CEFUROXIME PIVOXETIL

Details

Stereochemistry	MIXED
Molecular Formula	C23H28N4O11S
Molecular Weight	568.554
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 3
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12SCC(COC(N)=O)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\C3=CC=CO3)C(=O)OC(C)OC(=O)C(C)(C)OC

InChI

InChIKey=MGYPWVCKENORQX-KMMUMHRISA-N

InChI=1S/C23H28N4O11S/c1-11(38-21(31)23(2,3)33-4)37-20(30)16-12(9-36-22(24)32)10-39-19-15(18(29)27(16)19)25-17(28)14(26-34-5)13-7-6-8-35-13/h6-8,11,15,19H,9-10H2,1-5H3,(H2,24,32)(H,25,28)/b26-14-/t11?,15-,19-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C23H28N4O11S
Molecular Weight	568.554
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	2 / 3
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15781398 | https://www.ncbi.nlm.nih.gov/pubmed/16270182

Cefuroxime Pivoxetil is an ester prodrug of cefuroxime, a semisynthetic, broad-spectrum, beta-lactamase-resistant, second-generation cephalosporin with antibacterial activity. Cefuroxime binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This results in the weakening of the bacterial cell wall and causes cell lysis.

Originator

Approval Year

PubMed

Title	Date	PubMed
Atom, atom-type, and total nonstochastic and stochastic quadratic fingerprints: a promising approach for modeling of antibacterial activity.	2005 Apr 15	15781398

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:35:00 GMT 2023` Edited by `admin` on `Fri Dec 15 16:35:00 GMT 2023`
Record UNII	LR90117565
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CEFUROXIME PIVOXETIL

Official Name

English

CCI-23628

Code

English

CCI 23628

Code

English

CEFUROXIME PIVOXETIL [USAN]

Common Name

English

5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 3-(((AMINOCARBONYL)OXY)METHYL)-7-((2-FURANYL(METHOXYIMINO)ACETYL)AMINO)-8-OXO-, 1-(2-METHOXY-2-METHYL-1-OXOPROPOXY)ETHYL ESTER, (6R-(6.ALPHA.,7.BETA.(Z)))-

Common Name

English

1-HYDROXYETHYL (6R,7R)-7-(2-(2-FURYL)GLYOXYLAMIDO)-3-(HYDROXYMETHYL)-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLATE, 7^2-(Z)-(O-METHYLOXIME), 3-CARBAMATE 1-(2-METHOXY-2-METHYLPROPIONATE)

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C357