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

Molecular Formula C16H18N2O7S2
Molecular Weight 414.453
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

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. III. Antigenic specificity of rat anti-cephalosporin-OvA IgE sera.
1981 Jan
IgE antibodies for penicillins and cephalosporins in rats. II. Antigenic specificity of rat anti-penicillin-OvA IgE sera.
1981 Jan
Antigenicity of beta-lactam antibiotic preparations: production of IgE antibodies to beta-lactam antibiotic and their cross-reaction within the antibiotic group.
1982
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
A case of inadvertent anterior chamber and corneal stromal injection with antibiotics during cataract operation.
2006 Dec
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:36:57 GMT 2023
Edited
by admin
on Fri Dec 15 15:36:57 GMT 2023
Record UNII
Q2VYF0562D
Record Status Validated (UNII)
Record Version
  • Download
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
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
EVMPD
SUB15423MIG
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PRIMARY
ChEMBL
CHEMBL2103786
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PRIMARY
CAS
41744-40-5
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
PUBCHEM
20055036
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
MESH
D013408
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
NCI_THESAURUS
C90915
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
DRUG CENTRAL
4052
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
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
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
SMS_ID
100000078052
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
ECHA (EC/EINECS)
255-528-6
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
WIKIPEDIA
SULBENICILLIN
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
RXCUI
10168
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 RxNorm
EPA CompTox
DTXSID90873381
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
CHEBI
9322
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
INN
3146
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
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