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Merck

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

Product Name

Mecillinam, VETRANAL®, analytical standard

InChI key

BWWVAEOLVKTZFQ-ISVUSNJMSA-N

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

SMILES string

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

grade

analytical standard

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

Quality Level

100

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Application

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

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.

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCL7014
BCCK6777
BCCJ1890
BCCG4047
BCCC7806

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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
Aurélie Scherler et al.
Microorganisms, 8(1) (2020-01-16)
Chlamydiae, such as Chlamydia trachomatis and Chlamydia pneumoniae, can cause chronic infections. It is believed that persistent forms called aberrant bodies (ABs) might be involved in this process. AB formation seems to be a common trait of all members of
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