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

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H16N2O7S2.2Na
Molecular Weight 458.417
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULBENICILLIN SODIUM

SMILES

[Na+].[Na+].[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=FWRNIJIOFYDBES-ZQDFAFASSA-L
InChI=1S/C16H18N2O7S2.2Na/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);;/q;2*+1/p-2/t9-,10-,11+,14-;;/m1../s1

HIDE SMILES / InChI

Molecular Formula C16H16N2O7S2
Molecular Weight 412.437
Charge -2
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Analysis of beta-lactam antibiotics by high performance liquid chromatography-atmospheric pressure chemical ionization mass spectrometry using bromoform.
2002 Nov 7
A case of inadvertent anterior chamber and corneal stromal injection with antibiotics during cataract operation.
2006 Dec
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:18:44 GMT 2023
Edited
by admin
on Fri Dec 15 15:18:44 GMT 2023
Record UNII
29SO9LIM1Q
Record Status Validated (UNII)
Record Version
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Name Type Language
SULBENICILLIN SODIUM
MART.   WHO-DD  
Common Name English
KEDACILLIN
Brand Name English
4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 3,3-DIMETHYL-7-OXO-6-((2-PHENYL-2-SULFOACETYL)AMINO)-, SODIUM SALT (1:2), (2S,5R,6R)-
Common Name English
SULBENICILLIN SODIUM [MART.]
Common Name English
DISODIUM SALT OF (6R)-6-(2-PHENYL-2-SULPHOACETAMIDO)PENICILLANIC ACID
Common Name English
D-(-)-.ALPHA.-SULFOBENZYLPENICILLIN SODIUM SALT
Common Name English
SULBENICILLIN DISODIUM
Common Name English
SULBENICILLIN SODIUM [JAN]
Common Name English
SULFOCILLIN
Common Name English
Sulbenicillin sodium [WHO-DD]
Common Name English
Code System Code Type Description
PUBCHEM
45357485
Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023
PRIMARY
CHEBI
32160
Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023
PRIMARY
EVMPD
SUB21912
Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023
PRIMARY
CAS
36417-90-0
Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023
PRIMARY
CAS
28002-18-8
Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023
ALTERNATIVE
EPA CompTox
DTXSID2048618
Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023
PRIMARY
FDA UNII
29SO9LIM1Q
Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023
PRIMARY
ChEMBL
CHEMBL2103786
Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023
PRIMARY
SMS_ID
100000087618
Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023
PRIMARY
ECHA (EC/EINECS)
253-025-6
Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY