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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
KEDACILLIN® for Injection
Curative
KEDACILLIN® for Injection
Curative
KEDACILLIN® for Injection
Curative
KEDACILLIN® for Injection
Curative
KEDACILLIN® for Injection
Curative
KEDACILLIN® for Injection

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
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
Record UNII
Q2VYF0562D
Record Status Validated (UNII)
Record Version