144-80-9 Usage
Chemical Properties
white crystalline powder
Originator
Sulamyd,Schering,US,1941
Uses
Different sources of media describe the Uses of 144-80-9 differently. You can refer to the following data:
1. Sulfacetamide is an antibiotic used for the treatment of skin infections and urinary tract infections. Sulfacetamide is also used to treat acne and seborrheic dermatitis. Sulfacetamide was investigated for potential anti-inflammatory properties
2. Sulfacetamide is an antibiotic used for the treatment of skin infections and urinary tract infections. Sulfacetamide is also used to treat acne and seborrheic dermatitis. Sulfacetamide was investigate
d for potential anti-inflammatory properties
Definition
ChEBI: A sulfonamide that is sulfanilamide acylated on the sulfonamide nitrogen.
Manufacturing Process
17.2 grams of 4-aminobenzene-sulfonamide are heated to boiling with 75 cc
of acetic anhydride for 1 hour and thereupon the diacetyl product caused to
separate by stirring into ice water. After recrystallization from alcohol the 4-
acetylaminobenzene-sulfonacetyl-amide forms colorless prisms of melting
point 253°C with decomposition. The product is easily soluble in alkalies and
forms neutral salts. The acetylation can also take place with acetyl chloride.
Instead of the 4-aminobenzene-sulfonamide also 4-acetylaminobenzenesulfonamide
can be employed. The action of 4-acetylaBy heating the diacetyl compound with sodium hydroxide solution partial
saponification of the acetyl groups takes place. 25.6 grams of diacetyl
compound are heated to boiling for some hours with 100 cc of 2N sodium
hydroxide solution. The precipitate produced by acidification of the solution
with acetic acid is filtered off and treated with dilute sodium carbonate
solution. The 4-aminobenzene-sulfonacetylamide passes into solution while
the simultaneously formed 4-acetylaminobenzene-sulfonamide remains
undissolved. It is filtered with suction and the filtrate again acidified with
acetic acid. The 4-aminobenzene-sulfon-acetamide separates out and is
recrystallized from water. It forms colorless lustrous rhombic crystals of MP
181°C.
Therapeutic Function
Antimicrobial
General Description
Different sources of media describe the General Description of 144-80-9 differently. You can refer to the following data:
1. Sulfacetamide’s plasmahalf-life is 7 hours. This compound is a white crystallinepowder, soluble in water (1:62.5 at 37°C) and in alcohol. It is very soluble in hot water, and its water solution is acidic.It has a pKa of 5.4.
2. White powder.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
N-((4-Aminophenyl)sulfonyl)acetamide is an amide. Organic amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generate mixed oxides of nitrogen (NOx)
Fire Hazard
Flash point data for N-((4-Aminophenyl)sulfonyl)acetamide are not available. N-((4-Aminophenyl)sulfonyl)acetamide is probably combustible.
Pharmaceutical Applications
N-acetylsulfanilamide. It is very soluble in water and was
formerly used in urinary tract infection. It is available in
some countries in ophthalmic preparations and as a component
(with sulfathiazole and sulfabenzamide) of a triple
sulfonamide cream for the topical treatment of bacterial
vaginosis.
Sulfacetamide is one of the least active sulfonamides. It
is well absorbed when given orally and is excreted in the
urine with a half-life of around 9 h. About 70% is excreted
unchanged, the remainder being present as the acetyl metabolite.
Adverse reactions are those common to the group.
Stevens–Johnson syndrome has been reported several times
after topical use in conjunctivitis.
Biochem/physiol Actions
Sulfacetamide is a sulfonamide antibiotic that blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase. Sulfacetamide is a competitive inhibitor of bacterial para-aminobenzoic acid (PABA), which is required for bacterial synthesis of folic acid. It is active against Gram positive bacteria, Gram negative bacteria and Chlamydia. Mode of resistance is via the alteration of dihydropteroate synthase or alternative pathway for folic acid synthesis.
Safety Profile
Mildly toxic by ingestion and intravenous routes. An experimental teratogen. Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and SOx.
