Amoxicillin sodium

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H18N3O5S.Na
Molecular Weight	387.386
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)C3=CC=C(O)C=C3)C(=O)N2[C@H]1C([O-])=O

InChI

InChIKey=BYHDFCISJXIVBV-YWUHCJSESA-M

InChI=1S/C16H19N3O5S.Na/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);/q;+1/p-1/t9-,10-,11+,14-;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C16H18N3O5S
Molecular Weight	364.396
Charge	-1
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	Na
Molecular Weight	22.98976928
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/050542s026s027s028,050754s013s014s017,050760s012s013s015,050761s012s013s015lbl.pdf

Amoxicillin is one of the widely prescribed antibacterial agents, which was discovered by scientists at Beecham Research Laboratories in 1972. In the US GlaxoSmithKline markets it under the original brand name Amoxil. It is the first line treatment for middle ear infections. It is also used for strep throat, pneumonia, skin infections, and urinary tract infections it is taken by mouth. Amoxicillin inhibits the third and final stage of bacterial cell wall synthesis by preferentially binding to specific penicillin-binding proteins (PBPs) that are located inside the bacterial cell wall. This results in a formation of defective cell wall and a cell death. Common side effects include nausea and rash. It may also increase the risk of yeast infections and, when used in combination with clavulanic acid, diarrhea. It should not be used in those who are allergic to penicillin.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 234 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12461003	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Infections of the ear, nose, and throat 5 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/050542s026s027s028,050754s013s014s017,050760s012s013s015,050761s012s013s015lbl.pdf	Curative	Approved 8583	AMOXIL Approved Use AMOXICILLIN is indicated in the treatment of infections due to susceptible (ONLY β-lactamase–negative) strains of the designated microorganisms in the conditions listed below: Infections of the ear, nose and throat - due to Streptococcus spp. (α- and β-hemolytic strains only), S. pneumoniae, Staphylococcus spp., or H. influenzae. Infections of the genitourinary tract - due to E. coli, P. mirabilis, or E. faecalis. Infections of the skin and skin structure - due to Streptococcus spp. (α- and β-hemolytic strains only), Staphylococcus spp., or E. coli. Infections of the lower respiratory tract - due to Streptococcus spp. (α- and β-hemolytic strains only), S. pneumoniae, Staphylococcus spp., or H. influenzae. Gonorrhea, acute uncomplicated (ano-genital and urethral infections) - due to N. gonorrhoeae (males and females). H. pylori eradication to reduce the risk of duodenal ulcer recurrence Triple Therapy: AMOXICILLIN/clarithromycin/lansoprazole AMOXICILLIN, in combination with clarithromycin plus lansoprazole as triple therapy, is indicated for the treatment of patients with H.pylori infection and duodenal ulcer disease (active or 1-year history of a duodenal ulcer) to eradiate H. pylori. Eradication of H. pylori has been shown to reduce the risk of duodenal ulcer recurrence. (See CLINICAL STUDIES and DOSAGE AND ADMINISTRATION.) Dual Therapy: AMOXICILLIN/lansoprazole AMOXICILLIN, in combination with lansoprazole delayed-release capsules as dual therapy, is indicated for the treatment of patients with H.pylori infection and duodenal ulcer disease (active or 1-year history of a duodenal ulcer) who are either allergic or intolerant to clarithromycin or in whom resistance to clarithromycin is known or suspected. (See the clarithromycin package insert, MICROBIOLOGY.) Eradication of H.pylori has been shown to reduce the risk of duodenal ulcer recurrence. (See CLINICAL STUDIES and DOSAGE AND ADMINISTRATION.) To reduce the development of drug-resistant bacteria and maintain the effectiveness of AMOXICILLIN and other antibacterial drugs, AMOXICILLIN should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Indicated surgical procedures should be performed. Launch Date 1980
Infections of the genitourinary tract 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/050542s026s027s028,050754s013s014s017,050760s012s013s015,050761s012s013s015lbl.pdf	Curative	Approved 8583	AMOXIL Approved Use AMOXICILLIN is indicated in the treatment of infections due to susceptible (ONLY β-lactamase–negative) strains of the designated microorganisms in the conditions listed below: Infections of the ear, nose and throat - due to Streptococcus spp. (α- and β-hemolytic strains only), S. pneumoniae, Staphylococcus spp., or H. influenzae. Infections of the genitourinary tract - due to E. coli, P. mirabilis, or E. faecalis. Infections of the skin and skin structure - due to Streptococcus spp. (α- and β-hemolytic strains only), Staphylococcus spp., or E. coli. Infections of the lower respiratory tract - due to Streptococcus spp. (α- and β-hemolytic strains only), S. pneumoniae, Staphylococcus spp., or H. influenzae. Gonorrhea, acute uncomplicated (ano-genital and urethral infections) - due to N. gonorrhoeae (males and females). H. pylori eradication to reduce the risk of duodenal ulcer recurrence Triple Therapy: AMOXICILLIN/clarithromycin/lansoprazole AMOXICILLIN, in combination with clarithromycin plus lansoprazole as triple therapy, is indicated for the treatment of patients with H.pylori infection and duodenal ulcer disease (active or 1-year history of a duodenal ulcer) to eradiate H. pylori. Eradication of H. pylori has been shown to reduce the risk of duodenal ulcer recurrence. (See CLINICAL STUDIES and DOSAGE AND ADMINISTRATION.) Dual Therapy: AMOXICILLIN/lansoprazole AMOXICILLIN, in combination with lansoprazole delayed-release capsules as dual therapy, is indicated for the treatment of patients with H.pylori infection and duodenal ulcer disease (active or 1-year history of a duodenal ulcer) who are either allergic or intolerant to clarithromycin or in whom resistance to clarithromycin is known or suspected. (See the clarithromycin package insert, MICROBIOLOGY.) Eradication of H.pylori has been shown to reduce the risk of duodenal ulcer recurrence. (See CLINICAL STUDIES and DOSAGE AND ADMINISTRATION.) To reduce the development of drug-resistant bacteria and maintain the effectiveness of AMOXICILLIN and other antibacterial drugs, AMOXICILLIN should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Indicated surgical procedures should be performed. Launch Date 1980
Skin and skin structure infections 81 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/050542s026s027s028,050754s013s014s017,050760s012s013s015,050761s012s013s015lbl.pdf	Curative	Approved 8583	AMOXIL Approved Use AMOXICILLIN is indicated in the treatment of infections due to susceptible (ONLY β-lactamase–negative) strains of the designated microorganisms in the conditions listed below: Infections of the ear, nose and throat - due to Streptococcus spp. (α- and β-hemolytic strains only), S. pneumoniae, Staphylococcus spp., or H. influenzae. Infections of the genitourinary tract - due to E. coli, P. mirabilis, or E. faecalis. Infections of the skin and skin structure - due to Streptococcus spp. (α- and β-hemolytic strains only), Staphylococcus spp., or E. coli. Infections of the lower respiratory tract - due to Streptococcus spp. (α- and β-hemolytic strains only), S. pneumoniae, Staphylococcus spp., or H. influenzae. Gonorrhea, acute uncomplicated (ano-genital and urethral infections) - due to N. gonorrhoeae (males and females). H. pylori eradication to reduce the risk of duodenal ulcer recurrence Triple Therapy: AMOXICILLIN/clarithromycin/lansoprazole AMOXICILLIN, in combination with clarithromycin plus lansoprazole as triple therapy, is indicated for the treatment of patients with H.pylori infection and duodenal ulcer disease (active or 1-year history of a duodenal ulcer) to eradiate H. pylori. Eradication of H. pylori has been shown to reduce the risk of duodenal ulcer recurrence. (See CLINICAL STUDIES and DOSAGE AND ADMINISTRATION.) Dual Therapy: AMOXICILLIN/lansoprazole AMOXICILLIN, in combination with lansoprazole delayed-release capsules as dual therapy, is indicated for the treatment of patients with H.pylori infection and duodenal ulcer disease (active or 1-year history of a duodenal ulcer) who are either allergic or intolerant to clarithromycin or in whom resistance to clarithromycin is known or suspected. (See the clarithromycin package insert, MICROBIOLOGY.) Eradication of H.pylori has been shown to reduce the risk of duodenal ulcer recurrence. (See CLINICAL STUDIES and DOSAGE AND ADMINISTRATION.) To reduce the development of drug-resistant bacteria and maintain the effectiveness of AMOXICILLIN and other antibacterial drugs, AMOXICILLIN should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Indicated surgical procedures should be performed. Launch Date 1980
