SULTAMICILLIN

Possibly Marketed Outside US

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 Search

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

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 65 Target ID: CHEMBL352 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18974644	Inhibitor 8228
Bacillus subtilis 8 Target ID: CHEMBL359 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18974644	Inhibitor 8228
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 8228
Escherichia coli 80 Target ID: CHEMBL354 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9527765	Inhibitor 8228
Bacterial penicillin-binding protein 232 Target ID: CHEMBL2354204 Sources: http://www.genome.jp/dbget-bin/www_bget?D05972	Inhibitor 8228
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 8228

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 8360	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 5.363712E11
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 8360	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 5.363712E11
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 8360	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 5.363712E11

PubMed

Title	Date	PubMed
Biodegradable polyhydroxyalkanoate implants for osteomyelitis therapy: in vitro antibiotic release.	2001	11403236
Effect of granulocyte-macrophage colony-stimulating factor on treatment of acute osteomyelitis. An experimental investigation in rats.	2001	11262785
A randomized, double-blind comparison of ampicillin/sulbactam and ceftriaxone in the prevention of surgical-site infections after neurosurgery.	2001 Aug	11558864
Pharmacokinetics of antibiotic prophylaxis in major orthopedic surgery and blood-saving techniques.	2001 Jul	11478553
Use of ampicillin/sulbactam and sultamicillin in pediatric infections: a re-evaluation.	2001 Jul-Aug	11675898
Parallel analysis of individual and aggregated data on antibiotic exposure and resistance in gram-negative bacilli.	2001 Nov 1	11588690
Comparison of Neisseria gonorrhoeae isolates from the genital tract and pharynx of two gonorrhea patients.	2001 Sep	11810580
Role of sultamicillin and ampicillin/sulbactam in the treatment of upper and lower bacterial respiratory tract infections.	2001 Sep	11673031
Antimicrobial susceptibility of coagulase-negative staphylococci isolated from bovine mastitis in Argentina.	2002 Aug	12214983
Shorter courses of parenteral antibiotic therapy do not appear to influence response rates for children with acute hematogenous osteomyelitis: a systematic review.	2002 Aug 14	12181082
Chronic intrauterine infection and inflammation in the preterm rabbit, despite antibiotic therapy.	2002 Feb	11854641
[The efficacy of combining antibiotic treatment with topical intranasal steroid administration in the treatment of chronic otitis media with effusion].	2002 Jul-Aug	12422079
[A case of bronchopulmonary actinomycosis diagnosed by transbronchial biopsy of a bronchial polypoid tumor].	2002 Jun	12325338
Comparison of ampicillin-sulbactam and imipenem-cilastatin for the treatment of acinetobacter ventilator-associated pneumonia.	2002 Jun 1	12015687
Extended-spectrum beta-lactamase-producing Escherichia coli and Klebsiella species: risk factors for colonization and impact of antimicrobial formulary interventions on colonization prevalence.	2002 May	12026150
Reports of osteopenia/rickets of prematurity are on the increase because of improved survival rates of low birthweight infants.	2002 Oct	12426026
The effect of high single dose parenteral vitamin A in addition to antibiotic therapy on healing of maxillary sinusitis in experimental acute sinusitis.	2002 Sep 24	12242137
[The impact of antibiotic use on hospital-acquired pneumonia: data of etiology tests].	2003	12695638
Lung abscess caused by Actinomyces odontolyticus.	2003 Aug	12924500
Roseomonas infection associated with a left ventricular assist device.	2003 Dec	14700415
HPLC for in-process control in the production of sultamicillin.	2003 Feb 26	12609671
Acute otitis media and facial nerve paralysis in adults.	2003 Jan	12544039
The effect of antibiotic therapy on intrauterine infection-induced preterm parturition in rabbits.	2003 Jul	14563094
Antibiotic therapy in preterm premature rupture of membranes: Are seven days necessary? A preliminary, randomized clinical trial.	2003 Jun	12824971
[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
Meningitis with multidrug-resistant Acinetobacter baumannii treated with ampicillin/sulbactam.	2004 Apr	15066747
Beta-lactam antibiotic-induced pseudoporphyria.	2004 Aug	15280819
[Isolation of Listeria monocytogenes from a patient with sealed ruptured thoracoabdominal aortic aneurysm].	2004 Dec	15678977
Biological treatability of raw and ozonated penicillin formulation effluent.	2004 Dec 10	15561374
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
Localized linear IgA disease induced by ampicillin/sulbactam.	2004 Jul	15243532
Antibiotic prophylaxis in clean neck dissections.	2004 Mar	15068519
[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
Reappraisal of clindamycin IV monotherapy for treatment of mild-to-moderate aspiration pneumonia in elderly patients.	2005 Apr	15821205
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
[Ampicillin and sulbactam concentrations in the irradiated mandible after oral squamous cell cancer].	2005 Jul	15926086
Triple, standard quadruple and ampicillin-sulbactam-based quadruple therapies for H. pylori eradication: a comparative three-armed randomized clinical trial.	2006 Aug 14	16937475
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
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
Acinetobacter baumannii mediastinitis after cardiopulmonary bypass: case report and literature review.	2008 Apr	18426353
Necrotizing fasciitis of eyelid secondary to parotitis.	2008 Jan-Feb	18203098
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.

Substance Class	Chemical Created by `admin` on `Thu Jul 06 02:23:09 UTC 2023` Edited by `admin` on `Thu Jul 06 02:23:09 UTC 2023`
Record UNII	65DT0ML581
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SULTAMICILLIN

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