EthambutolCAS# 74-55-5 |
- BMS-303141
Catalog No.:BCC4097
CAS No.:943962-47-8
Quality Control & MSDS
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| Cas No. | 74-55-5 | SDF | Download SDF |
| PubChem ID | 14052 | Appearance | Powder |
| Formula | C10H24N2O2 | M.Wt | 204.31 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Synonyms | Emb | ||
| Solubility | Soluble in DMSO | ||
| Chemical Name | (2S)-2-[2-[[(2S)-1-hydroxybutan-2-yl]amino]ethylamino]butan-1-ol | ||
| SMILES | CCC(CO)NCCNC(CC)CO | ||
| Standard InChIKey | AEUTYOVWOVBAKS-UWVGGRQHSA-N | ||
| Standard InChI | InChI=1S/C10H24N2O2/c1-3-9(7-13)11-5-6-12-10(4-2)8-14/h9-14H,3-8H2,1-2H3/t9-,10-/m0/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Ethambutol is a bacteriostatic antimycobacterial agent, which obstructs the formation of cell wall by inhibiting arabinosyl transferases.
Target: Antibacterial
Ethambutol directly affects two polymers, arabinogalactan (AG) and lipoarabinomannan (LAM) in Mycobacterium smegmatis. In M. smegmatis, Ethambutol inhibits synthesis of arabinan completely and inhibits AG synthesis most likely as a consequence of this; more than 50% of the cell arabinan is released from the bacteria following Ethambutol treatment, whereas no galactan is released. Ethambutol main targets against embB gene product in M. avium. Ethambutol induces 60% changes in the embB gene in M. tuberculosis resistant mutants [1]. Ethambutol is effective against actively growing microorganisms of the genus Mycobacterium, including M. tuberculosis. Nearly all strains of M. tuberculosis and M. kansasii as well as a number of strains of the M. aviumcomplex (MAC) are sensitive to Ethambutol. [1] Ethambutol is potency against M. tuberculosis (H37Rv) with MIC of 0.5 μg/mL in vitro [2]. Ethambutol is efficient on treatment of mycobacterial-infected macrophages. When M. tuberculosis infected macrophages are treated with 6 μg/mL Ethambutol, the log CFUs following treatment for 3 days is 4.17, while value in control group is 4.8. The MICs for M. avium (MTCC 1723) and M. smegmatis (MTCC 6) are 15 μg/mL and 0.18 μg/mL, respectively. Ethambutol is efficient in animal model. 100 mg/kg Ethambutol given orally 15 days post i.v. infection 1 ×/week for 5 weeks, induces a lower log CFU compared with untreatment (4.59 vs 5.07) [3]. References: | |||||
Ethambutol Dilution Calculator
Ethambutol Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 4.8945 mL | 24.4726 mL | 48.9452 mL | 97.8905 mL | 122.3631 mL |
| 5 mM | 0.9789 mL | 4.8945 mL | 9.789 mL | 19.5781 mL | 24.4726 mL |
| 10 mM | 0.4895 mL | 2.4473 mL | 4.8945 mL | 9.789 mL | 12.2363 mL |
| 50 mM | 0.0979 mL | 0.4895 mL | 0.9789 mL | 1.9578 mL | 2.4473 mL |
| 100 mM | 0.0489 mL | 0.2447 mL | 0.4895 mL | 0.9789 mL | 1.2236 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Ethambutol is a bacteriostatic antimycobacterial agent, which obstructs the formation of cell wall by inhibiting arabinosyl transferases.
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The rare ethambutol-induced optic neuropathy: A case-report and literature review.[Pubmed:28079833]
Medicine (Baltimore). 2017 Jan;96(2):e5889.
RATIONALE: Ethambutol-induced optic neuropathy (EON) is a well-known complication that results from the use of Ethambutol. The ocular manifestations of EON include painless loss of central vision and cecocentral scotomas in the visual field. PATIENT CONCERNS: A 75-year-old Chinese Han man suffered from this rare ocular disorder because he took Ethambutol for about 8 months. DIAGNOSES: He was diagnosed as EON based on series of ophthalmic examinations performed. INTERVENTIONS: Since he has stopped taking this drug for 3 months, we just offered some neurotrophic agents to him. OUTCOMES: One month later, he came back for return visit. The ophthalmic examinations indicated recovery of the visual function very well. LESSONS: The EON is a reversible optic neuropathy if the ocular toxicity is monitored closely among the tuberculosis patients that take Ethambutol.
The Antituberculosis Drug Ethambutol Selectively Blocks Apical Growth in CMN Group Bacteria.[Pubmed:28174310]
MBio. 2017 Feb 7;8(1). pii: mBio.02213-16.
