SULBACTAM

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 Search

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
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050608s040lbl.pdf
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

Primary Target	Pharmacology	Condition	Potency
Beta-lactamase TEM 11 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 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050608s040lbl.pdf	Inhibitor 7701		0.062 µM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Staphylococcus aureus (beta-lactamase and non-beta-lactamase producing) 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050608s040lbl.pdf	Curative	Approved 7997	UNASYN Approved Use Sulbactam Launch Date 5.8501438E11
Staphylococcus epidermidis (beta-lactamase and non-beta-lactamase producing) 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050608s040lbl.pdf	Curative	Approved 7997	UNASYN Approved Use Sulbactam Launch Date 5.8501438E11
Hemophilus influenzae (beta-lactamase and non-beta-lactamase producing) 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050608s040lbl.pdf	Curative	Approved 7997	UNASYN Approved Use Sulbactam Launch Date 5.8501438E11
Moraxella (Branhamella) catarrhalis (beta-lactamase and non-beta-lactamase producing) 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050608s040lbl.pdf	Curative	Approved 7997	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
Peptostreptococcus species 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050608s040lbl.pdf	Curative	Approved 7997	UNASYN Approved Use Sulbactam Launch Date 5.8501438E11
Bacterial infections 230 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050608s040lbl.pdf	Curative	Approved 7997	UNASYN Approved Use Sulbactam Launch Date 5.8501438E11

C_max

Value	Dose	Co-administered	Analyte	Population
15.36 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2338029	0.5 g single, intramuscular dose: 0.5 g route of administration: Intramuscular experiment type: SINGLE co-administered: AMPICILLIN	AMPICILLIN	SULBACTAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
40.33 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2338029	0.5 g single, intramuscular dose: 0.5 g route of administration: Intramuscular experiment type: SINGLE co-administered: AMPICILLIN	AMPICILLIN	SULBACTAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
40.71 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2338029	0.5 g 1 times / day steady-state, intravenous dose: 0.5 g route of administration: Intravenous experiment type: STEADY-STATE co-administered: AMPICILLIN	AMPICILLIN	SULBACTAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
83.79 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2338029	1 g 1 times / day steady-state, intravenous dose: 1 g route of administration: Intravenous experiment type: STEADY-STATE co-administered: AMPICILLIN	AMPICILLIN	SULBACTAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.26 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2338029	0.5 g single, intramuscular dose: 0.5 g route of administration: Intramuscular experiment type: SINGLE co-administered: AMPICILLIN	AMPICILLIN	SULBACTAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1.15 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2338029	0.5 g 1 times / day steady-state, intravenous dose: 0.5 g route of administration: Intravenous experiment type: STEADY-STATE co-administered: AMPICILLIN	AMPICILLIN	SULBACTAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1.14 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2338029	1 g 1 times / day steady-state, intravenous dose: 1 g route of administration: Intravenous experiment type: STEADY-STATE co-administered: AMPICILLIN	AMPICILLIN	SULBACTAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050608s040lbl.pdf			SULBACTAM serum	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
62% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050608s040lbl.pdf			SULBACTAM serum	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/28052852 Page: p.5	unhealthy n = 13 Health Status: unhealthy Condition: Ventilator-associated pneumonia, caused by colistin-resistant A. baumannii infection Population Size: 13 Sources: https://pubmed.ncbi.nlm.nih.gov/28052852 Page: p.5	Sources: https://pubmed.ncbi.nlm.nih.gov/28052852 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: https://www.mims.com/malaysia/drug/info/sulperazon?type=full	unhealthy Health Status: unhealthy Condition: Bacterial infections Sources: https://www.mims.com/malaysia/drug/info/sulperazon?type=full	Sources: https://www.mims.com/malaysia/drug/info/sulperazon?type=full

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	OAT1 290 MRP4 73

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
MRP4 73	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/17939016/	yes
OAT1 290	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/29277663/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:9321	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9321
ChemicalBook	CB1419201	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1419201
MolPort	MolPort-002-499-832	https://www.molport.com/shop/molecule-link/MolPort-002-499-832
Selleck Chemicals	sulbactam	http://www.selleckchem.com/products/sulbactam.html
ZINC	ZINC000000897244	http://zinc15.docking.org/substances/ZINC000000897244
eMolecules	2735250	https://www.emolecules.com/cgi-bin/more?vid=2735250

