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

Details

Stereochemistry ABSOLUTE
Molecular Formula C8H10NO5S.Na
Molecular Weight 255.223
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULBACTAM SODIUM

SMILES

[Na+].[H][C@@]12CC(=O)N1[C@@H](C([O-])=O)C(C)(C)S2(=O)=O

InChI

InChIKey=NKZMPZCWBSWAOX-IBTYICNHSA-M
InChI=1S/C8H11NO5S.Na/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);/q;+1/p-1/t5-,6+;/m1./s1

HIDE SMILES / InChI

Molecular Formula C8H10NO5S
Molecular Weight 232.234
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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
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
[New aspects of antibiotic resistance and possibilities of its prevention].
2001 Aug
Hepatotoxic reactions induced by beta-lactamase inhibitors.
2001 Dec 17
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
Effect of single-dose prophylactic ampicillin and sulbactam on wound infection after tension-free inguinal hernia repair with polypropylene mesh: the randomized, double-blind, prospective trial.
2001 Jan
In vivo application of biodegradable controlled antibiotic release systems for the treatment of implant-related osteomyelitis.
2001 Jan
Use of ampicillin/sulbactam and sultamicillin in pediatric infections: a re-evaluation.
2001 Jul-Aug
Investigation of oxacillin-hydrolyzing beta-lactamase in borderline methicillin-resistant clinical isolates of Staphylococcus aureus.
2001 Jul-Aug
An anaphylactic reaction possibly associated with an intraoperative coronary artery spasm during general anesthesia.
2001 May
Epigallocatechin gallate synergy with ampicillin/sulbactam against 28 clinical isolates of methicillin-resistant Staphylococcus aureus.
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
Bacteriology and antimicrobial susceptibility of gram-positive cocci isolated from pus specimens of orofacial odontogenic infections.
2002 Apr
The impact of carbapenemases on antimicrobial development and 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
Prevalence of and resistance to anti-microbial drugs in selected microbial species isolated from bulk milk samples.
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
The emergence of beta-lactamase resistance in respiratory pathogens.
2002 Mar
The role of cefoperazone-sulbactam for treatment of severe melioidosis.
2002 Mar 1
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
[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
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
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;
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:26:09 GMT 2023
Edited
by admin
on Fri Dec 15 15:26:09 GMT 2023
Record UNII
DKQ4T82YE6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SULBACTAM SODIUM
EP   MART.   ORANGE BOOK   USAN   USP   VANDF   WHO-DD  
USAN  
Official Name English
SULBACTAM SODIUM COMPONENT OF SULPERAZONE
Brand Name English
SULBACTAM SODIUM [MART.]
Common Name English
SULBACTAM SODIUM [VANDF]
Common Name English
SULBACTAM SODIUM [EP MONOGRAPH]
Common Name English
SULBACTAM SODIUM [ORANGE BOOK]
Common Name English
SULBACTAM SODIUM [JAN]
Common Name English
SULBACTAM (AS SODIUM)
Common Name English
Sulbactam sodium [WHO-DD]
Common Name English
XACDURO COMPONENT SULBACTAM SODIUM
Brand Name English
SULBACTAM SODIUM [USAN]
Common Name English
SULBACTAM SODIUM [USP MONOGRAPH]
Common Name English
SULBACTAM SODIUM COMPONENT OF XACDURO
Brand Name English
SULBACTAM SODIUM [EP IMPURITY]
Common Name English
SULPERAZONE COMPONENT SULBACTAM SODIUM
Brand Name English
SULBACTAM SODIUM SALT
MI  
Common Name English
SULBACTAM SODIUM SALT [MI]
Common Name English
SULBACTAM SODIUM [USP IMPURITY]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C260
Created by admin on Fri Dec 15 15:26:09 GMT 2023 , Edited by admin on Fri Dec 15 15:26:09 GMT 2023
Code System Code Type Description
PUBCHEM
23663973
Created by admin on Fri Dec 15 15:26:09 GMT 2023 , Edited by admin on Fri Dec 15 15:26:09 GMT 2023
PRIMARY
RS_ITEM_NUM
1623671
Created by admin on Fri Dec 15 15:26:09 GMT 2023 , Edited by admin on Fri Dec 15 15:26:09 GMT 2023
PRIMARY
RXCUI
82100
Created by admin on Fri Dec 15 15:26:09 GMT 2023 , Edited by admin on Fri Dec 15 15:26:09 GMT 2023
PRIMARY RxNorm
DRUG BANK
DBSALT001310
Created by admin on Fri Dec 15 15:26:09 GMT 2023 , Edited by admin on Fri Dec 15 15:26:09 GMT 2023
PRIMARY
CAS
69388-84-7
Created by admin on Fri Dec 15 15:26:09 GMT 2023 , Edited by admin on Fri Dec 15 15:26:09 GMT 2023
PRIMARY
ECHA (EC/EINECS)
273-984-4
Created by admin on Fri Dec 15 15:26:09 GMT 2023 , Edited by admin on Fri Dec 15 15:26:09 GMT 2023
PRIMARY
MERCK INDEX
m10291
Created by admin on Fri Dec 15 15:26:09 GMT 2023 , Edited by admin on Fri Dec 15 15:26:09 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C47732
Created by admin on Fri Dec 15 15:26:09 GMT 2023 , Edited by admin on Fri Dec 15 15:26:09 GMT 2023
PRIMARY
DAILYMED
DKQ4T82YE6
Created by admin on Fri Dec 15 15:26:09 GMT 2023 , Edited by admin on Fri Dec 15 15:26:09 GMT 2023
PRIMARY
EPA CompTox
DTXSID401026661
Created by admin on Fri Dec 15 15:26:09 GMT 2023 , Edited by admin on Fri Dec 15 15:26:09 GMT 2023
PRIMARY
EVMPD
SUB04617MIG
Created by admin on Fri Dec 15 15:26:09 GMT 2023 , Edited by admin on Fri Dec 15 15:26:09 GMT 2023
PRIMARY
ChEMBL
CHEMBL403
Created by admin on Fri Dec 15 15:26:09 GMT 2023 , Edited by admin on Fri Dec 15 15:26:09 GMT 2023
PRIMARY
FDA UNII
DKQ4T82YE6
Created by admin on Fri Dec 15 15:26:09 GMT 2023 , Edited by admin on Fri Dec 15 15:26:09 GMT 2023
PRIMARY
SMS_ID
100000090027
Created by admin on Fri Dec 15 15:26:09 GMT 2023 , Edited by admin on Fri Dec 15 15:26:09 GMT 2023
PRIMARY
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
EP
PARENT -> SALT/SOLVATE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
Ph.Eur.; USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
Ph.Eur.; USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
Ph.Eur.; USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
Ph.Eur.; USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
Ph.Eur.; USP
IMPURITY -> PARENT
UNSPECIFIED IMPURITY
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY