Sisomicin
(Synonyms: 紫苏霉素) 目录号 : GC44894A broad-spectrum aminoglycoside antibiotic
Cas No.:32385-11-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Sisomicin is a broad-spectrum aminoglycoside antibiotic originally isolated from M. inyoensis. It is active against Gram-positive and Gram-negative bacteria including B. subtilis, S. aureus, E. coli, and P. aeruginosa among others (MICs = 0.01-0.75 µg/ml) but is less active against P. multocida and V. coli (MICs = 7.5 and 2.4 µg/ml, respectively). Sisomicin is protective against Gram-positive and Gram-negative bacterial infections in mice with 50% protective dose (PD50s) values ranging from 0.5 to 6 mg/kg.
| Cas No. | 32385-11-8 | SDF | |
| 别名 | 紫苏霉素 | ||
| Canonical SMILES | N[C@H]1[C@](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@@]3([H])OC[C@](C)(O)[C@H](NC)[C@H]3O)[C@H]2O)([H])OC(CN)=CC1 | ||
| 分子式 | C19H37N5O7 | 分子量 | 447.5 |
| 溶解度 | DMF: 25 mg/ml,DMSO: 30 mg/ml,Ethanol: 25 mg/ml,PBS (pH 7.2): 5 mg/ml | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.2346 mL | 11.1732 mL | 22.3464 mL |
| 5 mM | 0.4469 mL | 2.2346 mL | 4.4693 mL |
| 10 mM | 0.2235 mL | 1.1173 mL | 2.2346 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Sisomicin, netilmicin and dibekacin. A review of their antibacterial activity and therapeutic use
Drugs 1984 Jun;27(6):548-78.PMID:6376062DOI:10.2165/00003495-198427060-00003.
Sisomicin is a naturally occurring aminoglycoside antibiotic produced by Micromonospora inyoensis, while dibekacin and netilmicin are both semisynthetic aminoglycosides. Dibekacin is 3',4'-dideoxykanamycin B and netilmicin is 1-N-ethyl Sisomicin. In both cases, these modifications render the agents insusceptible to some of the enzymes found in resistant strains of bacteria which inactivate the parent compounds. Antibacterial activity: All 3 drugs show bactericidal activity against a wide range of Gram-negative bacteria (including E. coli, Enterobacter, Klebsiella and Proteus spp. and Ps. aeruginosa) and also against staphylococci; however, in common with other amino-glycosides, streptococci are usually resistant (except when beta-lactam antibiotics are used in combination) and anaerobic organisms are not sensitive. Sisomicin is closely related structurally to gentamicin Cla, but in vitro studies have shown it to have superior activity to gentamicin against Ps. aeruginosa, closely paralleling the activity of tobramycin, while still possessing the high activity of gentamicin against Serratia and other Gram-negative rods. However, Sisomicin is inactivated by virtually all bacterial enzymes which inactivate gentamicin and tobramycin. Nevertheless, it retains useful activity against a number of gentamicin-resistant strains of Ps. aeruginosa which are resistant by non-enzymatic (possibly permeability barrier) mechanisms; in this respect it closely resembles tobramycin. Dibekacin closely resembles tobramycin structurally and in vitro it seems to have a very similar antibacterial spectrum, including activity against some strains of Ps. aeruginosa resistant to gentamicin. Netilmicin has a generally broader antibacterial spectrum than gentamicin, tobramycin, Sisomicin or debekacin and is resistant to inactivation by phosphorylating and adenylylating enzymes; however, it is inactivated by all acetylases, apart from acetylase 3-I. Its spectrum is therefore not as wide as that of amikacin against 'gentamicin-resistant' strains. Nonetheless, it is intrinsically more active than amikacin, weight-for-weight, against sensitive strains, apart possibly from Ps. aeruginosa. In fact, its activity against species of the Enterobacteriaceae and staphylococci sensitive to gentamicin is of the same order as the latter and possibly better for Klebsiella-Enterobacter species. All 3 agents show marked antibacterial synergy with a variety of beta-lactam antibiotics against a range of bacteria. Pharmacokinetically, Sisomicin, netilmicin and dibekacin all behave like gentamicin. All 3 drugs are excreted in the urine unchanged and have beta-phase elimination half-lives of around 2 to
Micromonospora-produced Sisomicin components
J Antibiot (Tokyo) 1976 Jul;29(7):677-84.PMID:956052DOI:10.7164/antibiotics.29.677.
