SULTAMICILLIN

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 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
Bacterial pathogens and outcome determinants of childhood pyogenic meningitis in Ilorin, Nigeria.	2001 Dec	14510107
In vitro investigation of the susceptibility of Acinetobacter baumannii strains isolated from clinical specimens to ampicillin/sulbactam alone and in combination with amikacin.	2002 Nov	12431877
Reports of osteopenia/rickets of prematurity are on the increase because of improved survival rates of low birthweight infants.	2002 Oct	12426026
Lung abscess caused by Actinomyces odontolyticus.	2003 Aug	12924500
Roseomonas infection associated with a left ventricular assist device.	2003 Dec	14700415
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
Nosocomial multi-drug resistant Acinetobacter baumannii bloodstream infection: risk factors and outcome with ampicillin-sulbactam treatment.	2003 May	12767844
[Synthesis and in vitro antibacterial activities of new 3,5-disubstituted oxazolidinone compounds].	2003 Oct	14730898
Successful treatment of necrotizing fasciitis due to group A streptococcus with impending toxic shock syndrome.	2003 Sep	14518693
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
Community-acquired pneumonia due to Pasteurella multocida.	2004 Dec	15571646
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
Treating foot infections in diabetic patients: a randomized, multicenter, open-label trial of linezolid versus ampicillin-sulbactam/amoxicillin-clavulanate.	2004 Jan 1	14679443
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
Effect of the formulation on the bioequivalence of sultamicillin: tablets and suspension.	2004 Sep	15497673
Reappraisal of clindamycin IV monotherapy for treatment of mild-to-moderate aspiration pneumonia in elderly patients.	2005 Apr	15821205
Antibiotic prophylaxis of early onset pneumonia in critically ill comatose patients. A randomized study.	2005 Apr	15754197
Enterococcal meningitis caused by Enterococcus casseliflavus. First case report.	2005 Jan 14	15649336
[Critical odontogenic infection involving the mediastinum. Case report].	2005 Jul	15926085
Compatibility of tramadol hydrochloride injection with selected drugs and solutions.	2005 Jun 15	15947129
Pulmonary abscess due to leflunomide use in rheumatoid arthritis: a case report.	2005 Mar	15322813
Septic arthritis secondary to fusobacterium necrophorum in a 4-year-old girl: case report and review of the literature.	2005 Sep	16148860
Synergy of arbekacin-based combinations against vancomycin hetero-intermediate Staphylococcus aureus.	2006 Apr	16614499
Triple, standard quadruple and ampicillin-sulbactam-based quadruple therapies for H. pylori eradication: a comparative three-armed randomized clinical trial.	2006 Aug 14	16937475
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
Ceftriaxone-related hemolysis and acute renal failure.	2006 May	16491410
Ampicillin-sulbactam versus amoxycillin in quadruple therapy for Helicobacter pylori eradication: a preliminary study.	2006 May-Jun	16877845
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
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
High-dose ampicillin-sulbactam as an alternative treatment of late-onset VAP from multidrug-resistant Acinetobacter baumannii.	2007	17366011
Nonoperative treatment of acute appendicitis in children.	2007 Aug	17706511
Good pregnancy outcome with emergent cerclage placed in the presence of intra-amniotic microbial invasion.	2007 Aug	17597442
Burkholderia cepacia complex nasal isolation in immunocompetent patients with sinonasal polyposis not associated with cystic fibrosis.	2007 Jan	17180349
In vitro susceptibilities of Escherichia coli and Klebsiella spp. to ampicillin-sulbactam and amoxicillin-clavulanic acid.	2007 Jul	17642541
Clindamycin versus Unasyn in the treatment of facial cellulitis of odontogenic origin in children.	2007 Mar	17325089
Simultaneous determination of ampicillin, cefoperazone, and sulbactam in pharmaceutical formulations by HPLC with beta-cyclodextrin stationary phase.	2007 Oct	17685376
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
Midterm clinical and first reproductive results of a randomized controlled trial comparing uterine fibroid embolization and myomectomy.	2008 Jan-Feb	17943348
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 `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

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