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

CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=CC=C3)S(O)(=O)=O)C(=O)N2[C@H]1C(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.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
252 μg/mL
2 g single, intravenous
dose: 2 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
SULBENICILLIN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
70 min
4 g single, intravenous
dose: 4 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
SULBENICILLIN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
97 min
2 g single, intravenous
dose: 2 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
SULBENICILLIN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
30%
4 g single, intravenous
dose: 4 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
SULBENICILLIN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
5 g 2 times / day multiple, intravenous
Studied dose
Dose: 5 g, 2 times / day
Route: intravenous
Route: multiple
Dose: 5 g, 2 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Other AEs: Rash, Eosinophilia...
Other AEs:
Rash (1.28%)
Eosinophilia (2.1%)
Transaminase glutamic-oxalacetic increased (2%)
Transaminase glutamic-pyruvic increased (2%)
ALP increased (0.7%)
Sources:
AEs

AEs

AESignificanceDosePopulation
ALP increased 0.7%
5 g 2 times / day multiple, intravenous
Studied dose
Dose: 5 g, 2 times / day
Route: intravenous
Route: multiple
Dose: 5 g, 2 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Rash 1.28%
5 g 2 times / day multiple, intravenous
Studied dose
Dose: 5 g, 2 times / day
Route: intravenous
Route: multiple
Dose: 5 g, 2 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Transaminase glutamic-oxalacetic increased 2%
5 g 2 times / day multiple, intravenous
Studied dose
Dose: 5 g, 2 times / day
Route: intravenous
Route: multiple
Dose: 5 g, 2 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Transaminase glutamic-pyruvic increased 2%
5 g 2 times / day multiple, intravenous
Studied dose
Dose: 5 g, 2 times / day
Route: intravenous
Route: multiple
Dose: 5 g, 2 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Eosinophilia 2.1%
5 g 2 times / day multiple, intravenous
Studied dose
Dose: 5 g, 2 times / day
Route: intravenous
Route: multiple
Dose: 5 g, 2 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
PubMed