A Sisomicin fermentation carried out in the presence of (methyl-14C)-L-methionine resulted in a crude mixture, composed of methyl-14C-labeled Sisomicin as a major component; and two 4''-C-desmethylsisomicin (66-40B and 66-40D) isomer-like components, an unidentified component and a gentamicin A-like antibiotic as minor components. When (methyl-14C)-L-methionine was added in an early stage of the fermentation (24 hours), incorporation of methyl-14C-label into polar components (e.g., gentamicin A-like antibiotic) preceded that into Sisomicin. Chromatographic evidence for the bioconversion of (methyl-14C)-gentamicin A to a radioactive sisomicin-like product (possibly (3''-N-methyl-14C)-sisomicin) was seen, when a Micromonospora blocked mutant was incubated in the presence of the former antibiotic.
Analysis of histamine and Sisomicin in gentamicin: Search for the causative agents of adverse effects
Arch Pharm (Weinheim) 2021 Dec;354(12):e2100260.PMID:34427364DOI:10.1002/ardp.202100260.
In 1998, the aminoglycoside antibiotic gentamicin sulfate caused several cases of deaths in the United States, after the switch from twice- to once-daily application. Endotoxins were discussed as the cause for the adverse effects and Sisomicin was identified as the lead impurity; batches containing Sisomicin were contaminated with more impurities and were responsible for the fatalities. In 2016, anaphylactic reactions in horses, and later in humans with one fatality, were observed after application of gentamicin sulfate contaminated with histamine. To determine whether histamine was responsible for the 1990s death cases as well, histamine was quantified by means of liquid chromatography-tandem mass spectrometry (LC-MS/MS) in 30 samples of gentamicin sulfate analyzed in previous studies. Furthermore, a relative quantification of Sisomicin was performed to check for a correlation between histamine and the lead impurity. A maximum amount of 11.52 ppm histamine was detected, which is below the limit for anaphylactic reactions of 16 ppm, and no correlation of the two impurities was observed. However, the European Medicines Agency recommends a stricter limit with regard to the maximum single dose of gentamicin sulfate to reach a greater gap between the maximum histamine exposition of 4.3 µg and the quantity known to cause hypotension of 7 µg. The low amounts of histamine and the fact that there is no connection with the contamination with Sisomicin showed that histamine was not the cause for the death cases in the United States in 1998, and endotoxins remain the most probable explanation.
Clinical pharmacology of Sisomicin
Antimicrob Agents Chemother 1975 Jan;7(1):38-41.PMID:1137357DOI:10.1128/AAC.7.1.38.
Studies were conducted in 30 patients with neoplastic diseases. Twelve patients received Sisomicin intramuscularly at doses of 20 mg/m(2) and 40 mg/m(2). The mean peak serum concentration occurred at 1 h and was 2.5 mug/ml and 4.0 mug/ml, respectively. Ten patients received intravenous Sisomicin at doses of 30 mg/m(2) during 30-min infusion. Mean peak serum level determined at 30 min was 5.1 mug/ml. The levels gradually decreased and at 6 h was 0.6 mug/ml. The serum half-life was 160 min. Serum levels determined in eight patients who received Sisomicin by continuous infusion at doses of 30 mg/m(2) every 6 h were greater than 1.4 mug/ml during the 6-h period. The urinary excretion of Sisomicin during the 6-h period after intramuscular administration of 20 mg/m(2) and 40 mg/m(2) was 49 and 61%, respectively. The pharmacology of Sisomicin is similar to gentamicin.
Sisomicin: a review of eight years' experience
Rev Infect Dis 1980 Mar-Apr;2(2):182-95.PMID:6994206DOI:10.1093/clinids/2.2.182.
Sisomicin is a new broad-spectrum aminoglycoside most closely related structurally to gentamicin C1a. In vitro and in experimental infections, Sisomicin has been found to be more potent than or nearly as potent as the most active of the other available aminoglycosides. Although susceptible to many (but not all) aminoglycoside-inactivating enzymes, Sisomicin is active against many microorganisms that are resistant to other aminoglycosides by nonenzymatic mechanisms. Sisomicin has been shown to interact synergistically with various beta-lactam antibiotics against enterococci, staphylocicci, Enterobacteriaceae, and nonfermentative gram-negative bacilli. The pharmacokinetics and toxicity of Sisomicin in humans appear to be similar to those of gentamicin, despite earlier reports of greater acute toxicity in animals. Sisomicin has been shown to be effective for treatment of severe infections in humans, including some infections caused by gentamicin-resistant bacteria.