Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C16H18N2O7S2 |
Molecular Weight | 414.453 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@@H](C3=CC=CC=C3)S(O)(=O)=O)C(O)=O
InChI
InChIKey=JETQIUPBHQNHNZ-NJBDSQKTSA-N
InChI=1S/C16H18N2O7S2/c1-16(2)11(15(21)22)18-13(20)9(14(18)26-16)17-12(19)10(27(23,24)25)8-6-4-3-5-7-8/h3-7,9-11,14H,1-2H3,(H,17,19)(H,21,22)(H,23,24,25)/t9-,10-,11+,14-/m1/s1
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/3114912
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/3114912
Sulbenicillin (INN) is a penicillin antibiotic, product name: KEDACILLIN (SODIUM SULBENICILLIN) is effective against gram-negative bacteria, including Pseudomonas aeruginosa and anaerobic Bacteroides, and is also effective against gram-positive bacteria sensitive to Penicillin – G. It’s excreted into the urine and bile in high concentration. Therefore, urinary levels, well above those required to eradicate urinary pathogens, are achieved. It is indicated to treat urinary tract infections: pyelonephritis, pyelitis, pyonephrosis, cystitis and urethritis. Bile-duct infections: cholecystitis and cholangitis. Respiratory tract infections: acute and chronic bronchitis, bronchiectasis, bronchopneumonia, pneumonia and pulmonary suppuration. Obstetrics and Gynecology: intrauterine infection, adnexitis, intrapelvic infection and Bartholinitis. Superfacial suppurative diseases: folliculitis, furuncle, carbuncle, abscess, panaris, phlegmon, tonsilitis, peritonsilitis, peritonsillar abscess, erysipelas, ophthalmia, blepharitis, corneal ulcer, dacryocystitis, stye, post-operative wound infection and traumatic and burn infections. Peritonitis. Septicemia and sub-acute bacterial endocarditis. Sulbenicillin caused elongation of the bacterial cells. At the early stage of elongation, no demonstrable changes of ultrastructure of the cell wall were observed. At the late stage, lysis of the peptidoglycan layer occurred and spheroplast was formed. However, most of the outer membrane of the cell wall remained intact. Sulbenicillin acts upon the peptidoglycan layer, but not on the outer membrane.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: bacterial cell wall Sources: http://www.ncbi.nlm.nih.gov/pubmed/3114912 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | KEDACILLIN® for Injection Approved UseIt is indicated the following infections due to Sulbenicillin susceptible Pseudomonas aeruginosa, Proteus, Retgerella, Klebsiella, Enterobacter, E. coli, Citrobacter cloacae, Pfeiffer's bacilli, Staphylococci, Streptococci, Pneumococcus and Bacteroides.
Urinary tract infections : pyelonephritis, pyelitis, pyonephrosis, cystitis and urethritis.
Bile-duct infections : cholecystitis and cholangitis.
Respiratory tract infections : acute and chronic bronchitis, bronchiectasis, bronchopneumonia, pneumonia and pulmonary suppuration.
Obstetrics and Gynecology : intrauterine infection, adnexitis, intrapelvic infection and Bartholinitis.
Otorhinological infections : otitis media, sinusitis, parotitis, submaxillitis, furuncle of the ear and furuncle of the nose.
Superfacial suppurative diseases : folliculitis, furuncle, carbuncle, abscess, panaris, phlegmon, tonsilitis, peritonsilitis, peritonsillar abscess, erysipelas, ophthalmia, blepharitis, corneal ulcer, dacryocystitis, stye, post-operative wound infection and traumatic and burn infections.
Peritonitis.
Septicemia and sub-acute bacterial endocarditis. |
|||
Curative | KEDACILLIN® for Injection Approved UseIt is indicated the following infections due to Sulbenicillin susceptible Pseudomonas aeruginosa, Proteus, Retgerella, Klebsiella, Enterobacter, E. coli, Citrobacter cloacae, Pfeiffer's bacilli, Staphylococci, Streptococci, Pneumococcus and Bacteroides.
Urinary tract infections : pyelonephritis, pyelitis, pyonephrosis, cystitis and urethritis.
Bile-duct infections : cholecystitis and cholangitis.
Respiratory tract infections : acute and chronic bronchitis, bronchiectasis, bronchopneumonia, pneumonia and pulmonary suppuration.
Obstetrics and Gynecology : intrauterine infection, adnexitis, intrapelvic infection and Bartholinitis.
Otorhinological infections : otitis media, sinusitis, parotitis, submaxillitis, furuncle of the ear and furuncle of the nose.
Superfacial suppurative diseases : folliculitis, furuncle, carbuncle, abscess, panaris, phlegmon, tonsilitis, peritonsilitis, peritonsillar abscess, erysipelas, ophthalmia, blepharitis, corneal ulcer, dacryocystitis, stye, post-operative wound infection and traumatic and burn infections.
Peritonitis.
Septicemia and sub-acute bacterial endocarditis. |
|||
Curative | KEDACILLIN® for Injection Approved UseIt is indicated the following infections due to Sulbenicillin susceptible Pseudomonas aeruginosa, Proteus, Retgerella, Klebsiella, Enterobacter, E. coli, Citrobacter cloacae, Pfeiffer's bacilli, Staphylococci, Streptococci, Pneumococcus and Bacteroides.
Urinary tract infections : pyelonephritis, pyelitis, pyonephrosis, cystitis and urethritis.
Bile-duct infections : cholecystitis and cholangitis.
Respiratory tract infections : acute and chronic bronchitis, bronchiectasis, bronchopneumonia, pneumonia and pulmonary suppuration.
