Thioacetazone

Thioacetazone

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	J04AM04 (WHO)
Identifiers
IUPAC name N-{4-[(ethanethioamidoimino)methyl]phenyl}acetamide
Synonyms	N-[4-[(carbamothioylhydrazinylidene) methyl]phenyl]acetamide
CAS Number	104-06-3
PubChem (CID)	9568512
ChemSpider	7843221
UNII	MMG78X7SSR
KEGG	D08584
ChEMBL	CHEMBL375492
ECHA InfoCard	100.002.882
Chemical and physical data
Formula	C10H12N4OS
Molar mass	236.3
3D model (Jmol)	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 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

1. Rieder HL, Arnadottir T, Trebucq A, Enarson DA (2001). "Tuberculosis treatment: dangerous regimens?". Int J Tuberc Lung Dis. 5 (1): 1–3. PMID 11263509.
2. 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.