SULTAMICILLIN TOSYLATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H30N4O9S2.C7H8O3S
Molecular Weight	766.859
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC=C(C=C1)S(O)(=O)=O.[H][C@]23SC(C)(C)[C@@H](N2C(=O)[C@H]3NC(=O)[C@H](N)C4=CC=CC=C4)C(=O)OCOC(=O)[C@@H]5N6C(=O)C[C@@]6([H])S(=O)(=O)C5(C)C

InChI

InChIKey=FFCSPKNZHGIDQM-CGAOXQFVSA-N

InChI=1S/C25H30N4O9S2.C7H8O3S/c1-24(2)17(29-20(32)16(21(29)39-24)27-19(31)15(26)12-8-6-5-7-9-12)22(33)37-11-38-23(34)18-25(3,4)40(35,36)14-10-13(30)28(14)18;1-6-2-4-7(5-3-6)11(8,9)10/h5-9,14-18,21H,10-11,26H2,1-4H3,(H,27,31);2-5H,1H3,(H,8,9,10)/t14-,15-,16-,17+,18+,21-;/m1./s1

HIDE SMILES / InChI

Description
Sources: http://www.astrumhealthcare.com/pdf/monograph_ampirok.pdf | https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050608s044lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/2661196

Sultamicillin is the mutual prodrug of sulbactam and ampicillin. It is the tosylate salt of the double ester of sulbactam plus ampicillin. Sulbactam is a semisynthetic ß-lactamase inhibitor which, in combination with ampicillin, extends the antibacterial activity of the latter to include some ß-lactamase-producing strains of bacteria that would otherwise be resistant. The combination of sulbactam plus ampicillin for parenteral use has previously been shown to be clinically and bacteriologically effective in a variety of infections. Sultamicillin is marketed under a trade name Unasyn among others.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Staphylococcus aureus 67 Target ID: CHEMBL352 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18974644	Inhibitor 8297
Bacillus subtilis 8 Target ID: CHEMBL359 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18974644	Inhibitor 8297
Bacterial beta-lactamase TEM 10 Target ID: CHEMBL2364670 Sources: http://www.astrumhealthcare.com/pdf/monograph_ampirok.pdf \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050608s044lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/1646771	Inhibitor 8297
Escherichia coli 82 Target ID: CHEMBL354 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9527765	Inhibitor 8297
Bacterial penicillin-binding protein 233 Target ID: CHEMBL2354204 Sources: http://www.genome.jp/dbget-bin/www_bget?D05972	Inhibitor 8297
Beta-lactamase TEM 12 Target ID: CHEMBL2065 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10103192 \| http://www.astrumhealthcare.com/pdf/monograph_ampirok.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/8851602	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Escherichia coli infections 15 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050608s044lbl.pdf https://www.ncbi.nlm.nih.gov/pubmed/9021203 https://www.ncbi.nlm.nih.gov/pubmed/10103192	Curative	Approved 8429	UNASYN Approved Use UNASYN is indicated for the treatment of infections due to susceptible strains of the designated microorganisms in the conditions listed below. Skin and Skin Structure Infections caused by beta-lactamase producing strains of Staphylococcus aureus, Escherichia coli,* Klebsiella spp.* (including K. pneumoniae), Proteus mirabilis, Bacteroides fragilis,* Enterobacter spp.,* and Acinetobacter calcoaceticus.* Intra-Abdominal Infections caused by beta-lactamase producing strains of Escherichia coli, Klebsiella spp. (including K. pneumoniae), Bacteroides spp. (including B. fragilis), and Enterobacter spp. Gynecological Infections caused by beta-lactamase producing strains of Escherichia coli,* and Bacteroides spp.* (including B. fragilis*). Launch Date 1986
Skin infections caused by beta-lactamase producing strains of Staphylococcus aureus 4 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050608s044lbl.pdf	Curative	Approved 8429	UNASYN Approved Use UNASYN is indicated for the treatment of infections due to susceptible strains of the designated microorganisms in the conditions listed below. Skin and Skin Structure Infections caused by beta-lactamase producing strains of Staphylococcus aureus, Escherichia coli,* Klebsiella spp.* (including K. pneumoniae), Proteus mirabilis, Bacteroides fragilis,* Enterobacter spp.,* and Acinetobacter calcoaceticus.* Intra-Abdominal Infections caused by beta-lactamase producing strains of Escherichia coli, Klebsiella spp. (including K. pneumoniae), Bacteroides spp. (including B. fragilis), and Enterobacter spp. Gynecological Infections caused by beta-lactamase producing strains of Escherichia coli,* and Bacteroides spp.* (including B. fragilis*). Launch Date 1986
Intra-abdominal infections caused by beta-lactamase producing strains of E. coli, Klebsiella spp., Bacteroides spp. and Enterobacter spp. 4 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050608s044lbl.pdf https://www.ncbi.nlm.nih.gov/pubmed/19621991 https://www.ncbi.nlm.nih.gov/pubmed/17706511	Curative	Approved 8429	UNASYN Approved Use UNASYN is indicated for the treatment of infections due to susceptible strains of the designated microorganisms in the conditions listed below. Skin and Skin Structure Infections caused by beta-lactamase producing strains of Staphylococcus aureus, Escherichia coli,* Klebsiella spp.* (including K. pneumoniae), Proteus mirabilis, Bacteroides fragilis,* Enterobacter spp.,* and Acinetobacter calcoaceticus.* Intra-Abdominal Infections caused by beta-lactamase producing strains of Escherichia coli, Klebsiella spp. (including K. pneumoniae), Bacteroides spp. (including B. fragilis), and Enterobacter spp. Gynecological Infections caused by beta-lactamase producing strains of Escherichia coli,* and Bacteroides spp.* (including B. fragilis*). Launch Date 1986

