thioacetazone

Thioacetazone
Systematic (IUPAC) name
	N-{4-[(ethanethioamidoimino)methyl]phenyl}acetamide
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
Identifiers
CAS Number	104-06-3
ATC code	J04AM04
PubChem	CID: 9568512
ChemSpider	7843221
UNII	MMG78X7SSR
KEGG	D08584
ChEMBL	CHEMBL375492
Synonyms	N-[4-[(carbamothioylhydrazinylidene) methyl]phenyl]acetamide
Chemical data
Formula	C10H12N4OS
Molecular mass	236.3
	SMILES O=C(Nc1ccc(cc1)\C=N\NC(=S)N)C ;
	InChI 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+ ; Key:SRVJKTDHMYAMHA-WUXMJOGZSA-N ;
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チオアセタゾン

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/12/06 20:02:54」(JST)

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Thioacetazone (INN and BAN) is also called thiocetazone, thiacetazone, thiosemicarbazone, benzothiozane or amithiozone (USAN); abbreviated T.

Thioacetazone is used in the treatment of tuberculosis; it has only weak activity against Mycobacterium tuberculosis and is only useful in preventing resistance to more powerful drugs like isoniazid and rifampicin. It is never used on its own to treat tuberculosis; it is used in a similar way to ethambutol. Thioacetazone is the only anti-TB drug that is ineffective when given intermittently.

There is no advantage to using thioacetazone if the regimen used already contains ethambutol, but many countries in sub-Saharan Africa still use thioacetazone because it is extremely cheap. Use of thioacetazone is declining because it can cause severe (sometimes fatal) skin reactions in HIV positive patients.^[1]^[2]

References

^ Rieder HL, Arnadottir T, Trebucq A, Enarson DA (2001). "Tuberculosis treatment: dangerous regimens?". Int J Tuberc Lung Dis 5 (1): 1–3. PMID 11263509.
^ Nunn P, Porter J, Winstanley P (1993). "Thiacetazone—avoid like poison or use with care?". Trans R Soc Trop Med Hyg 87 (5): 578–82. doi:10.1016/0035-9203(93)90096-9. PMID 7505496.

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UpToDate Contents

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1. 薬剤耐性結核の診断、治療、および予防 diagnosis treatment and prevention of drug resistant tuberculosis

English Journal

Thiosemicarbazones and their antimycobacterial effects.

Opletalová V, Doležel J.SourceCharles University in Prague Faculty of Pharmacy in Hradec Králové, Department of Pharmaceutical Chemistry and Drug Analysis, Czech Republic. veronika.opletalova@faf.cuni.cz
Ceská a Slovenská farmacie : casopis Ceské farmaceutické spolecnosti a Slovenské farmaceutické spolecnosti.Ceska Slov Farm.2013 Apr;62(2):78-83.
Antimycobacterial effects of thiosemicarbazones were discovered in the late 1940s. The best known representative of these compounds is thioacetazone that has been used in the therapy of tuberculosis since the turn of the 1940s and 1950s. At present, it is used only rarely since it exhibits severe si
PMID 23822572

Recycling and refurbishing old antitubercular drugs: the encouraging case of inhibitors of mycolic acid biosynthesis.

Belardinelli JM, Morbidoni HR.SourceCátedra de Microbiología, Facultad de Ciencias Médicas, Universidad Nacional de Rosario, Santa Fe 3100 (2000), Rosario, Argentina.
Expert review of anti-infective therapy.Expert Rev Anti Infect Ther.2013 Apr;11(4):429-40. doi: 10.1586/eri.13.24.
One of the first approaches undertaken in the quest for antitubercular compounds was that of understanding the mechanism of action of old drugs and proposing chemical modifications or other strategies to improve their activity, generally lost to the mechanisms of resistance developed by Mycobacteriu
PMID 23566152

Synthesis, antitubercular activity and mechanism of resistance of highly effective thiacetazone analogues.

Coxon GD, Craig D, Corrales RM, Vialla E, Gannoun-Zaki L, Kremer L.SourceStrathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, Glasgow, United Kingdom. geoff.coxon@strath.ac.uk
PloS one.PLoS One.2013;8(1):e53162. doi: 10.1371/journal.pone.0053162. Epub 2013 Jan 3.
Defining the pharmacological target(s) of currently used drugs and developing new analogues with greater potency are both important aspects of the search for agents that are effective against drug-sensitive and drug-resistant Mycobacterium tuberculosis. Thiacetazone (TAC) is an anti-tubercular drug
PMID 23301038