U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C8H11NO5S
Molecular Weight 233.243
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULBACTAM

SMILES

CC1(C)[C@]([H])(C(=O)O)N2C(=O)C[C@@]2([H])S1(=O)=O

InChI

InChIKey=FKENQMMABCRJMK-RITPCOANSA-N
InChI=1S/C8H11NO5S/c1-8(2)6(7(11)12)9-4(10)3-5(9)15(8,13)14/h5-6H,3H2,1-2H3,(H,11,12)/t5-,6+/m1/s1

HIDE SMILES / InChI

Description
Curator's Comment:: description was created based on several sources, including https://en.wikipedia.org/wiki/Sulbactam http://www.drugbank.ca/drugs/DB09324

Sulbactam is a β-lactamase inhibitor given in combination with β-lactam antibiotics to inhibit β-lactamase, an enzyme produced by bacteria that destroys the antibiotics. Sulbactam in combination with semisynthetic antibiotic ampicillin sodium is indicated for the treatment of infections due to susceptible strains of the designated microorganisms: Skin and Skin Structure Infections caused by beta-lactamase producing strains of Staphylococcus aureus, Escherichia coli etc; Intra-Abdominal Infections caused by beta-lactamase producing strains of Escherichia coli, Klebsiella spp. (including K. Pneumoniae) tec; Gynecological Infections caused by beta-lactamase producing strains of Escherichia coli, and Bacteroides spp. (including B. fragilis).

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P62593
Gene ID: 10076131|||10076142|||13876868|||13877052|||13903673|||13905334|||13905363|||13906404|||13906709|||13906924|||13909533|||13909568|||14612524|||17824300|||17824435|||18157686|||20466965|||20466993|||20467118|||20468340|||20471961|||20491414|||20491639|||20492529|||20492626|||20493584|||2716540|||3244915|||3722457|||4924718|||5961992|||6276043|||8319064|||8319163|||9537966|||9538101|||9846067
Gene Symbol: bla|||blaT-3|||blaT-4|||blaT-5|||blaT-6
Target Organism: Escherichia coli
0.062 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
UNASYN

Approved Use

Sulbactam

Launch Date

5.8501438E11
Curative
UNASYN

Approved Use

Sulbactam

Launch Date

5.8501438E11
Curative
UNASYN

Approved Use

Sulbactam

Launch Date

5.8501438E11
Curative
UNASYN

Approved Use

UNASYN is an injectable antibacterial combination consisting of the semisynthetic antibiotic ampicillin sodium and the beta-lactamase inhibitor sulbactam sodium for intravenous and intramuscular administration

Launch Date

5.8501438E11
Curative
UNASYN

Approved Use

Sulbactam

Launch Date

5.8501438E11
Curative
UNASYN

Approved Use

Sulbactam

Launch Date

5.8501438E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
15.36 μg/mL
0.5 g single, intramuscular
dose: 0.5 g
route of administration: Intramuscular
experiment type: SINGLE
co-administered: AMPICILLIN
SULBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
40.33 μg × h/mL
0.5 g single, intramuscular
dose: 0.5 g
route of administration: Intramuscular
experiment type: SINGLE
co-administered: AMPICILLIN
SULBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
40.71 μg × h/mL
0.5 g 1 times / day steady-state, intravenous
dose: 0.5 g
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: AMPICILLIN
SULBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
83.79 μg × h/mL
1 g 1 times / day steady-state, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: AMPICILLIN
SULBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.26 h
0.5 g single, intramuscular
dose: 0.5 g
route of administration: Intramuscular
experiment type: SINGLE
co-administered: AMPICILLIN
SULBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1.15 h
0.5 g 1 times / day steady-state, intravenous
dose: 0.5 g
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: AMPICILLIN
SULBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1.14 h
1 g 1 times / day steady-state, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: AMPICILLIN
SULBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1 h
SULBACTAM serum
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
62%
SULBACTAM serum
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
4 g 3 times / day multiple, intravenous
Highest studied dose
Dose: 4 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 4 g, 3 times / day
Co-administed with::
ampicillin, i.v(8 g, t.i.d)
meropenem, i.v(2g, t.i.d)
polymyxin B, i.v(1.43 mg/kg, b.i.d)
Sources: Page: p.5
unhealthy
n = 13
Health Status: unhealthy
Condition: Ventilator-associated pneumonia, caused by colistin-resistant A. baumannii infection
Population Size: 13
Sources: Page: p.5
2 g 2 times / day multiple, intravenous
Recommended
Dose: 2 g, 2 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 2 times / day
Co-administed with::
cefoperazone, i.v
Sources:
unhealthy
Health Status: unhealthy
Condition: Bacterial infections
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
yes
PubMed