PubMed

Title	Date	PubMed
In vitro effect of ampicillin/sulbactam on Acinetobacter species.	2001	11548205
Group F streptococcal bacteremia complicating a Bartholin's abscess.	2001	11368261
Effect of granulocyte-macrophage colony-stimulating factor on treatment of acute osteomyelitis. An experimental investigation in rats.	2001	11262785
Hepatotoxic reactions induced by beta-lactamase inhibitors.	2001 Dec 17	11772541
Epidemiology, resistance, and outcomes of Acinetobacter baumannii bacteremia treated with imipenem-cilastatin or ampicillin-sulbactam.	2001 Feb	11213849
Inhibition of the SHV-1 beta-lactamase by sulfones: crystallographic observation of two reaction intermediates with tazobactam.	2001 Feb 13	11327849
[The inducibility of Amp C enzyme of Enterobacter cloacae and its susceptibility to enzyme inhibitor].	2001 Feb 25	11798880
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	11141221
In vivo application of biodegradable controlled antibiotic release systems for the treatment of implant-related osteomyelitis.	2001 Jan	11085386
Use of ampicillin/sulbactam and sultamicillin in pediatric infections: a re-evaluation.	2001 Jul-Aug	11675898
Investigation of oxacillin-hydrolyzing beta-lactamase in borderline methicillin-resistant clinical isolates of Staphylococcus aureus.	2001 Jul-Aug	11399858
Penicillins and beta-lactamase inhibitor combinations.	2001 Jun 15	11417732
Role of sultamicillin and ampicillin/sulbactam in the treatment of upper and lower bacterial respiratory tract infections.	2001 Sep	11673031
An unusual form of Actinomycosis of the mandible with a resultant gross sequester in a 4-year-old child: a case report.	2001 Spring	12049085
Eradication of multi-drug resistant Acinetobacter from an intensive care unit.	2001 Winter	12593705
Beta-lactam/beta-lactamase inhibitor combinations in empiric management of pediatric infections.	2002	11921490
Nontraditional dosing of ampicillin-sulbactam for multidrug-resistant Acinetobacter baumannii meningitis.	2002 Apr	11939689
Application of micellar electrokinetic chromatography to the determination of sultamicillin in oral pharmaceutical preparations.	2002 Dec 6	12498263
Chronic intrauterine infection and inflammation in the preterm rabbit, despite antibiotic therapy.	2002 Feb	11854641
[Analysis of prophylactic antibiotics for cesarean section].	2002 Jan	11953060
[A case of bronchopulmonary actinomycosis diagnosed by transbronchial biopsy of a bronchial polypoid tumor].	2002 Jun	12325338
Low dose sultamicillin in acute sinusitis.	2002 Mar	12700441
The emergence of beta-lactamase resistance in respiratory pathogens.	2002 Mar	12014854
Multiresistant Acinetobacter infections: a role for sulbactam combinations in overcoming an emerging worldwide problem.	2002 Mar	12010169
Antibiotic resistance among clinical isolates of Acinetobacter in the UK, and in vitro evaluation of tigecycline (GAR-936).	2002 Mar	11864948
Bacteriology and antimicrobial susceptibility in biliary tract disease: an audit of 10-year's experience.	2002 May	12197428
[The efficacy of prophylactic administration of SBT/ABPC for postoperative infection in neurosurgical operations].	2002 Oct	12404767
Development of an assay for beta-lactam hydrolysis using the pH-dependence of enhanced green fluorescent protein.	2002 Oct 15	12413455
[The impact of antibiotic use on hospital-acquired pneumonia: data of etiology tests].	2003	12695638
Current status of drug resistance among gram-negative bacilli isolated from admitted cases in a tertiary care centre.	2003 Jan	12693450
Spirocyclopropyl beta-lactams as mechanism-based inhibitors of serine beta-lactamases. Synthesis by rhodium-catalyzed cyclopropanation of 6-diazopenicillanate sulfone.	2003 Jun 19	12801220
[beta-Lactamase-inhibitor combinations].	2003 Mar	12717975
Nosocomial multi-drug resistant Acinetobacter baumannii bloodstream infection: risk factors and outcome with ampicillin-sulbactam treatment.	2003 May	12767844
Considerations in control and treatment of nosocomial infections due to multidrug-resistant Acinetobacter baumannii.	2003 May 15	12746772

Patents

Sample Use Guides

In Vivo Use Guide

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

ampicillin-sulbactam 2 ug/ml;

Name

Type

Language

SULBACTAM

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