Gonorrhea, acute uncomplicated 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/050542s026s027s028,050754s013s014s017,050760s012s013s015,050761s012s013s015lbl.pdf	Curative	Approved 8583	AMOXIL Approved Use AMOXICILLIN is indicated in the treatment of infections due to susceptible (ONLY β-lactamase–negative) strains of the designated microorganisms in the conditions listed below: Infections of the ear, nose and throat - due to Streptococcus spp. (α- and β-hemolytic strains only), S. pneumoniae, Staphylococcus spp., or H. influenzae. Infections of the genitourinary tract - due to E. coli, P. mirabilis, or E. faecalis. Infections of the skin and skin structure - due to Streptococcus spp. (α- and β-hemolytic strains only), Staphylococcus spp., or E. coli. Infections of the lower respiratory tract - due to Streptococcus spp. (α- and β-hemolytic strains only), S. pneumoniae, Staphylococcus spp., or H. influenzae. Gonorrhea, acute uncomplicated (ano-genital and urethral infections) - due to N. gonorrhoeae (males and females). H. pylori eradication to reduce the risk of duodenal ulcer recurrence Triple Therapy: AMOXICILLIN/clarithromycin/lansoprazole AMOXICILLIN, in combination with clarithromycin plus lansoprazole as triple therapy, is indicated for the treatment of patients with H.pylori infection and duodenal ulcer disease (active or 1-year history of a duodenal ulcer) to eradiate H. pylori. Eradication of H. pylori has been shown to reduce the risk of duodenal ulcer recurrence. (See CLINICAL STUDIES and DOSAGE AND ADMINISTRATION.) Dual Therapy: AMOXICILLIN/lansoprazole AMOXICILLIN, in combination with lansoprazole delayed-release capsules as dual therapy, is indicated for the treatment of patients with H.pylori infection and duodenal ulcer disease (active or 1-year history of a duodenal ulcer) who are either allergic or intolerant to clarithromycin or in whom resistance to clarithromycin is known or suspected. (See the clarithromycin package insert, MICROBIOLOGY.) Eradication of H.pylori has been shown to reduce the risk of duodenal ulcer recurrence. (See CLINICAL STUDIES and DOSAGE AND ADMINISTRATION.) To reduce the development of drug-resistant bacteria and maintain the effectiveness of AMOXICILLIN and other antibacterial drugs, AMOXICILLIN should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Indicated surgical procedures should be performed. Launch Date 1980
Helicobacter pylori infection and duodenal ulcer disease 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/050542s026s027s028,050754s013s014s017,050760s012s013s015,050761s012s013s015lbl.pdf	Curative	Approved 8583	AMOXIL Approved Use AMOXICILLIN is indicated in the treatment of infections due to susceptible (ONLY β-lactamase–negative) strains of the designated microorganisms in the conditions listed below: Infections of the ear, nose and throat - due to Streptococcus spp. (α- and β-hemolytic strains only), S. pneumoniae, Staphylococcus spp., or H. influenzae. Infections of the genitourinary tract - due to E. coli, P. mirabilis, or E. faecalis. Infections of the skin and skin structure - due to Streptococcus spp. (α- and β-hemolytic strains only), Staphylococcus spp., or E. coli. Infections of the lower respiratory tract - due to Streptococcus spp. (α- and β-hemolytic strains only), S. pneumoniae, Staphylococcus spp., or H. influenzae. Gonorrhea, acute uncomplicated (ano-genital and urethral infections) - due to N. gonorrhoeae (males and females). H. pylori eradication to reduce the risk of duodenal ulcer recurrence Triple Therapy: AMOXICILLIN/clarithromycin/lansoprazole AMOXICILLIN, in combination with clarithromycin plus lansoprazole as triple therapy, is indicated for the treatment of patients with H.pylori infection and duodenal ulcer disease (active or 1-year history of a duodenal ulcer) to eradiate H. pylori. Eradication of H. pylori has been shown to reduce the risk of duodenal ulcer recurrence. (See CLINICAL STUDIES and DOSAGE AND ADMINISTRATION.) Dual Therapy: AMOXICILLIN/lansoprazole AMOXICILLIN, in combination with lansoprazole delayed-release capsules as dual therapy, is indicated for the treatment of patients with H.pylori infection and duodenal ulcer disease (active or 1-year history of a duodenal ulcer) who are either allergic or intolerant to clarithromycin or in whom resistance to clarithromycin is known or suspected. (See the clarithromycin package insert, MICROBIOLOGY.) Eradication of H.pylori has been shown to reduce the risk of duodenal ulcer recurrence. (See CLINICAL STUDIES and DOSAGE AND ADMINISTRATION.) To reduce the development of drug-resistant bacteria and maintain the effectiveness of AMOXICILLIN and other antibacterial drugs, AMOXICILLIN should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Indicated surgical procedures should be performed. Launch Date 1980

