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Merck
CN

SML0817

Sigma-Aldrich

Pivmecillinam

≥98% (HPLC)

Synonym(s):

Amdinocillin pivoxil

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About This Item

Empirical Formula (Hill Notation):
C21H33N3O5S
CAS Number:
32886-97-8
Molecular Weight:
439.57
EC Number:
251-276-6
MDL number:
MFCD00865080
UNSPSC Code:
51111800
PubChem Substance ID:
329825603
NACRES:
NA.77

Key Documents

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Quality Level

100

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D +215 to +245°, c = 1 in ethanol

color

white to beige

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

−20°C

SMILES string

CC1(C)[C@H](C(OCOC(C(C)(C)C)=O)=O)N2C([C@](/N=C/N3CCCCCC3)([H])[C@@]2([H])S1)=O

InChI

1S/C21H33N3O5S/c1-20(2,3)19(27)29-13-28-18(26)15-21(4,5)30-17-14(16(25)24(15)17)22-12-23-10-8-6-7-9-11-23/h12,14-15,17H,6-11,13H2,1-5H3/b22-12+/t14-,15+,17-/m1/s1

InChI key

NPGNOVNWUSPMDP-UTEPHESZSA-N

Related Categories

Application

Pivmecillinam has been used to test its efficacy as a breast cancer stem cells (CSCs) targeting agent.

Biochem/physiol Actions

Pivmecillinam is a β-lactam antibiotic and a pivaloyl-containing pro-drug. It belongs to the class of amidinopenicillin. Pivmecillinam is an oral anti-microbial agent that can be considered for treating E. coli urinary tract infection (UTI).
Pivmecillinam is a gram negative antibiotic, and inhibitor of penicillin-binding protein 2 (PBP2).
Pivmecillinam is a gram negative antibiotic, and inhibitor of penicillin-binding protein 2 (PBP2). Pivmecillinam has been shown to have synergistic effects with several antibiotics including novobiocin and rifampin in gram negative bacteria.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000440302
0000440305
0000440305
0000440302
0000407744

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Beta-lactam antibiotics
Meyler's Side Effects of Drugs: The International Encyclopedia of Adverse Drug Reactions and (2015)
Miika Bergman et al.
Antimicrobial agents and chemotherapy, 53(3), 912-917 (2008-12-24)
During a 9-year study period from 1997 through 2005, the association between antimicrobial resistance rates in Escherichia coli and outpatient antimicrobial consumption was investigated in 20 hospital districts in Finland. A total of 754,293 E. coli isolates, mainly from urine
Sven A Ferry et al.
Scandinavian journal of primary health care, 25(1), 49-57 (2007-03-14)
To analyse associations between symptoms and bacteriuria in uncomplicated lower urinary tract infection in women (LUTIW) and to evaluate outcome of therapy with three different regimens of pivmecillinam or placebo. Prospective, multicentre, randomized, double-blind, and placebo-controlled therapy study. Symptoms registered
C-M Lokrantz et al.
Acta neurologica Scandinavica, 109(4), 297-301 (2004-03-16)
We describe the clinical and neurophysiological findings in a case of hyperammonemic encephalopathy. A 72-year-old woman taking valproate (VPA), as monotherapy for her partial epilepsy developed urinary tract infection. She was treated with pivmecillinam 600 mg daily. The following days
Maria Loose et al.
Antibiotics (Basel, Switzerland), 9(6) (2020-07-08)
Given the increasing antimicrobial resistance in urinary tract infections (UTI), alternative strategies need to be investigated. Determination of minimal inhibitory and bactericidal concentrations of essential oils from cajeput, lemongrass, tea tree, and thyme in artificial urine, revealed bactericidal activity of
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