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Key Documents

SML3203

Sigma-Aldrich

Tebipenem

≥98% (HPLC)

Synonym(s):

(1R,5S,6S)-2-[1-(1,3-Thiazolin-2-yl)azetidin-3-yl]thio-6-[(R)-1-hydroxyeth yl]-1-methyl-carbapen-2-em-3-carboxylic acid, (4R,5S,6S)-3-[[1-(4,5-Dihydro-2-thiazolyl)-3-azetidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, L-084 active drug, LJC 11,036, LJC 11036, ME1211 active drug, SPR 859, SPR 994 active drug, SPR-859, SPR-994 active drug, SPR859, SPR994 active drug, TBM, TBM-PI active drug, Tebi-pivoxil active drug, [4R-[4α,5β,6β(R*)]]-3-[[1-(4,5-Dihydro-2-thiazolyl)-3-azetidinyl]thio]-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C16H21N3O4S2
CAS Number:
161715-21-5
Molecular Weight:
383.49
MDL number:
MFCD00936545
UNSPSC Code:
51111800
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

InChI

1S/C16H21N3O4S2/c1-7-11-10(8(2)20)14(21)19(11)12(15(22)23)13(7)25-9-5-18(6-9)16-17-3-4-24-16/h7-11,20H,3-6H2,1-2H3,(H,22,23)/t7-,8-,10-,11-/m1/s1

InChI key

GXXLUDOKHXEFBQ-YJFSRANCSA-N

Biochem/physiol Actions

Tebipenem (LJC 11,036; SPR859; TBM) is a carbapenem class broad-spectrum β-lactam antibiotic against both gram-positive and gram-negative bacteria, including penicillin-resistant S. pneumoniae (PRSP) and many β-lactamase-producing strains (respective MIC ≤6-200 and ≤25-390 ng/mL), while being less effective against methicillin-resistant S. aureus (MRSA), S. marcescens, and P. aeruginosa (respective MIC ranges 0.2 to12.5, 0.05 to100, 3.13 to >100 μg/mL). TBM is 2- to 64-fold more potent than imipenem, cefdinir, and faropenem against clinical isolates from respiratory and urinary-tract infections.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Aileen Rubio et al.
ACS infectious diseases, 4(10), 1436-1438 (2018-08-18)
Carbapenems are potent antibacterials with broad-spectrum activity. However, poor oral absorption generally confines this important drug class to in-hospital use by intravenous (IV) administration. The continued rise in drug resistant pathogens creates a need for alternative oral therapies with broad-spectrum
Qi Yao et al.
Molecules (Basel, Switzerland), 21(1), 62-62 (2016-01-12)
To systemically investigate the in vitro and in vivo antibacterial properties of tebipenem pivoxil tablet. In addition, acute toxicity of this preparation was also studied. In vitro, minimum inhibitory concentration (MIC) or minimal inhibitory concentration (MBC) were determined by using
Visanu Thamlikitkul et al.
Journal of the Medical Association of Thailand = Chotmaihet thangphaet, 97(12), 1259-1268 (2015-03-15)
To determine in vitro and in vivo activity of tebipenem against ESBL-producing E. coli. Minimum inhibitory concentration (MIC) of tebipenem against 100 clinical isolates of ESBL-producing E. coli was performed by broth micro-dilution technique. Blood and urine samples from 10
Mario A Bianchet et al.
BMC biochemistry, 18(1), 8-8 (2017-05-27)
The carbapenem subclass of β-lactams is among the most potent antibiotics available today. Emerging evidence shows that, unlike other subclasses of β-lactams, carbapenems bind to and inhibit non-classical transpeptidases (L,D-transpeptidases) that generate 3 → 3 linkages in bacterial peptidoglycan. The
Koichi Fujimoto et al.
Antimicrobial agents and chemotherapy, 57(2), 697-707 (2012-11-14)
SM-295291 and SM-369926 are new parenteral 2-aryl carbapenems with strong activity against major causative pathogens of community-acquired infections such as methicillin-susceptible Staphylococcus aureus, Streptococcus pneumoniae (including penicillin-resistant strains), Streptococcus pyogenes, Enterococcus faecalis, Klebsiella pneumoniae, Moraxella catarrhalis, Haemophilus influenzae (including β-lactamase-negative
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