PubMed

TitleDatePubMed
Synthesis of novel hapten and production of generic monoclonal antibody for immunoassay of penicillins residues in milk.
2013
Gemella species-associated late-onset endophthalmitis after trabeculectomy with adjunctive mitomycin C.
2009-08
An intractable case of Pseudomonas aeruginosa infection after scleral buckling for rhegmatogenous retinal detachment.
2008-03
A case of inadvertent anterior chamber and corneal stromal injection with antibiotics during cataract operation.
2006-12
Placental transfer of antibiotics administered to the mother: a review.
2006-02
Analysis of beta-lactam antibiotics by high performance liquid chromatography-atmospheric pressure chemical ionization mass spectrometry using bromoform.
2002-11-07
[Antibiotic ophthalmic solutions evaluated by pharmacokinetic parameters of maximum concentration in the aqueous].
2002-04
Stereoselective binding and degradation of sulbenicillin in the presence of human serum albumin.
2001-05-15
Methicillin-resistant staphylococci and ofloxacin-resistant bacteria from clinically healthy conjunctivas.
2001-05-08
Epitope analysis of aztreonam by antiaztreonam monoclonal antibodies and possible consequences in beta-lactams hypersensitivity.
1992
Antigenicity of beta-lactam antibiotic preparations: production of IgE antibodies to beta-lactam antibiotic and their cross-reaction within the antibiotic group.
1982
IgE antibodies for penicillins and cephalosporins in rats. III. Antigenic specificity of rat anti-cephalosporin-OvA IgE sera.
1981-01
IgE antibodies for penicillins and cephalosporins in rats. II. Antigenic specificity of rat anti-penicillin-OvA IgE sera.
1981-01
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 Mon Mar 31 18:03:03 GMT 2025
Edited
by admin
on Mon Mar 31 18:03:03 GMT 2025
Record UNII
Q2VYF0562D
Record Status Validated (UNII)
Record Version
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Name Type Language
.ALPHA.-SULFOBENZYLPENICILLIN
Preferred Name English
SULBENICILLIN
INN   MI   WHO-DD  
INN  
Official 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 Mon Mar 31 18:03:03 GMT 2025 , Edited by admin on Mon Mar 31 18:03:03 GMT 2025
WHO-VATC QJ01CA16
Created by admin on Mon Mar 31 18:03:03 GMT 2025 , Edited by admin on Mon Mar 31 18:03:03 GMT 2025
WHO-ATC J01CA16
Created by admin on Mon Mar 31 18:03:03 GMT 2025 , Edited by admin on Mon Mar 31 18:03:03 GMT 2025
Code System Code Type Description
DRUG BANK
DB13693
Created by admin on Mon Mar 31 18:03:03 GMT 2025 , Edited by admin on Mon Mar 31 18:03:03 GMT 2025
PRIMARY
EVMPD
SUB15423MIG
Created by admin on Mon Mar 31 18:03:03 GMT 2025 , Edited by admin on Mon Mar 31 18:03:03 GMT 2025
PRIMARY
ChEMBL
CHEMBL2103786
Created by admin on Mon Mar 31 18:03:03 GMT 2025 , Edited by admin on Mon Mar 31 18:03:03 GMT 2025
PRIMARY
CAS
41744-40-5
Created by admin on Mon Mar 31 18:03:03 GMT 2025 , Edited by admin on Mon Mar 31 18:03:03 GMT 2025
PRIMARY
PUBCHEM
20055036
Created by admin on Mon Mar 31 18:03:03 GMT 2025 , Edited by admin on Mon Mar 31 18:03:03 GMT 2025
PRIMARY
MESH
D013408
Created by admin on Mon Mar 31 18:03:03 GMT 2025 , Edited by admin on Mon Mar 31 18:03:03 GMT 2025
PRIMARY
NCI_THESAURUS
C90915
Created by admin on Mon Mar 31 18:03:03 GMT 2025 , Edited by admin on Mon Mar 31 18:03:03 GMT 2025
PRIMARY
DRUG CENTRAL
4052
Created by admin on Mon Mar 31 18:03:03 GMT 2025 , Edited by admin on Mon Mar 31 18:03:03 GMT 2025
PRIMARY
FDA UNII
Q2VYF0562D
Created by admin on Mon Mar 31 18:03:03 GMT 2025 , Edited by admin on Mon Mar 31 18:03:03 GMT 2025
PRIMARY
MERCK INDEX
m10292
Created by admin on Mon Mar 31 18:03:03 GMT 2025 , Edited by admin on Mon Mar 31 18:03:03 GMT 2025
PRIMARY Merck Index
SMS_ID
100000078052
Created by admin on Mon Mar 31 18:03:03 GMT 2025 , Edited by admin on Mon Mar 31 18:03:03 GMT 2025
PRIMARY
ECHA (EC/EINECS)
255-528-6
Created by admin on Mon Mar 31 18:03:03 GMT 2025 , Edited by admin on Mon Mar 31 18:03:03 GMT 2025
PRIMARY
WIKIPEDIA
SULBENICILLIN
Created by admin on Mon Mar 31 18:03:03 GMT 2025 , Edited by admin on Mon Mar 31 18:03:03 GMT 2025
PRIMARY
RXCUI
10168
Created by admin on Mon Mar 31 18:03:03 GMT 2025 , Edited by admin on Mon Mar 31 18:03:03 GMT 2025
PRIMARY RxNorm
EPA CompTox
DTXSID90873381
Created by admin on Mon Mar 31 18:03:03 GMT 2025 , Edited by admin on Mon Mar 31 18:03:03 GMT 2025
PRIMARY
CHEBI
9322
Created by admin on Mon Mar 31 18:03:03 GMT 2025 , Edited by admin on Mon Mar 31 18:03:03 GMT 2025
PRIMARY
INN
3146
Created by admin on Mon Mar 31 18:03:03 GMT 2025 , Edited by admin on Mon Mar 31 18:03:03 GMT 2025
PRIMARY
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