Members of the genus Mycobacterium are the most prevalent cause of infectious diseases. Mycobacteria have a complex cell envelope containing a peptidoglycan layer and an additional arabinogalactan polymer to which a mycolic acid bilayer is linked; this complex, multilayered cell wall composition (mAGP) is conserved among all CMN group bacteria. The arabinogalactan and mycolic acid synthesis pathways constitute effective drug targets for tuberculosis treatment. Ethambutol (EMB), a classical antituberculosis drug, inhibits the synthesis of the arabinose polymer. Although EMB acts bacteriostatically, its underlying molecular mechanism remains unclear. Here, we used Corynebacterium glutamicum and Mycobacterium phlei as model organisms to study the effects of EMB at the single-cell level. Our results demonstrate that EMB specifically blocks apical cell wall synthesis, but not cell division, explaining the bacteriostatic effect of EMB. Furthermore, the data suggest that members of the family Corynebacterineae have two dedicated machineries for cell elongation (elongasome) and cytokinesis (divisome). IMPORTANCE: Antibiotic treatment of bacterial pathogens has contributed enormously to the increase in human health. Despite the apparent importance of antibiotic treatment of bacterial infections, surprisingly little is known about the molecular functions of antibiotic actions in the bacterial cell. Here, we analyzed the molecular effects of Ethambutol, a first-line antibiotic against infections caused by members of the genus Mycobacterium We find that this drug selectively blocks apical cell growth but still allows for effective cytokinesis. As a consequence, cells survive Ethambutol treatment and adopt a pneumococcal cell growth mode with cell wall synthesis only at the site of cell division. However, combined treatment of Ethambutol and beta-lactam antibiotics acts synergistically and effectively stops cell proliferation.
Substitution of ethambutol with linezolid during the intensive phase of treatment of pulmonary tuberculosis: study protocol for a prospective, multicenter, randomized, open-label, phase II trial.[Pubmed:28193240]
Trials. 2017 Feb 13;18(1):68.
BACKGROUND: Linezolid, an oxazolidinone, substantially improves treatment outcomes of multidrug-resistant tuberculosis and extensively drug-resistant tuberculosis. We started a trial to test whether the use of linezolid instead of Ethambutol could increase the rate of sputum culture conversion as of 8 weeks of treatment in patients with drug-susceptible tuberculosis. METHODS/DESIGN: This is a phase II, multicenter, randomized study with three arms. We are enrolling patients with pulmonary tuberculosis without rifampicin resistance screened by the Xpert MTB/RIF(R) assay. The standard treatment arm uses isoniazid (6 months), rifampicin (6 months), pyrazinamide (2 months), and Ethambutol (2 months). Experimental arm 1 uses linezolid (600 mg/day) for 4 weeks instead of Ethambutol. Experimental arm 2 uses linezolid (600 mg/day) for 2 weeks instead of Ethambutol. The primary outcome is the sputum culture conversion rate on liquid media after 2 months of treatment. Secondary outcomes include the sputum culture conversion rate on solid media after 2 months of treatment, time to sputum culture conversion on liquid and solid media, cure rate, and treatment success rate. The frequencies of total adverse events (AEs) and serious AEs will be described and documented. Based on an alpha = 0.05 level of significance, a power of 85%, a 15% difference in the culture conversion rate after 2 months between the control arm and experimental arm 1 (75% vs. 90%), a 10% default (loss to follow-up) rate, and a 10% culture failure, the required number per arm was calculated to be 143 (429 in total). DISCUSSION: This trial will reveal the effectiveness and safety of 2 or 4 weeks of use of linezolid instead of Ethambutol for patients with drug-susceptible pulmonary tuberculosis. If a new regimen including linezolid shows a higher culture conversion rate by week 8, and is safe, it could be tested as a 4-month antituberculosis treatment regimen in the future. TRIAL REGISTRATION: ClincalTrials.gov, NCT01994460 . Registered on 13 November 2013.
Primary ethambutol resistance among Iranian pulmonary tuberculosis patients: a systematic review.[Pubmed:28149517]
Ther Adv Infect Dis. 2016 Oct;3(5):133-138.
INTRODUCTION: Ethambutol (EMB) is an anti-mycobacterial agent that is most commonly used in combination with other anti-tuberculosis (TB) drugs in the treatment of TB. Studies have shown that primary resistance rates of Mycobacterium tuberculosis to EMB vary widely, that is, from 1% to as high as 14%. In this study, we aimed to determine the exact prevalence of primary EMB resistance among pulmonary TB cases. METHODS: Several databases, including Medline, Embase, and Iranian databases, were searched from March 2000 to January 2016 to identify studies addressing EMB-resistant TB in Iran. Comprehensive meta-analysis (V2.2, Biostat) software was used to analyze the data. RESULTS: Of the 112 records identified from the databases, 10 studies fulfilled the eligibility criteria. The pooled prevalence of primary EMB-resistant TB was estimated at 4.2% [95% confidence interval (CI) 1.8-9.0]. No evidence of publication bias was observed among the included studies (p = 0.4 for Begg rank correlation analysis; p = 0.2 for Egger weighted regression analysis). CONCLUSION: Results of systematic review and meta-analyses indicated that effective strategies to minimize the acquired drug resistance, to improve the drug susceptibility testing (DST) capability, and to control the transmission of resistance should be attached importance for control of TB in Iran.
