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MedKoo Cat#: 571118 | Name: Thioacetazone
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Description:

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

Thioacetazone is a thiosemicarbazone that is used in association with other antimycobacterial agents in the initial and continuation phases of antituberculosis regimens. Thiacetazone containing regimens are less effective than the short-course regimen recommended by the International Union Against Tuberculosis and are used in some developing countries to reduce drug costs.

Chemical Structure

Thioacetazone
Thioacetazone
CAS#104-06-3

Theoretical Analysis

MedKoo Cat#: 571118

Name: Thioacetazone

CAS#: 104-06-3

Chemical Formula: C10H12N4OS

Exact Mass: 236.0732

Molecular Weight: 236.29

Elemental Analysis: C, 50.83; H, 5.12; N, 23.71; O, 6.77; S, 13.57

Price and Availability

Size Price Availability Quantity
250mg USD 425.00
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Related CAS #
No Data
Synonym
Thioacetazone; Diazam; Neotibil; Neustab;
IUPAC/Chemical Name
Acetamide, N-(4-(((aminothioxomethyl)hydrazono)methyl)phenyl)-
InChi Key
SRVJKTDHMYAMHA-WUXMJOGZSA-N
InChi Code
InChI=1S/C10H12N4OS/c1-7(15)13-9-4-2-8(3-5-9)6-12-14-10(11)16/h2-6H,1H3,(H,13,15)(H3,11,14,16)/b12-6+
SMILES Code
CC(NC1=CC=C(/C=N/NC(N)=S)C=C1)=O
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 236.29 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: Khairullah AR, Moses IB, Kusala MKJ, Tyasningsih W, Ayuti SR, Rantam FA, Fauziah I, Silaen OSM, Puspitasari Y, Aryaloka S, Raharjo HM, Hasib A, Yanestria SM, Nurhidayah N. Unveiling insights into bovine tuberculosis: A comprehensive review. Open Vet J. 2024 Jun;14(6):1330-1344. doi: 10.5455/OVJ.2024.v14.i6.2. Epub 2024 Jun 30. PMID: 39055751; PMCID: PMC11268907. 2: Jowsey WJ, Cook GM, McNeil MB. Antibiotic resistance in Mycobacterium tuberculosis alters tolerance to cell wall-targeting inhibitors. JAC Antimicrob Resist. 2024 Jun 4;6(3):dlae086. doi: 10.1093/jacamr/dlae086. PMID: 38836195; PMCID: PMC11148391. 3: Singh V, Grzegorzewicz AE, Fienberg S, Müller R, Khonde LP, Sanz O, Alfonso S, Urones B, Drewes G, Bantscheff M, Ghidelli-Disse S, Ioerger TR, Angala B, Liu J, Lee RE, Sacchettini JC, Krieger IV, Jackson M, Chibale K, Ghorpade SR. 1,3-Diarylpyrazolyl-acylsulfonamides Target HadAB/BC Complex in Mycobacterium tuberculosis. ACS Infect Dis. 2022 Nov 11;8(11):2315-2326. doi: 10.1021/acsinfecdis.2c00392. Epub 2022 Nov 3. PMID: 36325756; PMCID: PMC9673142. 4: Singh P, Rawat S, Agrahari AK, Singh M, Chugh S, Gurcha S, Singh A, Abrahams K, Besra GS, Asthana S, Rawat DS, Singh R. NSC19723, a Thiacetazone-Like Benzaldehyde Thiosemicarbazone Improves the Efficacy of TB Drugs In Vitro and In Vivo. Microbiol Spectr. 2022 Dec 21;10(6):e0259222. doi: 10.1128/spectrum.02592-22. Epub 2022 Oct 31. PMID: 36314972; PMCID: PMC9769743. 5: Liu S, Xu Y, An B, Zhang D. Interaction of rod decussation and crack growth in enamel. Comput Methods Biomech Biomed Engin. 2023 May;26(6):700-709. doi: 10.1080/10255842.2022.2084333. Epub 2022 Jul 11. PMID: 35815376. 6: Singh BK, Singha M, Basak S, Biswas R, Das AK, Basak A. Fluorescently labelled thioacetazone for detecting the interaction with Mycobacterium dehydratases HadAB and HadBC. Org Biomol Chem. 2022 Feb 16;20(7):1444-1452. doi: 10.1039/d1ob02080c. PMID: 35084426. 7: de Freitas Paulo T, Duhayon C, de França Lopes LG, Silva Sousa EH, Chauvin R, Bernardes-Génisson V. Further Insights into the Oxidative Pathway of Thiocarbonyl-Type Antitubercular Prodrugs: Ethionamide, Thioacetazone, and Isoxyl. Chem Res Toxicol. 2021 Aug 16;34(8):1879-1889. doi: 10.1021/acs.chemrestox.1c00164. Epub 2021 Jul 28. PMID: 34319702. 