C_max

Value	Dose	Co-administered	Analyte	Population
11.8 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/836010/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:		AMOXICILLIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
37.6 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/836010/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:		AMOXICILLIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
0.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/836010/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:		AMOXICILLIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
775 mg 1 times / day steady, oral Dose: 775 mg, 1 times / day Route: oral Route: steady Dose: 775 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/050813s000medr.pdf	unhealthy, > 12 years Health Status: unhealthy Age Group: > 12 years Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/050813s000medr.pdf	Disc. AE: Pharyngolaryngeal pain... Other AEs: Nausea, Pharyngotonsillitis... AEs leading to discontinuation/dose reduction: Pharyngolaryngeal pain (severe, 0.6%) Other AEs: Nausea (1.5%) Pharyngotonsillitis (0.9%) Vulvovaginal candidiasis (0.9%) Headache (0.7%) Diarrhea (0.5%) Abdominal pain (0.5%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/050813s000medr.pdf

AEs

AE	Significance	Dose	Population
Abdominal pain	0.5%	775 mg 1 times / day steady, oral Dose: 775 mg, 1 times / day Route: oral Route: steady Dose: 775 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/050813s000medr.pdf	unhealthy, > 12 years Health Status: unhealthy Age Group: > 12 years Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/050813s000medr.pdf
Diarrhea	0.5%	775 mg 1 times / day steady, oral Dose: 775 mg, 1 times / day Route: oral Route: steady Dose: 775 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/050813s000medr.pdf	unhealthy, > 12 years Health Status: unhealthy Age Group: > 12 years Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/050813s000medr.pdf
Headache	0.7%	775 mg 1 times / day steady, oral Dose: 775 mg, 1 times / day Route: oral Route: steady Dose: 775 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/050813s000medr.pdf	unhealthy, > 12 years Health Status: unhealthy Age Group: > 12 years Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/050813s000medr.pdf
Pharyngotonsillitis	0.9%	775 mg 1 times / day steady, oral Dose: 775 mg, 1 times / day Route: oral Route: steady Dose: 775 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/050813s000medr.pdf	unhealthy, > 12 years Health Status: unhealthy Age Group: > 12 years Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/050813s000medr.pdf
Vulvovaginal candidiasis	0.9%	775 mg 1 times / day steady, oral Dose: 775 mg, 1 times / day Route: oral Route: steady Dose: 775 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/050813s000medr.pdf	unhealthy, > 12 years Health Status: unhealthy Age Group: > 12 years Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/050813s000medr.pdf
Nausea	1.5%	775 mg 1 times / day steady, oral Dose: 775 mg, 1 times / day Route: oral Route: steady Dose: 775 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/050813s000medr.pdf	unhealthy, > 12 years Health Status: unhealthy Age Group: > 12 years Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/050813s000medr.pdf
Pharyngolaryngeal pain	severe, 0.6% Disc. AE	775 mg 1 times / day steady, oral Dose: 775 mg, 1 times / day Route: oral Route: steady Dose: 775 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/050813s000medr.pdf	unhealthy, > 12 years Health Status: unhealthy Age Group: > 12 years Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/050813s000medr.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP3A5 136 CYP2C8 1057 BSEP 550 CYP2A6 879 PEPT1 27 PEPT2 13 OAT1 725 CYP2C19 2057 MRP2 499 P-gp 1741 OATP1B1 1079 CYP2J2 33 CYP2E1 1060 BCRP 910 OATP1B3 961 MRP3 246 CYP19A1 429 CYP1A2 2153 OATP2B1 157 ABCB6 3 MRP4 290	OCT2 434 chicken BCRP 3 OAT1 395 chicken P-gp 3 OAT3 391 PEPT1 60 OATP1B1 503 PEPT2 37 OATP2B1 122 OATP1B3 435 OCT1 393

Drug as perpetrator

Target	Modality	Activity
CYP2J2 36	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1210069#sid=103296891	inconclusive [IC50 50 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/625245#sid=103296891	no [IC50 >10 uM]
CYP2A6 911	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/625246#sid=103296891	no [IC50 >10 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/625247#sid=103296891	no [IC50 >10 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/625250#sid=103296891	no [IC50 >10 uM]
BSEP 554	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP2 625	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP3 326	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP4 345	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
ABCB6 3	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/602162#sid=855939	no
BCRP 985	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1325#sid=855939	no
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/743139#sid=144204855	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26763401/	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26763401/	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26763401/	no
CYP3A5 201	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26763401/	no
P-gp 1932	activator 342 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/799#sid=855939	no
P-gp 1932	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1325#sid=855939	no
OAT1 730	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16434549/	unlikely [Ki 11000 uM]
PEPT1 29	inhibitor 4027	unlikely [Ki 66200 uM]
PEPT2 17	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16434549/	unlikely [Ki 733 uM]
CYP2C8 1117	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26763401/	yes [IC50 0.83 uM]
OATP1B3 970	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26976869/	yes [IC50 28.9 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26976869/	yes [IC50 36.2 uM]
OATP2B1 162	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26976869/	yes [IC50 56.6 uM]

Drug as victim

Target	Modality	Activity
OATP1B1 503	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/30012768/	likely
OCT1 393	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/30012768/	likely
OCT2 434	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/30012768/	likely
OAT1 395	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/30012768/	no
OATP1B3 435	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/30012768/	no
OATP2B1 122	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/30012768/	no
chicken BCRP 3	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/29725709/	no
chicken P-gp 3	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/29725709/	no
PEPT2 37	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16434549/	yes [Km 1040 uM]
OAT3 391	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/30012768/	yes [Km 161.4 uM]
PEPT1 60	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16434549/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/20064605/