PubMed

TitleDatePubMed
[Activity of new fluoroquinolones against clinical isolates of Acinetobacter baumannii].
2001 Dec
[Guideline of antimicrobial therapy in the area of cardiovascular surgery].
2001 Dec
Hepatotoxic reactions induced by beta-lactamase inhibitors.
2001 Dec 17
Comparison of Neisseria gonorrhoeae isolates from the genital tract and pharynx of two gonorrhea patients.
2001 Sep
In vitro activity of sulperazon against recent isolates of ceftazidime-resistant bacteria.
2001 Sep
An unusual form of Actinomycosis of the mandible with a resultant gross sequester in a 4-year-old child: a case report.
2001 Spring
Eradication of multi-drug resistant Acinetobacter from an intensive care unit.
2001 Winter
Beta-lactam/beta-lactamase inhibitor combinations in empiric management of pediatric infections.
2002
Surgical antibiotic prophylaxis in a Turkish university hospital.
2002 Aug
Antimicrobial susceptibility of coagulase-negative staphylococci isolated from bovine mastitis in Argentina.
2002 Aug
Pharmacokinetics of an ampicillin/sulbactam (2:1) combination in rabbits.
2002 Aug
Pandrug-resistant Acinetobacter baumannii causing nosocomial infections in a university hospital, Taiwan.
2002 Aug
Molecular dynamics at the root of expansion of function in the M69L inhibitor-resistant TEM beta-lactamase from Escherichia coli.
2002 Aug 14
Efficacy of amoxicillin-sulbactam, given twice-a-day, for the treatment of community-acquired pneumonia: a clinical trial based on a pharmacodynamic model.
2002 Dec
Application of micellar electrokinetic chromatography to the determination of sultamicillin in oral pharmaceutical preparations.
2002 Dec 6
Antibacterial activities of beta-lactamase inhibitors associated with morphological changes of cell wall in Helicobacter pylori.
2002 Feb
Chronic intrauterine infection and inflammation in the preterm rabbit, despite antibiotic therapy.
2002 Feb
[Analysis of prophylactic antibiotics for cesarean section].
2002 Jan
[The efficacy of combining antibiotic treatment with topical intranasal steroid administration in the treatment of chronic otitis media with effusion].
2002 Jul-Aug
[A case of bronchopulmonary actinomycosis diagnosed by transbronchial biopsy of a bronchial polypoid tumor].
2002 Jun
[Microbiological and clinical studies of Haemophilus influenzae isolated at Kitakyushu Municipal Medical Center from 1996 through 1999].
2002 Jun
Comparison of ampicillin-sulbactam and imipenem-cilastatin for the treatment of acinetobacter ventilator-associated pneumonia.
2002 Jun 1
Low dose sultamicillin in acute sinusitis.
2002 Mar
Multiresistant Acinetobacter infections: a role for sulbactam combinations in overcoming an emerging worldwide problem.
2002 Mar
Malakoplakia of liver diagnosed by a needle core biopsy: a case report and review of the literature.
2002 Mar
The role of cefoperazone-sulbactam for treatment of severe melioidosis.
2002 Mar 1
In vitro antibiotic release from poly(3-hydroxybutyrate-co-3-hydroxyvalerate) rods.
2002 Mar-Apr
Bacteriology and antimicrobial susceptibility in biliary tract disease: an audit of 10-year's experience.
2002 May
In vitro investigation of the susceptibility of Acinetobacter baumannii strains isolated from clinical specimens to ampicillin/sulbactam alone and in combination with amikacin.
2002 Nov