PubMed

Title	Date	PubMed
[Synthesis and in vitro antibacterial activities of new 3,5-disubstituted oxazolidinone compounds].	2003 Oct	14730898
Double-disk synergy test positivity in Stenotrophomonas maltophilia clinical strains.	2004	15114869
Beta-lactam antibiotic-induced pseudoporphyria.	2004 Aug	15280819
Community-acquired pneumonia due to Pasteurella multocida.	2004 Dec	15571646
Restricting the use of ampicillin-sulbactam.	2004 Feb	15019231
[A case of tricuspid valve infective endocarditis presenting with multiple nodular shadows in both lungs without known predisposing factors].	2004 Feb	15007919
[Comparison of the effects of prophylactic antibiotic therapy and cost-effectiveness between cefazolin (CEZ) and Sulbactam/Ampicillin (SBT/ABPC) in gastric cancer surgery employing clinical pathway].	2004 Nov	15516808
Effect of the formulation on the bioequivalence of sultamicillin: tablets and suspension.	2004 Sep	15497673
Reappraisal of clindamycin IV monotherapy for treatment of mild-to-moderate aspiration pneumonia in elderly patients.	2005 Apr	15821205
Antibiotic prophylaxis of early onset pneumonia in critically ill comatose patients. A randomized study.	2005 Apr	15754197
Effect of bovine lactoferrin on the MICs of ampicillin/sulbactam (UNASYN), amoxicillin/clavulanic acid (Augmentin), ticarcillin clavulanate (Timentin), and piperacillin-tazobactam (ZOSYN), against clinical and environmental isolates of motile Aeromonas.	2005 Jan	15710671
Enterococcal meningitis caused by Enterococcus casseliflavus. First case report.	2005 Jan 14	15649336
[Two leptospirosis cases and review of the national literature].	2005 Jul	16358497
[Ampicillin and sulbactam concentrations in the irradiated mandible after oral squamous cell cancer].	2005 Jul	15926086
[Critical odontogenic infection involving the mediastinum. Case report].	2005 Jul	15926085
Compatibility of tramadol hydrochloride injection with selected drugs and solutions.	2005 Jun 15	15947129
A case of right-side infective endocarditis with ventricular septal defect.	2005 Mar	15888981
Pharmacokinetics of an ampicillin-sulbactam combination after intravenous and intramuscular administration to neonatal calves.	2005 May	15848786
Septic arthritis secondary to fusobacterium necrophorum in a 4-year-old girl: case report and review of the literature.	2005 Sep	16148860
An open-label, randomized study comparing efficacy and safety of intravenous piperacillin/tazobactam and ampicillin/sulbactam for infected diabetic foot ulcers.	2005 Spring	15865549
Synergy of arbekacin-based combinations against vancomycin hetero-intermediate Staphylococcus aureus.	2006 Apr	16614499
Pharmacokinetics of an ampicillin-sulbactam (2:1) combination after intravenous and intramuscular administration to chickens.	2006 Apr	16437304
Triple, standard quadruple and ampicillin-sulbactam-based quadruple therapies for H. pylori eradication: a comparative three-armed randomized clinical trial.	2006 Aug 14	16937475
The value of chemoprophylaxis against Enterococcus species in elective cholecystectomy: a randomized study of cefuroxime vs ampicillin-sulbactam.	2006 Dec	17178957
Synthesis and potent antimicrobial activities of some novel retinoidal monocationic benzimidazoles.	2006 Feb	16470650
Efficacy and safety of Sultamicillin (Ampicillin/Sulbactan) and Amoxicillin/Clavulanic acid in the treatment of upper respiratory tract infections in adults--an open-label, multicentric, randomized trial.	2006 Jan-Feb	16917560
Ceftriaxone-related hemolysis and acute renal failure.	2006 May	16491410
Ampicillin-sulbactam versus amoxycillin in quadruple therapy for Helicobacter pylori eradication: a preliminary study.	2006 May-Jun	16877845
[Liver abscess and infective endocarditis cases caused by Ruminococcus productus].	2006 Oct	17205698
RN not at fault for failure to give epinephrin. Taylor v. Jackson-Madison Cnty. Gen. Hosp., No.W2005-02471-COA-R3-CV (Tenn. App. 8/23/06) -Tn.	2006 Oct	17117601
[Case of anaphylactic shock induced by an antibiotic after induction of anesthesia].	2006 Oct	17051993
Internal jugular vein thrombosis associated with acute mastoiditis in a pediatric age.	2006 Oct	17006344
Molecular findings and antibiotic-resistance in an outbreak of Acinetobacter baumannii in an intensive care unit.	2007	17536158
Bioequivalence study of sultamicillin suspensions.	2007	17515294
High-dose ampicillin-sulbactam as an alternative treatment of late-onset VAP from multidrug-resistant Acinetobacter baumannii.	2007	17366011
Nonoperative treatment of acute appendicitis in children.	2007 Aug	17706511
Good pregnancy outcome with emergent cerclage placed in the presence of intra-amniotic microbial invasion.	2007 Aug	17597442
Pasteurella multocida urinary tract infection in a pediatric patient with end-stage renal disease.	2007 Feb	17259887
Burkholderia cepacia complex nasal isolation in immunocompetent patients with sinonasal polyposis not associated with cystic fibrosis.	2007 Jan	17180349
In vitro susceptibilities of Escherichia coli and Klebsiella spp. to ampicillin-sulbactam and amoxicillin-clavulanic acid.	2007 Jul	17642541
[Listeriosis in a patient with hemodialysis and iron overload].	2007 Jun 15	17571224
Clindamycin versus Unasyn in the treatment of facial cellulitis of odontogenic origin in children.	2007 Mar	17325089
Simultaneous determination of ampicillin, cefoperazone, and sulbactam in pharmaceutical formulations by HPLC with beta-cyclodextrin stationary phase.	2007 Oct	17685376
Methicillin-resistant ascending facial and orbital cellulitis in an operation Iraqi Freedom troop population.	2007 Sep-Oct	17881993
Acinetobacter baumannii mediastinitis after cardiopulmonary bypass: case report and literature review.	2008 Apr	18426353
Moxifloxacin vs ampicillin/sulbactam in aspiration pneumonia and primary lung abscess.	2008 Feb	18231720
Necrotizing fasciitis of eyelid secondary to parotitis.	2008 Jan-Feb	18203098
Midterm clinical and first reproductive results of a randomized controlled trial comparing uterine fibroid embolization and myomectomy.	2008 Jan-Feb	17943348
Ampicillin/sulbactam compared with polymyxins for the treatment of infections caused by carbapenem-resistant Acinetobacter spp.	2008 Jun	18367459
A retrospective review of ampicillin-sulbactam and amoxicillin + clavulanate vs cefazolin/cephalexin and erythromycin in the setting of preterm premature rupture of membranes: maternal and neonatal outcomes.	2008 May	18455521

