Compound ID | 3270

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Amoxicillin + clavulanic acid

Synonym(s): amoxicillin + clavulanate  |  amoxyclav  |  co-amoxyclav  |  Augmentin

Class: Beta-lactam (penicillin) + beta-lactamase inhibitor

Spectrum of activity: Gram-positive  &  Gram-negative
Details of activity: Active against methicillin-resistant beta-lactamase producing Staphylococcus aureus and beta-lactamase producing Neisseria sp.
Combined with other compounds: Yes
Description: Semi-synthetic compound (amoxycillin) and natural product from Streptomyces clavuligerus (clavulanic acid); other formulations exists but have been discontinued for clinical use
Year first mentioned: 1978
Highest developmental phase: Approved by FDA in 2002
Development status: Approved
Chemical structure(s):
Amoxicillin
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Molecular weight: 365.41
Iso. SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=C(C=C3)O)N)C(=O)O)C
InChI Key: LSQZJLSUYDQPKJ-NJBDSQKTSA-N
Can. SMILES: CC1(C)[C@H](C(=O)O)N2C(=O)[C@H]([C@H]2S1)NC(=O)[C@@H](C3=CC=C(C=C3)O)N
InChI: InChI=1S/C16H19N3O5S/c1-16(2)11(15(23)24)19-13(22)10(14(19)25-16)18-12(21)9(17)7-3-5-8(20)6-4-7/h3-6,9-11,14,20H,17H2,1-2H3,(H,18,21)(H,23,24)/t9-,10-,11+,14-/m1/s1
Clauvulanic acid
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Molecular weight: 199.16
Iso. SMILES: C1[C@@H]2N(C1=O)[C@H](/C(=C/CO)/O2)C(=O)O
InChI Key: HZZVJAQRINQKSD-PBFISZAISA-N
Can. SMILES: C(=C/1\[C@H](C(=O)O)N2C(=O)C[C@H]2O1)/CO
InChI: InChI=1S/C8H9NO5/c10-2-1-4-7(8(12)13)9-5(11)3-6(9)14-4/h1,6-7,10H,2-3H2,(H,12,13)/b4-1-/t6-,7-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/33613
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/5280980
Citations:
  • https://doi.org/10.1016/s0140-6736(80)91118-6
  • https://www.ncbi.nlm.nih.gov/books/NBK538164/#:~:text=This%20drug%20combination%20offers%20broader,%CE%B2%2Dlactamase%E2%80%93producing%20strains.
  • https://doi.org/10.1128/aac.13.3.389

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