
参考文献:一种泰妙菌素的制备方法
标题:一种泰妙菌素的制备方法
摘要:本发明公开了一种泰妙菌素的制备方法,合成路线如下:以式1化合物-截短侧耳素为原料,经对甲苯磺酰化,合成出中间体对甲苯磺酸酯后,不需分离,直接与β‑巯基乙醇经亲核取代反应制备出式2中间体-14‑o‑[(1‑羟基丙烷‑2‑基)巯乙酰基]姆体林,所述式2中间体经卤化试剂或磺酰化试剂活化后,形成式3中间体,无需分离,直接与二乙胺反应合成出式4化合物-泰妙菌素.该方法避开使用受监管的2‑二乙氨基乙硫醇,解决了当前制约泰妙菌素产量的主要不利因素,以成本低廉,条件温和,环境友好的,适合于工艺化生产的合成路线制备泰妙菌素.

海关参考信息

2901210000-乙烯
2901220000-丙烯
2905122000-异丙醇
2905399002-1,4-丁二醇
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主要参考文献

1: Liu K, Xia J, Li Y, Li BB, Wang MQ, Zhou Q, Ma ML, He QR, Yang WQ, Liu DF, Wang ZY, Yang LL, Zhang YY. Discovery of Novel Coumarin Pleuromutilin Derivatives as Potent Anti-MRSA Agents. J Med Chem. 2024 Dec 12;67(23):21030-21048. doi: 10.1021/acs.jmedchem.4c01678. Epub 2024 Nov 27.
282:117061. doi: 10.1016/j.ejmech.2024.117061. Epub 2024 Nov 13.
39:170-174. doi: 10.1016/j.jgar.2024.09.004. Epub ahead of print.