Thioacetazone

Thioacetazone
Clinical data
Trade names	Conteben
Other names	Thiacetazone; Thiocetazone; Thioparamizone; Benzothiozane; 4-Acetylaminobenzaldehyde thiosemicarbazone; N-[4-[(Carbamothioylhydrazinylidene) methyl]phenyl]acetamide
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	J04AM04 (WHO) ;
Identifiers
	IUPAC name N-{4-[(Ethanethioamidoimino)methyl]phenyl}acetamide;
CAS Number	104-06-3 ;
PubChem CID	9568512;
ChemSpider	7843221 ;
UNII	MMG78X7SSR;
KEGG	D08584 ;
ChEMBL	ChEMBL375492 ;
CompTox Dashboard (EPA)	DTXSID80859179 DTXSID2022593, DTXSID80859179 ;
ECHA InfoCard	100.002.882
Chemical and physical data
Formula	C10H12N4OS
Molar mass	236.29 g·mol−1
3D model (JSmol)	Interactive image;
	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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Thioacetazone (INN, BAN), also known as amithiozone (USAN), is an oral antibiotic which is used in the treatment of tuberculosis.^[1]^[2]^[3]^[4] It has fallen into almost complete disuse due to toxicity and the introduction of improved anti-tuberculosis drugs like isoniazid.^[5] The drug has only weak activity against Mycobacterium tuberculosis and is only useful in preventing resistance to more powerful drugs such as isoniazid and rifampicin. It is never used on its own to treat tuberculosis; it is used in a similar way to ethambutol.

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.^[6]^[7]

The biological target of thioacetazone has proven elusive and its mechanism of action remains unknown, although it is thought to interfere with mycolic acid synthesis.^[4]

^ Buckingham J (2 December 1993). Dictionary of Natural Products. CRC Press. pp. 208–. ISBN 978-0-412-46620-5.
^ Martindale: The Extra Pharmacopoeia (30th ed.). London: The Pharmaceutical Press. 1993. p. 217. ISBN 978-0-85369-300-0.
^ "List of Antituberculosis agents - Generics Only". Drugs.com.
^ ^a ^b Grayson ML, Crowe SM, McCarthy JS, Mills J, Mouton JW, Norrby SR, Paterson DL, Pfaller MA (29 October 2010). "Thioacetazone". Kucers' The Use of Antibiotics: A Clinical Review of Antibacterial, Antifungal and Antiviral Drugs (Sixth ed.). CRC Press. pp. 1673–. ISBN 978-1-4441-4752-0.
^ Schaaf HS, Seddon JA, Caminero JA (2011). "Second-line Antituberculosis Drugs: Current Knowledge, Recent Research Findings and Controversies". In Donald PR, Van Helden PD (eds.). Antituberculosis Chemotherapy. Karger Medical and Scientific Publishers. pp. 92–. ISBN 978-3-8055-9627-5.
^ Rieder HL, Arnadottir T, Trébucq A, Enarson DA (January 2001). "Tuberculosis treatment: dangerous regimens?". The International Journal of Tuberculosis and Lung Disease. 5 (1): 1–3. PMID 11263509.
^ Nunn P, Porter J, Winstanley P (1993). "Thiacetazone--avoid like poison or use with care?". Transactions of the Royal Society of Tropical Medicine and Hygiene. 87 (5): 578–582. doi:10.1016/0035-9203(93)90096-9. PMID 7505496.

[Buckingham1993-1] Buckingham J (2 December 1993). Dictionary of Natural Products. CRC Press. pp. 208–. ISBN 978-0-412-46620-5.

[2] Martindale: The Extra Pharmacopoeia (30th ed.). London: The Pharmaceutical Press. 1993. p. 217. ISBN 978-0-85369-300-0.

[Drugs.com-3] "List of Antituberculosis agents - Generics Only". Drugs.com.

[GraysonCrowe2010-4] Grayson ML, Crowe SM, McCarthy JS, Mills J, Mouton JW, Norrby SR, Paterson DL, Pfaller MA (29 October 2010). "Thioacetazone". Kucers' The Use of Antibiotics: A Clinical Review of Antibacterial, Antifungal and Antiviral Drugs (Sixth ed.). CRC Press. pp. 1673–. ISBN 978-1-4441-4752-0.

[DonaldHelden2011-5] Schaaf HS, Seddon JA, Caminero JA (2011). "Second-line Antituberculosis Drugs: Current Knowledge, Recent Research Findings and Controversies". In Donald PR, Van Helden PD (eds.). Antituberculosis Chemotherapy. Karger Medical and Scientific Publishers. pp. 92–. ISBN 978-3-8055-9627-5.

[Rieder2001-6] Rieder HL, Arnadottir T, Trébucq A, Enarson DA (January 2001). "Tuberculosis treatment: dangerous regimens?". The International Journal of Tuberculosis and Lung Disease. 5 (1): 1–3. PMID 11263509.

[Nunn1993-7] Nunn P, Porter J, Winstanley P (1993). "Thiacetazone--avoid like poison or use with care?". Transactions of the Royal Society of Tropical Medicine and Hygiene. 87 (5): 578–582. doi:10.1016/0035-9203(93)90096-9. PMID 7505496.

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