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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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Cite NPCDR
Visitor Map
Correspondence

X. N. Sun, Y. T. Zhang, Y. Zhou, X. C. Lian, L. L. Yan, T. Pan, T. Jin, H. Xie, Z. M. Liang, W. Q. Qiu, J. X. Wang, Z. R. Li, F. Zhu*, X. B. Sui*. NPCDR: natural product-based drug combination and its disease-specific molecular regulation. Nucleic Acids Research. 50(D1): 1324-1333 (2020). PMID: 34664659

Prof. Feng ZHU  (zhufeng@zju.edu.cn)

College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, China


Prof. Xinbing SUI  (hzzju@hznu.edu.cn)

School of Pharmacy and Department of Medical Oncology, the Affiliated Hospital of Hangzhou Normal University, Hangzhou Normal University, Hangzhou, China