Piperacillin & Tazobactam

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Also known as: Tazocin (tn), Zosyn (tn), Piperacillin-tazobactam mixt., Piperacillin-tazobactam mixture, Niosh/xi0191450, Piperacillin sodium and tazobactam

Molecular Formula

C₃₃H₃₈N₉NaO₁₂S₂

Molecular Weight

839.8 g/mol

InChI Key

TUPFOYXHAYOHIB-WZGOVNIISA-M

Piperacillin-Tazobactam is a combination formulation of the antibiotic piperacillin and the beta-lactamase inhibitor tazobactam with antibacterial activity. Piperacillin, a broad-spectrum, semisynthetic penicillin, binds to and inactivates penicillin-binding proteins (PBP) located on the inner membrane of the bacterial cell wall, thereby interfering with the cross-linking of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. As a result, the cell wall is weakened and the cell lyses. Tazobactam, a penicillanic acid sulfone derivative, irreversibly binds to and inhibits bacterial beta-lactamase at or near its active site, thereby preventing the destruction of the beta-lactamase susceptible piperacillin by this bacterial enzyme.

1 2D Structure

Piperacillin & Tazobactam

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

sodium;(2S,5R,6R)-6-[[(2S)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;(2S,3S,5R)-3-methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-46-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

2.1.2 InChI

InChI=1S/C23H27N5O7S.C10H12N4O5S.Na/c1-4-26-10-11-27(19(32)18(26)31)22(35)25-13(12-8-6-5-7-9-12)16(29)24-14-17(30)28-15(21(33)34)23(2,3)36-20(14)28;1-10(5-13-3-2-11-12-13)8(9(16)17)14-6(15)4-7(14)20(10,18)19;/h5-9,13-15,20H,4,10-11H2,1-3H3,(H,24,29)(H,25,35)(H,33,34);2-3,7-8H,4-5H2,1H3,(H,16,17);/q;;+1/p-1/t13-,14+,15-,20+;7-,8+,10+;/m01./s1

2.1.3 InChI Key

TUPFOYXHAYOHIB-WZGOVNIISA-M

2.1.4 Canonical SMILES

CCN1CCN(C(=O)C1=O)C(=O)NC(C2=CC=CC=C2)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)[O-].CC1(C(N2C(S1(=O)=O)CC2=O)C(=O)O)CN3C=CN=N3.[Na+]

2.1.5 Isomeric SMILES

CCN1CCN(C(=O)C1=O)C(=O)N[C@@H](C2=CC=CC=C2)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)[O-].C[C@@]1([C@@H](N2[C@H](S1(=O)=O)CC2=O)C(=O)O)CN3C=CN=N3.[Na+]

2.2 Synonyms

2.2.1 Depositor-Supplied Synonyms

1. Tazocin (tn)

2. Zosyn (tn)

3. Piperacillin-tazobactam Mixt.

4. Piperacillin-tazobactam Mixture

5. Niosh/xi0191450

6. Piperacillin Sodium And Tazobactam

7. Dtxsid001016418

8. Tazobactam And Piperacillin (jp17)

9. Piperacillin-tazobactam Mixt. (4:1)

10. Tazobactam-piperacillin Mixt. (1:4)

11. Xi01914500

12. D02505

13. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 3-methyl-7-oxo-3-(1h-1,2,3-triazol-1-ylmethyl)-, 4,4-dioxide, (2s-(2-alpha,3-beta,5-alpha))-, Mixt. With (2s-(2-alpha,5-alpha,6-beta(s*)))-6-(((((4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl)amino)phenylacetyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid (1:4)

14. Sodium;(2s,5r,6r)-6-[[(2s)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;(2s,3s,5r)-3-methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

2.3 Create Date

2008-02-08

3 Chemical and Physical Properties

Molecular Formula	C₃₃H₃₈N₉NaO₁₂S₂
Molecular Weight	839.8 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	15
Rotatable Bond Count	9
Exact Mass	839.19790431 g/mol
Monoisotopic Mass	839.19790431 g/mol
Topological Polar Surface Area	315 Å²
Heavy Atom Count	57
Formal Charge	0
Complexity	1560
Isotope Atom Count	0
Defined Atom Stereocenter Count	7
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	3