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MedKoo Cat#: 584371 | Name: Ethambutol
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ethambutol is an antitubercular agent that inhibits the transfer of mycolic acids into the cell wall of the tubercle bacillus. It may also inhibit the synthesis of spermidine in mycobacteria. The action is usually bactericidal, and the drug can penetrate human cell membranes to exert its lethal effect.

Chemical Structure

Ethambutol
Ethambutol
CAS#74-55-5 (SS free base)

Theoretical Analysis

MedKoo Cat#: 584371

Name: Ethambutol

CAS#: 74-55-5 (SS free base)

Chemical Formula: C10H24N2O2

Exact Mass: 204.1838

Molecular Weight: 204.31

Elemental Analysis: C, 58.79; H, 11.84; N, 13.71; O, 15.66

Price and Availability

Size Price Availability Quantity
1mg USD 250.00 2 Weeks
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Related CAS #
74-55-5 (SS free base) 1070-11-7 (SS 2HCl) 10054-05-4 (RR free base)
Synonym
Ethambutol; Etambutol; Aethambutolum; Diambutol; Purderal; Tibutol; Myambutol; Ethambutolum; D-Ethambutol; (+)-S,S-Ethambutol;
IUPAC/Chemical Name
(2S)-2-[2-[[(2S)-1-hydroxybutan-2-yl]amino]ethylamino]butan-1-ol
InChi Key
AEUTYOVWOVBAKS-UWVGGRQHSA-N
InChi Code
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
SMILES Code
CC[C@H](NCCN[C@@H](CC)CO)CO
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 204.31 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Safi H, Lingaraju S, Amin A, Kim S, Jones M, Holmes M, McNeil M, Peterson SN, Chatterjee D, Fleischmann R, Alland D. Evolution of high-level ethambutol-resistant tuberculosis through interacting mutations in decaprenylphosphoryl-β-D-arabinose biosynthetic and utilization pathway genes. Nat Genet. 2013 Oct;45(10):1190-7. doi: 10.1038/ng.2743. Epub 2013 Sep 1. PubMed PMID: 23995136. 2: Wu Y, Sims RC, Zhou A. AFM resolves effects of ethambutol on nanomechanics and nanostructures of single dividing mycobacteria in real-time. Phys Chem Chem Phys. 2014 Sep 28;16(36):19156-64. doi: 10.1039/c4cp01317d. PubMed PMID: 24965038. 3: Kandel H, Adhikari P, Shrestha GS, Ruokonen EL, Shah DN. Visual function in patients on ethambutol therapy for tuberculosis. J Ocul Pharmacol Ther. 2012 Apr;28(2):174-8. doi: 10.1089/jop.2011.0095. Epub 2011 Dec 2. PubMed PMID: 22136146. 4: Xu J, Jin H, Zhu H, Zheng M, Wang B, Liu C, Chen M, Zhou L, Zhao W, Fu L, Lu Y. Oral bioavailability of rifampicin, isoniazid, ethambutol, and pyrazinamide in a 4-drug fixed-dose combination compared with the separate formulations in healthy Chinese male volunteers. Clin Ther. 2013 Feb;35(2):161-8. doi: 10.1016/j.clinthera.2013.01.003. PubMed PMID: 23410999. 5: Shewiyo DH, Kaale E, Risha PG, Dejaegher B, Smeyers-Verbeke J, Vander Heyden Y. Optimization of a reversed-phase-high-performance thin-layer chromatography method for the separation of isoniazid, ethambutol, rifampicin and pyrazinamide in fixed-dose combination antituberculosis tablets. J Chromatogr A. 2012 Oct 19;1260:232-8. doi: 10.1016/j.chroma.2012.08.044. Epub 2012 Aug 30. PubMed PMID: 22981506. 6: El-Ridy MS, Yehia SA, Kassem MA, Mostafa DM, Nasr EA, Asfour MH. Niosomal encapsulation of ethambutol hydrochloride for increasing its efficacy and safety. Drug Deliv. 