Sultamicillin

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Sultamicillin
Clinical data
Trade namesUnasyn, Unacid PD oral
AHFS/Drugs.comInternational Drug Names
Routes of
administration		By mouth
ATC code
Pharmacokinetic data
Bioavailability80%
ExcretionMainly via kidney
Identifiers
  • [(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
JSmol)
  • 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=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 checkY
  • Key:OPYGFNJSCUDTBT-PMLPCWDUSA-N checkY
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Sultamicillin, sold under the brand name Unasyn among others, is an oral form of the

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

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]

Medical uses

Medical uses for sultamicillin include:

Contraindications

Sultamicillin is contraindicated in people with penicillin allergy and those with

mononucleosis, as these have an increased risk of developing severe rashes.[1][5]

Adverse effects

The most common side effect, as with many other antibiotics, is

Haemorrhagic colitis caused by Clostridium difficile infections is a rare complication.[1][5]

Interactions

Interactions with other drugs are similar to other penicillins: allopurinol increases the risk for patients to develop rashes. Penicillins slow down the elimination of methotrexate, potentially increasing its adverse effects. Conversely, the elimination of sultamicillin's active constituents (ampicillin and sulbactam) is reduced by probenecid and probably by the nonsteroidal anti-inflammatory drugs (NSAIDs) aspirin, indometacin and phenylbutazone.[1]

Pharmacology

Pharmacokinetics

The constituents of sultamicillin: ampicillin (blue), sulbactam (red), and the acylal link (black).

Sultamicillin is a

elimination half-lives are 45–80 minutes and 40–70 minutes, respectively. Both drugs are mainly eliminated via the kidneys: within eight hours after intake, 46 to 80% of the ampicillin and 41 to 66% of the sulbactam are found in the urine.[2][5]

Mechanism of action

Further information: Ampicillin § Mechanism of action, and β-Lactamase inhibitor § Mechanism of action

Ampicillin, a

beta-lactamase inhibitor, irreversibly inhibits many beta-lactamases that occur in resistant bacteria strains.[1]

Chemistry

Ampicillin and sulbactam are linked via a

tosylate salt.[2][5]

References

  1. ^ a b c d e f g h i Haberfeld H, ed. (2020). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Unasyn-Filmtabletten.
  2. ^
    ISBN 978-3-8047-2898-1
    .
  3. ISBN 978-3-527-60749-5
    .
  4. ISBN 978-3-8047-2898-1
    .
  5. ^
    S2CID 195693347
    .
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