General Information of Drug (ID: DR0104)
Drug Name
Amoxicillin
Synonyms
Amoclen; Amolin; Amopen; Amopenixin; Amoxi-Mast; Amoxicilina; Amoxicillin anhydrous; Amoxicilline; Amoxicilline [INN-French]; Amoxicillinum; Amoxicillinum [INN-Latin]; Amoxiden; Amoxil; Amoxivet; Amoxycillin; Anemolin; Aspenil; Bristamox; Cemoxin; Clamoxyl; D-Amoxicillin; Delacillin; DisperMox; Efpenix; Flemoxin; Hiconcil; Histocillin; Ibiamox; Imacillin; Metafarma capsules; Metifarma capsules; Moxacin; Ospamox; Piramox; Robamox; Sawamox PM; Unicillin; Utimox; Vetramox; amoxicillin; p-Hydroxyampicillin; 26787-78-0; AMPC; Amoxi; Moxal; Sumox; Wymox
Indication Acute otitis media [ICD11: AB00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 365.4 Topological Polar Surface Area 158
Heavy Atom Count 25 Rotatable Bond Count 4
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
33613
PubChem SID
9045 ; 625395 ; 855939 ; 7978697 ; 8173210 ; 10321668 ; 11466385 ; 11467505 ; 11486110 ; 14803689 ; 14852747 ; 34675405 ; 46507578 ; 47277019 ; 47500930 ; 48020429 ; 48244812 ; 49698452 ; 50050650 ; 50124271 ; 51091783 ; 56310905 ; 56312972 ; 56464141 ; 57288747 ; 57311544 ; 75691305 ; 85148361 ; 85787504 ; 92125419 ; 92711519 ; 96099939 ; 103296891 ; 103914155 ; 104170168 ; 104178892 ; 104316487 ; 119525230 ; 121362635 ; 121363090 ; 124766400 ; 124799877 ; 126630772 ; 126657267 ; 134337739 ; 134997708 ; 135769296 ; 136357150 ; 137002906 ; 139157548
ChEBI ID
ChEBI:2676
CAS Number
26787-78-0
TTD Drug ID
D0F6EO
Formula
C16H19N3O5S
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Amoxicillin metabolite M1 DM001354 N. A. Oxidation - Hydroxylation 1 [23]
Amoxicillin metabolite M2 DM001355 N. A. Oxidation - Oxidative Deamination 1 [23]
Amoxicillin metabolite M3 DM001351 N. A. Oxidation - Oxidation 1 [23]
Amoxicillin metabolite M6 DM001356
156531442
Oxidation - Oxidative Decarboxylation 1 [23]
Amoxicillin metabolite M7 DM001357 N. A. Conjugation - O-Glucuronidation 1 [23]
Amoxicillin metabolite M8 DM001358 N. A. Oxidation - Oxidative Deamination 1 [23]
Amoxicillin metabolite M4 DM001352 N. A. Oxidation - Oxidation 2 [24]
Amoxicillin metabolite M5 DM001353 N. A. Oxidation - Oxidation 3 [24]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000211 Amoxicillin Amoxicillin metabolite M3 Oxidation - Oxidation Unclear [23]
MR000212 Amoxicillin Amoxicillin metabolite M1 Oxidation - Hydroxylation Unclear [23]
MR000213 Amoxicillin Amoxicillin metabolite M2 Oxidation - Oxidative Deamination Unclear [23]
MR000214 Amoxicillin Amoxicillin metabolite M6 Oxidation - Oxidative Decarboxylation Unclear [23]
MR000215 Amoxicillin Amoxicillin metabolite M7 Conjugation - O-Glucuronidation Unclear [23]
MR000216 Amoxicillin Amoxicillin metabolite M8 Oxidation - Oxidative Deamination Unclear [23]
MR000209 Amoxicillin metabolite M3 Amoxicillin metabolite M4 Oxidation - Oxidation Unclear [24]
MR000210 Amoxicillin metabolite M4 Amoxicillin metabolite M5 Oxidation - Oxidation Unclear [24]
⏷ Show the Full List of 8 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Beta-lactamase (blaB) DME1020 Acidaminococcus fermentans
Q9XBM2_ACIFE
3.5.2.6
[2]
Beta-lactamase (blaB) DME1094 Citrobacter freundii
AMPC_CITFR
3.5.2.6
[3]
Beta-lactamase (blaB) DME1314 Photorhabdus asymbiotica
B6VMJ3_PHOAA
3.5.2.6
[4] , [5]
Beta-lactamase (blaB) DME1300 Capnocytophaga ochracea
O32372_CAPOC
3.5.2.6
[6]
Beta-lactamase (blaB) DME1319 Bacteroides intestinalis
A0A412YFL9_9BACE
3.5.2.6
[7]
Beta-lactamase (blaB) DME1880 Klebsiella aerogenes
BLA1_KLEPN
3.5.2.6
[8]
