Tazobactam

Not to be confused with Teixobactin.

Tazobactam
Clinical data


AHFS/Drugs.com	International Drug Names
Pregnancy category	B
Routes of administration	Intravenous
ATC code	J01CG02 (WHO)
Legal status
Legal status	℞ (Prescription only)
Identifiers
IUPAC name (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
CAS Number	89786-04-9^Y
PubChem (CID)	123630
DrugBank	DB01606^Y
ChemSpider	110216^Y
UNII	SE10G96M8W^Y
KEGG	D00660^Y
ChEBI	CHEBI:9421^N
ChEMBL	CHEMBL404^Y
ECHA InfoCard	100.108.321
Chemical and physical data
Formula	C₁₀H₁₂N₄O₅S
Molar mass	300.289 g/mol
3D model (Jmol)	Interactive image
SMILES O=S2(=O)[C@]([C@@H](N1C(=O)C[C@H]12)C(=O)O)(Cn3nncc3)C
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^Y Key:LPQZKKCYTLCDGQ-WEDXCCLWSA-N^Y
^NY (what is this?) (verify)

Tazobactam is a pharmaceutical drug that inhibits the action of bacterial β-lactamases, especially those belonging to the SHV-1 and TEM groups. It is commonly used as its sodium salt, tazobactam sodium.

Tazobactam is combined with the extended spectrum β-lactam antibiotic piperacillin in the drug piperacillin/tazobactam, used in infections due Pseudomonas aeruginosa. Tazobactam broadens the spectrum of piperacillin by making it effective against organisms that express β-lactamase and would normally degrade piperacillin.^[1]

Tazobactam is a heavily modified penicillin and a sulfone.

References

↑ Yang Y, Rasmussen BA, Shlaes DM (1999). "Class A beta-lactamases—enzyme-inhibitor interactions and resistance". Pharmacol Ther. 83: 141–151. doi:10.1016/S0163-7258(99)00027-3.

Antibacterials: cell envelope antibiotics (J01C-J01D)

Intracellular

Inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
DADAL/AR inhibitors (Cycloserine)
bactoprenol inhibitors (Bacitracin)

Glycopeptide

Inhibit PG chain elongation: Vancomycin^# (Oritavancin
Telavancin)
Teicoplanin (Dalbavancin)
Ramoplanin

β-lactams/
(inhibit PBP
cross-links)

Penicillins
(Penams)

Narrow spectrum

β-lactamase sensitive (1st generation)	Benzylpenicillin (G)^# Benzathine benzylpenicillin^# Procaine benzylpenicillin^# Phenoxymethylpenicillin (V)^# Propicillin^‡ Pheneticillin^‡ Azidocillin^‡ Clometocillin^‡ Penamecillin^‡

β-lactamase resistant (2nd generation)	Cloxacillin^# (Dicloxacillin Flucloxacillin) Oxacillin Nafcillin Methicillin^‡

Extended spectrum

Aminopenicillins (3rd generation)	Amoxicillin^# Ampicillin^# (Pivampicillin Hetacillin^‡ Bacampicillin^‡ Metampicillin^‡ Talampicillin^‡) Epicillin^‡

Carboxypenicillins (4th generation)	Ticarcillin Carbenicillin^‡ / Carindacillin^‡ Temocillin^‡

Ureidopenicillins (4th generation)	Piperacillin Azlocillin^‡ Mezlocillin^‡

Other	Mecillinam^‡ (Pivmecillinam^‡) Sulbenicillin^‡

Penems

Faropenem^‡

Carbapenems

Cephalosporins/Cephamycins
(Cephems)

1st generation (P Ec K)	Cefazolin^# Cefalexin ^# Cefadroxil Cefapirin Cefazedone^‡ Cefazaflur^‡ Cefradine^‡ Cefroxadine^‡ Ceftezole^‡ Cefaloglycin^‡ Cefacetrile^‡ Cefalonium^‡ Cefaloridine^‡ Cefalotin^‡ Cefatrizine^‡

2nd generation (H E N)	Cefaclor Cefotetan Cephamycin (Cefoxitin Cefprozil Cefuroxime Cefuroxime axetil Cefamandole^‡ Cefminox^‡ Cefonicid^‡ Ceforanide^‡ Cefotiam^‡ Cefbuperazone^‡ Cefuzonam^‡ Cefmetazole)^‡ Carbacephem^‡ (Loracarbef^‡)

3rd generation	Cefixime^# Ceftriaxone^# Antipseudomonal (Ceftazidime^# Cefoperazone) Cefdinir Cefcapene Cefdaloxime Ceftizoxime Cefmenoxime Cefotaxime Cefpiramide Cefpodoxime Ceftibuten Cefditoren Cefetamet^‡ Cefodizime^‡ Cefpimizole^‡ Cefsulodin^‡ Cefteram^‡ Ceftiolene^‡ Oxacephem (Flomoxef^‡ Latamoxef^‡)

4th generation (Pseudomonas)	Cefepime Cefozopran^‡ Cefpirome^‡ Cefquinome^‡

5th generation	Ceftaroline fosamil Ceftolozane Ceftobiprole

Veterinary	Ceftiofur Cefquinome Cefovecin

Monobactams

β-lactamase inhibitors

Combinations

Other

polymyxins/detergent
- Colistin
- Polymyxin B
depolarizing
- Daptomycin
Hydrolyze NAM-NAG
- lysozyme
Tyrothricin
- Gramicidin
- Tyrocidine
Isoniazid
Teixobactin

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

This article is issued from Wikipedia - version of the 10/14/2016. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.

Tazobactam

See also

References