8: Madacki J, Kopál M, Jackson M, Korduláková J. Mycobacterial Epoxide Hydrolase EphD Is Inhibited by Urea and Thiourea Derivatives. Int J Mol Sci. 2021 Mar 12;22(6):2884. doi: 10.3390/ijms22062884. PMID: 33809178; PMCID: PMC7998700. 9: Farjallah A, Chiarelli LR, Forbak M, Degiacomi G, Danel M, Goncalves F, Carayon C, Seguin C, Fumagalli M, Záhorszká M, Vega E, Abid S, Grzegorzewicz A, Jackson M, Peixoto A, Korduláková J, Pasca MR, Lherbet C, Chassaing S. A Coumarin-Based Analogue of Thiacetazone as Dual Covalent Inhibitor and Potential Fluorescent Label of HadA in Mycobacterium tuberculosis. ACS Infect Dis. 2021 Mar 12;7(3):552-565. doi: 10.1021/acsinfecdis.0c00325. Epub 2021 Feb 22. PMID: 33617235; PMCID: PMC8022203. 10: Stigliani JL, Bernardes-Génisson V. New insights into the chemical behavior of S-oxide derivatives of thiocarbonyl-containing antitubercular drugs and the influence on their mechanisms of action and toxicity. Ann Pharm Fr. 2019 Mar;77(2):126-135. doi: 10.1016/j.pharma.2018.11.004. Epub 2019 Jan 29. PMID: 30709547. 11: Pang H, Jiang Y, Wan K. Drug Susceptibility of 33 Reference Strains of Slowly Growing Mycobacteria to 19 Antimicrobial Agents. Biomed Res Int. 2017;2017:1584658. doi: 10.1155/2017/1584658. Epub 2017 Apr 20. PMID: 28512635; PMCID: PMC5415667. 12: Halloum I, Viljoen A, Khanna V, Craig D, Bouchier C, Brosch R, Coxon G, Kremer L. Resistance to Thiacetazone Derivatives Active against Mycobacterium abscessus Involves Mutations in the MmpL5 Transcriptional Repressor MAB_4384. Antimicrob Agents Chemother. 2017 Mar 24;61(4):e02509-16. doi: 10.1128/AAC.02509-16. PMID: 28096157; PMCID: PMC5365672. 13: Fox GJ, Benedetti A, Cox H, Koh WJ, Viiklepp P, Ahuja S, Pasvol G, Menzies D; Collaborative Group for Meta-Analysis of Individual Patient Data in MDR-TB. Group 5 drugs for multidrug-resistant tuberculosis: individual patient data meta-analysis. Eur Respir J. 2017 Jan 3;49(1):1600993. doi: 10.1183/13993003.00993-2016. PMID: 28049171. 14: Choi J, Jee JG. Repositioning of Thiourea-Containing Drugs as Tyrosinase Inhibitors. Int J Mol Sci. 2015 Dec 2;16(12):28534-48. doi: 10.3390/ijms161226114. PMID: 26633377; PMCID: PMC4691061. 15: Chen M, Deng J, Li W, Su C, Xia Y, Wang M, Li X, Abuaku BK, Tan H, Wen SW. The relationship between chitotriosidase activity and tuberculosis. Epidemiol Infect. 2015 Nov;143(15):3196-202. doi: 10.1017/S095026881500062X. PMID: 26418349; PMCID: PMC4594044. 16: Pang H, Li G, Zhao X, Liu H, Wan K, Yu P. Drug Susceptibility Testing of 31 Antimicrobial Agents on Rapidly Growing Mycobacteria Isolates from China. Biomed Res Int. 2015;2015:419392. doi: 10.1155/2015/419392. Epub 2015 Aug 13. PMID: 26351633; PMCID: PMC4550772. 17: Shimokawa Y, Yoda N, Kondo S, Yamamura Y, Takiguchi Y, Umehara K. Inhibitory Potential of Twenty Five Anti-tuberculosis Drugs on CYP Activities in Human Liver Microsomes. Biol Pharm Bull. 2015;38(9):1425-9. doi: 10.1248/bpb.b15-00313. Epub 2015 Jun 20. PMID: 26094899. 18: Carrère-Kremer S, Blaise M, Singh VK, Alibaud L, Tuaillon E, Halloum I, van de Weerd R, Guérardel Y, Drancourt M, Takiff H, Geurtsen J, Kremer L. A new dehydratase conferring innate resistance to thiacetazone and intra-amoebal survival of Mycobacterium smegmatis. Mol Microbiol. 2015 Jun;96(5):1085-102. doi: 10.1111/mmi.12992. Epub 2015 Mar 28. PMID: 25754266. 19: Gopal P, Dick T. The new tuberculosis drug Perchlozone® shows cross- resistance with thiacetazone. Int J Antimicrob Agents. 2015 Apr;45(4):430-3. doi: 10.1016/j.ijantimicag.2014.12.026. Epub 2015 Feb 3. PMID: 25704063. 20: Falzon D, Hill G, Pal SN, Suwankesawong W, Jaramillo E. Pharmacovigilance and tuberculosis: applying the lessons of thioacetazone. Bull World Health Organ. 2014 Dec 1;92(12):918-9. doi: 10.2471/BLT.14.142570. Epub 2014 Oct 7. PMID: 25552777; PMCID: PMC4264398.