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-0028	http://www.3bsc.com/index/pro_info.php?id=19384
Aaron Chemicals	AR006UMZ	http://www.aaronchem.com/26787-78-0
abcr GmbH	AB439985	http://www.abcr.com/shop/en/AB439985
AbMole Bioscience	M4095	http://www.abmole.com/products/notoginsenoside-fe.html
Achemtek	0104-023910	http://www.achemtek.com/26787-78-0
Acorn PharmaTech	ACN-044355	http://www.acornpharmatech.com/
Acros Organics	AC455140010	https://www.fishersci.com/shop/products/amoxicillin-96-acros-organics-2/AC455140010
Acros Organics	AC455140050	https://www.fishersci.com/shop/products/amoxicillin-96-acros-organics-1/AC455140050
Acros Organics	AC455140250	https://www.fishersci.com/shop/products/amoxicillin-96-acros-organics/AC455140250
Alsachim	723	http://www.alsachim.com/product-C2651-glo.bal-view.html
Aurora Fine Chemicals LLC	A13.142.375	http://online.aurorafinechemicals.com/info?ID=A13.142.375
Aurum Pharmatech LLC	NE41275	http://www.Aurumpharmatech.com/Product/ProductDetails/NE41275
AvaChem Scientific	2773A	http://www.avachem.com/productSearch.asp?2773A
BioCrick	BCC4625	http://www.biocrick.com/Amoxicillin-BCC4625.html
BLD Pharm	BD233963	http://www.bldpharm.com/products/26787-78-0.html
Boerchem	BC204303	http://www.boerchem.com/?product_34374.html
Chem Scene	CS-2612	http://www.chemscene.com/26787-78-0.html
ChemMol	30102056	http://www.chemmol.com/chemmol/30102056.html
ChemMol	44001791	http://www.chemmol.com/chemmol/44001791.html
ChemMol	99055597	http://www.chemmol.com/chemmol/99055597.html
Chemspace	CSSB00000693552	https://chem-space.com/CSSB00000693552
CSNpharm	CSN13145	https://www.csnpharm.com/products/amoxicillin.html
eNovation Chemicals	D673782	https://www.enovationchem.com/ProductDetails.asp?ProductID=D673782
eNovation Chemicals	D764547	https://www.enovationchem.com/ProductDetails.asp?ProductID=D764547
eNovation Chemicals	D783616	https://www.enovationchem.com/ProductDetails.asp?ProductID=D783616
Hairui	HR130838	http://www.hairuichem.com/en/product/61336-70-7.html
iChemical	EBD2203797	http://www.ichemical.com/products/26787-78-0.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network	LN00239840	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00239840
mcule	MCULE-5710225015	https://mcule.com/MCULE-5710225015/
MedChem Express	HY-B0467A	https://www.medchemexpress.com/amoxicillin.html
Selleck Chemicals	S3015	http://www.selleckchem.com/products/amoxicillin-amoxycillin.html
Sigma-Aldrich	A8523_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/a8523?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S584747	https://www.smolecule.com/products/s584747
THE BioTek	bt-298733	https://www.thebiotek.com/product/others/bt-298733
Yuhao Chemical	LQ4576	http://www.chemyuhao.com/26787-78-0.html

