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Safety Information

SML0817

Sigma-Aldrich

Pivmecillinam

≥98% (HPLC)

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Synonym(s):
Amdinocillin pivoxil
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

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 has been shown to have synergistic effects with several antibiotics including novobiocin and rifampin in gram negative bacteria.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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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
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
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
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
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
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