127-69-5 Hazards Identification
Pictogram(s):
Signal:
Warning
GHS Hazard Statements:
H315 (95.45%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (95.45%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
Precautionary Statement Codes:
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501
Hazard Classes and Categories:
Skin Irrit. 2 (95.45%)
Eye Irrit. 2 (95.45%)
STOT SE 3 (100%)
127-69-5 Usage
Uses
Used in Pharmaceutical Industry:
Sulfisoxazole is used as an antibacterial agent for the treatment of infections caused by sulfonamide-sensitive bacteria. It is particularly effective in the treatment of gram-negative urinary infections.
Used in Veterinary Medicine:
Sulfisoxazole is also used in veterinary medicine for the treatment of bacterial infections in animals, targeting a wide spectrum of gram-negative and gram-positive bacteria.
Brand Name:
Gantrisin (Roche) is a brand name under which Sulfisoxazole is marketed.
Originator
Gantrisin,Roche,US,1949
Manufacturing Process
112 parts of 3,4-dimethyl-5-amino-isoxazole were dissolved in a mixture of
100 volume parts of pyridine and 200 volume parts of acetone. The mixture is
cooled with cold water and 240 parts p-acetamino-benzene sulfonic acid
chloride are added in small portions under stirring at temperatures of below
30°C. The mixture is left standing overnight at 20° to 30°C and then the 5-
acetamino-benzene-sulfonylamino-3,4-dimethyl-isoxazole is precipitated by the addition of water. Recrystallized from acetic acid or alcohol it forms small
prisms of the melting point 210°C.100 parts of the 5-acetamino-benzene-sulfonyl-amino-3,4-dimethyl-isoxazole
are boiled under reflux with 500 volume parts 15 to 20% aqueous
hydrochloric acid for 30 to 45 minutes until all is dissolved. 500 parts
crystallized sodium acetate are added and the liquid left cooling for
crystallization. The sulfanilamido-3,4-dimethyl-isoxazole is sucked off, washed
with water and dried. In the pure state it forms white prisms with the melting
point of 193°C.
Therapeutic Function
Antibacterial
Antimicrobial activity
Like all examined sulfanilamides, this drug is effective in treating infections caused by
streptococci, gonococci, pneumococci, staphylococci, and also colon bacillus. However,
about 90% of it binds with proteins in the plasma after oral administration, and it diffuses mostly to tissues and tissue fluids, which makes it the drug of choice for many systemic infections. Synonyms of this drug are gantrisin, fultrxin, sulfazin, sulfolar, and
others.
Air & Water Reactions
May be sensitive to prolonged exposure to air and light. Sensitive to heat. Slightly soluble in water.
Fire Hazard
Flash point data for Sulfisoxazole are not available; however, Sulfisoxazole is probably combustible.
Pharmaceutical Applications
3,4-Dimethyl-5-sulfanilamidoisoxazole. It is highly soluble,
even in acid urine. The spectrum and potency are typical of
the group. It is well absorbed, achieving a concentration of
around 20 mg/L 3–4 h after a 2 g oral dose.
Side effects are those common to other sulfonamides. It
is less prone than some other members of the group to cause
renal problems. Its principal use is in urinary tract infection,
and is present in some ophthalmic preparations.
Biological Activity
A selective ET A endothelin receptor antagonist (IC 50 values are 600 and 2200 nM for ET A and ET B receptors respectively).
Safety Profile
Mildly toxic by ingestion. An experimental teratogen. Questionable carcinogen. Mutation data reported. When heated to decomposition it emits very toxic fumes of SOx and NOx.
Synthesis
Sulfisoxazole, N1
-(3,4-dimethyl-5-isoxazolyl)sulfanilamide (33.1.19), is
synthesized by reacting 4-acetylaminobenzenesulfonyl chloride with 5-amino-3,
4-dimethylisoxazol (33.1.17), which is in turn synthesized by heterocyclization of 2-methylacetylacetonitrile with hydroxylamine, and subsequent acidic hydrolysis (hydrochloric acid)
of the protective acetyl group in the resulting product (33.1.18).
Check Digit Verification of cas no
The CAS Registry Mumber 127-69-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 7 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 127-69:
(5*1)+(4*2)+(3*7)+(2*6)+(1*9)=55
55 % 10 = 5
So 127-69-5 is a valid CAS Registry Number.
