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

[H][C@@]12CC(=O)N1[C@@H](C(O)=O)C(C)(C)S2(=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 8297		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 8429	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 8429	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 8429	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 8429	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 8429	UNASYN Approved Use Sulbactam Launch Date 1988
Bacterial infections 234 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050608s040lbl.pdf	Curative	Approved 8429	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
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 326 MRP4 77

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
MRP4 77	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/17939016/	yes
OAT1 326	substrate 3367 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
Effect of cefaperazone/sulbactam and ampicillin/sulbactam on the in vitro activity of human erythrocyte glucose-6-phosphate dehydrogenase.	2001	11868906
[Activity of new fluoroquinolones against clinical isolates of Acinetobacter baumannii].	2001 Dec	11856982
[Guideline of antimicrobial therapy in the area of cardiovascular surgery].	2001 Dec	11828708
Use of ampicillin/sulbactam and sultamicillin in pediatric infections: a re-evaluation.	2001 Jul-Aug	11675898
Comparison of Neisseria gonorrhoeae isolates from the genital tract and pharynx of two gonorrhea patients.	2001 Sep	11810580
Eradication of multi-drug resistant Acinetobacter from an intensive care unit.	2001 Winter	12593705
Experience with ampicillin/sulbactam in severe infections.	2002	11921491
Probing substrate binding to metallo-beta-lactamase L1 from Stenotrophomonas maltophilia by using site-directed mutagenesis.	2002	11876827
[Acinetobacter, a nosocomial pathogen. Contribution of experimental models].	2002 Apr 13	11995384
Surgical antibiotic prophylaxis in a Turkish university hospital.	2002 Aug	12420855
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
Efficacy of amoxicillin-sulbactam, given twice-a-day, for the treatment of community-acquired pneumonia: a clinical trial based on a pharmacodynamic model.	2002 Dec	12583551
Application of micellar electrokinetic chromatography to the determination of sultamicillin in oral pharmaceutical preparations.	2002 Dec 6	12498263
Antibacterial activities of beta-lactamase inhibitors associated with morphological changes of cell wall in Helicobacter pylori.	2002 Feb	11886472
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
[The efficacy of combining antibiotic treatment with topical intranasal steroid administration in the treatment of chronic otitis media with effusion].	2002 Jul-Aug	12422079
[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
Comparison of ampicillin-sulbactam and imipenem-cilastatin for the treatment of acinetobacter ventilator-associated pneumonia.	2002 Jun 1	12015687
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
Multiresistant Acinetobacter infections: a role for sulbactam combinations in overcoming an emerging worldwide problem.	2002 Mar	12010169
[Nocardia farcinica: life-threatening chorioiditis under systemic immunosuppression].	2002 Mar	11987046
Antibiotic resistance among clinical isolates of Acinetobacter in the UK, and in vitro evaluation of tigecycline (GAR-936).	2002 Mar	11864948
Malakoplakia of liver diagnosed by a needle core biopsy: a case report and review of the literature.	2002 Mar	11860319
In vitro antibiotic release from poly(3-hydroxybutyrate-co-3-hydroxyvalerate) rods.	2002 Mar-Apr	11837970
Bacteriology and antimicrobial susceptibility in biliary tract disease: an audit of 10-year's experience.	2002 May	12197428
In vitro investigation of the susceptibility of Acinetobacter baumannii strains isolated from clinical specimens to ampicillin/sulbactam alone and in combination with amikacin.	2002 Nov	12431877
First occurrence of transferable extended-spectrum beta-lactamase hydrolyzing cefoperazone in multiresistant nosocomial strains of Klebsiella pneumoniae from two hospitals in Czech and Slovak Republics.	2002 Oct	12462425
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
Development of an assay for beta-lactam hydrolysis using the pH-dependence of enhanced green fluorescent protein.	2002 Oct 15	12413455
[Activity of 14 antimicrobials against Eikenella corrodens].	2002 Oct-Dec	12600009
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
Biochemical characterization of a novel extended-spectrum beta-lactamase from Pseudomonas aeruginosa 802.	2002 Spring	12002654
[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
HPLC for in-process control in the production of sultamicillin.	2003 Feb 26	12609671
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
Group 1 beta-lactamases of Aeromonas caviae and their resistance to beta-lactam antibiotics.	2003 Mar	12795407

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 [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

CP-458992

Code

English

Sulbactam [WHO-DD]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000175930