BIOMAT Database Logo BIOMAT Database Logo

A novel carbapenem antibiotic, SM-7338 structure-activity relationships. 1990

M Sunagawa, and H Matsumura, and T Inoue, and M Fukasawa, and M Kato
Research Laboratories, Sumitomo Pharmaceuticals Co., Ltd., Osaka, Japan.

A series of new carbapenem compounds, which have a pyrrolidin-3'-ylthio group substituted with various aminocarbonyl group at C-5' position as C-2 side chain, have been prepared. The antibacterial activity and the stability to renal dehydropeptidase-I of these compounds were investigated, and the structure-activity relationships were discussed. In this series, SM-7338; (1R,5S,6S)-2-[(3S,5S)-5-dimethylaminocarbonylpyrrolidin-3-ylthi o]-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid (5a) was the most interesting compound.

UI MeSH Term Description Entries
D008826 Microbial Sensitivity Tests Any tests that demonstrate the relative efficacy of different chemotherapeutic agents against specific microorganisms (i.e., bacteria, fungi, viruses). Bacterial Sensitivity Tests,Drug Sensitivity Assay, Microbial,Minimum Inhibitory Concentration,Antibacterial Susceptibility Breakpoint Determination,Antibiogram,Antimicrobial Susceptibility Breakpoint Determination,Bacterial Sensitivity Test,Breakpoint Determination, Antibacterial Susceptibility,Breakpoint Determination, Antimicrobial Susceptibility,Fungal Drug Sensitivity Tests,Fungus Drug Sensitivity Tests,Sensitivity Test, Bacterial,Sensitivity Tests, Bacterial,Test, Bacterial Sensitivity,Tests, Bacterial Sensitivity,Viral Drug Sensitivity Tests,Virus Drug Sensitivity Tests,Antibiograms,Concentration, Minimum Inhibitory,Concentrations, Minimum Inhibitory,Inhibitory Concentration, Minimum,Inhibitory Concentrations, Minimum,Microbial Sensitivity Test,Minimum Inhibitory Concentrations,Sensitivity Test, Microbial,Sensitivity Tests, Microbial,Test, Microbial Sensitivity,Tests, Microbial Sensitivity
D002621 Chemistry A basic science concerned with the composition, structure, and properties of matter; and the reactions that occur between substances and the associated energy exchange.
D000077731 Meropenem A thienamycin derivative antibacterial agent that is more stable to renal dehydropeptidase I than IMIPENEM, but does not need to be given with an enzyme inhibitor such as CILASTATIN. It is used in the treatment of bacterial infections, including infections in immunocompromised patients. 3-(5-Dimethylcarbamoylpyrrolidin-3-ylthio)-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid,Merrem,Penem,Ronem,SM 7338,SM-7338,SM7338
D001419 Bacteria One of the three domains of life (the others being Eukarya and ARCHAEA), also called Eubacteria. They are unicellular prokaryotic microorganisms which generally possess rigid cell walls, multiply by cell division, and exhibit three principal forms: round or coccal, rodlike or bacillary, and spiral or spirochetal. Bacteria can be classified by their response to OXYGEN: aerobic, anaerobic, or facultatively anaerobic; by the mode by which they obtain their energy: chemotrophy (via chemical reaction) or PHOTOTROPHY (via light reaction); for chemotrophs by their source of chemical energy: CHEMOLITHOTROPHY (from inorganic compounds) or chemoorganotrophy (from organic compounds); and by their source for CARBON; NITROGEN; etc.; HETEROTROPHY (from organic sources) or AUTOTROPHY (from CARBON DIOXIDE). They can also be classified by whether or not they stain (based on the structure of their CELL WALLS) with CRYSTAL VIOLET dye: gram-negative or gram-positive. Eubacteria
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D013845 Thienamycins Beta-lactam antibiotics that differ from PENICILLINS in having the thiazolidine sulfur atom replaced by carbon, the sulfur then becoming the first atom in the side chain. They are unstable chemically, but have a very broad antibacterial spectrum. Thienamycin and its more stable derivatives are proposed for use in combinations with enzyme inhibitors. Antibiotics, Thienamycin,Thienamycin Antibiotics
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D015780 Carbapenems A group of beta-lactam antibiotics in which the sulfur atom in the thiazolidine ring of the penicillin molecule is replaced by a carbon atom. THIENAMYCINS are a subgroup of carbapenems which have a sulfur atom as the first constituent of the side chain. Antibiotics, Carbapenem,Carbapenem,Carbapenem Antibiotics
D055598 Chemical Phenomena The composition, structure, conformation, and properties of atoms and molecules, and their reaction and interaction processes. Chemical Concepts,Chemical Processes,Physical Chemistry Concepts,Physical Chemistry Processes,Physicochemical Concepts,Physicochemical Phenomena,Physicochemical Processes,Chemical Phenomenon,Chemical Process,Physical Chemistry Phenomena,Physical Chemistry Process,Physicochemical Phenomenon,Physicochemical Process,Chemical Concept,Chemistry Process, Physical,Chemistry Processes, Physical,Concept, Chemical,Concept, Physical Chemistry,Concept, Physicochemical,Concepts, Chemical,Concepts, Physical Chemistry,Concepts, Physicochemical,Phenomena, Chemical,Phenomena, Physical Chemistry,Phenomena, Physicochemical,Phenomenon, Chemical,Phenomenon, Physicochemical,Physical Chemistry Concept,Physicochemical Concept,Process, Chemical,Process, Physical Chemistry,Process, Physicochemical,Processes, Chemical,Processes, Physical Chemistry,Processes, Physicochemical

