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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
In vitro effect of ampicillin/sulbactam on Acinetobacter species.
2001
Group F streptococcal bacteremia complicating a Bartholin's abscess.
2001
Effect of granulocyte-macrophage colony-stimulating factor on treatment of acute osteomyelitis. An experimental investigation in rats.
2001
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
Inhibition of the SHV-1 beta-lactamase by sulfones: crystallographic observation of two reaction intermediates with tazobactam.
2001 Feb 13
[The inducibility of Amp C enzyme of Enterobacter cloacae and its susceptibility to enzyme inhibitor].
2001 Feb 25
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
Penicillins and beta-lactamase inhibitor combinations.
2001 Jun 15
Role of sultamicillin and ampicillin/sulbactam in the treatment of upper and lower bacterial respiratory tract infections.
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
Nontraditional dosing of ampicillin-sulbactam for multidrug-resistant Acinetobacter baumannii meningitis.
2002 Apr
Application of micellar electrokinetic chromatography to the determination of sultamicillin in oral pharmaceutical preparations.
2002 Dec 6
Chronic intrauterine infection and inflammation in the preterm rabbit, despite antibiotic therapy.
2002 Feb
[Analysis of prophylactic antibiotics for cesarean section].
2002 Jan
[A case of bronchopulmonary actinomycosis diagnosed by transbronchial biopsy of a bronchial polypoid tumor].
2002 Jun
Low dose sultamicillin in acute sinusitis.
2002 Mar
The emergence of beta-lactamase resistance in respiratory pathogens.
2002 Mar
Multiresistant Acinetobacter infections: a role for sulbactam combinations in overcoming an emerging worldwide problem.
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
[The efficacy of prophylactic administration of SBT/ABPC for postoperative infection in neurosurgical operations].
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
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
[beta-Lactamase-inhibitor combinations].
2003 Mar
Nosocomial multi-drug resistant Acinetobacter baumannii bloodstream infection: risk factors and outcome with ampicillin-sulbactam treatment.
2003 May
Considerations in control and treatment of nosocomial infections due to multidrug-resistant Acinetobacter baumannii.
2003 May 15
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
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PRIMARY
EPA CompTox
68373-14-8
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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
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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
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PRIMARY
USP_CATALOG
1623670
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PRIMARY USP-RS
DRUG CENTRAL
2492
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PRIMARY
PUBCHEM
130313
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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
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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