Patents

Sample Use Guides

In Vivo Use Guide

UNASYN (Sultamicillin) may be administered by either the IV or the IM routes. For IV administration, the dose can be given by slow intravenous injection over at least 10–15 minutes or can also be delivered in greater dilutions with 50–100 mL of a compatible diluent as an intravenous infusion over 15–30 minutes. UNASYN may be administered by deep intramuscular injection. 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. This 1.5 to 3 g range represents the total of ampicillin content plus the sulbactam content of UNASYN, and corresponds to a range of 1 g ampicillin/0.5 g sulbactam to 2 g ampicillin/1 g sulbactam. The total dose of sulbactam should not exceed 4 grams per day. Pediatric Patients 1 Year of Age or Older: The recommended daily dose of UNASYN in pediatric patients is 300 mg per kg of body weight administered via intravenous infusion in equally divided doses every 6 hours. This 300 mg/kg/day dosage represents the total ampicillin content plus the sulbactam content of UNASYN, and corresponds to 200 mg ampicillin/100 mg sulbactam per kg per day.

Route of Administration: Other

In Vitro Use Guide

Against methicillin-susceptible strains of S.aureus the activity of ampicillin plus sulbactam (Sultamicillin) was equal to that of cephalexin (MIC90 = 4 mg/L) and against methicillin-resistant strains of S. aureus the MIC90 of ampicillin plus sulbactam was 16 mg/L.

Name

Type

Language

SULTAMICILLIN TOSYLATE

Common Name

English

BACIMEX

Brand Name

English

UNACID

Brand Name

English

Sultamicillin tosilate [WHO-DD]

Common Name

English

SULTAMICILLIN TOSILATE

Common Name

English

SULTAMICILLIN TOSYLATE [MI]

Common Name

English

Code System Code Type Description

PUBCHEM

444021