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

Stereochemistry ABSOLUTE
Molecular Formula C8H11NO5S
Molecular Weight 233.242
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULBACTAM

SMILES

CC1(C)[C@@H](N2[C@@H](CC2=O)S1(=O)=O)C(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

1988
Curative
UNASYN

Approved Use

Sulbactam

Launch Date

1988
Curative
UNASYN

Approved Use

Sulbactam

Launch Date

1988
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

1988
Curative
UNASYN

Approved Use

Sulbactam

Launch Date

1988
Curative
UNASYN

Approved Use

Sulbactam

Launch Date

1988
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
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
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
1.15 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
1.26 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 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
Sources:
unhealthy
Health Status: unhealthy
Sources:
2 g 2 times / day multiple, intravenous
Recommended
Dose: 2 g, 2 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 2 times / day
Sources:
unhealthy
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
yes
PubMed

PubMed

TitleDatePubMed
Antibiotic susceptibility, serum response and surface properties of Klebsiella species.
2001
Effect of granulocyte-macrophage colony-stimulating factor on treatment of acute osteomyelitis. An experimental investigation in rats.
2001
[Fundamental and clinical studies on beta-lactamase inhibitors].
2001 Apr
Sulbactam efficacy in experimental models caused by susceptible and intermediate Acinetobacter baumannii strains.
2001 Apr
Rationale for treating community-acquired lower respiratory tract infections with amoxicillin/sulbactam combination through pharmacodynamic analysis in the setting of aminopenicillin-resistant organisms.
2001 Aug
[Guideline of antimicrobial therapy in the area of cardiovascular surgery].
2001 Dec
Hepatotoxic reactions induced by beta-lactamase inhibitors.
2001 Dec 17
Epidemiology, resistance, and outcomes of Acinetobacter baumannii bacteremia treated with imipenem-cilastatin or ampicillin-sulbactam.
2001 Feb
Incidence of beta-lactamase production and antimicrobial susceptibility of anaerobic gram-negative rods isolated from pus specimens of orofacial odontogenic infections.
2001 Feb
Inhibition of the SHV-1 beta-lactamase by sulfones: crystallographic observation of two reaction intermediates with tazobactam.
2001 Feb 13
Sepsis and multiple brain abscesses caused by Salmonella paratyphi B in an infant: successful treatment with sulbactam-ampicillin and surgical drainage.
2001 Jan-Mar
Use of ampicillin/sulbactam and sultamicillin in pediatric infections: a re-evaluation.
2001 Jul-Aug
[Clinical analysis of neutropenic fever associated with hematological disorders].
2001 Mar
An anaphylactic reaction possibly associated with an intraoperative coronary artery spasm during general anesthesia.
2001 May
Parallel analysis of individual and aggregated data on antibiotic exposure and resistance in gram-negative bacilli.
2001 Nov 1
The penetration of cefoperazone and sulbactam into the lumbar intervertebral discs.
2001 Oct
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
Beta-lactam/beta-lactamase inhibitor combinations in empiric management of pediatric infections.
2002
Probing substrate binding to metallo-beta-lactamase L1 from Stenotrophomonas maltophilia by using site-directed mutagenesis.
2002
Nontraditional dosing of ampicillin-sulbactam for multidrug-resistant Acinetobacter baumannii meningitis.
2002 Apr
[Acinetobacter, a nosocomial pathogen. Contribution of experimental models].
2002 Apr 13
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
Surveillance for antimicrobial resistance in Croatia.
2002 Jan
[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
Prevalence of and resistance to anti-microbial drugs in selected microbial species isolated from bulk milk samples.
2002 Jun
Pharmacokinetics of cefoperazone and sulbactam in liver transplant patients.
2002 Jun
CE versus LC for simultaneous determination of amoxicillin/clavulanic acid and ampicillin/sulbactam in pharmaceutical formulations for injections.
2002 Jun 20
Low dose sultamicillin in acute sinusitis.
2002 Mar
The emergence of beta-lactamase resistance in respiratory pathogens.
2002 Mar
Antibiotic resistance among clinical isolates of Acinetobacter in the UK, and in vitro evaluation of tigecycline (GAR-936).
