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Tazobactam sodium

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Tazobactam sodium Basic information

Product Name:
Tazobactam sodium
Synonyms:
  • TAZOBACTAM SODIUM
  • TAZOBACTAM SODIUM SALT
  • 2-alpha-methyl-2-beta-(1,2,3-triazol-1-ylmethyl)penam-3-alpha-carboxylicacid
  • 3-methyl-7-oxo-3-(1h-1,2,3-triazol-1-ylmethyl)-,4,4-dioxide,sodiumsalt,(2s-(2-alpha,3-beta,5-alp4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylicaci
  • 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylicacid,3-methyl-7-oxo-3-(1h-1,2,3
  • cl307579
  • [2s-(2α,3β,5α)]-3-methyl-7-oxo-3(1h,2,3-triazol-1-ylmethyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide
  • CL-298741, YTR-830H, [2S-(2α, 3β, 5α)]-3-Methyl-7-oxo-3(1H,2,3-triazol-1-ylmethyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide
CAS:
89785-84-2
MF:
C10H12N4NaO5S
MW:
323.28
EINECS:
685-629-4
Product Categories:
  • Antibiotic
  • pharmaceutical
  • Active Pharmaceutical Ingredients
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
Mol File:
89785-84-2.mol
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Tazobactam sodium Chemical Properties

Melting point:
140-147°C
Boiling point:
77℃
Flash point:
>110°(230°F)
storage temp. 
Keep in dark place,Inert atmosphere,2-8°C
solubility 
H2O: 50 mg/mL, clear, colorless
form 
powder
color 
white
optical activity
[α]/D 144±4°, c = 0.1 in H2O
Water Solubility 
Soluble in water.Soluble in water and methanol.
Stability:
Hygroscopic
CAS DataBase Reference
89785-84-2(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
22-24/25-36-26
WGK Germany 
3
RTECS 
XI0191500
HS Code 
2941900000

MSDS

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Tazobactam sodium Usage And Synthesis

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

Lactamase inhibitor, used with ?lactam antibiotics to enhance their effect

Uses

β-Lactamase inhibitor, used with β-lactam antibiotics to enhance their effect.

Uses

A β-lactamase inhibitor and antibacterial agent

Uses

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.

Definition

ChEBI: Tazobactam sodium is an organic sodium salt having tazobactam(1-) as the counterion; used in combination with ceftolozane sulfate for treatment of complicated intra-abdominal infections and complicated urinary tract infections. It has a role as an antimicrobial agent, an antiinfective agent and an EC 3.5.2.6 (beta-lactamase) inhibitor. It contains a tazobactam(1-).

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

Tazobactam sodium Preparation Products And Raw materials

Preparation Products

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