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

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

Molecular Formula	C8H11NO5S
Molecular Weight	233.242
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

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	Inhibitor 8,297		0.062 µM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Staphylococcus aureus (beta-lactamase and non-beta-lactamase producing) 4	Curative	Approved 8,429	UNASYN
Staphylococcus epidermidis (beta-lactamase and non-beta-lactamase producing) 4	Curative	Approved 8,429	UNASYN
Hemophilus influenzae (beta-lactamase and non-beta-lactamase producing) 4	Curative	Approved 8,429	UNASYN
Moraxella (Branhamella) catarrhalis (beta-lactamase and non-beta-lactamase producing) 4	Curative	Approved 8,429	UNASYN
Peptostreptococcus species 4	Curative	Approved 8,429	UNASYN
Bacterial infections 234	Curative	Approved 8,429	UNASYN

C_max

Value	Dose	Co-administered	Analyte	Population
15.36 μg/mL	0.5 g single, intramuscular	AMPICILLIN	SULBACTAM plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
83.79 μg × h/mL	1 g 1 times / day steady-state, intravenous	AMPICILLIN	SULBACTAM plasma	Homo sapiens
40.71 μg × h/mL	0.5 g 1 times / day steady-state, intravenous	AMPICILLIN	SULBACTAM plasma	Homo sapiens
40.33 μg × h/mL	0.5 g single, intramuscular	AMPICILLIN	SULBACTAM plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.14 h	1 g 1 times / day steady-state, intravenous	AMPICILLIN	SULBACTAM plasma	Homo sapiens
1.15 h	0.5 g 1 times / day steady-state, intravenous	AMPICILLIN	SULBACTAM plasma	Homo sapiens
1.26 h	0.5 g single, intramuscular	AMPICILLIN	SULBACTAM plasma	Homo sapiens
1 h			SULBACTAM serum	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
62%			SULBACTAM serum	Homo sapiens

Doses

Doses

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Dose	Population	Adverse events
4 g 3 times / day multiple, intravenous Highest studied dose	unhealthy
2 g 2 times / day multiple, intravenous Recommended	unhealthy

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	OAT1 326 MRP4 77

Drug as victim

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Target	Modality	Activity	Metabolite	Clinical evidence
MRP4 77	substrate 3,367	yes
OAT1 326	substrate 3,367	yes

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Sourcing

Sourcing

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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

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PubMed

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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
Hepatotoxic reactions induced by beta-lactamase inhibitors.	2001 Dec 17	11772541
[The inducibility of Amp C enzyme of Enterobacter cloacae and its susceptibility to enzyme inhibitor].	2001 Feb 25	11798880

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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;