First occurrence of transferable extended-spectrum beta-lactamase hydrolyzing cefoperazone in multiresistant nosocomial strains of Klebsiella pneumoniae from two hospitals in Czech and Slovak Republics.
2002 Oct
Reports of osteopenia/rickets of prematurity are on the increase because of improved survival rates of low birthweight infants.
2002 Oct
[The efficacy of prophylactic administration of SBT/ABPC for postoperative infection in neurosurgical operations].
2002 Oct
Antimicrobial susceptibility of major pathogens of orofacial odontogenic infections to 11 beta-lactam antibiotics.
2002 Oct
Development of an assay for beta-lactam hydrolysis using the pH-dependence of enhanced green fluorescent protein.
2002 Oct 15
[Activity of 14 antimicrobials against Eikenella corrodens].
2002 Oct-Dec
The effect of high single dose parenteral vitamin A in addition to antibiotic therapy on healing of maxillary sinusitis in experimental acute sinusitis.
2002 Sep 24
Biochemical characterization of a novel extended-spectrum beta-lactamase from Pseudomonas aeruginosa 802.
2002 Spring
[The impact of antibiotic use on hospital-acquired pneumonia: data of etiology tests].
2003
Catalytic properties of an endogenous beta-lactamase responsible for the resistance of Azospirillum lipoferum to beta-lactam antibiotics.
2003 Feb
HPLC for in-process control in the production of sultamicillin.
2003 Feb 26
Current status of drug resistance among gram-negative bacilli isolated from admitted cases in a tertiary care centre.
2003 Jan
Acute otitis media and facial nerve paralysis in adults.
2003 Jan
Severe nosocomial infections with imipenem-resistant Acinetobacter baumannii treated with ampicillin/sulbactam.
2003 Jan
Spirocyclopropyl beta-lactams as mechanism-based inhibitors of serine beta-lactamases. Synthesis by rhodium-catalyzed cyclopropanation of 6-diazopenicillanate sulfone.
2003 Jun 19
Group 1 beta-lactamases of Aeromonas caviae and their resistance to beta-lactam antibiotics.
2003 Mar
[beta-Lactamase-inhibitor combinations].
2003 Mar
Nosocomial multi-drug resistant Acinetobacter baumannii bloodstream infection: risk factors and outcome with ampicillin-sulbactam treatment.
2003 May
In vitro activity of penicillin G/sulbactam compared with penicillin and other antibiotics against common organisms causing ear, nose and throat (ENT) infections.
2003 May
Considerations in control and treatment of nosocomial infections due to multidrug-resistant Acinetobacter baumannii.
2003 May 15
Spectrum and antibiotic sensitivity of bacteria contaminating the upper gut in patients with malabsorption syndrome from the tropics.
2003 May 24
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: UNASYN should be administered by slow intravenous injection over at least 10–15 minutes or can also be delivered in greater dilutions with 50–100 mL of a compatible diluent as an intravenous infusion over 15–30 minutes.
The recommended adult dosage of UNASYN is 1.5 g (1 g ampicillin as the sodium salt plus 0.5 g sulbactam as the sodium salt) to 3 g (2 g ampicillin as the sodium salt plus 1 g sulbactam as the sodium salt) every six hours
Route of Administration: Intravenous
In Vitro Use Guide
Curator's Comment:: The combination of sulbactam and ampicillin was extremely effective in vitro against anaerobic bacteria, including those which demonstrated high-level resistance to ampicillin
ampicillin-sulbactam 2 ug/ml;
Name Type Language
SULBACTAM
