SULBACTAM BENZATHINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H20N2.2C8H11NO5S
Molecular Weight	706.827
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
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.[H][C@@]34CC(=O)N3[C@@H](C(O)=O)C(C)(C)S4(=O)=O.C(CNCC5=CC=CC=C5)NCC6=CC=CC=C6

InChI

InChIKey=YSEPFTSCLHUBNH-HFKSPEPWSA-N

InChI=1S/C16H20N2.2C8H11NO5S/c1-3-7-15(8-4-1)13-17-11-12-18-14-16-9-5-2-6-10-16;2*1-8(2)6(7(11)12)9-4(10)3-5(9)15(8,13)14/h1-10,17-18H,11-14H2;2*5-6H,3H2,1-2H3,(H,11,12)/t;2*5-,6+/m.11/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
In vitro effect of ampicillin/sulbactam on Acinetobacter species.	2001	11548205
Biodegradable polyhydroxyalkanoate implants for osteomyelitis therapy: in vitro antibiotic release.	2001	11403236
Group F streptococcal bacteremia complicating a Bartholin's abscess.	2001	11368261
Antibiotic susceptibility, serum response and surface properties of Klebsiella species.	2001	11297012
Transferable antibiotic resistance in multiresistant nosocomial Acinetobacter baumannii strains from seven clinics in the Slovak and Czech Republics.	2001 Apr	11330360
[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
[New aspects of antibiotic resistance and possibilities of its prevention].	2001 Aug	11678026
A randomized, double-blind comparison of ampicillin/sulbactam and ceftriaxone in the prevention of surgical-site infections after neurosurgery.	2001 Aug	11558864
Hepatotoxic reactions induced by beta-lactamase inhibitors.	2001 Dec 17	11772541
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
Piperacillin, beta-lactam inhibitor plus gentamicin as empirical therapy of a sequential regimen in febrile neutropenia of pediatric cancer patients.	2001 Jul	11497392
Pharmacokinetics of antibiotic prophylaxis in major orthopedic surgery and blood-saving techniques.	2001 Jul	11478553
Index of suspicion. Case 2. Diagnosis: Ludwig angina.	2001 Jul	11464817
Randomized, double-blind, controlled study of cefoperazone-sulbactam plus cotrimoxazole versus ceftazidime plus cotrimoxazole for the treatment of severe melioidosis.	2001 Jul 1	11389491
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
[Clinical analysis of neutropenic fever associated with hematological disorders].	2001 Mar	11321778
[Escherichia coli eradication from the blader urine by amoxicillin-sulbactam. Intrinsic activity of the inhibitor].	2001 May	11446908
An anaphylactic reaction possibly associated with an intraoperative coronary artery spasm during general anesthesia.	2001 May	11377162
Hand infections in patients with diabetes mellitus.	2001 Nov	11727802
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
Epigallocatechin gallate synergy with ampicillin/sulbactam against 28 clinical isolates of methicillin-resistant Staphylococcus aureus.	2001 Sep	11533000
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
Probing substrate binding to metallo-beta-lactamase L1 from Stenotrophomonas maltophilia by using site-directed mutagenesis.	2002	11876827
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
The impact of carbapenemases on antimicrobial development and therapy.	2002 Feb	12020049
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
Surveillance for antimicrobial resistance in Croatia.	2002 Jan	11749742
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
In vitro antibiotic release from poly(3-hydroxybutyrate-co-3-hydroxyvalerate) rods.	2002 Mar-Apr	11837970
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
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
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

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 BENZATHINE

Official Name

English

SULBACTAM BENZATHINE [USAN]

Common Name

English

CP-45,899-99

Code

English

4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 3,3-DIMETHYL-7-OXO-, 4,4-DIOXIDE, (2S,5R)-, COMPD. WITH N,N'-BIS(PHENYLMETHYL)-1,2-ETHANEDIAMINE (2:1)

Systematic Name

English

CP-45899-99

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C471