InChI:InChI=1/C11H13N3O3S/c1-7-8(2)13-17-11(7)14-18(15,16)10-5-3-9(12)4-6-10/h3-6,14H,12H2,1-2H3
127-69-5Relevant academic research and scientific papers
N-Acylated derivatives of sulfamethoxazole and sulfafurazole inhibit intracellular growth of chlamydia trachomatis
Marwaha, Sania,Uvell, Hanna,Salin, Olli,Lindgren, Anders E. G.,Silver, Jim,Elofsson, Mikael,Gylfe, ?sa
supporting information, p. 2968 - 2971 (2014/05/06)
Antibacterial compounds with novel modes of action are needed for management of bacterial infections. Here we describe a high-content screen of 9,800 compounds identifying acylated sulfonamides as novel growth inhibitors of the sexually transmitted pathogen Chlamydia trachomatis. The effect was bactericidal and distinct from that of sulfonamide antibiotics, as para-Aminobenzoic acid did not reduce efficacy. Chemical inhibitors play an important role in Chlamydia research as probes of potential targets and as drug development starting points. Copyright
Sulfonamide molecular crystals: Structure, sublimation thermodynamic characteristics, molecular packing, hydrogen bonds networks
Perlovich, German L.,Ryzhakov, Alex M.,Tkachev, Valery V.,Hansen, Lars Kr.,Raevsky, Oleg A.
, p. 4002 - 4016 (2013/09/24)
The crystal structures of ten sulfonamides have been determined by X-ray diffraction. On the basis of our previous data, the obtained results and literature data crystal properties including molecular conformational states, packing architecture, and hydrogen bond networks were comparatively analyzed using graph set notations. Conformational flexibility of the bridge connecting two phenyl rings was studied. It was found out that the most frequently occurring graphs for compounds with a single hydrogen bond are infinite chains with four atoms included. The molecular packing architecture of the selected crystals may be conditionally divided into three different groups. The idea underlying such classification is the difference in structure and composition of molecular layers that can be singled out for most packings. The influence of various molecular fragments on crystal lattice energy was analyzed. A correlation between melting points and fragmental molecular interactions in the crystal lattices was obtained. The thermodynamic aspects of the sulfonamide sublimation were studied by determining the temperature dependence of vapor pressure using the transpiration method. A correlation between the Gibbs energy of the sublimation process and the melting points was found. Besides, a regression equation was derived to describe the correlation between the sublimation entropy terms and crystal density data calculated from X-ray diffraction results.
Virtual screening leads to the discovery of novel non-nucleotide P2Y 1 receptor antagonists
Costanzi, Stefano,Santhosh Kumar,Balasubramanian, Ramachandran,Kendall Harden,Jacobson, Kenneth A.
, p. 5254 - 5261 (2012/11/07)
The P2Y1 receptor (P2Y1R) is a G protein-coupled receptor naturally activated by extracellular ADP. Its stimulation is an essential requirement of ADP-induced platelet aggregation, thus making antagonists highly sought compounds for the development of antithrombotic agents. Here, through a virtual screening campaign based on a pharmacophoric representation of the common characteristics of known P2Y1R ligands and the putative shape and size of the receptor binding pocket, we have identified novel antagonist hits of μM affinity derived from a N,N′-bis-arylurea chemotype. Unlike the vast majority of known P2Y 1R antagonists, these drug-like compounds do not have a nucleotidic scaffold or highly negatively charged phosphate groups. Hence, our compounds may provide a direction for the development of receptor probes with altered physicochemical properties.
Discovery and synthesis of a potent sulfonamide ET(B) selective antagonist
Kanda, Yasuhiko,Takahashi, Tadashi,Araki, Yoshitaka,Konoike, Toshiro,Mihara, Shin-ichi,Fujimoto, Masafumi
, p. 1875 - 1878 (2007/10/03)
The synthesis and structure-activity relationships of a series of sulfonamide endothelin antagonists are described. In the course of our modification studies, we discovered ET(B) selective antagonists. The most potent compound 15f displays IC50 values of 1.7 μM and 0.002 μM to ET(A) and ET(B) receptors, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.
Process for formulating a synthetic drug for use in animal feed, and resulting formulation
-
, (2008/06/13)
A method of formulating a synthetic drug for use in animal feed, for the purpose of reducing carry-over of the synthetic drug to subsequent lots of animal feed in the feed mill.
