3511-16-8 Usage
Description
7-(2,2-DIMETHYL-5-OXO-4-PHENYL-IMIDAZOLIDIN-1-YL)-3,3-DIMETHYL-6-OXO-2-THIA-5-AZABICYCLO[3.2.0]HEPTANE-4-CARBOXYLIC ACID is a complex organic compound with a unique chemical structure. It belongs to the class of β-lactam antibiotics, which are widely used in the medical field for their potent antibacterial properties. This specific compound is characterized by its imidazolidinyl and phenyl groups, as well as its thia-azabicyclo[3.2.0]heptane core, which contribute to its biological activity and potential applications.
Uses
Used in Pharmaceutical Industry:
7-(2,2-DIMETHYL-5-OXO-4-PHENYL-IMIDAZOLIDIN-1-YL)-3,3-DIMETHYL-6-OXO-2-THIA-5-AZABICYCLO[3.2.0]HEPTANE-4-CARBOXYLIC ACID is used as a β-lactam antibiotic for the treatment of bacterial infections. Its potent antibacterial activity makes it a valuable asset in combating various types of bacterial pathogens, including those resistant to other antibiotics.
Used in Medical Research:
In addition to its direct application as an antibiotic, this compound may also be used in medical research to study the mechanisms of bacterial resistance and the development of new antibiotics. Its unique chemical structure can provide insights into the design and synthesis of novel antibacterial agents.
Brand Name:
The brand name for this compound, when formulated as a pharmaceutical product, is Hetacillin, which is marketed under the brand name Versapen-K by Bristol-Myers Squibb. This formulation is specifically designed to enhance the bioavailability and efficacy of the antibiotic, making it a more effective treatment option for patients suffering from bacterial infections.
Originator
Natacillin,Bristol Banyu,Japan,1970
Manufacturing Process
To 100 grams of α-aminobenzylpenicillin slurried in 2,500 ml of acetone is
added 200 ml of a 22% solution of potassium ethylhexanoate in dry n-butanol
and the mixture is warmed to 45°C whereupon the acid dissolves. After the
mixture is agitated for 1 hour at 40° to 45°C, the product begins to crystallize
out. Agitation is continued for 4 hours at 45°C after which the product, the
potassium salt of hetacillin, is collected by filtration, washed with 500 ml of
dry acetone, dried for 17 hours at 40°C and found to weigh 70.0 grams.
Therapeutic Function
Antibacterial
Check Digit Verification of cas no
The CAS Registry Mumber 3511-16-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,5,1 and 1 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 3511-16:
(6*3)+(5*5)+(4*1)+(3*1)+(2*1)+(1*6)=58
58 % 10 = 8
So 3511-16-8 is a valid CAS Registry Number.
InChI:InChI=1/C19H23N3O4S/c1-18(2)13(17(25)26)21-15(24)12(16(21)27-18)22-14(23)11(20-19(22,3)4)10-8-6-5-7-9-10/h5-9,11-13,16,20H,1-4H3,(H,25,26)/t11-,12-,13+,16-/m1/s1
3511-16-8Relevant articles and documents
Chemical reactivity of penicillins and cephalosporins. Intramolecular involvement of the acyl-amido side chain
Llinas, Antonio,Vilanova, Bartolome,Frau, Juan,Munoz, Francisco,Donoso, Josefa,Page, Michael I.
, p. 9052 - 9060 (2007/10/03)
The rate of degradation of 6-epi-ampicillin in acidic, neutral, and alkaline aqueous solutions was followed at 35 °C and an ionic strength of 0.5 mol dm-3 (KCl) by high-performance liquid chromatography (HPLC) and spectrophotometric assays. Pseudo-first-order rate constants were determined in a variety of buffer solutions, and the overall pH-rate profile was obtained by extrapolation to zero buffer concentration. The hydrolysis of 6- epi-ampicillin is subject to acid and hydroxide-ion catalysis and, for a penicillin, an unusual pH-independent reaction. Intramolecular general base- catalyzed hydrolysis by the side chain amido group is proposed to explain the enhanced rate of neutral hydrolysis of 6-epi-ampicillin and cephalosporins. The β-lactam of 6-epi-ampicillin also undergoes intramolecular aminolysis by nucleophilic attack of the 6-α side chain amino group to give a stable piperazine-2,5-dione derivative. The low effective molarity for intramolecular aminolysis of only 40 M is partly attributed to the unfavorable trans to cis isomerization about the 6-amide side chain required for ring closure. Theoretical calculations show that the intramolecular aminolysis of 6-epi-ampicillin nucleophilic attack occurs from the α-face of the β-lactam ring with an activation energy of 14.4 kcal/mol.