Thioacetazone

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 470606762

| IUPAC_name = N-{4-[(Ethanethioamidoimino)methyl]phenyl}acetamide

| image = Thioacetazone.svg

| alt = Structural formula of thioacetazone

| width = 250

| image2 = Thioacetazone 3D spacefill.png

| alt2 = Space-filling model of thioacetazone

| width2 = 225

| tradename = Conteben

| Drugs.com = {{drugs.com|international|thioacetazone}}

| routes_of_administration = Oral

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 104-06-3

| ATC_prefix = J04

| ATC_suffix = AM04

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 375492

| PubChem = 9568512

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 7843221

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = MMG78X7SSR

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D08584

| C=10 | H=12 | N=4 | O=1 | S=1

| smiles = O=C(Nc1ccc(cc1)\C=N\NC(=S)N)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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+

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = SRVJKTDHMYAMHA-WUXMJOGZSA-N

| synonyms = Thiacetazone; Thiocetazone; Thioparamizone; Benzothiozane; 4-Acetylaminobenzaldehyde thiosemicarbazone; N-[4-[(Carbamothioylhydrazinylidene) methyl]phenyl]acetamide

}}

Thioacetazone (INN, BAN), also known as amithiozone (USAN), is an oral antibiotic which is used in the treatment of tuberculosis.{{cite book| vauthors = Buckingham J |title=Dictionary of Natural Products|url=https://books.google.com/books?id=1W0NUD42fA4C&pg=PA208|date=2 December 1993|publisher=CRC Press|isbn=978-0-412-46620-5|pages=208–}}{{cite book |title=Martindale: The Extra Pharmacopoeia |date=1993 |publisher=The Pharmaceutical Press |location=London |isbn=978-0-85369-300-0 |edition=30th | page = 217}}{{Cite web|url=https://www.drugs.com/international/thioacetazone.html|title=List of Antituberculosis agents - Generics Only | work = Drugs.com }} It has fallen into almost complete disuse due to toxicity and the introduction of improved anti-tuberculosis drugs like isoniazid.{{cite book| vauthors = Schaaf HS, Seddon JA, Caminero JA | chapter = Second-line Antituberculosis Drugs: Current Knowledge, Recent Research Findings and Controversies | veditors = Donald PR, Van Helden PD |title=Antituberculosis Chemotherapy | chapter-url=https://books.google.com/books?id=r37jwNmr4sMC&pg=PA92|year=2011|publisher=Karger Medical and Scientific Publishers|isbn=978-3-8055-9627-5|pages=92–}} 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.{{cite journal | vauthors = Rieder HL, Arnadottir T, Trébucq A, Enarson DA | title = Tuberculosis treatment: dangerous regimens? | journal = The International Journal of Tuberculosis and Lung Disease | volume = 5 | issue = 1 | pages = 1–3 | date = January 2001 | pmid = 11263509 }}{{cite journal | vauthors = Nunn P, Porter J, Winstanley P | title = Thiacetazone--avoid like poison or use with care? | journal = Transactions of the Royal Society of Tropical Medicine and Hygiene | volume = 87 | issue = 5 | pages = 578–582 | year = 1993 | pmid = 7505496 | doi = 10.1016/0035-9203(93)90096-9 }}

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.{{cite book | vauthors = Grayson ML, Crowe SM, McCarthy JS, Mills J, Mouton JW, Norrby SR, Paterson DL, Pfaller MA | chapter = Thioacetazone |title= Kucers' The Use of Antibiotics: A Clinical Review of Antibacterial, Antifungal and Antiviral Drugs | edition = Sixth | chapter-url= https://books.google.com/books?id=XR3cBQAAQBAJ&pg=PA1673 |date= 29 October 2010 |publisher= CRC Press |isbn= 978-1-4441-4752-0 |pages= 1673–}}