Sultamicillin

Sultamicillin
Clinical data
Trade names	Unasyn, Unacid PD oral
AHFS/Drugs.com	International Drug Names
Routes of; administration	By mouth
ATC code	J01CR04 (WHO) ;
Pharmacokinetic data
Bioavailability	80%
Excretion	Mainly via kidney
Identifiers
	IUPAC name [(2R)-3,3-Dimethyl-4,4,7-trioxy-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carbonyl]oxymethyl(2R)-6-{[(2S)-2-amino-2-phenyl-acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;
CAS Number	76497-13-7 ;
PubChem CID	444022;
ChemSpider	392048 ;
UNII	65DT0ML581;
KEGG	D05972 ;
ChEBI	CHEBI:51770 ;
ChEMBL	ChEMBL506110 ;
CompTox Dashboard (EPA)	DTXSID501010077 ;
Chemical and physical data
Formula	C25H30N4O9S2
Molar mass	594.65 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(OCOC(=O)[C@@H]2N1C(=O)C[C@H]1S(=O)(=O)C2(C)C)[C@@H]4N5C(=O)[C@@H](NC(=O)[C@@H](c3ccccc3)N)[C@H]5SC4(C)C;
	InChI 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 ; Key:OPYGFNJSCUDTBT-PMLPCWDUSA-N ;
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Sultamicillin, sold under the brand name Unasyn among others, is an oral form of the penicillin antibiotic combination ampicillin/sulbactam. It is used for the treatment of bacterial infections of the upper and lower respiratory tract, the kidneys and urinary tract, skin and soft tissues, among other organs. It contains esterified ampicillin and sulbactam.^[1]

Sultamicillin is better absorbed from the gut than ampicillin/sulbactam, decreasing the chances of diarrhea and dysentery. The inclusion of sulbactam extends ampicillin's spectrum of action to beta-lactamase producing strains of bacteria.^[2] Oral sulbactam with the intravenous form provides a regimen of continuous sulbactam therapy throughout the treatment, resulting in better clinical results.^{[citation needed]}

It was patented in 1979 and approved for medical use in 1987.^[3]

^ Haberfeld H, ed. (2020). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Unasyn-Filmtabletten.
^ Mutschler E (2013). Arzneimittelwirkungen (in German) (10 ed.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. pp. 745, 748. ISBN 978-3-8047-2898-1.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 491. ISBN 978-3-527-60749-5.

[AC-1] Haberfeld H, ed. (2020). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Unasyn-Filmtabletten.

[Mutschler-2] Mutschler E (2013). Arzneimittelwirkungen (in German) (10 ed.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. pp. 745, 748. ISBN 978-3-8047-2898-1.

[Fis2006-3] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 491. ISBN 978-3-527-60749-5.

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