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^N
PubChem (CID)	9568512
ChemSpider	7843221^Y
UNII	MMG78X7SSR^Y
KEGG	D08584^Y
ChEMBL	CHEMBL375492^Y
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+^Y Key:SRVJKTDHMYAMHA-WUXMJOGZSA-N^Y
^NY (what is this?) (verify)

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.

Antibacterials: protein synthesis inhibitors (J01A, J01B, J01F, J01G, QJ01XQ)

30S

Aminoglycosides
(initiation inhibitors)

-mycin (Streptomyces)	Streptomycin^# Dihydrostreptomycin Neomycin^# Framycetin Paromomycin Ribostamycin Kanamycin^# Amikacin Arbekacin Bekanamycin Dibekacin Tobramycin Spectinomycin^# Hygromycin B Paromomycin

-micin (Micromonospora)	Gentamicin^# Netilmicin Sisomicin Plazomicin^† Isepamicin Verdamicin Astromicin

Tetracycline antibiotics
(tRNA binding)

Tetracyclines	Doxycycline^# Chlortetracycline Clomocycline Demeclocycline Lymecycline Meclocycline Metacycline Minocycline Oxytetracycline Penimepicycline Rolitetracycline Tetracycline

Glycylcyclines	Tigecycline

Fluorocyclines	Eravacycline^†

50S

Oxazolidinone
(initiation inhibitors)

Peptidyl transferase

Amphenicols	Chloramphenicol^# Azidamfenicol Thiamphenicol Florfenicol

Pleuromutilins	Retapamulin Tiamulin Valnemulin

MLS (transpeptidation/translocation)

Macrolides	Azithromycin^# Clarithromycin Dirithromycin Erythromycin^# Flurithromycin Josamycin Midecamycin Miocamycin Oleandomycin Rokitamycin Roxithromycin Spiramycin Troleandomycin Tylosin Ketolides Telithromycin Cethromycin Solithromycin^†

Lincosamides	Clindamycin^# Lincomycin Pirlimycin

Streptogramins	Pristinamycin Quinupristin/dalfopristin Virginiamycin

EF-G

Steroid antibacterials	Fusidic acid

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Antibacterials: cell envelope antibiotics (J01C-J01D)

Intracellular

Inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
DADAL/AR inhibitors (Cycloserine)
bactoprenol inhibitors (Bacitracin)

Glycopeptide

Inhibit PG chain elongation: Vancomycin^# (Oritavancin
Telavancin)
Teicoplanin (Dalbavancin)
Ramoplanin

β-lactams/
(inhibit PBP
cross-links)

Penicillins
(Penams)

Narrow spectrum

β-lactamase sensitive (1st generation)	Benzylpenicillin (G)^# Benzathine benzylpenicillin^# Procaine benzylpenicillin^# Phenoxymethylpenicillin (V)^# Propicillin^‡ Pheneticillin^‡ Azidocillin^‡ Clometocillin^‡ Penamecillin^‡

β-lactamase resistant (2nd generation)	Cloxacillin^# (Dicloxacillin Flucloxacillin) Oxacillin Nafcillin Methicillin^‡

Extended spectrum

Aminopenicillins (3rd generation)	Amoxicillin^# Ampicillin^# (Pivampicillin Hetacillin^‡ Bacampicillin^‡ Metampicillin^‡ Talampicillin^‡) Epicillin^‡

Carboxypenicillins (4th generation)	Ticarcillin Carbenicillin^‡ / Carindacillin^‡ Temocillin^‡

Ureidopenicillins (4th generation)	Piperacillin Azlocillin^‡ Mezlocillin^‡

Other	Mecillinam^‡ (Pivmecillinam^‡) Sulbenicillin^‡

Penems

Faropenem^‡

Carbapenems

Cephalosporins/Cephamycins
(Cephems)

1st generation (P Ec K)	Cefazolin^# Cefalexin ^# Cefadroxil Cefapirin Cefazedone^‡ Cefazaflur^‡ Cefradine^‡ Cefroxadine^‡ Ceftezole^‡ Cefaloglycin^‡ Cefacetrile^‡ Cefalonium^‡ Cefaloridine^‡ Cefalotin^‡ Cefatrizine^‡

2nd generation (H E N)	Cefaclor Cefotetan Cephamycin (Cefoxitin Cefprozil Cefuroxime Cefuroxime axetil Cefamandole^‡ Cefminox^‡ Cefonicid^‡ Ceforanide^‡ Cefotiam^‡ Cefbuperazone^‡ Cefuzonam^‡ Cefmetazole)^‡ Carbacephem^‡ (Loracarbef^‡)

3rd generation	Cefixime^# Ceftriaxone^# Antipseudomonal (Ceftazidime^# Cefoperazone) Cefdinir Cefcapene Cefdaloxime Ceftizoxime Cefmenoxime Cefotaxime Cefpiramide Cefpodoxime Ceftibuten Cefditoren Cefetamet^‡ Cefodizime^‡ Cefpimizole^‡ Cefsulodin^‡ Cefteram^‡ Ceftiolene^‡ Oxacephem (Flomoxef^‡ Latamoxef^‡)

4th generation (Pseudomonas)	Cefepime Cefozopran^‡ Cefpirome^‡ Cefquinome^‡

5th generation	Ceftaroline fosamil Ceftolozane Ceftobiprole

Veterinary	Ceftiofur Cefquinome Cefovecin

Monobactams

β-lactamase inhibitors

Combinations

Other

polymyxins/detergent
- Colistin
- Polymyxin B
depolarizing
- Daptomycin
Hydrolyze NAM-NAG
- lysozyme
Tyrothricin
- Gramicidin
- Tyrocidine
Isoniazid
Teixobactin

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Antibacterials: nucleic acid inhibitors (J01E, J01M)

Antifolates
(inhibits
purine metabolism,
thereby inhibiting
DNA and RNA synthesis)

DHFR inhibitor

2,4-Diaminopyrimidine
- Trimethoprim^#
- Brodimoprim
- Tetroxoprim
- Iclaprim^†

Sulfonamides
(DHPS inhibitor)

Short- acting	Sulfaisodimidine Sulfamethizole Sulfadimidine Sulfapyridine Sulfafurazole Sulfanilamide Prontosil Sulfathiazole Sulfathiourea

Intermediate- acting	Sulfamethoxazole Sulfadiazine^# Sulfamoxole

Long- acting	Sulfadimethoxine Sulfadoxine Sulfalene Sulfametomidine Sulfametoxydiazine Sulfamethoxypyridazine Sulfaperin Sulfamerazine Sulfaphenazole Sulfamazone

Other/ungrouped	Sulfacetamide Sulfadicramide Sulfametrole

Combinations

Trimethoprim/sulfamethoxazole^#

Topoisomerase
inhibitors/
quinolones/
(inhibits
DNA replication)

1st g.

Fluoro-
quinolones

2nd g.	Ciprofloxacin^# Ofloxacin Enoxacin^‡ Fleroxacin^‡ Lomefloxacin^‡ Nadifloxacin^‡ Norfloxacin^‡ Pefloxacin^‡ Rufloxacin^‡

3rd g.	Levofloxacin Balofloxacin^‡ Grepafloxacin^‡ Pazufloxacin^‡ Sparfloxacin^‡ Temafloxacin^‡ Tosufloxacin^‡

4th g.	Besifloxacin Gatifloxacin Finafloxacin Gemifloxacin Moxifloxacin Clinafloxacin^† Garenoxacin^‡ Prulifloxacin^‡ Sitafloxacin^‡ Trovafloxacin^‡/Alatrofloxacin^‡

Vet.	Danofloxacin Difloxacin Enrofloxacin Ibafloxacin Marbofloxacin Orbifloxacin Pradofloxacin Sarafloxacin

Newer non-fluorinated

Nemonoxacin

Related (DG)

Aminocoumarins: Novobiocin

Anaerobic DNA
inhibitors

Nitro- imidazole derivatives	Metronidazole^# Tinidazole Ornidazole

Nitrofuran derivatives	Nitrofurantoin^# Furazolidone^‡ Nifurtoinol

RNA synthesis

Rifamycins/ RNA polymerase	Rifampicin^# Rifabutin Rifapentine Rifaximin Rifalazil^§

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Antibacterials: others (J01X)

Other/ungrouped	bornane: Xibornol cresol: Clofoctol polyamine: Methenamine alpha hydroxy acid: Mandelic acid nitroquinoline: Nitroxoline pyran/fatty acid: Isoleucine-tRNA ligase inhibitors (Mupirocin)

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