33447

Supelco

Mecillinam

VETRANAL®, analytical standard

Empirical Formula (Hill Notation):
C15H23N3O3S
CAS Number:
Molecular Weight:
325.43
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.24
Pricing and availability is not currently available.

Quality Level

grade

analytical standard

product line

VETRANAL®

form

neat

shelf life

limited shelf life, expiry date on the label

application(s)

HPLC: suitable
gas chromatography (GC): suitable

Featured Industry

Clinical
Forensics and Toxicology
Pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

SMILES string

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2\N=C\N3CCCCCC3)C(O)=O

InChI

1S/C15H23N3O3S/c1-15(2)11(14(20)21)18-12(19)10(13(18)22-15)16-9-17-7-5-3-4-6-8-17/h9-11,13H,3-8H2,1-2H3,(H,20,21)/b16-9+/t10-,11+,13-/m1/s1

InChI key

BWWVAEOLVKTZFQ-ISVUSNJMSA-N

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General description

Chemical structure: ß-lactam
Mecillinam is a beta-lactam antibiotic, specific to penicillin-binding protein 2 (PBP2) in Escherichia coli, which tends to block cell wall elongation and indirectly blocks cell division.

Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Legal Information

VETRANAL is a registered trademark of Sigma-Aldrich Chemie GmbH

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 2

Certificate of Analysis
Certificate of Origin
Mecillinam resistance in Escherichia coli is conferred by loss of a second activity of the AroK protein
Vinella D, et al.
Journal of Bacteriology, 178, 3818-3828 (1996)
Karen L Nielsen et al.
Journal of medical microbiology, 63(Pt 4), 582-589 (2014-01-28)
Urinary tract infections (UTIs) are primarily caused by Escherichia coli with the patient's own faecal flora acting as a reservoir for the infecting E. coli. Here we sought to characterize the E. coli faecal flora of UTI patients and healthy...
Elisabeth Thulin et al.
EBioMedicine, 23, 111-118 (2017-09-01)
Mecillinam (amdinocillin) is a β-lactam antibiotic used to treat uncomplicated urinary tract infections (UTIs). We have previously shown that inactivation of the Escherichia coli cysB gene is the major cause of mecillinam resistance (Mec
Niki Lampri et al.
The Journal of antimicrobial chemotherapy, 67(10), 2424-2428 (2012-06-06)
Extended-spectrum β-lactamases (ESBLs) have emerged as an important mechanism of β-lactam resistance among community uropathogens. We characterized the ESBLs of a collection of Escherichia coli isolates recovered from outpatients with urinary tract infection during nationwide surveillance conducted from 2005 to...
Christina A Ahlstrom et al.
Scientific reports, 8(1), 7361-7361 (2018-05-11)
Antimicrobial resistance (AMR) in bacterial pathogens threatens global health, though the spread of AMR bacteria and AMR genes between humans, animals, and the environment is still largely unknown. Here, we investigated the role of wild birds in the epidemiology of...

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