SULBACTAM

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 Search

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
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 12 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 8504		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 8583	UNASYN Approved Use Sulbactam Launch Date 1988
Staphylococcus epidermidis (beta-lactamase and non-beta-lactamase producing) 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050608s040lbl.pdf	Curative	Approved 8583	UNASYN Approved Use Sulbactam Launch Date 1988
Hemophilus influenzae (beta-lactamase and non-beta-lactamase producing) 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050608s040lbl.pdf	Curative	Approved 8583	UNASYN Approved Use Sulbactam Launch Date 1988
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 8583	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
Peptostreptococcus species 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050608s040lbl.pdf	Curative	Approved 8583	UNASYN Approved Use Sulbactam Launch Date 1988
Bacterial infections 235 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050608s040lbl.pdf	Curative	Approved 8583	UNASYN Approved Use Sulbactam Launch Date 1988

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
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
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
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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
1.15 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
1.26 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 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 Sources: https://pubmed.ncbi.nlm.nih.gov/28052852	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/28052852	Sources: https://pubmed.ncbi.nlm.nih.gov/28052852
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: https://www.mims.com/malaysia/drug/info/sulperazon?type=full	unhealthy Health Status: unhealthy 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 395 MRP4 91

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
MRP4 91	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17939016/	yes
OAT1 395	substrate 4014 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
eMolecules	2735250	https://www.emolecules.com/cgi-bin/more?vid=2735250
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

PubMed

Title	Date	PubMed
Antibiotic susceptibility, serum response and surface properties of Klebsiella species.	2001	11297012
Effect of granulocyte-macrophage colony-stimulating factor on treatment of acute osteomyelitis. An experimental investigation in rats.	2001	11262785
[Fundamental and clinical studies on beta-lactamase inhibitors].	2001 Apr	11305004
Sulbactam efficacy in experimental models caused by susceptible and intermediate Acinetobacter baumannii strains.	2001 Apr	11266426
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	11589483
[Guideline of antimicrobial therapy in the area of cardiovascular surgery].	2001 Dec	11828708
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
Incidence of beta-lactamase production and antimicrobial susceptibility of anaerobic gram-negative rods isolated from pus specimens of orofacial odontogenic infections.	2001 Feb	11169133
Inhibition of the SHV-1 beta-lactamase by sulfones: crystallographic observation of two reaction intermediates with tazobactam.	2001 Feb 13	11327849
Sepsis and multiple brain abscesses caused by Salmonella paratyphi B in an infant: successful treatment with sulbactam-ampicillin and surgical drainage.	2001 Jan-Mar	11297167
Use of ampicillin/sulbactam and sultamicillin in pediatric infections: a re-evaluation.	2001 Jul-Aug	11675898
[Clinical analysis of neutropenic fever associated with hematological disorders].	2001 Mar	11321778
An anaphylactic reaction possibly associated with an intraoperative coronary artery spasm during general anesthesia.	2001 May	11377162
Parallel analysis of individual and aggregated data on antibiotic exposure and resistance in gram-negative bacilli.	2001 Nov 1	11588690
The penetration of cefoperazone and sulbactam into the lumbar intervertebral discs.	2001 Oct	11586148
In vitro activity of sulperazon against recent isolates of ceftazidime-resistant bacteria.	2001 Sep	11732084
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
Beta-lactam/beta-lactamase inhibitor combinations in empiric management of pediatric infections.	2002	11921490
Probing substrate binding to metallo-beta-lactamase L1 from Stenotrophomonas maltophilia by using site-directed mutagenesis.	2002	11876827
Nontraditional dosing of ampicillin-sulbactam for multidrug-resistant Acinetobacter baumannii meningitis.	2002 Apr	11939689
[Acinetobacter, a nosocomial pathogen. Contribution of experimental models].	2002 Apr 13	11995384
Antimicrobial susceptibility of coagulase-negative staphylococci isolated from bovine mastitis in Argentina.	2002 Aug	12214983
Pharmacokinetics of an ampicillin/sulbactam (2:1) combination in rabbits.	2002 Aug	12213113
Pandrug-resistant Acinetobacter baumannii causing nosocomial infections in a university hospital, Taiwan.	2002 Aug	12141969
Molecular dynamics at the root of expansion of function in the M69L inhibitor-resistant TEM beta-lactamase from Escherichia coli.	2002 Aug 14	12167037
Surveillance for antimicrobial resistance in Croatia.	2002 Jan	11749742
[A case of bronchopulmonary actinomycosis diagnosed by transbronchial biopsy of a bronchial polypoid tumor].	2002 Jun	12325338
[Microbiological and clinical studies of Haemophilus influenzae isolated at Kitakyushu Municipal Medical Center from 1996 through 1999].	2002 Jun	12199114
Prevalence of and resistance to anti-microbial drugs in selected microbial species isolated from bulk milk samples.	2002 Jun	12121041
Pharmacokinetics of cefoperazone and sulbactam in liver transplant patients.	2002 Jun	12043952
CE versus LC for simultaneous determination of amoxicillin/clavulanic acid and ampicillin/sulbactam in pharmaceutical formulations for injections.	2002 Jun 20	12062667
Low dose sultamicillin in acute sinusitis.	2002 Mar	12700441
The emergence of beta-lactamase resistance in respiratory pathogens.	2002 Mar	12014854
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
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	12026150
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	12052544
Reports of osteopenia/rickets of prematurity are on the increase because of improved survival rates of low birthweight infants.	2002 Oct	12426026
[The efficacy of prophylactic administration of SBT/ABPC for postoperative infection in neurosurgical operations].	2002 Oct	12404767
Antimicrobial susceptibility of major pathogens of orofacial odontogenic infections to 11 beta-lactam antibiotics.	2002 Oct	12354209
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	12242137
[The impact of antibiotic use on hospital-acquired pneumonia: data of etiology tests].	2003	12695638
Catalytic properties of an endogenous beta-lactamase responsible for the resistance of Azospirillum lipoferum to beta-lactam antibiotics.	2003 Feb	12624206
Current status of drug resistance among gram-negative bacilli isolated from admitted cases in a tertiary care centre.	2003 Jan	12693450
Acute otitis media and facial nerve paralysis in adults.	2003 Jan	12544039
Severe nosocomial infections with imipenem-resistant Acinetobacter baumannii treated with ampicillin/sulbactam.	2003 Jan	12507838
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
Spectrum and antibiotic sensitivity of bacteria contaminating the upper gut in patients with malabsorption syndrome from the tropics.	2003 May 24	12769832

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

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