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104-06-3,MFCD00022157
Catalog No.:AA00HA6D

104-06-3 | N-(4-((2-Carbamothioylhydrazono)methyl)phenyl)acetamide

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100mg
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500mg
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1g
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00HA6D
Chemical Name:
N-(4-((2-Carbamothioylhydrazono)methyl)phenyl)acetamide
CAS Number:
104-06-3
Molecular Formula:
C10H12N4OS
Molecular Weight:
236.2935
MDL Number:
MFCD00022157
SMILES:
CC(=O)Nc1ccc(cc1)/C=N/NC(=S)N
NSC Number:
3550
Properties
Computed Properties
 
Complexity:
285  
Covalently-Bonded Unit Count:
1  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
16  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
3  
XLogP3:
1  

Downstream Synthesis Route

[1]Taniyamaetal.[YakugakuZasshi/JournalofthePharmaceuticalSocietyofJapan,1954,vol.74,p.374,378][Chem.Abstr.,1955,p.5442]

57-57-8    104-06-3   
3-(4-acetylamino-benzylidenehydrazono)-amino-methylsulfanyl-propionicacid 

[1]CurrentPatentAssignee:CIBAPHARMACEUTICALPRODUCTS,INC.-US2672463,1951,A

4-acetylamino-benzaldehydehydrazone 
  1147550-11-5    104-06-3 

[1]Puetzeretal.[JournaloftheAmericanChemicalSociety,1951,vol.73,p.2958]Das;Mukherjee[JournaloftheAmericanChemicalSociety,1953,vol.75,p.1241]

[1]Amal;Egernc[IstanbulUniversitesiFenFakultesiMecmuasi,1958,vol.<C>23,p.38,40]

[1]Bernsteinetal.[JournaloftheAmericanChemicalSociety,1951,vol.73,p.906,908]Eckensteinetal.[HelveticaChimicaActa,1950,vol.33,p.1353,1360]Maffiietal.[Farmaco,EdizioneScientifica,1958,vol.13,p.187,196]Medowschtschikowa;Postowskii[ZhurnalObshcheiKhimii,1954,vol.24,p.2024,2026;engl.Ausg.S.1989]

Literature

Title: A common mechanism of inhibition of the Mycobacterium tuberculosis mycolic acid biosynthetic pathway by isoxyl and thiacetazone.

Journal: The Journal of biological chemistry 20121109

Title: Mutations in the essential FAS II β-hydroxyacyl ACP dehydratase complex confer resistance to thiacetazone in Mycobacterium tuberculosis and Mycobacterium kansasii.

Journal: Molecular microbiology 20121101

Title: Exposure of mycobacteria to cell wall-inhibitory drugs decreases production of arabinoglycerolipid related to Mycolyl-arabinogalactan-peptidoglycan metabolism.

Journal: The Journal of biological chemistry 20120330

Title: Preclinical pharmacokinetics of KBF611, a new antituberculosis agent in mice and rabbits, and comparison with thiacetazone.

Journal: Xenobiotica; the fate of foreign compounds in biological systems 20100301

Title: Simultaneous determination of a new antituberculosis agent KBF-611 and its de-acetylated metabolite in mouse and rabbit plasma by HPLC.

Journal: Archives of pharmacal research 20091001

Title: Synthesis, activity, and pharmacophore development for isatin-beta-thiosemicarbazones with selective activity toward multidrug-resistant cells.

Journal: Journal of medicinal chemistry 20090528

Title: Mycolic acid methyltransferase, MmaA4, is necessary for thiacetazone susceptibility in Mycobacterium tuberculosis.

Journal: Molecular microbiology 20090301

Title: Human flavin-containing monooxygenase 2.1 catalyzes oxygenation of the antitubercular drugs thiacetazone and ethionamide.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20090101

Title: In silico fasciolicide activity of three experimental compounds in sheep.

Journal: Annals of the New York Academy of Sciences 20081201

Title: Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.

Journal: Journal of medicinal chemistry 20081113

Title: EthA, a common activator of thiocarbamide-containing drugs acting on different mycobacterial targets.

Journal: Antimicrobial agents and chemotherapy 20070301

Title: The lipophilicity estimation of 5-arylidene derivatives of (2-thio)hydantoin with antimycobacterial activity.

Journal: Biomedical chromatography : BMC 20070301

Title: [A case of multidrug-resistant pulmonary tuberculosis cured by the regimen including thiacetazone].

Journal: Kekkaku : [Tuberculosis] 20070101

Title: Haemorheological variables in Nigeria pulmonary tuberculosis patients undergoing therapy.

Journal: Clinical hemorheology and microcirculation 20070101

Title: Thiacetazone, an antitubercular drug that inhibits cyclopropanation of cell wall mycolic acids in mycobacteria.

Journal: PloS one 20070101

Title: Extension of the intensive phase reduces unfavourable outcomes with the 8-month thioacetazone regimen.

Journal: The international journal of tuberculosis and lung disease : the official journal of the International Union against Tuberculosis and Lung Disease 20061101

Title: Oxidative activation of thiacetazone by the Mycobacterium tuberculosis flavin monooxygenase EtaA and human FMO1 and FMO3.

