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Chemical Structure| 536-33-4 Chemical Structure| 536-33-4

Structure of Ethionamide
CAS No.: 536-33-4

Chemical Structure| 536-33-4

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Ethionamide is a second-line antitubercular agent which can inhibit mycolic acid synthesis.

Synonyms: 2-Ethylthioisonicotinamide; NSC 255115; Bayer 5312

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Product Details of Ethionamide

CAS No. :536-33-4
Formula : C8H10N2S
M.W : 166.24
SMILES Code : NC(C1=CC(CC)=NC=C1)=S
Synonyms :
2-Ethylthioisonicotinamide; NSC 255115; Bayer 5312
MDL No. :MFCD00057361
InChI Key :AEOCXXJPGCBFJA-UHFFFAOYSA-N
Pubchem ID :2761171

Safety of Ethionamide

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335-H351-H361
Precautionary Statements:P261-P305+P351+P338

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
Wharton’s jelly-derived mesenchymal stem cells (WJ-MSCs) 100 μM 72 hours Ethionamide preconditioning enhanced the proliferation of WJ-MSCs by activating PI3K/Akt and MEK/ERK1/2 signaling pathways. Int J Mol Sci. 2020 Sep 23;21(19):7013
Human lung microsomes 200 μM 5 minutes To study the metabolism of ethionamide in human lung microsomes, it was found that the FMO2 genetic polymorphism affects the metabolism of ethionamide. Toxicol Appl Pharmacol. 2008 Dec 15;233(3):420-7
Mouse liver and lung microsomes 200 μM 5 minutes To study the metabolism of ethionamide in mouse liver and lung microsomes, it was found that ethionamide was oxidized to ETASO, and this reaction was primarily catalyzed by FMOs rather than CYP. Toxicol Appl Pharmacol. 2008 Dec 15;233(3):420-7
Sf9 insect cells 200 μM 5 minutes To study the metabolism of ethionamide in Sf9 insect cells, it was found that all mouse and human FMOs (except hFMO5) oxidized ethionamide to ethionamide-S-oxide (ETASO). Toxicol Appl Pharmacol. 2008 Dec 15;233(3):420-7
Mycobacterium tuberculosis 50 μg/ml 7 days To evaluate the effect of CinA deletion on the bactericidal effect of Ethionamide. Results showed that CinA deletion enhanced the killing of non-replicating Mtb by Ethionamide. Nat Commun. 2022 Apr 22;13(1):2203

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
Swiss mice Tuberculosis model Gavage 50 mg/kg 5 days per week for 6 months To evaluate the bactericidal and sterilizing activity of a second-line antituberculous regimen containing ethionamide. Results showed higher relapse rates for fluoroquinolone-resistant strains compared to the wild-type, correlating with resistance levels. Antimicrob Agents Chemother. 2013 Sep;57(9):4496-500
BALB/c mice Latent tuberculosis infection model Gavage 50 mg/kg Daily administration for 6 months Evaluate the efficacy of ethionamide combined with moxifloxacin in treating latent tuberculosis infection. Results showed that the combination of ethionamide and moxifloxacin was more effective than the recommended regimen of pyrazinamide plus ethambutol. Am J Respir Crit Care Med. 2005 Dec 1;172(11):1452-6
BALB/c mice Tuberculosis model Oral 50 mg/kg 5 days per week for 2-7 months To evaluate the bactericidal and sterilizing activity of Ethionamide in second-line regimens containing fluoroquinolones. Results showed that Ethionamide, when combined with moxifloxacin or high-dose levofloxacin and extended use of pyrazinamide, significantly enhanced sterilizing activity. Am J Respir Crit Care Med. 2013 Jul 1;188(1):97-102
Mice Wild-type C57BL/6J and Fmo1/2/4 knockout mice Oral gavage 125 mg/kg Single dose, observation time from 0.25 to 3.5 hours To assess the impact of the FMO2 genetic polymorphism on the pharmacokinetics of ETA. Results showed that in WT mice, plasma concentrations of the metabolite ETASO were higher than the parent ETA, whereas in KO mice, ETA concentrations were higher than ETASO. Pharmaceuticals (Basel). 2012;5(11):1147-59
BALB/c female mice Pulmonary tuberculosis mouse model 10 mg/kg/day Once daily, 5 days a week, for 4 weeks To evaluate the synergistic effect of PPs with ETH in a pulmonary tuberculosis mouse model, results showed that the bacterial load in the lungs was significantly lower in the combination group than in the ETH-alone group. Antibiotics (Basel). 2022 Oct 4;11(10):1349
Mice Mycobacterium tuberculosis H37Rv-infected mice Oral and inhalation Oral: 4.7 mg ETO + 2.35 mg DCS; Inhalation: 70 μg ETO + 35 μg DCS 20 daily doses for 4 weeks To evaluate the pharmacokinetics and anti-tuberculosis efficacy of DCS and ETO combination. Inhalation significantly reduced the bacterial load in lungs and spleen, showing bactericidal activity. Antimicrob Agents Chemother. 2019 May 24;63(6):e00099-19
Mice Tuberculosis model Oral 50 mg/kg 5 times per week for 2 months Evaluate the therapeutic effect of Ethionamide in combination with other drugs on multidrug-resistant tuberculosis. Results showed that R207910-containing regimens were significantly more active than non-R207910-containing regimens. Antimicrob Agents Chemother. 2006 Nov;50(11):3543-7

Clinical Trial:

