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33447

Mecillinam

VETRANAL®, analytical standard

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About This Item

Empirical Formula (Hill Notation):
C15H23N3O3S
CAS Number:
32887-01-7
Molecular Weight:
325.43
NACRES:
NA.24
PubChem Substance ID:
329754550
UNSPSC Code:
41116107
EC Number:
251-277-1
MDL number:
MFCD00056869
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grade

analytical standard

Quality Level

100

product line

VETRANAL®

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

application(s)

clinical testing

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

Related Categories

General description

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.
Chemical structure: β-lactam

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 Merck KGaA, Darmstadt, Germany

Storage Class

11 - Combustible Solids

wgk

WGK 2

ppe

Eyeshields, Gloves, type N95 (US)

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Daniel Vinella et al.
Molecular microbiology, 56(4), 958-970 (2005-04-28)
In Escherichia coli the beta-lactam mecillinam specifically inhibits penicillin-binding protein 2 (PBP2), a peptidoglycan transpeptidase essential for maintaining rod shape. We have previously shown that PBP2 inactivation results in a cell division block and that an increased concentration of the
Filip Jansåker et al.
Antibiotics (Basel, Switzerland), 8(2) (2019-05-10)
Objectives: To investigate pivmecillinam´s efficacy in uncomplicated lower urinary tract infection (UTI) caused by Staphylococcus saprophyticus-considered non-susceptible to mecillinam. Methods: Participants with confirmed UTIs caused by S. saprophyticus from four randomized controlled trials, where pivmecillinam was empirically given to females
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
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)
Aneta Karczmarek et al.
Molecular microbiology, 65(1), 51-63 (2007-06-22)
The bacterial actin homologue MreB forms a helix underneath the cytoplasmic membrane and was shown to be essential in the morphogenesis of the rod-shaped cells. Additionally, MreB was implicated to be involved in DNA segregation. However, in our hands the
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