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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

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

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 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Asa Sullivan et al.
Antimicrobial agents and chemotherapy, 49(1), 170-175 (2004-12-24)
The knowledge of the effects of antimicrobial agents on the normal vaginal microflora is limited. The objective of the present study was to study the ecological impact of pivmecillinam on the normal vaginal microflora. In 20 healthy women, the estimated
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
Karen Ejrnaes et al.
Journal of clinical microbiology, 44(5), 1776-1781 (2006-05-05)
The primary infecting Escherichia coli strains from 156 women with community-acquired uncomplicated urinary tract infection (UTI) randomized to pivmecillinam or placebo and the E. coli strains causing UTI at two follow-up visits were typed using pulsed-field gel electrophoresis (PFGE). In
51 - Chemotherapy of infections
Medical Pharmacology and Therapeutics (Fifth Edition) (2018)
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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