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MedKoo Cat#: 414109 | Name: Ethionamide HCl

Description:

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

Ethionamide HCl is the salt form of Ethionamide, a second-line antitubercular agent that inhibits mycolic acid synthesis. Ethionamide is a nicotinamide derivative, with antibacterial activity, used to treat tuberculosis. Although the exact mechanism of action of ethionamide is unknown, it may inhibit the synthesis of mycolic acid, a saturated fatty acid found in the bacterial cell wall, thereby inhibiting bacterial cell wall synthesis. This eventually leads to bacterial cell wall disruption and cell lysis. Ethionamide may be bacteriostatic or bactericidal in action, depending on the concentration of the drug at the site of infection and the susceptibility of the organism involved. It binds with NAD+ to form an adduct.

Chemical Structure

Ethionamide HCl
Ethionamide HCl
CAS#3684-73-9 (HCl)

Theoretical Analysis

MedKoo Cat#: 414109

Name: Ethionamide HCl

CAS#: 3684-73-9 (HCl)

Chemical Formula: C8H11ClN2S

Exact Mass:

Molecular Weight: 202.70

Elemental Analysis: C, 47.40; H, 5.47; Cl, 17.49; N, 13.82; S, 15.82

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
3684-73-9 (HCl) 536-33-4 (free base)
Synonym
Ethionamide HCl; Ethionamide hydrochloride; Amidazine; Trecator
IUPAC/Chemical Name
2-Ethylthioisonicotinamide monohydrochloride
InChi Key
YNKSYHUKAKUZAR-UHFFFAOYSA-N
InChi Code
InChI=1S/C8H10N2S.ClH/c1-2-7-5-6(8(9)11)3-4-10-7;/h3-5H,2H2,1H3,(H2,9,11);1H
SMILES Code
NC(C1=CC=NC(CC)=C1)=S.[H]Cl
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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 202.70 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: Nikiforov PO, Surade S, Blaszczyk M, Delorme V, Brodin P, Baulard AR, Blundell TL, Abell C. A fragment merging approach towards the development of small molecule inhibitors of Mycobacterium tuberculosis EthR for use as ethionamide boosters. Org Biomol Chem. 2016 Jan 25. [Epub ahead of print] PubMed PMID: 26806381. 2: de Melo CC, da Silva CC, Pereira CC, Rosa PC, Ellena J. Mechanochemistry applied to reformulation and scale-up production of Ethionamide: Salt selection and solubility enhancement. Eur J Pharm Sci. 2016 Jan 1;81:149-56. doi: 10.1016/j.ejps.2015.10.007. Epub 2015 Oct 22. PubMed PMID: 26472469. 3: Rueda J, Realpe T, Mejia GI, Zapata E, Rozo JC, Ferro BE, Robledo J. Genotypic Analysis of Genes Associated with Independent Resistance and Cross-Resistance to Isoniazid and Ethionamide in Mycobacterium tuberculosis Clinical Isolates. Antimicrob Agents Chemother. 2015 Dec;59(12):7805-10. doi: 10.1128/AAC.01028-15. Epub 2015 Sep 14. PubMed PMID: 26369965; PubMed Central PMCID: PMC4649173. 4: Choi J, Park SJ, Jee JG. Analogues of ethionamide, a drug used for multidrug-resistant tuberculosis, exhibit potent inhibition of tyrosinase. Eur J Med Chem. 2015 Dec 1;106:157-66. doi: 10.1016/j.ejmech.2015.10.033. Epub 2015 Oct 19. PubMed PMID: 26544630. 5: Lakshmi R, Ramachandran R, Kumar DR, Sundar AS, Radhika G, Rahman F, Selvakumar N, Kumar V. Revisiting the susceptibility testing of Mycobacterium tuberculosis to ethionamide in solid culture medium. Indian J Med Res. 2015 Nov;142(5):538-42. doi: 10.4103/0971-5916.171278. PubMed PMID: 26658587. 6: Varma-Basil M, Prasad R. Dilemmas with ethionamide susceptibility testing of Mycobacterium tuberculosis: A microbiologist & physician's nightmare. Indian J Med Res. 2015 Nov;142(5):512-4. doi: 10.4103/0971-5916.171272. PubMed PMID: 26658583. 7: Cordeiro Rde A, Serpa R, Marques FJ, de Melo CV, Evangelista AJ, Mota VF, Brilhante RS, Bandeira Tde J, Rocha MF, Sidrim JJ. Inhibitory activity of isoniazid and ethionamide against Cryptococcus biofilms. Can J Microbiol. 