PubMed

Title	Date	PubMed
Cefpodoxime proxetil: a review of its use in the management of bacterial infections in paediatric patients.	2001	11269640
Amoxicillin plus metronidazole in the treatment of adult periodontitis patients. A double-blind placebo-controlled study.	2001 Apr	11314884
Use of antibiotics to treat bacteriuria of pregnancy in the Nordic countries. Which antibiotics are appropriate to treat bacteriuria of pregnancy?	2001 Apr	11295409
A prospective observational study of 5-, 7-, and 10-day antibiotic treatment for acute otitis media.	2001 Apr	11283494
Use of the t > MIC to choose between different dosing regimens of beta-lactam antibiotics.	2001 Apr	11266433
Analysis of metronidazole, clarithromycin and tetracycline resistance of Helicobacter pylori isolates from Korea.	2001 Apr	11266421
Efficacy, safety and tolerability of 3 day azithromycin versus 10 day co-amoxiclav in the treatment of children with acute lower respiratory tract infections.	2001 Apr	11266417
Effects of lansoprazole, clarithromycin and pH gradient on uptake of [14C]amoxycillin into rat gastric tissue.	2001 Apr	11266411
Helicobacter eradication versus prompt endoscopy for dyspepsia.	2001 Apr	11266397
Simultaneous determination of five beta-lactam antibiotics in bovine milk using liquid chromatography coupled with electrospray ionization tandem mass spectrometry.	2001 Apr 1	11321318
Complete remission of primary high-grade B-cell gastric lymphoma after cure of Helicobacter pylori infection.	2001 Apr 1	11283137
Comparison of amoxicillin and azithromycin in the prevention of recurrent acute otitis media.	2001 Apr 6	11249979
[Eradication therapy of Helicobacter pylori infection].	2001 Feb	11307304
[The history of Helicobacter pylori].	2001 Feb	11307300
Management of brain stem abscess.	2001 Feb	11303665
Cefprozil versus high-dose amoxicillin/clavulanate in children with acute otitis media.	2001 Feb	11293553
Differentiation between reinfection and recrudescence of helicobacter pylori strains using PCR-based restriction fragment length polymorphism analysis.	2001 Feb	11293500
The effect of postsurgical antibiotics on the healing of intrabony defects following treatment with enamel matrix proteins.	2001 Feb	11288792
Spectrophotometric determination of ampicillin, dicluxacillin, flucloxacillin and amoxicillin antibiotic drugs: ion-pair formation with molybdenum and thiocyanate.	2001 Feb	11272312
Bioequivalence study of a novel Solutab tablet formulation of amoxicillin/clavulanic acid versus the originator film-coated tablet.	2001 Feb	11270805
Do some patients with Helicobacter pylori infection benefit from an extension to 2 weeks of a proton pump inhibitor-based triple eradication therapy?	2001 Feb	11232676
Comparison of the efficacy and safety of different formulations of omeprazole-based triple therapies in the treatment of Helicobacter pylori-positive peptic ulcer.	2001 Feb	11227677
Early stage gastric MALT lymphoma with high-grade component cured by Helicobacter pylori eradication.	2001 Feb	11227668
[Prevention of bacterial endocarditis in patients with prosthetic heart valves].	2001 Feb 15	11284424
Improved phagocyte response by co-amoxiclav in renal transplant recipients.	2001 Feb 27	11258440
