U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of SULBENICILLIN

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

HIDE SMILES / InChI

Description
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

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
KEDACILLIN® for Injection

Approved Use

It 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 Use

It 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 Use

It 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 Use

It 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 Use

It 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 Use

It 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.
PubMed

PubMed

TitleDatePubMed
Stereoselective binding and degradation of sulbenicillin in the presence of human serum albumin.
2001 May 15
Methicillin-resistant staphylococci and ofloxacin-resistant bacteria from clinically healthy conjunctivas.
2001 May-Jun
Patents

Patents

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
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.
Name Type Language
SULBENICILLIN
INN   MI   WHO-DD  
INN  
Official Name English
.ALPHA.-SULFOBENZYLPENICILLIN
Common Name English
D-(-)-SULBENICILLIN
Common Name English
sulbenicillin [INN]
Common Name English
Sulbenicillin [WHO-DD]
Common Name English
4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 3,3-DIMETHYL-7-OXO-6-(((2R)-2-PHENYL-2-SULFOACETYL)AMINO)-, (2S,5R,6R)-
Common Name English
SULBENICILLIN [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1500
Created by admin on Fri Dec 15 15:36:58 GMT 2023 , Edited by admin on Fri Dec 15 15:36:58 GMT 2023
WHO-VATC QJ01CA16
Created by admin on Fri Dec 15 15:36:58 GMT 2023 , Edited by admin on Fri Dec 15 15:36:58 GMT 2023
WHO-ATC J01CA16
Created by admin on Fri Dec 15 15:36:58 GMT 2023 , Edited by admin on Fri Dec 15 15:36:58 GMT 2023
Code System Code Type Description
DRUG BANK
DB13693
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PRIMARY
EVMPD
SUB15423MIG
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PRIMARY
ChEMBL
CHEMBL2103786
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CAS
41744-40-5
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PUBCHEM
20055036
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MESH
D013408
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NCI_THESAURUS
C90915
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DRUG CENTRAL
4052
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PRIMARY
FDA UNII
Q2VYF0562D
Created by admin on Fri Dec 15 15:36:58 GMT 2023 , Edited by admin on Fri Dec 15 15:36:58 GMT 2023
PRIMARY
MERCK INDEX
m10292
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PRIMARY Merck Index
SMS_ID
100000078052
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PRIMARY
ECHA (EC/EINECS)
255-528-6
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WIKIPEDIA
SULBENICILLIN
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PRIMARY
RXCUI
10168
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PRIMARY RxNorm
EPA CompTox
DTXSID90873381
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PRIMARY
CHEBI
9322
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PRIMARY
INN
3146
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PRIMARY