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
SMILES
[Na+].[Na+].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=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
| 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 | 22.98976928 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/3114912
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
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: bacterial cell wall Sources: http://www.ncbi.nlm.nih.gov/pubmed/3114912 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | KEDACILLIN® for Injection Approved UseIt 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 UseIt 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 UseIt 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 UseIt 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 UseIt 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 UseIt 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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
252 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1120400/ |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
70 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1120400/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1120400/ |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
30% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1120400/ |
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
| Dose | Population | Adverse 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%) Sources: Eosinophilia (2.1%) Transaminase glutamic-oxalacetic increased (2%) Transaminase glutamic-pyruvic increased (2%) ALP increased (0.7%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| 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
| Title | Date | PubMed |
|---|---|---|
| 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
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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/3939120
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
Edited
Mon Mar 31 17:53:39 GMT 2025
by
admin
on
Mon Mar 31 17:53:39 GMT 2025
|
| Record UNII |
29SO9LIM1Q
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Preferred Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
45357485
Created by
admin on Mon Mar 31 17:53:39 GMT 2025 , Edited by admin on Mon Mar 31 17:53:39 GMT 2025
|
PRIMARY | |||
|
32160
Created by
admin on Mon Mar 31 17:53:39 GMT 2025 , Edited by admin on Mon Mar 31 17:53:39 GMT 2025
|
PRIMARY | |||
|
SUB21912
Created by
admin on Mon Mar 31 17:53:39 GMT 2025 , Edited by admin on Mon Mar 31 17:53:39 GMT 2025
|
PRIMARY | |||
|
36417-90-0
Created by
admin on Mon Mar 31 17:53:39 GMT 2025 , Edited by admin on Mon Mar 31 17:53:39 GMT 2025
|
PRIMARY | |||
|
28002-18-8
Created by
admin on Mon Mar 31 17:53:39 GMT 2025 , Edited by admin on Mon Mar 31 17:53:39 GMT 2025
|
ALTERNATIVE | |||
|
29SO9LIM1Q
Created by
admin on Mon Mar 31 17:53:39 GMT 2025 , Edited by admin on Mon Mar 31 17:53:39 GMT 2025
|
PRIMARY | |||
|
CHEMBL2103786
Created by
admin on Mon Mar 31 17:53:39 GMT 2025 , Edited by admin on Mon Mar 31 17:53:39 GMT 2025
|
PRIMARY | |||
|
100000087618
Created by
admin on Mon Mar 31 17:53:39 GMT 2025 , Edited by admin on Mon Mar 31 17:53:39 GMT 2025
|
PRIMARY | |||
|
DTXSID30873380
Created by
admin on Mon Mar 31 17:53:39 GMT 2025 , Edited by admin on Mon Mar 31 17:53:39 GMT 2025
|
PRIMARY | |||
|
253-025-6
Created by
admin on Mon Mar 31 17:53:39 GMT 2025 , Edited by admin on Mon Mar 31 17:53:39 GMT 2025
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
PARENT -> SALT/SOLVATE |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |