Tazobactam

Structural formula
General
Non-proprietary name	Tazobactam
other names	(2 S , 3 S , 5 R ) -3-methyl-4,4,7-trioxo-3- (1 H -1,2,3-triazol-1-ylmethyl) -4-thia-1-azabicyclo [ 3.2.0] heptane-2-carboxylic acid ( IUPAC ) ; Tazobactamum ( Latin ) ;
Molecular formula	C 10 H 12 N 4 O 5 S (tazobactam) ; C 10 H 11 N 4 NaO 5 S (tazobactam sodium) ;
External identifiers / databases
EC number	618-303-7
ECHA InfoCard	100.108.321
PubChem	123630
ChemSpider	110216
DrugBank	DB01606
Wikidata	Q423376
Drug information
ATC code	J01 CG02 ; J01 CR05 tazobactam + piperacillin ;
Drug class	β-lactamase inhibitor
properties
Molar mass	300,30 g · mol -1 (Tazobactam) ; 322.27 g · mol -1 (tazobactam sodium) ;
Melting point	> 170 ° C (tazobactam sodium, decomposition)
pK s value	2.1
solubility	Water: 50 g l −1 , (tazobactam sodium, clear, colorless solution)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
Toxicological data	> 5000 mg kg −1 ( LD 50 , rat , oral , tazobactam sodium) ; > 5000 mg kg −1 ( LD 50 , mouse , ip , tazobactam sodium) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tazobactam is a drug from the group of β-lactamase inhibitors . Tazobactam is only slightly antimicrobial, but broadens the antibiotic spectrum of the β-lactam antibiotic piperacillin . It is therefore only used in a fixed combination with piperacillin.

Both substances are not effective orally and are therefore administered parenterally .

pharmacology

The β-lactamase inhibitors have a similar chemical structure to β-lactam antibiotics and contain the β-lactam ring. By combining the β-lactamase- labile piperacillin with the β-lactamase inhibitor tazobactam, the antibiotic resistance of bacteria against β-lactamase-labile penicillins can be overcome. Tazobactam has hardly any direct antibacterial activity. It binds irreversibly to the clinically common enzyme β-lactamase, which is produced by some bacteria , and thus prevents the inactivation of the β-lactam antibiotics . Most plasmid-mediated penicillinases are inhibited, less or not at all the chromosomally mediated cephalosporinases .

Chemical-pharmaceutical information

The water-soluble sodium salt of tazobactam is used medicinally.

Varia

The combination of piperacillin / tazobactam is not recommended for perioperative prophylaxis.

Trade names

Combination preparations

Piperacillin / Tazobactam (D, A, CH), Pipitaz (A), Tazobac (D, CH), Tazonam (A)

literature

Hermann J. Roth: Medicinal Chemistry: Targets and Drugs; 157 tables . German Apotheker-Verlag, Stuttgart 2005, ISBN 3-7692-3483-9 .

Individual evidence

↑ ^a ^b Entry on tazobactam. In: Römpp Online . Georg Thieme Verlag, accessed on May 1, 2014.
↑ ^a ^b ^c data sheet Tazobactam sodium salt from Sigma-Aldrich , accessed on October 23, 2016 ( PDF ).
↑ ^a ^b Entry on tazobactam in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ Jörg Braun: Infectious Diseases. In: Jörg Braun, Roland Preuss (Ed.): Clinic Guide Intensive Care Medicine. 9th edition. Elsevier, Munich 2016, ISBN 978-3-437-23763-8 , pp. 437-519, here: pp. 485 f. ( Piperacillin / tazobactam ).

[roempp-1] Entry on tazobactam. In: Römpp Online . Georg Thieme Verlag, accessed on May 1, 2014.

[sigma-2] ta sheet Tazobactam sodium salt from Sigma-Aldrich , accessed on October 23, 2016 ( PDF ).

[ChemIDplus-3] Entry on tazobactam in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[4] Jörg Braun: Infectious Diseases. In: Jörg Braun, Roland Preuss (Ed.): Clinic Guide Intensive Care Medicine. 9th edition. Elsevier, Munich 2016, ISBN 978-3-437-23763-8 , pp. 437-519, here: pp. 485 f. ( Piperacillin / tazobactam ).