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Tazobactam acid

Product Name
Tazobactam acid
CAS No.
89786-04-9
Chemical Name
Tazobactam acid
Synonyms
TAZOBACTAM;(2S,3S,5R)-3-Methyl-7-oxo-3-(1H-1,2,3-triazol-1-ylmethyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;ytr83oh;cl298741;YTR-830H;Tazobactamum;7-Methyl-2H-1;He (the temple;TAZOBACTAN ACID;tazobactam acid
CBNumber
CB7473784
Molecular Formula
C10H12N4O5S
Formula Weight
300.29
MOL File
89786-04-9.mol
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Tazobactam acid Property

Melting point:
115-145℃
Boiling point:
77℃
Density 
1.92±0.1 g/cm3(Predicted)
RTECS 
XI0191400
Flash point:
>110°(230°F)
storage temp. 
Sealed in dry,Store in freezer, under -20°C
solubility 
DMSO (Slightly, Heated), Methanol (Slightly, Heated, Sonicated)
form 
Solid
pka
2.33±0.40(Predicted)
color 
White to Off-White
Water Solubility 
Soluble in water
Stability:
Light Sensitive
InChI
InChI=1S/C10H12N4O5S/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)/t7-,8+,10+/m1/s1
InChIKey
LPQZKKCYTLCDGQ-WEDXCCLWSA-N
SMILES
N12[C@@]([H])(CC1=O)S(=O)(=O)[C@@](C)(CN1C=CN=N1)[C@@H]2C(O)=O
CAS DataBase Reference
89786-04-9(CAS DataBase Reference)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
3
HS Code 
2941106000
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHR1686
Product name
Tazobactam
Purity
Pharmaceutical Secondary Standard; Certified Reference Material
Packaging
1g
Price
$111
Updated
2024/03/01
Sigma-Aldrich
Product number
1643383
Product name
Tazobactam
Packaging
200mg
Price
$474
Updated
2024/03/01
TCI Chemical
Product number
T3732
Product name
Tazobactam
Purity
>97.0%(HPLC)(T)
Packaging
1g
Price
$71
Updated
2024/03/01
TCI Chemical
Product number
T3732
Product name
Tazobactam
Purity
>97.0%(HPLC)(T)
Packaging
5g
Price
$212
Updated
2024/03/01
Alfa Aesar
Product number
J66483
Product name
Tazobactam
Purity
94%
Packaging
1g
Price
$127.65
Updated
2024/03/01
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Tazobactam acid Chemical Properties,Usage,Production

Description

Tazobactam often is coadministered with piperacillin because of tazobactam's ability to inhibit β-lactamases. T azobactam, like other β-lactamase inhibitors, has little or no antibacterial activity. This effect is analogous to that of clavulanic acid and sulbactam.

Chemical Properties

White or off-white powder

Originator

CL-307579,China Pharm Chemical Co.,,China

Uses

b-lactamase inhibitor

Uses

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

Definition

ChEBI: A member of the class of penicillanic acids that is sulbactam in which one of the exocyclic methyl hydrogens is replaced by a 1,2,3-triazol-1-yl group; used (in the form of its sodium salt) in combination with ceftolozane sulfate for treatment of complicat d intra-abdominal infections and complicated urinary tract infections.

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

Antimicrobial activity

Tazobactam exhibits little useful antimicrobial activity, although weak activity against Acinetobacter spp. and Borrelia burgdorferi has been reported.

Mechanism of action

Tazobactam functions as an irreversible inhibitor by covalently binding to β-lactamases, and prevents the enzyme hydrolysis of ceftolozane, thereby enhancing its activity against resistant ESBL-producing pathogens, along with expanding coverage to include anaerobes (e.g., Bacteroides spp.)