Synthesis
Sulfacetamide, N1
-acetylsulfanilamide (33.1.44), is synthesized either
by direct alkylation of acetamide with 4-aminobenzenesulfonyl chloride, or by reacting
4-aminobenzenesulfonamide with acetic anhydride and subsequent selective, reductive deacylation of the resulting acetamide 33.1.45 using a system of zinc–sodium hydroxide.
Purification Methods
Crystallise the amide from aqueous EtOH. [Beilstein 14 IV 2662.]
Check Digit Verification of cas no
The CAS Registry Mumber 144-80-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,4 and 4 respectively; the second part has 2 digits, 8 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 144-80:
(5*1)+(4*4)+(3*4)+(2*8)+(1*0)=49
49 % 10 = 9
So 144-80-9 is a valid CAS Registry Number.
InChI:InChI=1/C6H7NO3/c1-4(8)7-5(9)2-3-6(7)10/h2-3H2,1H3
144-80-9Relevant articles and documents
Exploring Ligand-Directed N-Acyl- N-alkylsulfonamide-Based Acylation Chemistry for Potential Targeted Degrader Development
Bae, Jae Hyun,Dhe-Paganon, Sirano,Donovan, Katherine A.,Ficarro, Scott B.,Fischer, Eric S.,Gray, Nathanael S.,Jiang, Jie,Marto, Jarrod A.,Seo, Hyuk-Soo,Teng, Mingxing,Zhang, Tinghu
, p. 1302 - 1307 (2021)
Ligand-directed bioconjugation strategies have been used for selective protein labeling in live cells or tissue samples in applications such as live-cell imaging. Here we hypothesized that a similar strategy could be used for targeted protein degradation. To test this possibility, we developed a series of CDK2-targeting N-acyl-N-alkylsulfonamide (NASA)-containing acylation probes. The probes featured three components: a CDK2 homing ligand, a CRL4CRBN E3 ligase recruiting ligand, and a NASA functionality. We determined that upon target binding, NASA-mediated reaction resulted in selective functionalization of Lys89 on purified or native CDK2. However, we were unable to observe CDK2 degradation, which is in contrast to the efficient degradation achieved by the use of a structurally similar reversible bivalent degrader. Our analysis suggests that the lack of degradation is due to the failure to form a productive CDK2:CRBN complex. Therefore, although this work demonstrates that NASA chemistry can be used for protein labeling, whether this strategy could enable efficient protein degradation remains an open question.
Ofloxacin-sulfacetamide hybrid drug as well as preparation method and application thereof
-
Paragraph 0030-0034; 042-0043, (2019/03/31)
The invention provides an ofloxacin-sulfacetamide hybrid drug as well as a preparation method and application thereof. The ofloxacin-sulfacetamide hybrid drug is prepared from acidized sulfacetamide sodium and ofloxacin under catalysis of dicyclohexylcarbodiimide. According to the ofloxacin-sulfacetamide hybrid drug disclosed by the invention, the ofloxacin is spliced onto sulfacetamide by formingcovalent bonds, so that the hybrid drug has properties of the ofloxacin and the sulfacetamide. Since mycobacterium tuberculosis difficultly produces drug resistance to sulfonamide drugs, the ofloxacin-sulfacetamide hybrid drug disclosed by the invention has excellent drug tolerance on the mycobacterium tuberculosis. Meanwhile, the ofloxacin and the sulfacetamide in the ofloxacin-sulfacetamide hybrid drug can be respectively combined with different targets, the pharmacological activity can be enhanced, and respective corresponding toxic and side effects are reduced.
Compound capable of inhibiting activity of NEDD8 kinase as well as preparation method and pharmaceutical application of compound
-
, (2016/10/10)
The invention belongs to the field of medicines and in particular relates to a compound with the structure of a formula I, a stereomer of the compound or pharmaceutically acceptable salts of the compound as well as a preparation method of the compound and application of the compound to preparation of anti-tumor medicines. A pharmacological experiment result shows that the compound can be used for inhibiting the activity of NEDD8 kinase and has the inhibition effect on proliferation of a plurality of types of tumor cells, so that the compound can be used as an NEDD8 kinase activity inhibitor for preparing the anti-tumor medicines. The formula I is shown in the description.