Beta-lactamase (blaB) DME1013 Pseudoflavonifractor capillosus
A6NX15_9FIRM
3.5.2.6
[9]
Beta-lactamase (blaB) DME1014 Acidaminococcus intestini
C0W968_9FIRM
3.5.2.6
[10]
Beta-lactamase (blaB) DME1015 Fusobacterium mortiferum
C3WC84_FUSMR
3.5.2.6
[11] , [12]
Beta-lactamase (blaB) DME1017 Odoribacter splanchnicus
F9Z530_ODOSD
3.5.2.6
[11] , [12]
Beta-lactamase (blaB) DME1225 Fusobacterium varium
C6JIU1_FUSVA
3.5.2.6
[11]
Beta-lactamase (blaB) DME1230 Prevotella nigrescens
A0A246EJV2_9BACT
3.5.2.6
[13] , [3]
Beta-lactamase (blaB) DME1308 Prevotella veroralis
C9MN73_9BACT
3.5.2.6
[3]
Beta-lactamase (blaB) DME1309 Alloprevotella tannerae
C9LD75_9BACT
3.5.2.6
[13]
Beta-lactamase (blaB) DME1310 Capnocytophaga gingivalis
C2M7J0_CAPGI
3.5.2.6
[6]
Beta-lactamase (blaB) DME1326 Capnocytophaga granulosa
A0A381DV31_9FLAO
3.5.2.6
[6]
Beta-lactamase (blaB) DME1334 Capnocytophaga sputigena
A0A2A3N1K0_CAPSP
3.5.2.6
[6]
Beta-lactamase (blaB) DME1335 Capnocytophaga leadbetteri
A0A250F962_9FLAO
3.5.2.6
[6]
Beta-lactamase (blaB) DME1354 Prevotella loescheii
A0A069QS91_PRELO
3.5.2.6
[3]
Beta-lactamase (blaB) DME1318 Bacteroides dorei
A0A413GBG0_9BACE
3.5.2.6
[7]
Beta-lactamase (blaB) DME1298 Shigella sonnei
Q2F4C6_SHISO
3.5.2.6
[14]
Beta-lactamase (blaB) DME1921 Prevotella copri
A0A2T4TNV5_9BACT
3.5.2.6
[15]
Beta-lactamase (blaB) DME1026 Bacteroides uniformis
BLAC_BACUN
3.5.2.6
[7]
Beta-lactamase (blaB) DME1095 Bacteroides fragilis
BLAB_BACFG
3.5.2.6
[7]
Beta-lactamase (blaB) DME1012 Bacteroides eggerthii
A0A414M273_9BACE
3.5.2.6
[16]
Beta-lactamase (blaB) DME1215 Bacteroides caccae
A0A4Q5I6I2_9BACE
3.5.2.6
[7]
Beta-lactamase (blaB) DME1216 Parabacteroides distasonis
B5WXV2_9BACT
3.5.2.6
[17]
Beta-lactamase (blaB) DME1218 Bacteroides ovatus
B5WXV3_BACOV
3.5.2.6
[7]
Beta-lactamase (blaB) DME1219 Bacteroides thetaiotaomicron
B5WXV7_BACT4
3.5.2.6
[7]
Beta-lactamase (blaB) DME1220 Bacteroides vulgatus
BLAC_BACVU
3.5.2.6
[7] , [18]
Beta-lactamase (blaB) DME1221 Capnocytophaga haemolytica
A0A2S0LB67_9FLAO
3.5.2.6
[3]
Beta-lactamase (blaB) DME1329 Prevotella denticola
A0A347B2J2_9BACT
3.5.2.6
[3]
Beta-lactamase (blaB) DME1016 Prevotella melaninogenica
Q8KT52_9BACT
3.5.2.6
[3] , [19]
Beta-lactamase (blaB) DME1018 Prevotella oralis
Q8KT51_9BACT
3.5.2.6
[11] , [12]
Beta-lactamase (blaB) DME1019 Prevotella bivia
Q8KT60_9BACT
3.5.2.6
[11] , [12]
Beta-lactamase (blaB) DME1229 Prevotella intermedia
Q9X4S7_PREIN
3.5.2.6
[13]
Beta-lactamase (blaB) DME1295 Prevotella buccae
Q8KT59_9BACT
3.5.2.6
[3]
Beta-lactamase (blaB) DME1485 Peptostreptococcus anaerobius
A0A095XPV0_9FIRM
3.5.2.6
[3]
Beta-lactamase (blaB) DME1227 Neisseria sicca
A0A1S1G219_9NEIS
3.5.2.6
[3]
Beta-lactamase (blaB) DME1347 Bacteroides stercoris
A0A120A1C6_BACSE
3.5.2.6
[7]
Beta-lactamase (blaB) DME1348 Bacteroides cellulosilyticus
A0A108T9G3_9BACE
3.5.2.6
[7]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[20]
Metallo-beta-lactamase (blaM) DME1881 Klebsiella pneumoniae
BLAN1_KLEPN
3.5.2.6
[8]
Metallo-beta-lactamase (blaM) DME1296 Achromobacter xylosoxidans
Q68K11_ALCXX
3.5.2.6
[8]
N-acylhomoserine lactone acylase (lacA) DME1021 Acidovorax ebreus
A0A0A1VBK6_9BURK
3.5.1.97
[21]
New delhi metallo-beta-lactamase NDM-1 (blaNDM) DME1732 Salmonella enterica
A0A345N7K5_SALET
3.5.2.6
[22]
⏷ Show the Full List of 46  DME(s)
References
1 Pantoprazole Sodium was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 ACI-1 from Acidaminococcus fermentans: characterization of the first beta-lactamase in Anaerobic cocci. Antimicrob Agents Chemother. 2000 Nov;44(11):3144-9.
