127-69-5 Usage
Chemical Properties
white to cream powder
Originator
Gantrisin,Roche,US,1949
Uses
Sulfisoxazole is a sulfonamide based antibacterial that exhibits activity against wide spectrum of gram-negative and gram-positive bacterium.
Definition
ChEBI: A sulfonamide antibacterial with an oxazole substituent. It has antibiotic activity against a wide range of gram-negative and gram-positive organisms.
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.
Brand name
Gantrisin (Roche).
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.
General Description
Different sources of media describe the General Description of 127-69-5 differently. You can refer to the following data:
1. Sulfisoxazole’s plasmahalf-life is 6 hours. This compound is a white, odorless,slightly bitter, crystalline powder. Its pKa is 5.0. At pH 6,this sulfonamide has a water solubility of 350 mg in100 mL, and its acetyl derivative has a solubility of 110 mgin 100 mL of water.Sulfisoxazole possesses the action and the uses of othersulfonamides and is used for infections involving sulfonamide-sensitive bacteria. It is claimed to be effective in thetreatment of Gram-negative urinary infections.
2. Odorless white to yellowish crystalline powder. Slightly bitter taste. Acid to litmus.
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 articles and documents
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
, 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
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.
HALOGEN SUBSTITUTION AT THE ISOXAZOLE RING ENHANCES THE ACTIVITY OF N-(ISOXAZOLYL)SULFONAMIDE ENDOTHELIN ANTAGONISTS
Chan, Ming Fai,Raju, B.,Kois, Adam,Castillo, Rosario S.,Verner, Erik J.,et al.
, p. 2393 - 2398 (2007/10/03)
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