Definite streptococcus bovis endocarditis: characteristics in 20 patients.	2001 Jan	11284936
[Multiresistant tuberculosis caused by Mycobacterium bovis and human immunodeficiency virus infection. Are there new therapeutic possibilities?].	2001 Jan	11256251
[Pneumococcal antibiotic resistance in 1999. Results from 19 registries for 1999].	2001 Jan	11242764
[Pneumococcal antibiotic resistance. Data from 6 regional registries for 1999].	2001 Jan	11242757
Meropenem in neonatal severe infections due to multiresistant gram-negative bacteria.	2001 Jan	11237230
A prospective study of antibiotic use and associated infections in young children.	2001 Jan	11237117
[Prevalence of Moraxella catarrhalis colonization in asymptomatic carriers under 6 years of age].	2001 Jan-Feb	11270281
Charm Safe-Level beta-Lactam Test for amoxicillin, ampicillin, ceftiofur, cephapirin, and penicillin G in raw commingled milk.	2001 Jan-Feb	11234843
[A prospective study on erysipelas and infectious cellulitis: how are they dealt within hospital?].	2001 Mar	11319360
Peptic ulcer occurrence in follow-up of chronic gastritis in patients with treated and not eradicated CagA-positive Helicobacter pylori infection.	2001 Mar	11318536
Standard case management of pneumonia in hospitalized children in Uruguay, 1997 to 1998.	2001 Mar	11303831
The effect of culture results for Helicobacter pylori on the choice of treatment following failure of initial eradication.	2001 Mar	11303370
Osseintegration following treatment of peri-implantitis and replacement of implant components. An experimental study in the dog.	2001 Mar	11284540
Antimicrobial susceptibility of Listeria monocytogenes isolated from meningoencephalitis in sheep.	2001 Mar	11282267
Lacrimal gland ductal cyst abscess.	2001 Mar	11281587
Screening method for identification of beta-lactams in bovine urine by use of liquid chromatography and a microbial inhibition test.	2001 Mar	11277195
A case of gastric plasmacytoma associated with Helicobacter pylori infection: improvement of abnormal endoscopic and EUS findings after H. pylori eradication.	2001 Mar	11231401
Tests for 2 x K contingency tables with clustered ordered categorical data.	2001 Mar 15	11241576
[Angina tonsillaris in children. Penicillin V can not be recommended here].	2001 Mar 22	11302079
Broad-spectrum antibiotics for spontaneous preterm labour: the ORACLE II randomised trial. ORACLE Collaborative Group.	2001 Mar 31	11293641
Broad-spectrum antibiotics for preterm, prelabour rupture of fetal membranes: the ORACLE I randomised trial. ORACLE Collaborative Group.	2001 Mar 31	11293640
Antibiotic resistance and antibiotic sensitivity based treatment in Helicobacter pylori infection: advantages and outcome.	2001 May	11316688
Simultaneous determination of amoxycillin and clavulanic acid in pharmaceutical dosage forms by LC with amperometric detection.	2001 May	11275440
Worldwide prevalence of antimicrobial resistance in Streptococcus pneumoniae, Haemophilus influenzae, and Moraxella catarrhalis in the SENTRY Antimicrobial Surveillance Program, 1997-1999.	2001 May 15	11320449
Prospective evaluation of the impact of amoxicillin, clarithromycin and their combination on human gastrointestinal colonization by Candida species.	2001 May-Jun	11306791

