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ampicillin/sulbactam

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ampicillin/sulbactam

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Also known as Ampicillin / Sulbactam

Ampicillin/sulbactam is a fixed-dose combination medication of the common penicillin-derived antibiotic ampicillin and sulbactam, an inhibitor of bacterial beta-lactamase. Two different forms of the drug exist. The first, developed in 1987 and marketed in the United States under the brand name Unasyn, generic only outside the United States, is an intravenous antibiotic. The second, an oral form called sultamicillin, is marketed under the brand name Ampictam outside the United States, and generic only in the United States. Ampicillin/sulbactam is used to treat infections caused by bacteria resi

Chemical data

Formula
C24H28N4Na2O9S2
Molecular weight
626.6 g/mol
IUPAC name
disodium;(2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;(2S,5R)-3,3-dimethyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
SMILES
CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)C(=O)[O-])C.CC1([C@@H](N2[C@H](S1(=O)=O)CC2=O)C(=O)[O-])C.[Na+].[Na+]
InChIKey
CVMHBXYXKYUCML-UBWQYZJSSA-L
Polar surface area
244 Ų
H-bond donors
2
H-bond acceptors
11
Formal charge
0

via PubChem

Wikidata facts

Subclass of
mixture
Has part
sulbactam
Has use
medication
Show 3 more facts
chemical formula
C₂₄H₂₈N₄Na₂O₉S₂
canonical SMILES
CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)[O-])C.CC1(C(N2C(S1(=O)=O)CC2=O)C(=O)[O-])C.[Na+].[Na+]
isomeric SMILES
CC1(C)S[C@@H]2[C@H](N=C([O-])[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(=O)[O-].CC1(C)[C@H](C(=O)O)N2C(=O)C[C@H]2S1(=O)=O.[Na+].[Na+]
Sources (2)

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~11 min read

Encyclopedic overview

13 sections
Contents
  • Medical uses
  • Contraindications
  • Adverse effects
  • Pharmacology
  • Pharmacodynamics and pharmacokinetics
  • Mechanism of action
  • Chemistry
  • History
  • Formulation
  • Society and culture
  • Names
  • References
  • External links

Ampicillin/sulbactam is a fixed-dose combination medication of the common penicillin-derived antibiotic ampicillin and sulbactam, an inhibitor of bacterial beta-lactamase. Two different forms of the drug exist. The first, developed in 1987 and marketed in the United States under the brand name Unasyn, generic only outside the United States, is an intravenous antibiotic. The second, an oral form called sultamicillin, is marketed under the brand name Ampictam outside the United States, and generic only in the United States. Ampicillin/sulbactam is used to treat infections caused by bacteria resistant to beta-lactam antibiotics. Sulbactam blocks the enzyme which breaks down ampicillin and thereby allows ampicillin to attack and kill the bacteria.

== Medical uses == Ampicillin/sulbactam has a wide array of medical use for many different types of infectious disease. It is usually reserved as a second-line therapy in cases where bacteria have become beta-lactamase resistant, rendering traditional penicillin-derived antibiotics ineffective. It is effective against certain gram positive bacteria, gram-negative bacteria, and anaerobes. Gram-positive bacteria: Staphylococcus aureus (beta-lactamase and non-beta-lactamase producing), Staphylococcus epidermidis (beta-lactamase and non-beta-lactamase producing), Staphylococcus saprophyticus (beta-lactamase and non-beta-lactamase producing), Enterococcus faecalis, Streptococcus pneumoniae, Streptococcus pyogenes, and Streptococcus viridans. Gram-negative bacteria: Haemophilus influenzae (beta-lactamase and non-beta-lactamase producing), Moraxella catarrhalis (beta-lactamase and non-beta-lactamase producing), Escherichia coli (beta-lactamase and non-beta-lactamase producing), Klebsiella spp. (all known species are beta-lactamase producing), Proteus mirabilis (beta-lactamase and non-beta-lactamase producing), Proteus vulgaris, Providencia rettgeri, Providencia stuartii, Morganella morganii, and Neisseria gonorrhoeae (beta-lactamase and non-beta-lactamase producing). Anaerobes: Clostridium spp., Peptococcus spp., Peptostreptococcus spp, Bacteroides spp. including B. fragilis. Gynecological Infections: Ampicillin/sulbactam can be used to treat gynecological infections caused by beta-lactamase producing strains of E. coli, and Bacteroides spp. (including B. fragilis). Bone and joint infections: Ampicillin/sulbactam can be used in the treatment of bone and joint infections caused by susceptible beta-lactamase producing bacteria. Intra-abdominal infections: Ampicillin/sulbactam can be used to treat intra-abdominal infections caused by beta-lactamase producing strains of E. coli, Klebsiella spp. (including K. pneumoniae), B. fragilis, and Enterobacter spp. Skin and skin structure Infections: This medication can be used to treat skin and skin structure infections caused from beta-lactamase-producing strains of S. aureus, Enterobacter spp., E. coli, Klebsiella spp. (including K. pneumoniae), P. mirabilis, B. fragilis, and Acinetobacter calcoaceticus. Examples of skin conditions treated with ampicillin-sulbactam are moderate to severe diabetic foot infections and type 1 Necrotizing fasciitis, commonly referred to as "flesh-eating bacteria".

Excerpted from Wikipedia’s “ampicillin/sulbactam” article, available under the CC BY-SA 4.0 licence.