Sultamicillin

Structural formula
General
Non-proprietary name	Sultamicillin
other names	[(2 R ) -3,3-dimethyl-4,4,7-trioxo-4λ 6 -thia-1-azabicyclo- [3.2.0] heptane-2-carbonyl] oxymethyl- (2 R ) -6- [ (2 S ) -2-amino-2-phenyl-acetyl] amino ( IUPAC )
Molecular formula	C 25 H 30 N 4 O 9 S 2
Brief description	white to almost white, crystalline, slightly hygroscopic powder
External identifiers / databases
PubChem	53512
ChemSpider	48332
Wikidata	Q617686
Drug information
ATC code	J01 CR04
Drug class	β-lactam antibiotics; β-lactamase inhibitor;
Mechanism of action	Inhibition of cell wall synthesis by sensitive bacteria and inactivation of numerous β-lactamases
properties
Molar mass	594.66 g mol −1
solubility	practically insoluble in water, very sparingly soluble in methanol , practically insoluble in ethanol
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Sultamicillin is a prodrug - antibiotic in which the β-lactam antibiotic ampicillin as a bactericidal component and sulbactam as an inhibitor of β-lactamase are chemically linked by an ester bond . This binding increases the absorption via the intestine ( oral bioavailability ) compared to the combination of both substances as free molecules. After absorption has taken place, the bond is split hydrolytically .

Sultamicillin is a broad spectrum antibiotic. It also has an effect on β-lactamase producers (including Staphylococcus aureus ) and anaerobic bacteria. Areas of application are mainly urinary and respiratory infections caused by bacteria sensitive to ampicillin, but also gonorrhea .

The plasma half-life is approximately one hour. Ampicillin and sulbactam are excreted renally unchanged . The main side effects described were diarrhea , allergic reactions are possible.


Structural formula of ampicillin	Sulbactam structural formula

Structural formula of sultamicillin, blue = ampicillin, red = sulbactam

Trade names

Monopreparations

Unacid PD oral (D), sultamicillin ratio 375 mg (D), Unasyn (D, A)

Individual evidence

↑ ^a ^b SULTAMICILLIN CRS data sheet (PDF) at EDQM , accessed on March 26, 2009.

↑ Infoportal Pfizer

↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

↑ JC Frölich, W. Kirch: Practical medicine therapy . Springer-Verlag, 2013, ISBN 978-3-662-09397-9 , pp. 949 ( limited preview in Google Book search).

^ Gustav Paumgartner, Gerhard Steinbeck: Therapy for internal diseases . Springer-Verlag, 2013, ISBN 978-3-662-10475-0 , pp. 1617 ( limited preview in Google Book search).

↑ ^a ^b R. Ho ̈hl: Oral antibiotics in clinic and practice Practice-oriented recommendations for antibiotic therapy of mild and moderate bacterial infections in adults in outpatient and inpatient areas . Springer-Verlag, 2009, ISBN 978-3-642-00522-0 , pp. 16 ( limited preview in Google Book search).

^ ^A ^b Franz von Bruchhausen: Hager's Handbook of Pharmaceutical Practice . Springer-Verlag, 1930, ISBN 978-3-540-52688-9 , pp. 749 ( limited preview in Google Book search).

[Ph._Eur.-1] SULTAMICILLIN CRS data sheet (PDF) at EDQM , accessed on March 26, 2009.

[INF-2] Infoportal Pfizer

[NV-3] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[J.C._Frölich,_W._Kirch-4] JC Frölich, W. Kirch: Practical medicine therapy . Springer-Verlag, 2013, ISBN 978-3-662-09397-9 , pp. 949 ( limited preview in Google Book search).

[Gustav_Paumgartner,_Gerhard_Steinbeck-5] Gustav Paumgartner, Gerhard Steinbeck: Therapy for internal diseases . Springer-Verlag, 2013, ISBN 978-3-662-10475-0 , pp. 1617 ( limited preview in Google Book search).

[R._Ho_̈hl-6] R. Ho ̈hl: Oral antibiotics in clinic and practice Practice-oriented recommendations for antibiotic therapy of mild and moderate bacterial infections in adults in outpatient and inpatient areas . Springer-Verlag, 2009, ISBN 978-3-642-00522-0 , pp. 16 ( limited preview in Google Book search).

[Franz_von_Bruchhausen-7] A ^b Franz von Bruchhausen: Hager's Handbook of Pharmaceutical Practice . Springer-Verlag, 1930, ISBN 978-3-540-52688-9 , pp. 749 ( limited preview in Google Book search).