Patents

Sample Use Guides

In Vivo Use Guide

In adults, 750-1750 mg/day in divided doses every 8-12 hours. In Pediatric Patients > 3 Months of Age, 20-45 mg/kg/day in divided doses every 8-12 hours. Treatment of gonorrhea is 3 grams as a single oral dose. The upper dose for neonates and infants ≤ 3 months is 30 mg/kg/day divided every 12 hours. Dosing for H. pylori Infection: Triple therapy: 1 gram AMOXIL, 500 mg clarithromycin, and 30 mg lansoprazole, all given twice daily (every 12 hours) for 14 days. Dual therapy: 1 gram AMOXIL and 30 mg lansoprazole, each given three times daily (every 8 hours) for 14 days.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:01:01 GMT 2025` Edited by `admin` on `Mon Mar 31 18:01:01 GMT 2025`
Record UNII	544Y3D6MYH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Amoxicillin sodium

Official Name

English

Amoxicillin sodium salt

Preferred Name

English

Sodium amoxycillin

Common Name

English

Amoxicillin sodium [WHO-DD]

Common Name

English

4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-, sodium salt (1:1), (2S,5R,6R)-

Systematic Name

English

Sodium ?-amino-p-hydroxybenzylpenicillin

Common Name

English

BRL-2333AB-B

Code

English

Amoxicillin (as the sodium salt)

Common Name

English

Amoxicillin sodium salt [MI]

Common Name

English

4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2R)-amino(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-, monosodium salt, (2S,5R,6R)-

Systematic Name

English

Amoxycillin sodium salt

Common Name

English

Amoxicillin sodium [MART.]

Common Name

English

Sodium amoxicillin

Common Name

English

Amoxicillin sodium [EP MONOGRAPH]

Common Name

English

Amoxicillin sodium [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1500