Clinical Use

Tazobactam is a penicillanic acid sulfone that is similar instructure to sulbactam. It is a more potent β-lactamaseinhibitor than sulbactam and has a slightly broader spectrumof activity than clavulanic acid. It has very weak antibacterialactivity. Tazobactam is available in fixed-dose, injectablecombinations with piperacillin, a broad-spectrum penicillinconsisting of an 8:1 ratio of piperacillin sodium to tazobactamsodium by weight and marketed under the trade name Zosyn.The pharmacokinetics of the two drugs are very similar. Bothhave short half-lives (t1/2 ~1 hour), are minimally proteinbound, experience very little metabolism, and are excreted inactive forms in the urine in high concentrations.
Approved indications for the piperacillin–tazobactamcombination include the treatment of appendicitis, postpartumendometritis, and pelvic inflammatory disease caused byβ-lactamase–producing E. coli and Bacteroides spp., skin andskin structure infections caused by β-lactamase–producingS. aureus, and pneumonia caused by β-lactamase–producingstrains of H. influenzae.

Veterinary Drugs and Treatments

Although veterinary experience is limited with piperacillin or piperacillin/ tazobactam, these drugs have expanded coverage against many bacteria and may be suitable for empiric use until culture and susceptibility data are available, or for surgical prophylaxis when gram-negative or mixed aerobic/anaerobic infections are concerns.

Drug interactions

Potentially hazardous interactions with other drugs
Reduced excretion of methotrexate - monitor methotrexate levels during concomitant treatment.
Enhanced action of vecuronium and similar neuromuscular blocking agents.

Metabolism

Piperacillin is metabolised to a minor microbiologically active desethyl metabolite. Tazobactam is metabolised to a single metabolite that has been found to be microbiologically inactive.
Piperacillin and tazobactam are eliminated via the kidney by glomerular filtration and tubular secretion. Piperacillin, tazobactam, and desethyl piperacillin are also secreted into the bile.

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Tazobactam acid Suppliers

Changzhou Red Sun Pharmaceutical Co., Ltd.
Tel
0519-85223897 13766960291
Fax
0519-85223902
Email
zjc@czredsunpharm.com
Country
China
ProdList
47
Advantage
58
Hubei widely chemical technology Co., Ltd.
Tel
027-59402396 13419635609
Fax
027-83989310
Email
13419635609@163.com
Country
China
ProdList
1966
Advantage
55
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
94657
Advantage
76
TAIYUAN RHF CO.,LTD.
Tel
+86 351 7031519
Fax
+86 351 7031519
Email
sales@RHFChem.com
Country
China
ProdList
2338
Advantage
56
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24529
Advantage
81
Pure Chemistry Scientific Inc.
Tel
001-857-928-2050 or 1-888-588-9418
Fax
001-617-206-9595
Email
sales@chemreagents.com
Country
United States
ProdList
10186
Advantage
62
Adamas Reagent, Ltd.
Tel
400-6009262 16621234537
Fax
021-64823266
Email
chenyj@titansci.com
Country
China
ProdList
14103
Advantage
59
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2123
Advantage
70
XiaoGan ShenYuan ChemPharm co,ltd
Tel
15527768850
Email
1791901229@qq.com
Country
China
ProdList
8843
Advantage
52
Sinopharm Chemical Reagent Co,Ltd.
Tel
86-21-63210123
Fax
86-21-63290778 86-21-63218885
Email
sj_scrc@sinopharm.com
Country
China
ProdList
9815
Advantage
79
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View Lastest Price from Tazobactam acid manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Tazobactam acid 89786-04-9
Price
US $0.00-0.00/Kg/Drum
Min. Order
1KG
Purity
98%min
Supply Ability
500kg
Release date
2021-09-14
Shaanxi Dideu Medichem Co. Ltd
Product
Tazobactam acid 89786-04-9
Price
US $1.00-1.00/KG
Min. Order
1g
Purity
99%
Supply Ability
50tons
Release date
2020-05-07
Hangzhou Hyper Chemicals Limited
Product
Tazobactam 89786-04-9
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99%, USP
Supply Ability
5,000KG
Release date
2024-08-02

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