3 Detection and characterization of beta-lactamase genes in subgingival bacteria from patients with refractory periodontitis. FEMS Microbiol Lett. 2005 Jan 15;242(2):319-24.
4 Yersinia enterocolitica and Photorhabdus asymbiotica beta-lactamases BlaA are exported by the twin-arginine translocation pathway. Int J Med Microbiol. 2013 Jan;303(1):16-24.
5 Xenorhabdus luminescens (DNA hybridization group 5) from human clinical specimens. J Clin Microbiol. 1989 Jul;27(7):1594-600. Case Reports
6 High prevalence of beta-lactam and macrolide resistance genes in human oral Capnocytophaga species. J Antimicrob Chemother. 2014 Feb;69(2):381-4.
7 Prevalence of antimicrobial resistance genes in Bacteroides spp. and Prevotella spp. Dutch clinical isolates. Clin Microbiol Infect. 2019 Sep;25(9):1156.e9-1156.e13.
8 Interspecies dissemination of a mobilizable plasmid harboring blaIMP-19 and the possibility of horizontal gene transfer in a single patient. Antimicrob Agents Chemother. 2016 Aug 22;60(9):5412-9.
9 The prevalence of beta-lactamase producing bacteria in subgingival plaque and their sensitivity to Augmentin. Br J Oral Maxillofac Surg. 1990 Jun;28(3):180-4.
10 ACI-1 beta-lactamase is widespread across human gut microbiomes in Negativicutes due to transposons harboured by tailed prophages. Environ Microbiol. 2018 Jun;20(6):2288-2300.
11 Beta-lactamase production and susceptibilities to amoxicillin, amoxicillin-clavulanate, ticarcillin, ticarcillin-clavulanate, cefoxitin, imipenem, and metronidazole of 320 non-Bacteroides fragilis Bacteroides isolates and 129 fusobacteria from 28 U.S. centers. Antimicrob Agents Chemother. 1990 Aug;34(8):1546-50.
12 Effect of CO2 on susceptibilities of anaerobes to erythromycin, azithromycin, clarithromycin, and roxithromycin. Antimicrob Agents Chemother. 1994 Feb;38(2):211-6.
13 Prevotella strains and lactamic resistance gene distribution in different oral environments of children with pulp necrosis. Int Endod J. 2018 Nov;51(11):1196-1204.
14 IncU plasmid harbouring bla CTX-M-8 in multidrug-resistant Shigella sonnei in Brazil. J Glob Antimicrob Resist. 2018 Sep;14:99-100.
15 High prevalence of cfxA beta-lactamase in aminopenicillin-resistant Prevotella strains isolated from periodontal pockets. Oral Microbiol Immunol. 2002 Apr;17(2):85-8.
16 Major phenylpropanoid-derived metabolites in the human gut can arise from microbial fermentation of protein. Mol Nutr Food Res. 2013 Mar;57(3):523-35.
17 Presence of the cfxA gene in Bacteroides distasonis. Res Microbiol. 2003 Jun;154(5):369-74.
18 Beta-lactamase production, beta-lactam sensitivity and resistance to synergy with clavulanate of 737 Bacteroides fragilis group organisms from thirty-three US centres. J Antimicrob Chemother. 1990 Sep;26(3):361-70.
19 Antimicrobial drugs used in the management of anaerobic infections in children. Drugs. 1983 Dec;26(6):520-9.
20 High-dose rabeprazole/amoxicillin therapy as the second-line regimen after failure to eradicate H. pylori by triple therapy with the usual doses of a proton pump inhibitor, clarithromycin and amoxicillin. Hepatogastroenterology. 2003 Nov-Dec;50(54):2274-8.
21 A novel quorum-quenching N-acylhomoserine lactone acylase from Acidovorax sp. strain MR-S7 mediates antibiotic resistance. Appl Environ Microbiol. 2017 Jun 16;83(13). pii: e00080-17.
22 Genomic characterization of an extensively-drug resistance Salmonella enterica serotype Indiana strain harboring bla NDM-1 gene isolated from a chicken carcass in China. Microbiol Res. 2017 Nov;204:48-54.
23 Identification of In Vitro Metabolites of Amoxicillin in Human Liver Microsomes by LC-ESI/MS Chromatographia. 2014;77(15):1027-1035. doi: 10.1007/s10337-014-2648-2.
24 DrugBank(Pharmacology-Metabolism)Amoxicillin

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