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Merck

SML0817

Sigma-Aldrich

Pivmecillinam

≥98% (HPLC)

Sinónimos:

Amdinocillin pivoxil

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About This Item

Fórmula empírica (notación de Hill):
C21H33N3O5S
Número de CAS:
Peso molecular:
439.57
EC Number:
MDL number:
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Mette Vinther Skriver et al.
Scandinavian journal of infectious diseases, 36(10), 733-737 (2004-10-30)
A previous study unexpectedly showed an increased, statistically imprecise, risk of low Apgar score in children of women redeeming prescriptions for pivmecillinam in late pregnancy. To improve statistical precision we extended the previous dataset with data for 5 more y
Lindsay E Nicolle et al.
Scandinavian journal of infectious diseases, 39(8), 748-749 (2007-07-27)
Oral therapy options for pyelonephritis caused by ESBL producing E. coli are limited. We describe a woman with relapsing pyelonephritis due to a CTX-M ESBL E. coli who was cured with a prolonged course of pivmecillinam. This suggests pivmecillinam may
Birgit Stattin Norinder et al.
Antimicrobial agents and chemotherapy, 50(4), 1528-1530 (2006-03-30)
Similar changes in the periurethral and vaginal microflora were observed in 19 women with recurrent urinary tract infection following treatment with norfloxacin (NOR) or pivmecillinam (PIV). Escherichia coli strains were suppressed by both treatments. Staphylococcus spp. and enterococci colony counts
Sven A Ferry et al.
Scandinavian journal of infectious diseases, 36(4), 296-301 (2004-06-17)
This prospective, multicentre, randomized, double-blind and placebo controlled study was performed to describe the natural course of uncomplicated lower urinary tract infection (UTI). A total of 1143 women 18 y and above, consulting at 18 primary health care centres in
Beatrix S Traa et al.
International journal of epidemiology, 39 Suppl 1, i70-i74 (2010-04-02)
Ciprofloxacin, ceftriaxone and pivmecillinam are the antibiotics currently recommended by the World Health Organization (WHO) for the treatment of dysentery in children; yet there have been no reviews of the clinical effectiveness of these antibiotics in recent years. We reviewed

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