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
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C3=CC=CC=C3)C(=O)OCOC(=O)[C@@H]4N5C(=O)C[C@@]5([H])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 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18974644 |
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Target ID: CHEMBL359 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18974644 |
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Target ID: CHEMBL354 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9527765 |
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Target ID: CHEMBL2354204 Sources: http://www.genome.jp/dbget-bin/www_bget?D05972 |
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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 |
---|---|---|
Double-disk synergy test positivity in Stenotrophomonas maltophilia clinical strains. | 2004 |
|
Meningitis with multidrug-resistant Acinetobacter baumannii treated with ampicillin/sulbactam. | 2004 Apr |
|
Beta-lactam antibiotic-induced pseudoporphyria. | 2004 Aug |
|
Community-acquired pneumonia due to Pasteurella multocida. | 2004 Dec |
|
Biological treatability of raw and ozonated penicillin formulation effluent. | 2004 Dec 10 |
|
Restricting the use of ampicillin-sulbactam. | 2004 Feb |
|
[A case of tricuspid valve infective endocarditis presenting with multiple nodular shadows in both lungs without known predisposing factors]. | 2004 Feb |
|
Treating foot infections in diabetic patients: a randomized, multicenter, open-label trial of linezolid versus ampicillin-sulbactam/amoxicillin-clavulanate. | 2004 Jan 1 |
|
Localized linear IgA disease induced by ampicillin/sulbactam. | 2004 Jul |
|
Antibiotic prophylaxis in clean neck dissections. | 2004 Mar |
|
[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 Nov |
|
[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 |
|
Effect of the formulation on the bioequivalence of sultamicillin: tablets and suspension. | 2004 Sep |
|
Enterococcal meningitis caused by Enterococcus casseliflavus. First case report. | 2005 Jan 14 |
|
[Two leptospirosis cases and review of the national literature]. | 2005 Jul |
|
[Ampicillin and sulbactam concentrations in the irradiated mandible after oral squamous cell cancer]. | 2005 Jul |
|
[Critical odontogenic infection involving the mediastinum. Case report]. | 2005 Jul |
|
A case of right-side infective endocarditis with ventricular septal defect. | 2005 Mar |
|
Pulmonary abscess due to leflunomide use in rheumatoid arthritis: a case report. | 2005 Mar |
|
An open-label, randomized study comparing efficacy and safety of intravenous piperacillin/tazobactam and ampicillin/sulbactam for infected diabetic foot ulcers. | 2005 Spring |
|
Synergy of arbekacin-based combinations against vancomycin hetero-intermediate Staphylococcus aureus. | 2006 Apr |
|
Pharmacokinetics of an ampicillin-sulbactam (2:1) combination after intravenous and intramuscular administration to chickens. | 2006 Apr |
|
Triple, standard quadruple and ampicillin-sulbactam-based quadruple therapies for H. pylori eradication: a comparative three-armed randomized clinical trial. | 2006 Aug 14 |
|
The value of chemoprophylaxis against Enterococcus species in elective cholecystectomy: a randomized study of cefuroxime vs ampicillin-sulbactam. | 2006 Dec |
|
Synthesis and potent antimicrobial activities of some novel retinoidal monocationic benzimidazoles. | 2006 Feb |
|
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 |
|
Ceftriaxone-related hemolysis and acute renal failure. | 2006 May |
|
Ampicillin-sulbactam versus amoxycillin in quadruple therapy for Helicobacter pylori eradication: a preliminary study. | 2006 May-Jun |
|
[Liver abscess and infective endocarditis cases caused by Ruminococcus productus]. | 2006 Oct |
|
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 |
|
[Case of anaphylactic shock induced by an antibiotic after induction of anesthesia]. | 2006 Oct |
|
Internal jugular vein thrombosis associated with acute mastoiditis in a pediatric age. | 2006 Oct |
|
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 |
|
Nonoperative treatment of acute appendicitis in children. | 2007 Aug |
|
Good pregnancy outcome with emergent cerclage placed in the presence of intra-amniotic microbial invasion. | 2007 Aug |
|
Pasteurella multocida urinary tract infection in a pediatric patient with end-stage renal disease. | 2007 Feb |
|
Burkholderia cepacia complex nasal isolation in immunocompetent patients with sinonasal polyposis not associated with cystic fibrosis. | 2007 Jan |
|
In vitro susceptibilities of Escherichia coli and Klebsiella spp. to ampicillin-sulbactam and amoxicillin-clavulanic acid. | 2007 Jul |
|
[Listeriosis in a patient with hemodialysis and iron overload]. | 2007 Jun 15 |
|
Clindamycin versus Unasyn in the treatment of facial cellulitis of odontogenic origin in children. | 2007 Mar |
|
Simultaneous determination of ampicillin, cefoperazone, and sulbactam in pharmaceutical formulations by HPLC with beta-cyclodextrin stationary phase. | 2007 Oct |
|
Methicillin-resistant ascending facial and orbital cellulitis in an operation Iraqi Freedom troop population. | 2007 Sep-Oct |
|
Acinetobacter baumannii mediastinitis after cardiopulmonary bypass: case report and literature review. | 2008 Apr |
|
Moxifloxacin vs ampicillin/sulbactam in aspiration pneumonia and primary lung abscess. | 2008 Feb |
|
Necrotizing fasciitis of eyelid secondary to parotitis. | 2008 Jan-Feb |
|
Midterm clinical and first reproductive results of a randomized controlled trial comparing uterine fibroid embolization and myomectomy. | 2008 Jan-Feb |
|
Ampicillin/sulbactam compared with polymyxins for the treatment of infections caused by carbapenem-resistant Acinetobacter spp. | 2008 Jun |
|
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 |
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
by
admin
on
Edited
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by
admin
on
Fri Dec 15 19:15:36 GMT 2023
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Record UNII |
65DT0ML581
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Record Status |
Validated (UNII)
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Record Version |
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WHO-ATC |
J01CR04
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WHO-VATC |
QJ01CR04
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NCI_THESAURUS |
C28823
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2539
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CHEMBL506110
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65DT0ML581
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Sultamicillin
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C035444
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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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)
EP
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ACTIVE MOIETY |