72-14-0 Usage
Chemical Properties
white to cream powder
Originator
Tiazol,C. and C.
Definition
ChEBI: A 1,3-thiazole compound having a 4-aminobenzenesulfonamido group at the 2-position.
Manufacturing Process
116 parts 4-acetamidobenzolsufonyl chloride (prepared from acetanilide and
chlorosulfonic acid) was mixed with 100 parts 2-aminothiasole in 1000 parts
water by cooling and stirred for some hours. The bis-amide obtained was
filtered off and re-crystallized from 50% ethanol to give bis-(pacetylaminobenzolsulfo)-
2-aminothiazol with MP: 129°C.10 parts above bis-amide was heated with 10% sodium hydroxide solution for
0.5 hour on water bath. On cooling and filtration the alkaline solution was
acidified with glacial acetic acid. The amide obtained was cleared by recrystallized
from water to give N1-2-thiazolylsulfanilamide; MP: 202°-203°C.
Brand name
Argazol;Bucosol;Chemiovis;Coryza;Crionil;Csp 500;Csp-250;Edifeno;Femakzem;Formotablin antidiarreico;Gyne-sulf;Gyn-sulf;Neosutrin;Polvos wilfe;Pomada wilfe;Prothiazol;Septex cream no. 2;Streptacillin;Sulfa-orzon;Sulfazol;Sulfhatose;Sulfintestin;Sulfopyrol;Sulfour;Sulfzol;Sulnac;Sulphatriad;Tampovagan pss;Thiadyl;Thiuramide;Tiadyl;Trimeto;Trisulpha;Trysul;Tylasul;Ufa 902-duo;Vetoprim mi;Wintrazol.
Therapeutic Function
Antibacterial
World Health Organization (WHO)
Sulfathiazole, a sulfonamide anti-infective agent, was introduced
more than 25 years ago for the treatment of bacterial infections. The importance of
sulfonamides has subsequently decreased as a result of increasing bacterial
resistance and their replacement by antibiotics which are generally more active
and less toxic. The sulfonamides are known to cause serious adverse effects such
as renal toxicity, sometimes fatal exfoliative dermatitis and erythema multiforma
and dangerous adverse reactions affecting blood formation such as
agranulocytosis and haemolytic or aplastic anaemia. Although preparations remain
available, use of the drug has been discontinued in many countries.
General Description
White crystalline powder. Is dimorphous: form I is consists of prismatic rods and form II of six-sided plates and prisms. Insoluble in water and soluble in dil aqueous acid and aqueous base.
Air & Water Reactions
May be sensitive to heat, air and light during long-term storage . Insoluble in water.
Reactivity Profile
Sulfathiazole is an amino acid.
Fire Hazard
Flash point data for Sulfathiazole are not available, but Sulfathiazole is probably combustible.
Pharmaceutical Applications
2-Sulfanilamidothiazole. A short-acting compound (half-life
c. 4 h) with relatively high activity. Protein binding is c. 75%.
Its use has declined because of a high incidence of side effects.
It is one of the constituents of triple sulfonamide mixtures, of
which local preparations are still available.
Two compounds, phthalylsulfathiazole (sulfathalidine) and
succinylsulfathiazole (sulfasuxidine) owe their activity to the
slow liberation of sulfathiazole in the bowel. They are poorly
soluble and very little is absorbed after oral administration.
They were formerly used in the treatment of intestinal infections
and in bowel preparation before surgery. They are available
in multi-ingredient preparations in some countries.
Biochem/physiol Actions
Sulfonamide antibiotic that blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase.Mode of Action: Inhibits folic acid synthesis in prokaryotes.Anti-microbial Spectrum: Gram positive, Gram negative, ChlamydiaMode of Resistance: Alteration of dihydropteroate synthase or alternative pathway for folic acid synthesis.
Safety Profile
Human poison by
unspecified route. Experimental poison by
intraperitoneal route, Moderately toxic by
intravenous, subcutaneous, and parenteral
routes. Mildly toxic by ingestion. Human
systemic effects by unspecified route:
conjunctiva irritation, tubule changes, and
allergic skin dermatitis. Experimental
reproductive effects. Questionable
carcinogen with experimental tumorigenic
data, Mutation data reported. When heated
to decomposition it emits very toxic fumes
of NOx and SOx.
Check Digit Verification of cas no
The CAS Registry Mumber 72-14-0 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 2 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 72-14:
(4*7)+(3*2)+(2*1)+(1*4)=40
40 % 10 = 0
So 72-14-0 is a valid CAS Registry Number.
InChI:InChI=1/C9H9N3O2S2/c10-7-1-3-8(4-2-7)16(13,14)12-9-11-5-6-15-9/h1-6H,10H2,(H,11,12)
72-14-0Relevant articles and documents
USE OF LIME SLURRIES FOR SAPONIFYING CARBOMETHOXYSULFATHIAZOLE IN THE MANUFACTURE OF SULFATHIAZOLE
Kushkin, V. V.,Tupikina, V. G.
, p. 434 - 435 (1981)
-
-
Noll et al.
, p. 340 (1951)
-
Intensified Crystallization Processes for 1:1 Drug-Drug Cocrystals of Sulfathiazole-Theophylline, and Sulfathiazole-Sulfanilamide
Yeh, Kuan Lin,Lee, Tu
, p. 1339 - 1349 (2018/03/13)
The chemical synthesis and crystallization steps were integrated successfully for directly producing a 1:1 cocrystal of sulfathiazole-theophylline and a 1:1 cocrystal of sulfathiazole-sulfanilamide. The benefits of this process intensification were the reduction of number of steps, and the amount of energy consumption and solvent used. In addition, the overall cocrystal yields by Intensified Method I were much higher than the ones by the conventional method. Intensified Method I also gave high-purity cocrystals of ≥99%. Sulfathiazole not forming cocrystals with sulfanilamide by Intensified Method I was dissolved in the mother liquor by taking advantage of the pH-dependent solubility of sulfathiazole. Cocrystals of both sulfathiazole-theophylline and sulfathiazole-sulfanilamide systems remained stable under conditions of 40 °C and 75% relative humidity for a month.
Structure-based virtual screening and optimization of modulators targeting Hsp90-Cdc37 interaction
Wang, Lei,Li, Li,Zhou, Zi-Han,Jiang, Zheng-Yu,You, Qi-Dong,Xu, Xiao-Li
, p. 63 - 73 (2017/05/10)
Identification of novel Hsp90 inhibitors to disrupt Hsp90-Cdc37 protein-protein interaction (PPI) could be an alternative strategy to achieve Hsp90 inhibition. In this paper, a series of small molecules targeting Hsp90-Cdc37 complex are addressed and characterized. The molecules' key characters are determined by utilizing a structure-based virtual screening workflow, derivatives synthesis, and biological evaluation. Structural optimization and structure–activity relationship (SAR) analysis were then carried out on the virtual hit of VS-8 with potent activity, which resulted in the discovery of compound 10 as a more potent regulator of Hsp90-Cdc37 interaction with a promising inhibitory effect (IC50?=?27?μM), a moderate binding capacity (KD?=?40?μM) and a preferable antiproliferative activity against several cancer lines including MCF-7, SKBR3 and A549?cell lines (IC50?=?26?μM, 15?μM and 38?μM respectively). All the data suggest that compound 10 exhibits moderate inhibitory effect on Hsp90-Cdc37 and could be regard as a first evidence of a non-natural compound targeting Hsp90-Cdc37 PPI.