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*)]]-
    Click to Show/Hide
Molecular Type
Small molecule
Disease Bacterial infection [ICD-11: 1A00-1C4Z] Approved [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absorption AUC
The area under the plot of plasma concentration (AUC) of drug is 27.29 +/- 4.72 mgh/L
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 3.93 +/- 1.13 mg/L
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 1.31 +/- 0.33 h
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability
Bioavailability
The bioavailability of drug is 60%
Clearance
The clearance of drug is 21.3 L/h
Elimination
125mg to 1g doses are 70-78% eliminated in the urine after 6 hours
Half-life
The concentration or amount of drug in body reduced by one-half in 61.3 minutes
Metabolism
The drug is metabolized via the liver
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 68.41612 micromolar/kg/day
Unbound Fraction
The unbound fraction of drug in plasma is 0.85%
Vd
The volume of distribution (Vd) of drug is 27.7 L
Water Solubility
The ability of drug to dissolve in water is measured as 3.5 mg/mL
    Click to Show/Hide
    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
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.
 Download Picture         KEGG Link      
 Download Picture         KEGG Link