2002 Mar
Bacteriology and antimicrobial susceptibility in biliary tract disease: an audit of 10-year's experience.
2002 May
Extended-spectrum beta-lactamase-producing Escherichia coli and Klebsiella species: risk factors for colonization and impact of antimicrobial formulary interventions on colonization prevalence.
2002 May
Substitution of Met-69 by Ala or Gly in TEM-1 beta-lactamase confer an increased susceptibility to clavulanic acid and other inhibitors.
2002 May 21
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
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
[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
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
[beta-Lactamase-inhibitor combinations].
2003 Mar
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
CP-458992
Preferred 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 [USP-RS]
Common Name English
SULTAMICILLIN IMPURITY A [EP IMPURITY]
Common Name English
SULBACTAM [MART.]
Common Name English
sulbactam [INN]
Common Name English
SULBACTAM [VANDF]
Common Name English
NSC-759886
Code English
Sulbactam [WHO-DD]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175930
Created by admin on Wed Apr 02 09:08:42 GMT 2025 , Edited by admin on Wed Apr 02 09:08:42 GMT 2025
LIVERTOX 905
Created by admin on Wed Apr 02 09:08:42 GMT 2025 , Edited by admin on Wed Apr 02 09:08:42 GMT 2025
WHO-ATC J01CG01
Created by admin on Wed Apr 02 09:08:42 GMT 2025 , Edited by admin on Wed Apr 02 09:08:42 GMT 2025
NDF-RT N0000000202
Created by admin on Wed Apr 02 09:08:42 GMT 2025 , Edited by admin on Wed Apr 02 09:08:42 GMT 2025
WHO-VATC QJ01CG01
Created by admin on Wed Apr 02 09:08:42 GMT 2025 , Edited by admin on Wed Apr 02 09:08:42 GMT 2025
NCI_THESAURUS C260
Created by admin on Wed Apr 02 09:08:42 GMT 2025 , Edited by admin on Wed Apr 02 09:08:42 GMT 2025
Code System Code Type Description
RS_ITEM_NUM
1623670
Created by admin on Wed Apr 02 09:08:42 GMT 2025 , Edited by admin on Wed Apr 02 09:08:42 GMT 2025
PRIMARY
MESH
D013407
Created by admin on Wed Apr 02 09:08:42 GMT 2025 , Edited by admin on Wed Apr 02 09:08:42 GMT 2025
PRIMARY
EPA CompTox
DTXSID1023605
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PRIMARY
CAS
68373-14-8
Created by admin on Wed Apr 02 09:08:42 GMT 2025 , Edited by admin on Wed Apr 02 09:08:42 GMT 2025
PRIMARY
SMS_ID
100000083256
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PRIMARY
ChEMBL
CHEMBL403
Created by admin on Wed Apr 02 09:08:42 GMT 2025 , Edited by admin on Wed Apr 02 09:08:42 GMT 2025
PRIMARY
LACTMED
Ampicillin and Sulbactam
Created by admin on Wed Apr 02 09:08:42 GMT 2025 , Edited by admin on Wed Apr 02 09:08:42 GMT 2025
PRIMARY
ECHA (EC/EINECS)
269-878-2
Created by admin on Wed Apr 02 09:08:42 GMT 2025 , Edited by admin on Wed Apr 02 09:08:42 GMT 2025
PRIMARY
RXCUI
10167
Created by admin on Wed Apr 02 09:08:42 GMT 2025 , Edited by admin on Wed Apr 02 09:08:42 GMT 2025
PRIMARY RxNorm
WIKIPEDIA
SULBACTAM
Created by admin on Wed Apr 02 09:08:42 GMT 2025 , Edited by admin on Wed Apr 02 09:08:42 GMT 2025
PRIMARY
NCI_THESAURUS
C61957
Created by admin on Wed Apr 02 09:08:42 GMT 2025 , Edited by admin on Wed Apr 02 09:08:42 GMT 2025
PRIMARY
CHEBI
9321
Created by admin on Wed Apr 02 09:08:42 GMT 2025 , Edited by admin on Wed Apr 02 09:08:42 GMT 2025
PRIMARY
DAILYMED
S4TF6I2330
Created by admin on Wed Apr 02 09:08:42 GMT 2025 , Edited by admin on Wed Apr 02 09:08:42 GMT 2025
PRIMARY
DRUG CENTRAL
2492
Created by admin on Wed Apr 02 09:08:42 GMT 2025 , Edited by admin on Wed Apr 02 09:08:42 GMT 2025
PRIMARY
PUBCHEM
130313
Created by admin on Wed Apr 02 09:08:42 GMT 2025 , Edited by admin on Wed Apr 02 09:08:42 GMT 2025
PRIMARY
FDA UNII
S4TF6I2330
Created by admin on Wed Apr 02 09:08:42 GMT 2025 , Edited by admin on Wed Apr 02 09:08:42 GMT 2025
PRIMARY
MERCK INDEX
m10291
Created by admin on Wed Apr 02 09:08:42 GMT 2025 , Edited by admin on Wed Apr 02 09:08:42 GMT 2025
PRIMARY Merck Index
EVMPD
SUB10676MIG
Created by admin on Wed Apr 02 09:08:42 GMT 2025 , Edited by admin on Wed Apr 02 09:08:42 GMT 2025
PRIMARY
INN
4845
Created by admin on Wed Apr 02 09:08:42 GMT 2025 , Edited by admin on Wed Apr 02 09:08:42 GMT 2025
PRIMARY
DRUG BANK
DB09324
Created by admin on Wed Apr 02 09:08:42 GMT 2025 , Edited by admin on Wed Apr 02 09:08:42 GMT 2025
PRIMARY
NSC
759886
Created by admin on Wed Apr 02 09:08:42 GMT 2025 , Edited by admin on Wed Apr 02 09:08:42 GMT 2025
PRIMARY