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SML1220

Sigma-Aldrich

Doripenem hydrate

≥98% (HPLC)

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Synonym(s):
(4R,5S,6S)-3-[[(3S,5S)-5-[[(Aminosulfonyl)amino]methyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid hydrate
Empirical Formula (Hill Notation):
C15H24N4O6S2 · H2O
CAS Number:
364622-82-2
Molecular Weight:
438.52
MDL number:
MFCD09749887
UNSPSC Code:
12352200
PubChem Substance ID:
329825727
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

H2O: 5 mg/mL, clear (warmed)

storage temp.

2-8°C

InChI

1S/C15H24N4O6S2.H2O/c1-6-11-10(7(2)20)14(21)19(11)12(15(22)23)13(6)26-9-3-8(17-5-9)4-18-27(16,24)25;/h6-11,17-18,20H,3-5H2,1-2H3,(H,22,23)(H2,16,24,25);1H2/t6-,7-,8+,9+,10-,11-;/m1./s1

InChI key

NTUBEBXBDGKBTJ-WGLOMNHJSA-N

Biochem/physiol Actions

Doripenem hydrate is used to treat complicated urinary infection including Pyelonephritis caused by E.coli. Doripenem hydrate is promoted in the United States as DORIBAX®. This drug is synthesized from p-nitrobenzyl-protected enolphosphate 2b and N-(p-nitrobenzyloxycarbonyl)-protected aminomethylpyrrolidine.
Doripenem is an ultra-broad spectrum carbopenem antibiotic. Doripenem is active against both gram-positive and gram-negative bacteria.

Legal Information

DORIBAX is a registered trademark of Shionogi Inc.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Improved Large-scale One-pot Synthesis of Pure Doripenem Hydrate (S-4661).
Raju K R, et al.
Organic Prep. and Proc. Int., 48(4), 342-349 (2016)
Practical large-scale synthesis of doripenem: A novel 1β-methylcarbapenem antibiotic.
Nishino Y, et al.
Organic Process Research & Development, 7(6), 846-850 (2003)
Lokender Kumar et al.
Frontiers in microbiology, 12, 598498-598498 (2021-02-16)
Pseudomonas aeruginosa utilizes the quorum sensing (QS) system to strategically coordinate virulence and biofilm formation. Targeting QS pathways may be a potential anti-infective approach to treat P. aeruginosa infections. In the present study, we define cephalosporins' anti-QS activity using Chromobacterium

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