2015 Jan;22(1):21-36. doi: 10.3109/10717544.2013.868556. Epub 2013 Dec 20. PubMed PMID: 24359403. 7: Özkaya E. Eczematous-type multiple drug allergy from isoniazid and ethambutol with positive patch test results. Cutis. 2013 Sep;92(3):121-4. PubMed PMID: 24153138. 8: Talbert Estlin KA, Sadun AA. Risk factors for ethambutol optic toxicity. Int Ophthalmol. 2010 Feb;30(1):63-72. doi: 10.1007/s10792-009-9293-z. Epub 2009 Feb 11. PubMed PMID: 19205626. 9: Alffenaar JW, van der Werf T. Dosing ethambutol in obese patients. Antimicrob Agents Chemother. 2010 Sep;54(9):4044; author reply 4044-5. doi: 10.1128/AAC.00412-10. PubMed PMID: 20716782; PubMed Central PMCID: PMC2935003. 10: Jönsson S, Davidse A, Wilkins J, Van der Walt JS, Simonsson US, Karlsson MO, Smith P, McIlleron H. Population pharmacokinetics of ethambutol in South African tuberculosis patients. Antimicrob Agents Chemother. 2011 Sep;55(9):4230-7. doi: 10.1128/AAC.00274-11. Epub 2011 Jun 20. PubMed PMID: 21690284; PubMed Central PMCID: PMC3165318. 11: Jacobson MA, Yajko D, Northfelt D, Charlebois E, Gary D, Brosgart C, Sanders CA, Hadley WK. Randomized, placebo-controlled trial of rifampin, ethambutol, and ciprofloxacin for AIDS patients with disseminated Mycobacterium avium complex infection. J Infect Dis. 1993 Jul;168(1):112-9. Erratum in: J Infect Dis 1993 Sep;168(3):802. PubMed PMID: 8515098. 12: Pattisson PR, Kun OJ, Friedmann AI, Darbyshire JH, Tall R. Ethambutol and intra-ocular pressure. Tubercle. 1978 Mar;59(1):33-40. PubMed PMID: 635991. 13: Chuenkongkaew W, Samsen P, Thanasombatsakul N. Ethambutol and optic neuropathy. J Med Assoc Thai. 2003 Jul;86(7):622-5. PubMed PMID: 12948256. 14: Coluccia M, Fanizzi FP, Giannini G, Giordano D, Intini FP, Lacidogna G, Loseto F, Mariggio MA, Nassi A, Natile G. Synthesis, mutagenicity, binding to pBR 322 DNA and antitumour activity of platinum(II) complexes with ethambutol. Anticancer Res. 1991 Jan-Feb;11(1):281-7. PubMed PMID: 2018362. 15: Kohno S, Koga H, Kaku M, Maesaki S, Hara K. Prospective comparative study of ofloxacin or ethambutol for the treatment of pulmonary tuberculosis. Chest. 1992 Dec;102(6):1815-8. PubMed PMID: 1446494. 16: Lounis N, Maslo C, Truffot-Pernot C, Grosset J, Boelaert RJ. Impact of iron loading on the activity of isoniazid or ethambutol in the treatment of murine tuberculosis. Int J Tuberc Lung Dis. 2003 Jun;7(6):575-9. PubMed PMID: 12797701. 17: Babalik A, Ulus IH, Bakirci N, Kuyucu T, Arpag H, Dagyildizi L, Capaner E. Plasma concentrations of isoniazid and rifampin are decreased in adult pulmonary tuberculosis patients with diabetes mellitus. Antimicrob Agents Chemother. 2013 Nov;57(11):5740-2. doi: 10.1128/AAC.01345-13. Epub 2013 Aug 26. PubMed PMID: 23979746; PubMed Central PMCID: PMC3811326. 18: Dickinson JM, Mitchison DA. Bactericidal activity in vitro and in the guinea-pig of isoniazid, rifampicin and ethambutol. Tubercle. 1976 Dec;57(4):251-8. PubMed PMID: 827836. 19: Ethambutol. Tuberculosis (Edinb). 2008 Mar;88(2):102-5. doi: 10.1016/S1472-9792(08)70008-8. Review. PubMed PMID: 18486042. 20: Aditya NP, Patankar S, Madhusudhan B. Assessment of in vivo antimalarial activity of rifampicin, isoniazide, and ethambutol combination therapy. Parasitol Res. 2010 May;106(6):1481-4. doi: 10.1007/s00436-010-1789-y. Epub 2010 Feb 18. PubMed PMID: 20165870.