INN   MART.   MI   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
SULBACTAM [MI]
Common Name English
(2S,5R)-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID 4,4-DIOXIDE
Systematic Name English
SULBACTAM [WHO-DD]
Common Name English
SULBACTAM [USP-RS]
Common Name English
SULBACTAM [MART.]
Common Name English
SULBACTAM [INN]
Common Name English
SULBACTAM [VANDF]
Common Name English
SULTAMICILLIN IMPURITY A [EP]
Common Name English
NSC-759886
Code English
CP-458992
Code English
Classification Tree Code System Code
NDF-RT N0000175930
Created by admin on Fri Jun 25 22:02:59 UTC 2021 , Edited by admin on Fri Jun 25 22:02:59 UTC 2021
LIVERTOX 905
Created by admin on Fri Jun 25 22:02:59 UTC 2021 , Edited by admin on Fri Jun 25 22:02:59 UTC 2021
WHO-ATC J01CG01
Created by admin on Fri Jun 25 22:02:59 UTC 2021 , Edited by admin on Fri Jun 25 22:02:59 UTC 2021
NDF-RT N0000000202
Created by admin on Fri Jun 25 22:02:59 UTC 2021 , Edited by admin on Fri Jun 25 22:02:59 UTC 2021
WHO-VATC QJ01CG01
Created by admin on Fri Jun 25 22:02:59 UTC 2021 , Edited by admin on Fri Jun 25 22:02:59 UTC 2021
NCI_THESAURUS C260
Created by admin on Fri Jun 25 22:02:59 UTC 2021 , Edited by admin on Fri Jun 25 22:02:59 UTC 2021
Code System Code Type Description
MESH
D013407
Created by admin on Fri Jun 25 22:02:59 UTC 2021 , Edited by admin on Fri Jun 25 22:02:59 UTC 2021
PRIMARY
EPA CompTox
68373-14-8
Created by admin on Fri Jun 25 22:02:59 UTC 2021 , Edited by admin on Fri Jun 25 22:02:59 UTC 2021
PRIMARY
CAS
68373-14-8
Created by admin on Fri Jun 25 22:02:59 UTC 2021 , Edited by admin on Fri Jun 25 22:02:59 UTC 2021
PRIMARY
ChEMBL
CHEMBL403
Created by admin on Fri Jun 25 22:02:59 UTC 2021 , Edited by admin on Fri Jun 25 22:02:59 UTC 2021
PRIMARY
LACTMED
Ampicillin and Sulbactam
Created by admin on Fri Jun 25 22:02:59 UTC 2021 , Edited by admin on Fri Jun 25 22:02:59 UTC 2021
PRIMARY
ECHA (EC/EINECS)
269-878-2
Created by admin on Fri Jun 25 22:02:59 UTC 2021 , Edited by admin on Fri Jun 25 22:02:59 UTC 2021
PRIMARY
RXCUI
10167
Created by admin on Fri Jun 25 22:02:59 UTC 2021 , Edited by admin on Fri Jun 25 22:02:59 UTC 2021
PRIMARY RxNorm
WIKIPEDIA
SULBACTAM
Created by admin on Fri Jun 25 22:02:59 UTC 2021 , Edited by admin on Fri Jun 25 22:02:59 UTC 2021
PRIMARY
NCI_THESAURUS
C61957
Created by admin on Fri Jun 25 22:02:59 UTC 2021 , Edited by admin on Fri Jun 25 22:02:59 UTC 2021
PRIMARY
USP_CATALOG
1623670
Created by admin on Fri Jun 25 22:02:59 UTC 2021 , Edited by admin on Fri Jun 25 22:02:59 UTC 2021
PRIMARY USP-RS
DRUG CENTRAL
2492
Created by admin on Fri Jun 25 22:02:59 UTC 2021 , Edited by admin on Fri Jun 25 22:02:59 UTC 2021
PRIMARY
PUBCHEM
130313
Created by admin on Fri Jun 25 22:02:59 UTC 2021 , Edited by admin on Fri Jun 25 22:02:59 UTC 2021
PRIMARY
FDA UNII
S4TF6I2330
Created by admin on Fri Jun 25 22:02:59 UTC 2021 , Edited by admin on Fri Jun 25 22:02:59 UTC 2021
PRIMARY
MERCK INDEX
M10291
Created by admin on Fri Jun 25 22:02:59 UTC 2021 , Edited by admin on Fri Jun 25 22:02:59 UTC 2021
PRIMARY Merck Index
EVMPD
SUB10676MIG
Created by admin on Fri Jun 25 22:02:59 UTC 2021 , Edited by admin on Fri Jun 25 22:02:59 UTC 2021
PRIMARY
INN
4845
Created by admin on Fri Jun 25 22:02:59 UTC 2021 , Edited by admin on Fri Jun 25 22:02:59 UTC 2021
PRIMARY
DRUG BANK
DB09324
Created by admin on Fri Jun 25 22:02:59 UTC 2021 , Edited by admin on Fri Jun 25 22:02:59 UTC 2021
PRIMARY