2015 Nov;61(11):827-36. doi: 10.1139/cjm-2015-0230. Epub 2015 Aug 6. PubMed PMID: 26362025. 8: Thee S, Garcia-Prats AJ, Donald PR, Hesseling AC, Schaaf HS. A review of the use of ethionamide and prothionamide in childhood tuberculosis. Tuberculosis (Edinb). 2015 Oct 19. pii: S1472-9792(15)30046-9. doi: 10.1016/j.tube.2015.09.007. [Epub ahead of print] Review. PubMed PMID: 26586647. 9: Lehloenya RJ, Muloiwa R, Dlamini S, Gantsho N, Todd G, Dheda K. Lack of cross-toxicity between isoniazid and ethionamide in severe cutaneous adverse drug reactions: a series of 25 consecutive confirmed cases. J Antimicrob Chemother. 2015 Sep;70(9):2648-51. doi: 10.1093/jac/dkv158. Epub 2015 Jul 3. PubMed PMID: 26142408. 10: Mallela AR, Koya R, Nagari SK, Mohapatra AK. Ethionamide: Unusual Cause of Hypothyroidism. J Clin Diagn Res. 2015 Aug;9(8):OD08-9. doi: 10.7860/JCDR/2015/13531.6331. Epub 2015 Aug 1. PubMed PMID: 26435990; PubMed Central PMCID: PMC4576583. 11: Gupta Y, Shah I. Ethionamide-induced Pellagra. J Trop Pediatr. 2015 Aug;61(4):301-3. doi: 10.1093/tropej/fmv021. Epub 2015 Mar 30. PubMed PMID: 25828829. 12: Vilchèze C, Jacobs WR Jr. Resistance to Isoniazid and Ethionamide in Mycobacterium tuberculosis: Genes, Mutations, and Causalities. Microbiol Spectr. 2014 Aug;2(4):MGM2-0014-2013. doi: 10.1128/microbiolspec.MGM2-0014-2013. Review. PubMed PMID: 26104204. 13: Korth-Bradley JM, Mayer P, Mansfield D, Tucker H, Wu D. Comparative bioavailability study of single-dose film-coated and sugar-coated ethionamide tablets in healthy volunteers. Clin Ther. 2014 Jun 1;36(6):982-7. doi: 10.1016/j.clinthera.2014.04.014. Epub 2014 May 13. PubMed PMID: 24832559. 14: Bhanushali CJ, Zidan AS, Rahman Z, Habib MJ. Ion-pair chromatography for simultaneous analysis of ethionamide and pyrazinamide from their porous microparticles. AAPS PharmSciTech. 2013 Dec;14(4):1313-20. doi: 10.1208/s12249-013-0025-3. Epub 2013 Aug 30. PubMed PMID: 23990078; PubMed Central PMCID: PMC3840777. 15: Tatum NJ, Villemagne B, Willand N, Deprez B, Liebeschuetz JW, Baulard AR, Pohl E. Structural and docking studies of potent ethionamide boosters. Acta Crystallogr C. 2013 Nov;69(Pt 11):1243-50. doi: 10.1107/S0108270113028126. Epub 2013 Oct 24. PubMed PMID: 24192167. 16: Machado D, Perdigão J, Ramos J, Couto I, Portugal I, Ritter C, Boettger EC, Viveiros M. High-level resistance to isoniazid and ethionamide in multidrug-resistant Mycobacterium tuberculosis of the Lisboa family is associated with inhA double mutations. J Antimicrob Chemother. 2013 Aug;68(8):1728-32. doi: 10.1093/jac/dkt090. Epub 2013 Mar 28. PubMed PMID: 23539241. 17: Lakshmi R, Ramachandran R, Devika K, Radhika G, Syam Sundar A, Rahman F, Selvakumar N, Kumar V. Modification of proportion sensitivity testing method for ethionamide. World J Microbiol Biotechnol. 2013 Jun;29(6):1117-9. doi: 10.1007/s11274-013-1255-y. Epub 2013 Jan 12. PubMed PMID: 23315266. 18: Lakshmi R, Ramachandran R, Syam Sundar A, Rehman F, Radhika G, Kumar V. Optimization of the conventional minimum inhibitory concentration method for drug susceptibility testing of ethionamide. Int J Mycobacteriol. 2013 Mar;2(1):29-33. doi: 10.1016/j.ijmyco.2012.11.005. Epub 2013 Jan 3. PubMed PMID: 26785785. 19: Vale N, Gomes P, Santos HA. Metabolism of the antituberculosis drug ethionamide. Curr Drug Metab. 2013 Jan;14(1):151-8. Review. PubMed PMID: 23215813. 20: Vadwai V, Ajbani K, Jose M, Vineeth VP, Nikam C, Deshmukh M, Shetty A, Soman R, Rodrigues C. Can inhA mutation predict ethionamide resistance? Int J Tuberc Lung Dis. 2013 Jan;17(1):129-30. doi: 10.5588/ijtld.12.0511. Epub 2012 Nov 8. PubMed PMID: 23146620.

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MA 144 S1

MA 144 S1