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
In vitro effect of ampicillin/sulbactam on Acinetobacter species.	2001	11548205
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
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
[New aspects of antibiotic resistance and possibilities of its prevention].	2001 Aug	11678026
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
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
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
Penicillins and beta-lactamase inhibitor combinations.	2001 Jun 15	11417732
[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
Role of sultamicillin and ampicillin/sulbactam in the treatment of upper and lower bacterial respiratory tract infections.	2001 Sep	11673031
Nontraditional dosing of ampicillin-sulbactam for multidrug-resistant Acinetobacter baumannii meningitis.	2002 Apr	11939689
Bacteriology and antimicrobial susceptibility of gram-positive cocci isolated from pus specimens of orofacial odontogenic infections.	2002 Apr	11929563
[Acinetobacter, a nosocomial pathogen. Contribution of experimental models].	2002 Apr 13	11995384
Pharmacokinetics of an ampicillin/sulbactam (2:1) combination in rabbits.	2002 Aug	12213113
Application of micellar electrokinetic chromatography to the determination of sultamicillin in oral pharmaceutical preparations.	2002 Dec 6	12498263
[Analysis of prophylactic antibiotics for cesarean section].	2002 Jan	11953060
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
The role of cefoperazone-sulbactam for treatment of severe melioidosis.	2002 Mar 1	11823963
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