Obstetrics and Gynecology : intrauterine infection, adnexitis, intrapelvic infection and Bartholinitis.
Otorhinological infections : otitis media, sinusitis, parotitis, submaxillitis, furuncle of the ear and furuncle of the nose.
Superfacial suppurative diseases : folliculitis, furuncle, carbuncle, abscess, panaris, phlegmon, tonsilitis, peritonsilitis, peritonsillar abscess, erysipelas, ophthalmia, blepharitis, corneal ulcer, dacryocystitis, stye, post-operative wound infection and traumatic and burn infections.
Peritonitis.
Septicemia and sub-acute bacterial endocarditis. |
|||
Curative | KEDACILLIN® for Injection Approved UseIt is indicated the following infections due to Sulbenicillin susceptible Pseudomonas aeruginosa, Proteus, Retgerella, Klebsiella, Enterobacter, E. coli, Citrobacter cloacae, Pfeiffer's bacilli, Staphylococci, Streptococci, Pneumococcus and Bacteroides.
Urinary tract infections : pyelonephritis, pyelitis, pyonephrosis, cystitis and urethritis.
Bile-duct infections : cholecystitis and cholangitis.
Respiratory tract infections : acute and chronic bronchitis, bronchiectasis, bronchopneumonia, pneumonia and pulmonary suppuration.
Obstetrics and Gynecology : intrauterine infection, adnexitis, intrapelvic infection and Bartholinitis.
Otorhinological infections : otitis media, sinusitis, parotitis, submaxillitis, furuncle of the ear and furuncle of the nose.
Superfacial suppurative diseases : folliculitis, furuncle, carbuncle, abscess, panaris, phlegmon, tonsilitis, peritonsilitis, peritonsillar abscess, erysipelas, ophthalmia, blepharitis, corneal ulcer, dacryocystitis, stye, post-operative wound infection and traumatic and burn infections.
Peritonitis.
Septicemia and sub-acute bacterial endocarditis. |
|||
Curative | KEDACILLIN® for Injection Approved UseIt is indicated the following infections due to Sulbenicillin susceptible Pseudomonas aeruginosa, Proteus, Retgerella, Klebsiella, Enterobacter, E. coli, Citrobacter cloacae, Pfeiffer's bacilli, Staphylococci, Streptococci, Pneumococcus and Bacteroides.
Urinary tract infections : pyelonephritis, pyelitis, pyonephrosis, cystitis and urethritis.
Bile-duct infections : cholecystitis and cholangitis.
Respiratory tract infections : acute and chronic bronchitis, bronchiectasis, bronchopneumonia, pneumonia and pulmonary suppuration.
Obstetrics and Gynecology : intrauterine infection, adnexitis, intrapelvic infection and Bartholinitis.
Otorhinological infections : otitis media, sinusitis, parotitis, submaxillitis, furuncle of the ear and furuncle of the nose.
Superfacial suppurative diseases : folliculitis, furuncle, carbuncle, abscess, panaris, phlegmon, tonsilitis, peritonsilitis, peritonsillar abscess, erysipelas, ophthalmia, blepharitis, corneal ulcer, dacryocystitis, stye, post-operative wound infection and traumatic and burn infections.
Peritonitis.
Septicemia and sub-acute bacterial endocarditis. |
|||
Curative | KEDACILLIN® for Injection Approved UseIt is indicated the following infections due to Sulbenicillin susceptible Pseudomonas aeruginosa, Proteus, Retgerella, Klebsiella, Enterobacter, E. coli, Citrobacter cloacae, Pfeiffer's bacilli, Staphylococci, Streptococci, Pneumococcus and Bacteroides.
Urinary tract infections : pyelonephritis, pyelitis, pyonephrosis, cystitis and urethritis.
Bile-duct infections : cholecystitis and cholangitis.
Respiratory tract infections : acute and chronic bronchitis, bronchiectasis, bronchopneumonia, pneumonia and pulmonary suppuration.
Obstetrics and Gynecology : intrauterine infection, adnexitis, intrapelvic infection and Bartholinitis.
Otorhinological infections : otitis media, sinusitis, parotitis, submaxillitis, furuncle of the ear and furuncle of the nose.
Superfacial suppurative diseases : folliculitis, furuncle, carbuncle, abscess, panaris, phlegmon, tonsilitis, peritonsilitis, peritonsillar abscess, erysipelas, ophthalmia, blepharitis, corneal ulcer, dacryocystitis, stye, post-operative wound infection and traumatic and burn infections.
Peritonitis.
Septicemia and sub-acute bacterial endocarditis. |
Sample Use Guides
Usually, 2-4 g daily for adults or 40-80 mg/kg body weight daily for children, intravenously, divided into two to four doses.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/3939120
The in vitro antibacterial activity of sulbenicillin against a number of mucoid and non-mucoid strains of Pseudomonas aeruginosa was investigated and compared with that of some other beta-lactam antibiotics. Sulbenicillin showed better anti-microbial activity than carbenicillin in almost all the tests run. Sulbenicillin appears to have a somewhat lower activity than piperacillin and cefotaxime; however, cefotaxime and particularly piperacillin are highly conditioned by the inoculum size and have a less favourable MBC to MIC ratio.
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NCI_THESAURUS |
C1500
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WHO-VATC |
QJ01CA16
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WHO-ATC |
J01CA16
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DB13693
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SUB15423MIG
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CHEMBL2103786
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41744-40-5
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20055036
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D013408
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C90915
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4052
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Q2VYF0562D
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m10292
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100000078052
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255-528-6
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SULBENICILLIN
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10168
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DTXSID90873381
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9322
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3146
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)