89785-84-2 Usage
Description
Tazobactam sodium is a new triazolylmethyl beta-lactamase inhibitor launched in
combination with the antibiotic piperacillin as tazocilline. Tazobactam sodium is
active against penicillinases and wide spectrum of beta-lactamases. The combination
product tazobactdpiperacillin is effective against a broad range of both
Gram-positive and -negative organisms and is indicated for the treatment of lower
respiratory tract, urinary tract, intra-abdominal, biliary and skin and soft tissue
infections. It is expected to compete against the combination product augmentin
(amoxicillidclavulanate).
Chemical Properties
White to off-white powder
Originator
Taiho (Japan)
Uses
Different sources of media describe the Uses of 89785-84-2 differently. You can refer to the following data:
1. Lactamase inhibitor, used with ?lactam antibiotics to enhance their effect
2. β-Lactamase inhibitor, used with β-lactam antibiotics to enhance their effect.
3. A β-lactamase inhibitor and antibacterial agent
4. Tazobactam sodium is a beta-Lactamase inhibitor, which is used with penicillinase inhibition studies and beta-lactam antibiotics to enhance their effect. It serves as an antibacterial penicillin derivative, which inhibits the action of bacterial beta-lactamases.
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.
Brand name
Tazocilline
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
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.