Journal: Chemical research in toxicology 20060301

Title: [The rates of resistance to second-line drugs in multidrug resistant Mycobacterium tuberculosis strains].

Journal: Mikrobiyoloji bulteni 20060101

Title: Tuberculosis in people with HIV.

Journal: Clinical evidence 20051201

Title: Differential antibiotic susceptibilities of starved Mycobacterium tuberculosis isolates.

Journal: Antimicrobial agents and chemotherapy 20051101

Title: SRI-286, a thiosemicarbazole, in combination with mefloquine and moxifloxacin for treatment of murine Mycobacterium avium complex disease.

Journal: Antimicrobial agents and chemotherapy 20040901

Title: Thiosemicarbazole (thiacetazone-like) compound with activity against Mycobacterium avium in mice.

Journal: Antimicrobial agents and chemotherapy 20030801

Title: Drug resistance in tuberculosis in Delhi: a 2 year profile (2001--2002).

Journal: The Journal of communicable diseases 20030601

Title: Clinical concentrations of thioridazine kill intracellular multidrug-resistant Mycobacterium tuberculosis.

Journal: Antimicrobial agents and chemotherapy 20030301

Title: Activities of moxifloxacin alone and in combination with other antimicrobial agents against multidrug-resistant Mycobacterium tuberculosis infection in BALB/c mice.

Journal: Antimicrobial agents and chemotherapy 20030101

Title: In vitro activity of thiacetazone on mycobacterial species belonging to the Mycobacterium tuberculosis complex.

Journal: The international journal of tuberculosis and lung disease : the official journal of the International Union against Tuberculosis and Lung Disease 20021001

Title: [Lyell syndrome in Senegal: responsibility of thiacetazone].

Journal: Annales de dermatologie et de venereologie 20011201

Title: [Multiresistant tuberculosis caused by Mycobacterium bovis and human immunodeficiency virus infection. Are there new therapeutic possibilities?].

Journal: Enfermedades infecciosas y microbiologia clinica 20010101

Title: Tuberculosis treatment: dangerous regimens?

Journal: The international journal of tuberculosis and lung disease : the official journal of the International Union against Tuberculosis and Lung Disease 20010101

Title: Pattern of some haematological indices in newly diagnosed pulmonary tuberculosis cases in Iwo, Nigeria: diagnostic and therapeutic implications.

Journal: Nigerian journal of medicine : journal of the National Association of Resident Doctors of Nigeria 20010101

Title: [Skin toxicity of thiacetazone (TB1) at a hospital service in Dakar].

Journal: Dakar medical 20010101

Title: Use of genomics and combinatorial chemistry in the development of new antimycobacterial drugs.

Journal: Biochemical pharmacology 20000201

Title: Green fluorescent protein reporter microplate assay for high-throughput screening of compounds against Mycobacterium tuberculosis.

Journal: Antimicrobial agents and chemotherapy 19980201

Title: Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium.

Journal: Antimicrobial agents and chemotherapy 19970501

Title: Antituberculosis activity of clarithromycin.

Journal: Antimicrobial agents and chemotherapy 19951201

Title: The Garrod Lecture. Understanding the chemotherapy of tuberculosis--current problems.

Journal: The Journal of antimicrobial chemotherapy 19920501

Title: Thiacetazone: in vitro activity against Mycobacterium avium and M. tuberculosis.

Journal: Tubercle 19901201

Title: Electrophysiological evidence of peripheral nerve damage in patients treated with isoniazid.

Journal: East African medical journal 19821201

Title: Aplastic anaemia associated with anti-tuberculosis chemotherapy.

Journal: Acta haematologica 19820101

Title: The early bactericidal activity of drugs in patients with pulmonary tuberculosis.

Journal: The American review of respiratory disease 19800601

Title: Protein synthesis in Mycobacterium tuberculosis H37Rv and the effect of streptomycin in streptomycin-susceptible and -resistant strains.

Journal: Antimicrobial agents and chemotherapy 19730901

Title: Antibacterial nitrofuran derivatives. I. 5-nitro-2-furaldehyde semicarbazones and thiosemicarbazones.

Journal: Journal of medicinal chemistry 19670701

Title: The chemical approach to the control of tuberculosis.

Journal: Science (New York, N.Y.) 19520808

Title: J L Stigliani, et al. 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.

Title: P Khanna, et al. Characteristics of a Cytosolic Arylacylamidase Metabolizing Thiacetazone. J Pharmacol Exp Ther. 1992 Sep;262(3):1225-31.

Title: Anuradha Alahari, et al. Thiacetazone, an Antitubercular Drug That Inhibits Cyclopropanation of Cell Wall Mycolic Acids in Mycobacteria. PLoS One. 2007 Dec 19;2(12):e1343.

Title: C A Peloquin, et al. Pharmacokinetic Evaluation of Thiacetazone. Pharmacotherapy. Sep-Oct 1996;16(5):735-41.

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