U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of SULTAMICILLIN

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

HIDE SMILES / InChI

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.

Originator

Curator's Comment: Sultamicillin was first developed in 1987 by Pfizer Inc and marketed under the trade name Unasyn # Pfizer

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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
Curative
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
Curative
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

PubMed

TitleDatePubMed
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
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:15:36 GMT 2023
Edited
by admin
on Fri Dec 15 19:15:36 GMT 2023
Record UNII
65DT0ML581
Record Status Validated (UNII)
Record Version
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Name Type Language
SULTAMICILLIN
EP   INN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
CP-49952
Code English
SULTAMICILLIN [MART.]
Common Name English
6'-(2-AMINO-2-PHENYLACETAMIDO)PENICILLANOYLOXYMETHYL PENICILLANATE 1,1-DIOXIDE
Common Name English
Sultamicillin [WHO-DD]
Common Name English
SULTAMICILLIN [EP MONOGRAPH]
Common Name English
1,1-DIOXOPENICILLANOYLOXYMETHYL 6-(D-.ALPHA.-AMINO-.ALPHA.-PHENYLACETAMIDO)PENICILLANATE
Common Name English
SULTAMICILLIN [USAN]
Common Name English
sultamicillin [INN]
Common Name English
SULTAMICILLIN [MI]
Common Name English
Hydroxymethyl (2S,5R,6R)-6-[(R)-(2-amino-2-phenylacetamido)]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate, (2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate (ester) S,S-dioxide
Common Name English
CP-49,952
Code English
VD-1827
Code English
Classification Tree Code System Code
WHO-ATC J01CR04
Created by admin on Fri Dec 15 19:15:36 GMT 2023 , Edited by admin on Fri Dec 15 19:15:36 GMT 2023
WHO-VATC QJ01CR04
Created by admin on Fri Dec 15 19:15:36 GMT 2023 , Edited by admin on Fri Dec 15 19:15:36 GMT 2023
NCI_THESAURUS C28823
Created by admin on Fri Dec 15 19:15:36 GMT 2023 , Edited by admin on Fri Dec 15 19:15:36 GMT 2023
Code System Code Type Description
EVMPD
SUB10761MIG
Created by admin on Fri Dec 15 19:15:36 GMT 2023 , Edited by admin on Fri Dec 15 19:15:36 GMT 2023
PRIMARY
DRUG BANK
DB12127
Created by admin on Fri Dec 15 19:15:36 GMT 2023 , Edited by admin on Fri Dec 15 19:15:36 GMT 2023
PRIMARY
MERCK INDEX
m10391
Created by admin on Fri Dec 15 19:15:36 GMT 2023 , Edited by admin on Fri Dec 15 19:15:36 GMT 2023
PRIMARY Merck Index
DRUG CENTRAL
2539
Created by admin on Fri Dec 15 19:15:36 GMT 2023 , Edited by admin on Fri Dec 15 19:15:36 GMT 2023
PRIMARY
ChEMBL
CHEMBL506110
Created by admin on Fri Dec 15 19:15:36 GMT 2023 , Edited by admin on Fri Dec 15 19:15:36 GMT 2023
PRIMARY
EPA CompTox
DTXSID501010077
Created by admin on Fri Dec 15 19:15:36 GMT 2023 , Edited by admin on Fri Dec 15 19:15:36 GMT 2023
PRIMARY
PUBCHEM
444022
Created by admin on Fri Dec 15 19:15:36 GMT 2023 , Edited by admin on Fri Dec 15 19:15:36 GMT 2023
PRIMARY
NCI_THESAURUS
C28823
Created by admin on Fri Dec 15 19:15:36 GMT 2023 , Edited by admin on Fri Dec 15 19:15:36 GMT 2023
PRIMARY
CHEBI
51770
Created by admin on Fri Dec 15 19:15:36 GMT 2023 , Edited by admin on Fri Dec 15 19:15:36 GMT 2023
PRIMARY
SMS_ID
100000093293
Created by admin on Fri Dec 15 19:15:36 GMT 2023 , Edited by admin on Fri Dec 15 19:15:36 GMT 2023
PRIMARY
FDA UNII
65DT0ML581
Created by admin on Fri Dec 15 19:15:36 GMT 2023 , Edited by admin on Fri Dec 15 19:15:36 GMT 2023
PRIMARY
WIKIPEDIA
Sultamicillin
Created by admin on Fri Dec 15 19:15:36 GMT 2023 , Edited by admin on Fri Dec 15 19:15:36 GMT 2023
PRIMARY
CAS
76497-13-7
Created by admin on Fri Dec 15 19:15:36 GMT 2023 , Edited by admin on Fri Dec 15 19:15:36 GMT 2023
PRIMARY
INN
5151
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PRIMARY
MESH
C035444
Created by admin on Fri Dec 15 19:15:36 GMT 2023 , Edited by admin on Fri Dec 15 19:15:36 GMT 2023
PRIMARY
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