Natural Product (NP) Details

General Information of the NP (ID: NP3076)
Name
Clavulanate
Synonyms
CLAVULANIC ACID; Clavulanate; 58001-44-8; Acido clavulanico; Acide clavulanique; Antibiotic MM 14151; acidum clavulanicum; Clavulansaeure; (2R,3Z,5R)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; MM 14151; BRL 14151; BRL-14151; Clavulanate acid; CHEBI:48947; CLAVULANATE POTASSIUM; UNII-23521W1S24; (Z)-(2R,5R)-3-(2-Hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo(3.2.0)heptane-2-carboxylic acid; CHEMBL777; rx-10100; Sodium Clavulanate; Clavulansaeure [INN]; 23521W1S24; CLAVULANATE LITHIUM; Clavulinic Acid; Acide clavulanique [INN-French]; Acido clavulanico [INN-Spanish]; Acidum clavulanicum [INN-Latin]; Clavulox (TN); BRL-14151K; Clavulanic acid (INN); EINECS 261-069-2; 3008-B; BRN 0787059; Clavulanic acid [INN:BAN]; clavulonic acid; BRL14151; (Z)-(2R,5R)-3-(2-Hydroxyethyliden)-7-oxo-4-oxa-1-azabicyclo(3.2.0)heptan-2-carbonsaeure; Epitope ID:117130; SCHEMBL6093; SCHEMBL34260; BSPBio_002430; DTXSID2022830; GTPL11128; ZINC3830569; BDBM50021959; AKOS016009164; DB00766; NCGC00188985-01; 4-Oxa-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3-(2-hydroxyethylidene)-7-oxo-, (2R-(2-alpha,3Z,5-alpha))-; SBI-0206779.P001; A12384; C06662; D07711; 49700-EP2275102A1; 49700-EP2295432A1; 49700-EP2308874A1; 49700-EP2311825A1; 001C448; Q415709; W-105420; Clavulanic acid, Antibiotic for Culture Media Use Only; (2R,5R)-3-(2-Hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2beta-carboxylic acid; 1365254-41-6; 4-Oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,3-(2-hydroxyethylidene)-7-oxo-,(2R,3Z,5R)-
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Species Origin Streptomyces clavuligerus ...     Click to Show/Hide
Streptomyces clavuligerus
SuperKingdom: Bacteria
Phylum: Actinobacteria
Class: Actinomycetia
Order: Streptomycetales
Family: Streptomycetaceae
Genus: Streptomyces
Species: Streptomyces clavuligerus
Disease Bacterial infection [ICD-11: 1A00-1C4Z] Approved [1]
Structure
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2D MOL

3D MOL

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Formula
C8H9NO5
PubChem CID
5280980
Canonical SMILES
C1C2N(C1=O)C(C(=CCO)O2)C(=O)O
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
InChIKey
HZZVJAQRINQKSD-PBFISZAISA-N
CAS Number
CAS 58001-44-8
ChEBI ID
CHEBI:48947
TTD Drug ID
D0X7JN
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Amoxicillin      Bacterial infection     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression BCL-2  Molecule Info 
Pathway MAP
                    In-vivo Model Clinical Trial
                    Experimental
                    Result(s)		 Amoxicillin/clavulanic acid is a useful therapeutic addition to the existing forms of treatment for amoxicillin-resistant respiratory tract infections.
          Amoxicillin + Gentamicin     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Staphylococcus aureus Microorganism model Staphylococcus aureus
Susceptible Saureus Microorganism model Susceptible Saureus
                    In-vivo Model Forty-two female New Zealand white rabbits were used as animal model in this study.
                    Experimental
                    Result(s)		 1,8-cineole showed a synergistic effect in combination with both AMC and gentamicin, which offer possibilities for reducing antibiotic usage.
Target and Pathway
Target(s) Staphylococcus beta-lactamase (Stap-coc blaZ)  Molecule Info  [5]
References
Reference 1 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 065063.
Reference 2 A combination of amoxicillin and clavulanic acid in the treatment of respiratory tract infections caused by amoxicillin-resistant haemophilus influenzae. Infection. 1981;9(5):244-8.
Reference 3 The Antistaphylococcal Activity of Amoxicillin/Clavulanic Acid, Gentamicin, and 1,8-Cineole Alone or in Combination and Their Efficacy through a Rabbit Model of Methicillin-Resistant Staphylococcus aureus Osteomyelitis. Evid Based Complement Alternat Med. 2020 Apr 28;2020:4271017.
Reference 4 In vitro activity of mupirocin and amoxicillin-clavulanate alone and in combination against staphylococci including those resistant to methicillin. Int J Antimicrob Agents. 2004 May;23(5):513-6.
Reference 5 A sensitive coupled HPLC/electrospray mass spectrometry assay for SPM-1 metallo-beta-lactamase inhibitors. Assay Drug Dev Technol. 2009 Apr;7(2):170-9.
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