SULTAMICILLIN HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H30N4O9S2.ClH
Molecular Weight	631.118
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of SULTAMICILLIN HYDROCHLORIDE

Structure Search

SMILES

Cl.[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=JLBADLWTHWGGNE-CGAOXQFVSA-N

InChI=1S/C25H30N4O9S2.ClH/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);1H/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
[Activity of new fluoroquinolones against clinical isolates of Acinetobacter baumannii].	2001 Dec	11856982
Role of sultamicillin and ampicillin/sulbactam in the treatment of upper and lower bacterial respiratory tract infections.	2001 Sep	11673031
Nontraditional dosing of ampicillin-sulbactam for multidrug-resistant Acinetobacter baumannii meningitis.	2002 Apr	11939689
Application of micellar electrokinetic chromatography to the determination of sultamicillin in oral pharmaceutical preparations.	2002 Dec 6	12498263
[The efficacy of combining antibiotic treatment with topical intranasal steroid administration in the treatment of chronic otitis media with effusion].	2002 Jul-Aug	12422079
Clinical effect of ampicillin with beta-lactamase inhibitor (sulbactam/ampicillin) on community-acquired pneumonia in the elderly.	2003 Jun	12825120
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
[Isolation of Listeria monocytogenes from a patient with sealed ruptured thoracoabdominal aortic aneurysm].	2004 Dec	15678977
Localized linear IgA disease induced by ampicillin/sulbactam.	2004 Jul	15243532
Reappraisal of clindamycin IV monotherapy for treatment of mild-to-moderate aspiration pneumonia in elderly patients.	2005 Apr	15821205
A case of right-side infective endocarditis with ventricular septal defect.	2005 Mar	15888981
The value of chemoprophylaxis against Enterococcus species in elective cholecystectomy: a randomized study of cefuroxime vs ampicillin-sulbactam.	2006 Dec	17178957
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
High-dose ampicillin-sulbactam as an alternative treatment of late-onset VAP from multidrug-resistant Acinetobacter baumannii.	2007	17366011
Burkholderia cepacia complex nasal isolation in immunocompetent patients with sinonasal polyposis not associated with cystic fibrosis.	2007 Jan	17180349
Clindamycin versus Unasyn in the treatment of facial cellulitis of odontogenic origin in children.	2007 Mar	17325089

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 HYDROCHLORIDE

Common Name

English

Code System Code Type Description

CAS

76203-99-1