NCT Number Conditions Phases Recruitment Completion Date Locations
NCT02099240 Osteomyelitis Early Phase 1 Recruiting September 2019 United States, Kentucky ... More >> University of Louisville Recruiting Louisville, Kentucky, United States, 40202 Contact: Julio A Ramirez, MD    502-852-1148    jarami01@louisville.edu    Contact: David Seligson, MD    502-852-0923    d0seli01@louisville.edu    Sub-Investigator: Forest Arnold, DO          Sub-Investigator: Timothy Wiemkwn, PhD          Sub-Investigator: Robert Kelley, PhD          Sub-Investigator: James Summersgill, PhD          Sub-Investigator: Ruth Carrico, PhD          Sub-Investigator: Julie Harting, PharmD          Sub-Investigator: Paula Peyrani, MD          Principal Investigator: David Seligson, MD          Sub-Investigator: Craig Roberts, MD          Principal Investigator: Julio Ramirez, MD Less <<
NCT02365623 Tuberculosis, Multidrug-Resist... More >>ant Less << Phase 2 Active, not recruiting September 12, 2020 Japan ... More >> Kiyose, Japan Sakai, Japan Less <<
NCT00000796 HIV Infections ... More >> Tuberculosis Less << Not Applicable Completed - United States, Illinois ... More >> Cook County Hosp Chicago, Illinois, United States, 60612 United States, Michigan Henry Ford Hosp Detroit, Michigan, United States, 48202 United States, New York Bronx Lebanon Hosp Ctr Bronx, New York, United States, 10456 Bronx Municipal Hosp Ctr/Jacobi Med Ctr Bronx, New York, United States, 10461 Comprehensive Health Care Ctr / Bronx Municipal Hosp Bronx, New York, United States, 10461 Montefiore Drug Treatment Ctr / Bronx Municipal Hosp Bronx, New York, United States, 10461 Montefiore Family Health Ctr / Bronx Municipal Hosp Bronx, New York, United States, 10461 Samaritan Village Inc / Bronx Municipal Hosp Bronx, New York, United States, 10461 Jack Weiler Hosp / Bronx Municipal Hosp Bronx, New York, United States, 10465 Montefiore Med Ctr / Bronx Municipal Hosp Bronx, New York, United States, 10467 North Central Bronx Hosp / Bronx Municipal Hosp Bronx, New York, United States, 10467 Interfaith Med Ctr Brooklyn, New York, United States, 112032098 SUNY / Health Sciences Ctr at Brooklyn Brooklyn, New York, United States, 112032098 Beth Israel Med Ctr New York, New York, United States, 10003 Clinical Directors Network of Region II New York, New York, United States, 10011 Bellevue Hosp / New York Univ Med Ctr New York, New York, United States, 10016 Saint Clare's Hosp and Health Ctr New York, New York, United States, 10019 Cornell Univ Med Ctr New York, New York, United States, 10021 Mount Sinai Med Ctr New York, New York, United States, 10029 Columbia Presbyterian Med Ctr New York, New York, United States, 100323784 Harlem AIDS Treatment Group / Harlem Hosp Ctr New York, New York, United States, 10037 Less <<
NCT03237182 Tuberculosis, Multidrug-Resist... More >>ant Less << Phase 4 Recruiting December 2021 South Africa ... More >> King Dinuzulu Hospital Recruiting Durban, Kwa-Zulu Natal, South Africa Contact: Nesri Padayatchi, MBcHB    0312604550    nesri.padayatchi@caprisa.org    Contact: Resha Boodhram, BTech    0828383651    resha.boodhram@caprisa.org Less <<
NCT02975570 Tuberculosis Multi Drug Resist... More >>ant Active Less << Phase 3 Withdrawn(The study could not ... More >>be conducted since funding was not obtained.) Less << August 2022 -
NCT02454205 Tuberculosis ... More >>Multidrug Resistant Tuberculosis Extensively-drug Resistant Tuberculosis Less << Phase 2 Phase 3 Recruiting January 2019 South Africa ... More >> Brooklyn Chest Hospital Recruiting Cape Town, Western Cape, South Africa, 7441 Contact: Ali Esmail, MD    0214047654 ext 6119    a.esmail@uct.ac.za    Contact: Lynelle Mottay, MD    0214046119 ext 6119    lynelle.mottay@uct.ac.za Less <<
NCT03625739 - Recruiting December 31, 2026 China ... More >> Beijing Children's Hospital of Capital Medical University Recruiting Beijing, China Contact: Adong Shen, Master    13370115087    shenad16@hotmail.com Less <<
NCT00042289 HIV Infections Phase 4 Recruiting September 30, 2019 -
NCT02727582 - Recruiting February 28, 2019 South Africa ... More >> Brooklyn Chest Hospital Recruiting Cape Town, Western Cape, South Africa, 7725 Contact: Richard G Court    +27214066779    richard.court@uct.ac.za    Contact: Nihal DeVries       Nihal.DeVries@westerncape.gov.za    Sub-Investigator: Richard G Court          Principal Investigator: Helen M McIlleron          DP Marias Hospital Recruiting Cape Town, Western Cape, South Africa, 7725 Contact: Richard Dr Court    +27214066779    richard.court@uct.ac.za    Contact: Joseph Dr Harding       Joseph.Harding@westerncape.gov.za    Principal Investigator: Helen McIlleron          Sub-Investigator: Richard Court Less <<

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

6.02mL

1.20mL

0.60mL

30.08mL

6.02mL

3.01mL

60.15mL

12.03mL

6.02mL

References

 

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