Related Publications

M Sunagawa, and H Matsumura, and T Inoue, and M Fukasawa, and M Kato
In vitro antibacterial activity of SM-7338, a carbapenem antibiotic with stability to dehydropeptidase I.
February 1989, Antimicrobial agents and chemotherapy,
M Sunagawa, and H Matsumura, and T Inoue, and M Fukasawa, and M Kato
The stability of a novel carbapenem antibiotic, meropenem (SM-7338), in a solid state formulation for injection.
November 1993, Chemical & pharmaceutical bulletin,
M Sunagawa, and H Matsumura, and T Inoue, and M Fukasawa, and M Kato
In vitro activity and beta-lactamase stability of a new carbapenem, SM-7338.
July 1989, Antimicrobial agents and chemotherapy,
M Sunagawa, and H Matsumura, and T Inoue, and M Fukasawa, and M Kato
Antibacterial activity of the new carbapenem meropenem (SM-7338) against clinical isolates.
December 1989, European journal of clinical microbiology & infectious diseases : official publication of the European Society of Clinical Microbiology,
M Sunagawa, and H Matsumura, and T Inoue, and M Fukasawa, and M Kato
Comparative in vitro antibacterial activity of the new carbapenem meropenem (SM-7338).
December 1989, European journal of clinical microbiology & infectious diseases : official publication of the European Society of Clinical Microbiology,
M Sunagawa, and H Matsumura, and T Inoue, and M Fukasawa, and M Kato
Multicenter in vitro evaluation of SM-7338, a new carbapenem.
April 1989, Antimicrobial agents and chemotherapy,
M Sunagawa, and H Matsumura, and T Inoue, and M Fukasawa, and M Kato
In vitro antibacterial activity and beta-lactamase stability of the new carbapenem SM-7338.
October 1989, European journal of clinical microbiology & infectious diseases : official publication of the European Society of Clinical Microbiology,
M Sunagawa, and H Matsumura, and T Inoue, and M Fukasawa, and M Kato
Antimicrobial activity of SM-17466, a novel carbapenem antibiotic with potent activity against methicillin-resistant Staphylococcus aureus.
April 1995, Antimicrobial agents and chemotherapy,
M Sunagawa, and H Matsumura, and T Inoue, and M Fukasawa, and M Kato
Stability of a 1 beta-methylcarbapenem antibiotic, meropenem (SM-7338) in aqueous solution.
April 1995, Chemical & pharmaceutical bulletin,
M Sunagawa, and H Matsumura, and T Inoue, and M Fukasawa, and M Kato
Synthesis and structure-activity relationships of a novel oral carbapenem, CS-834.
May 1997, The Journal of antibiotics,
Copied contents to your clipboard!