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

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
IgE antibodies for penicillins and cephalosporins in rats. II. Antigenic specificity of rat anti-penicillin-OvA IgE sera.
1981 Jan
Epitope analysis of aztreonam by antiaztreonam monoclonal antibodies and possible consequences in beta-lactams hypersensitivity.
1992
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
[Antibiotic ophthalmic solutions evaluated by pharmacokinetic parameters of maximum concentration in the aqueous].
2002 Apr
Analysis of beta-lactam antibiotics by high performance liquid chromatography-atmospheric pressure chemical ionization mass spectrometry using bromoform.
2002 Nov 7
Placental transfer of antibiotics administered to the mother: a review.
2006 Feb
An intractable case of Pseudomonas aeruginosa infection after scleral buckling for rhegmatogenous retinal detachment.
2008 Mar
Gemella species-associated late-onset endophthalmitis after trabeculectomy with adjunctive mitomycin C.
2009 Aug
Synthesis of novel hapten and production of generic monoclonal antibody for immunoassay of penicillins residues in milk.
2013
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 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