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HomeProduct name listTHIACETAZONE

THIACETAZONE

  • CAS NO.:104-06-3
  • Empirical Formula: C10H12N4OS
  • Molecular Weight: 236.29
  • MDL number: MFCD00022157
  • EINECS: 203-170-6
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-04 20:04:50
THIACETAZONE Structural

What is THIACETAZONE?

Chemical properties

Solid

The Uses of THIACETAZONE

Thiacetazone (cas# 104-06-3) is used in combination chemotherapy, in preparation of nucleosides as inhibitors of adenylate-forming enzyme MenE.

Indications

Thiacetazone is active against many strains of M. tuberculosis. It is not marketed in the United States. However, because of its low cost, it is used as a first-line agent in East Africa, especially in combination with compounds such as isoniazid. The most common side effects of thiacetazone include GI intolerance and development of rashes. It causes significant ototoxicity, especially when coadministered with streptomycin. Lifethreatening hypersensitivity reactions, such as hepatitis, transient marrow aplastic syndromes, neutropenia, and thrombocytopenia, have been reported.

Definition

ChEBI: Thioacetazone is a member of acetamides and an anilide.

Pharmaceutical Applications

Thioacetazone (USAN amithiozone) is a synthetic compound discovered during initial work on the sulfonamides, to which it is structurally related. It is only slightly soluble in water. It is a weak bacteristatic drug, with frequent serious side effects, particularly in HIV-positive persons to whom it must never knowingly be given. On the advice of the WHO it no longer has a place in the treatment of tuberculosis, except as a last resort in cases of extreme drug resistance.
In-vitro MICs vary considerably according to the medium used and bear little relation to in-vivo efficacy. Many strains of M. tuberculosis isolated in East Africa, India and Hong Kong are naturally more resistant than strains from Europe. Acquired resistance, as a result of monotherapy, is prevalent in the developing countries.
Thioacetazone is well absorbed, achieving a plasma concentration of 1–4 mg/L 2–4 h after a 100 mg oral dose. The plasma half-life is 8–12 h. Little is known about the distribution of the drug. Several metabolites are described. About 20% is eliminated in the urine; the fate of the remainder is unknown. Rashes are common, occurring in 2–4% of patients in Africa but much more frequently in those of Chinese ethnic origin. More severe skin reactions, exfoliative dermatitis and Stevens–Johnson syndrome occur in less than 0.5% of HIV-negative patients, but there is a 10-fold increase of these reactions in HIV-positive patients, proving fatal in up to 3% of such patients. Other common side effects include gastrointestinal reactions, vertigo and conjunctivitis. Less common reactions include hepatitis, erythema multiforme, hemolytic anemia and, rarely, agranulocytosis. Prolonged therapy may rarely lead to hypertrichosis, gynecomastia and osteoporosis. It is very rarely used, but may occasionally be considered (with other antituberculosis drugs) in extremely drug resistant tuberculosis.

Properties of THIACETAZONE

Melting point: 225-230 °C
Density  1.2752 (rough estimate)
refractive index  1.6440 (estimate)
storage temp.  Store at -20°C
solubility  Soluble in DMSO
form  powder to crystal
pka 11.35±0.70(Predicted)
color  White to Orange to Green

Safety information for THIACETAZONE

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
Precautionary Statement Codes P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P332+P313:IF SKIN irritation occurs: Get medical advice/attention.
P337+P313:IF eye irritation persists: Get medical advice/attention.

Computed Descriptors for THIACETAZONE

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