Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C25H30N4O9S2 |
| Molecular Weight | 594.657 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)C3=CC=CC=C3)C(=O)N2[C@H]1C(=O)OCOC(=O)[C@@H]4N5[C@@H](CC5=O)S(=O)(=O)C4(C)C
InChI
InChIKey=OPYGFNJSCUDTBT-PMLPCWDUSA-N
InChI=1S/C25H30N4O9S2/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/h5-9,14-18,21H,10-11,26H2,1-4H3,(H,27,31)/t14-,15-,16-,17+,18+,21-/m1/s1
| Molecular Formula | C25H30N4O9S2 |
| Molecular Weight | 594.657 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL352 |
|||
Target ID: CHEMBL359 |
|||
Target ID: CHEMBL354 |
|||
Target ID: CHEMBL2354204 |
|||
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | UNASYN Approved UseUNASYN 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 Date1986 |
|||
| Curative | UNASYN Approved UseUNASYN 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 Date1986 |
|||
| Curative | UNASYN Approved UseUNASYN 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 Date1986 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Ampicillin/sulbactam compared with polymyxins for the treatment of infections caused by carbapenem-resistant Acinetobacter spp. | 2008-06 |
|
| 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. | 2008-05 |
|
| Acinetobacter baumannii mediastinitis after cardiopulmonary bypass: case report and literature review. | 2008-04 |
|
| Moxifloxacin vs ampicillin/sulbactam in aspiration pneumonia and primary lung abscess. | 2008-02 |
|
| Necrotizing fasciitis of eyelid secondary to parotitis. | 2008-01-19 |
|
| Simultaneous determination of ampicillin, cefoperazone, and sulbactam in pharmaceutical formulations by HPLC with beta-cyclodextrin stationary phase. | 2007-10 |
|
| Methicillin-resistant ascending facial and orbital cellulitis in an operation Iraqi Freedom troop population. | 2007-09-21 |
|
| Nonoperative treatment of acute appendicitis in children. | 2007-08 |
|
| Good pregnancy outcome with emergent cerclage placed in the presence of intra-amniotic microbial invasion. | 2007-08 |
|
| In vitro susceptibilities of Escherichia coli and Klebsiella spp. to ampicillin-sulbactam and amoxicillin-clavulanic acid. | 2007-07 |
|
| [Listeriosis in a patient with hemodialysis and iron overload]. | 2007-06-15 |
|
| Midterm clinical and first reproductive results of a randomized controlled trial comparing uterine fibroid embolization and myomectomy. | 2007-03-08 |
|
| Clindamycin versus Unasyn in the treatment of facial cellulitis of odontogenic origin in children. | 2007-03 |
|
| Pasteurella multocida urinary tract infection in a pediatric patient with end-stage renal disease. | 2007-02 |
|
| Burkholderia cepacia complex nasal isolation in immunocompetent patients with sinonasal polyposis not associated with cystic fibrosis. | 2007-01 |
|
| Molecular findings and antibiotic-resistance in an outbreak of Acinetobacter baumannii in an intensive care unit. | 2007 |
|
| Bioequivalence study of sultamicillin suspensions. | 2007 |
|
| High-dose ampicillin-sulbactam as an alternative treatment of late-onset VAP from multidrug-resistant Acinetobacter baumannii. | 2007 |
|
| The value of chemoprophylaxis against Enterococcus species in elective cholecystectomy: a randomized study of cefuroxime vs ampicillin-sulbactam. | 2006-12 |
|
| [Liver abscess and infective endocarditis cases caused by Ruminococcus productus]. | 2006-10 |
|
| 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. | 2006-10 |
|
| [Case of anaphylactic shock induced by an antibiotic after induction of anesthesia]. | 2006-10 |
|
| Internal jugular vein thrombosis associated with acute mastoiditis in a pediatric age. | 2006-10 |
|
| Triple, standard quadruple and ampicillin-sulbactam-based quadruple therapies for H. pylori eradication: a comparative three-armed randomized clinical trial. | 2006-08-14 |
|
| Ampicillin-sulbactam versus amoxycillin in quadruple therapy for Helicobacter pylori eradication: a preliminary study. | 2006-08-01 |
|
| Ceftriaxone-related hemolysis and acute renal failure. | 2006-05 |
|
| Synergy of arbekacin-based combinations against vancomycin hetero-intermediate Staphylococcus aureus. | 2006-04 |
|
| Pharmacokinetics of an ampicillin-sulbactam (2:1) combination after intravenous and intramuscular administration to chickens. | 2006-04 |
|
| Synthesis and potent antimicrobial activities of some novel retinoidal monocationic benzimidazoles. | 2006-02 |
|
| Septic arthritis secondary to fusobacterium necrophorum in a 4-year-old girl: case report and review of the literature. | 2005-09 |
|
| [Two leptospirosis cases and review of the national literature]. | 2005-07 |
|
| [Ampicillin and sulbactam concentrations in the irradiated mandible after oral squamous cell cancer]. | 2005-07 |
|
| [Critical odontogenic infection involving the mediastinum. Case report]. | 2005-07 |
|
| Compatibility of tramadol hydrochloride injection with selected drugs and solutions. | 2005-06-15 |
|
| 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. | 2005-05-24 |
|
| Pharmacokinetics of an ampicillin-sulbactam combination after intravenous and intramuscular administration to neonatal calves. | 2005-05 |
|
| Reappraisal of clindamycin IV monotherapy for treatment of mild-to-moderate aspiration pneumonia in elderly patients. | 2005-04 |
|
| Antibiotic prophylaxis of early onset pneumonia in critically ill comatose patients. A randomized study. | 2005-04 |
|
| A case of right-side infective endocarditis with ventricular septal defect. | 2005-03 |
|
| Pulmonary abscess due to leflunomide use in rheumatoid arthritis: a case report. | 2005-03 |
|
| Enterococcal meningitis caused by Enterococcus casseliflavus. First case report. | 2005-01-14 |
|
| 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. | 2005-01 |
|
| An open-label, randomized study comparing efficacy and safety of intravenous piperacillin/tazobactam and ampicillin/sulbactam for infected diabetic foot ulcers. | 2005 |
|
| Biological treatability of raw and ozonated penicillin formulation effluent. | 2004-12-10 |
|
| [Isolation of Listeria monocytogenes from a patient with sealed ruptured thoracoabdominal aortic aneurysm]. | 2004-12 |
|
| Community-acquired pneumonia due to Pasteurella multocida. | 2004-12 |
|
| [Factors participating in development of bleeding varices in portal hypertension. Part I: bacterial infection and comparison of intravenous and peroral antibiotics effects--a randomised study]. | 2004-11 |
|
| [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]. | 2004-11 |
|
| Effect of the formulation on the bioequivalence of sultamicillin: tablets and suspension. | 2004-09 |
|
| Beta-lactam antibiotic-induced pseudoporphyria. | 2004-08 |
Patents
Sample Use Guides
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
| Substance Class |
Chemical
Created
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| Record UNII |
65DT0ML581
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Validated (UNII)
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QJ01CR04
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NCI_THESAURUS |
C28823
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Sultamicillin
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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METABOLITE ACTIVE -> PRODRUG |
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METABOLITE ACTIVE -> PRODRUG |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |
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