Ethionamide
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MedKoo CAT#: 317796

CAS#: 536-33-4 (free base)

Description: Ethionamide is 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

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Ethionamide
CAS# 536-33-4 (free base)
Instruction

Theoretical Analysis

MedKoo Cat#: 317796
Name: Ethionamide
CAS#: 536-33-4 (free base)
Chemical Formula: C8H10N2S
Exact Mass: 166.06
Molecular Weight: 166.240
Elemental Analysis: C, 57.80; H, 6.06; N, 16.85; S, 19.29

Price and Availability

Size Price Availability Quantity
5g USD 250 2 weeks
10g USD 450 2 weeks
25g USD 750 2 weeks
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Related CAS #: 3684-73-9 (HCl)   536-33-4 (free base)  

Synonym: Ethionamide; Trecator; Ethioniamide; Ethinamide; 2-ethylpyridine-4-carbothioamide; Trecator; Trecator SC; Trecator-SC; Wyeth Brand of Ethionamide;

IUPAC/Chemical Name: 2-ethylpyridine-4-carbothioamide

InChi Key: AEOCXXJPGCBFJA-UHFFFAOYSA-N

InChi Code: InChI=1S/C8H10N2S/c1-2-7-5-6(8(9)11)3-4-10-7/h3-5H,2H2,1H3,(H2,9,11)

SMILES Code: CCC1=NC=CC(=C1)C(=S)N

Appearance: Light yellow to yellow crystalline 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, not in water

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 166.24 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.