89785-84-2 Usage
Uses
Used in Pharmaceutical Industry:
Tazobactam sodium is used as a beta-lactamase inhibitor for enhancing the effect of β-lactam antibiotics. It is particularly effective in combination with penicillinase inhibition studies and other beta-lactam antibiotics, improving their efficacy against a broad range of both Gram-positive and Gram-negative organisms.
Tazobactam sodium is used as an antibacterial agent for the treatment of various infections, including lower respiratory tract, urinary tract, intra-abdominal, biliary, and skin and soft tissue infections. It is expected to compete against other combination products like augmentin (amoxicillin/clavulanate) in the market.
Originator
Taiho (Japan)
Manufacturing Process
A known β-lactam type antibiotic (for example, benzhydryl 2-β-chloromethyl-
2-α-methylpenam-3-α-carboxylate) was used for synthesis of new penicillinic
derivatives.A solution of 5.00 g of sodium azide in 53 ml of water was added to a solution
of benzhydryl 2-β-chloromethyl-2-α-methylpenam-3-α-carboxylate (5.13 g) in
dimethylformamide (155 ml). The mixture was stirred at room temperature
for 4 h. The resulting reaction mixture was poured into cooled water and the
mixture was extracted with ethyl acetate. The ethyl acetate layer was washed
with water, dried over magnesium sulfate and concentrated to provide 4.87 g
of the benzhydryl 2-β-azidomethyl-2-α-methylpenam-3-α-carboxylate as oil in
93% yield.To a solution of benzhydryl 2-β-azidomethyl-2-α-methylpenam-3-α-
carboxylate (7.03 g) in a mixture of acetic acid (240 ml) and water (40 ml)
was added potassium permanganate (6.02 g) over a period of more than 1 h.
The mixture was stirred at room temperature for 2.5 h. The resulting reaction
mixture was diluted with ice water. The precipitate was collected by filtration,
and washed with water. The resulting product was dissolved in ethyl acetate
and the solution was washed with an aqueous solution of sodium hydrogen
carbonate and dried over magnesium sulfate. Concentration gave 5.48 g of
the benzhydryl 2-β-azidomethyl-2-α-methylpenam-3-α-carboxylate-1,1-dioxide
in 72% yield.A 200 mg quantity of benzhydryl 2-β-azidomethyl-2-α-methylpenam-3-α-
carboxylate-1,1-dioxide was reacted with 10 ml of vinyl acetate in a sealed reactor at 100° to 110°C for 30 h. The reaction mixture was concentrated at
reduced pressure. The residue was crystallized with cooled chloroform. The
white crystals of benzhydryl 2-α-methyl-2-β-(1,2,3-triazol-1-yl)methylpenam-
3-α-carboxylate-1,1-dioxide have a melting point 206°-208°C, dec.Hydrogenation was conducted in 10 ml of ethyl acetate and 10 ml of water at
room temperature for 30 min by using 45 mg of benzhydryl 2-α-methyl-2-β-
(1,2,3-triazol-1-yl)methylpenam-3-α-carboxylate-1,1-dioxide, 15 mg of 10%
palladium charcoal and 16 mg of sodium hydrogen carbonate. The aqueous
layer was separated from the reaction mixture and washed once with ethyl
acetate. The aqueous solution was then purified with an MCl gel, CHP-20P
(product of Mitsubishi Kasei Co., Ltd., Japan). After freeze-drying, there was
obtained an amorphous product of sodium 2-α-methyl-2-β-(1,2,3-triazol-1-
yl)methylpenam-3-α-carboxylate-1,1-dioxide with a melting point 170°C, dec.
Therapeutic Function
Antibiotic
Check Digit Verification of cas no
The CAS Registry Mumber 89785-84-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,9,7,8 and 5 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 89785-84:
(7*8)+(6*9)+(5*7)+(4*8)+(3*5)+(2*8)+(1*4)=212
212 % 10 = 2
So 89785-84-2 is a valid CAS Registry Number.
InChI:InChI=1/C10H12N4O5S.Na/c1-10(5-13-3-2-11-12-13)8(9(16)17)14-6(15)4-7(14)20(10,18)19;/h2-3,7-8H,4-5H2,1H3,(H,16,17);/q;+1/p-1/t7-,8+,10+;/m0./s1
89785-84-2Relevant articles and documents
PRODUCTION METHOD OF 2 ALPHA-METHYL-2 BETA-(1,2,3-TRIAZOLE-1-YL)-METHYL PENAM-3 ALPHA-CARBOXYLIC ACID 1,1-DIOXIDE-SODIUM HYDRATE CRYSTAL
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Paragraph 0035; 0037; 0038; 0039; 0041; 0043; 0044, (2018/05/24)
PROBLEM TO BE SOLVED: To provide an industrially advantageous production method of tazobactam sodium monohydrate crystal. SOLUTION: The present invention is a production method of a 2 alpha-methyl-2 beta-(1,2,3-triazolyl-1-yl)-methylpenam-3 alpha-carboxylic acid 1,1-dioxide sodium monohydrate crystal includes a step of reacting a basic sodium compound and 2 alpha-methyl-2 beta-(1,2,3-triazol-1-yl)-methyl penam-3 alpha-carboxylic acid 1,1-dioxide in a mixed solvent of water and an organic solvent to form a crystal of 2 alpha-methyl-2 beta-(1,2,3-triazol-1-yl)-methylpenam-3 alpha-carboxylic acid 1,1-dioxide sodium monohydrate in the mixed solvent. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPO&INPIT
A process for preparing an injectable sterile pharmaceutical formulation containing at least piperacillin sodium and tazobactam sodium as active principles
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Page/Page column 2-3, (2008/06/13)
Mixtures of at least two active principles, e.g. of piperacillin and tazobactam of which at least one is the sodium salt, are precipitated from an organic solution containing the same active principles in salified or non-salified acid form.
Process for preparation of penam derivatives
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Page/Page column 9-12, (2008/06/13)
The invention relates to novel processes for preparing penam derivatives, such as Tazobactam and derivatives thereof. The processes according to the invention encompass procedures for the protection and deprotection of the carboxylic group as well as for the oxidation of the sulphur moiety of penam derivatives. Additionally, the present invention relates to new intermediates for the production of penam derivatives, allowing the desired penam-derivatives to be formulated with high purity and in good yields.
Synthesis and β-lactamase inhibitory properties of 2β-[1,2,3-triazol-1-yl)methyl]-2α-methylpenam-3α-carboxylic acid 1,1-dioxide and related triazolyl derivatives
Micetich,Maiti,Spevak,Hall,Yamabe,Ishida,Tanaka,Yamazaki,Nakai,Ogawa
, p. 1469 - 1474 (2007/10/02)
Benzhydryl 2β-[(1,2,3-triazol-yl)methyl]-2α-methylpenam-3α-carboxylate 1,1-dioxide was prepared by heating benzhydryl 2β-(azidomethyl)-2α-methylpenam-3α-carboxylate 1,1-dioxide with (trimethylsilyl)acetylene. The ester group was removed by hydrogenolysis to give sodium 2β-[(1,2,3-triazol-1-yl)methyl]-2α-methylpenam-3α-carboxylate 1,1-dioxide (3i, YTR-830), which was found to be a potent inhibitor of various bacterial β-lactamases. A series of related compounds was prepared in a similar way, and all of these compounds show excellent β-lactamase inhibitory properties.
