Drug Details

General Information of the Drug (ID: DR3931)
Name
Amoxicillin
Synonyms
amoxicillin; Amoxycillin; Amoxicillin anhydrous; 26787-78-0; Amoxicilline; p-Hydroxyampicillin; Amopenixin; Amolin; Moxal; D-Amoxicillin; Clamoxyl; Amoxil; Amoxicillinum; Amoxicilina; Imacillin; Hiconcil; Moxatag; Robamox; Amoxicilina [INN-Spanish]; Amoxicillin trihydrate; Amoxicilline [INN-French]; Amoxicillinum [INN-Latin]; alpha-Amino-p-hydroxybenzylpenicillin; Histocillin; Amoclen; Flemoxin; Unicillin; AMPC; Amoxycillin Trihydrate; BRL-2333; AMOXICILLIN CRYSTALLINE; 6-(p-Hydroxy-alpha-aminophenylacetamido)penicillanic acid; Amoxicillin (INN); Amoxicillin [INN]; CHEBI:2676; (2S,5R,6R)-6-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; UNII-9EM05410Q9; Amoxicillin hydrate; Bristamox; Delacillin; Amoxiden; Amoxivet; Anemolin; Aspenil; Cemoxin; Efpenix; Piramox; Vetramox; Amoxi; Sumox; (2S,5R,6R)-6-{[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; Amoxi-Mast; Sawamox PM; Metafarma capsules; Metifarma capsules; (2S,5R,6R)-6-((R)-2-Amino-2-(4-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; Ospamox; Amopen; Amoxicillin, 96%; 9EM05410Q9; NSC-277174; Amoxicaps; D-2-Amino-2-(4-hydroxyphenyl)acetamidopenicillanic acid; BRL 2333; Apo-Amoxi; AMOX; DSSTox_CID_17044; DSSTox_RID_79299; DSSTox_GSID_37044; AX; AMOXICILLIN PEDIATRIC; amoxicillanyl; Amoxicillin (anhydrous); AMOXICILLINTRIHYDRATE; BLP 1410; D-(-)-alpha-Amino-p-hydroxybenzylpenicillin; Amoxicillin (TN); (2S,5R,6R)-6-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; SMR000058707; Amoxicillin (Amoxycillin); Ro 10-8756; HSDB 3204; EINECS 248-003-8; BL-P 1410; 6-(D-(-)-p-Hydroxy-alpha-aminobenzyl)penicillin; NSC 277174; amoxycilin; Amoxi-Inject; Amoxi-Tabs; NSC277174; notoginsenoside-fe; 6-(D-(-)-alpha-Amino-p-hydroxyphenylacetamido)penicillanic acid; NCGC00016797-02; NCGC00094586-01; Prestwick_713; CAS-26787-78-0; (-)-6-(2-Amino-2-(P-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo-(3.2.0)heptane-2-carboxylic acid; MFCD00056860; Prestwick0_000357; Prestwick1_000357; Prestwick2_000357; Prestwick3_000357; Epitope ID:114241; Epitope ID:116054; EC 248-003-8; SCHEMBL3427; CHEMBL1082; BSPBio_000453; MLS000028632; MLS002222248; SPBio_002374; BPBio1_000499; DTXSID3037044; CHEBI:53712; GTPL10895; HY-B0467A; HMS1569G15; HMS2096G15; HMS2231K23; HMS3259P17; HMS3713G15; ZINC3830215; Tox21_111302; BDBM50350464; s3015; AKOS025395540; Tox21_111302_1; CCG-220357; DB01060; DS-3835; MCULE-5710225015; NC00670; NE41275; 6beta-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-2,2-dimethylpenam-3alpha-carboxylic acid; NCGC00179554-01; 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((2R)-amino(4-hydroxyphenyl)acetyl)amino)-3,3-dimethyl-7-oxo-, (2S,5R,6R)-; 4-Thia-1-azobicyclo(3.2.0)heptane-2-carboxylic acid, 6-((amino(4-hydroxyphenyl)acetyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta(S)))-; AC-12263; Amoxicillin, potency: >=900 mug per mg; co-amoxiclav (amoxicillin + clavulanic acid); C06827; D07452; Q201928; SR-01000721886; SR-01000721886-2; BRD-K55044200-001-03-9; BRD-K55044200-001-15-3; 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(2-amino-2-(p-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-, D- (8CI); 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[amino (4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-, [2S-[2.alpha.,5.alpha.,6.beta.(S*)]]-
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Molecular Type
Small molecule
Disease Bacterial infection [ICD-11: 1A00-1C4Z] Approved [1]
Structure
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2D MOL

3D MOL

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Formula
C16H19N3O5S
PubChem CID
33613
Canonical SMILES
CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=C(C=C3)O)N)C(=O)O)C
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
InChIKey
LSQZJLSUYDQPKJ-NJBDSQKTSA-N
CAS Number
CAS 26787-78-0
ChEBI ID
CHEBI:2676
TTD Drug ID
D0F6EO
DrugBank ID
DB01060
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Clavulanate      Streptomyces clavuligerus     Click to Show/Hide the Molecular Data of This NP
                 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.
          1,8-cineole + Clavulanate     Click to Show/Hide the Molecular Data of This NP
                 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.
          Mupirocin + Clavulanate     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Staphylococcus aureus Microorganism model Staphylococcus aureus
                    Experimental
                    Result(s)		 Mupirocin and amoxicillin-clavulanate were synergistic against 9 of 49 (18%) strains of methicillin-resistant and methicillin-susceptible Staphylococcus aureus and coagulase-negative staphylococci (CNS).
Target and Pathway
Target(s) Bacterial Cell membrane (Bact CM)  Molecule Info  [5]
References
Reference 1 Emerging therapies for the treatment and prevention of otitis media. Expert Opin Emerg Drugs. 2006 May;11(2):251-64.
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 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
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