U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H19N3O5S
Molecular Weight 365.404
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMOXICILLIN ANHYDROUS

SMILES

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=LSQZJLSUYDQPKJ-NJBDSQKTSA-N
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

HIDE SMILES / InChI

Description

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

PubMed

PubMed

TitleDatePubMed
Amoxicillin plus metronidazole in the treatment of adult periodontitis patients. A double-blind placebo-controlled study.
2001 Apr
Simultaneous determination of five beta-lactam antibiotics in bovine milk using liquid chromatography coupled with electrospray ionization tandem mass spectrometry.
2001 Apr 1
[Eradication therapy of Helicobacter pylori infection].
2001 Feb
[The history of Helicobacter pylori].
2001 Feb
[A prospective study on erysipelas and infectious cellulitis: how are they dealt within hospital?].
2001 Mar
Peptic ulcer occurrence in follow-up of chronic gastritis in patients with treated and not eradicated CagA-positive Helicobacter pylori infection.
2001 Mar
Standard case management of pneumonia in hospitalized children in Uruguay, 1997 to 1998.
2001 Mar
Antibiotic resistance and antibiotic sensitivity based treatment in Helicobacter pylori infection: advantages and outcome.
2001 May
Worldwide prevalence of antimicrobial resistance in Streptococcus pneumoniae, Haemophilus influenzae, and Moraxella catarrhalis in the SENTRY Antimicrobial Surveillance Program, 1997-1999.
2001 May 15
Prospective evaluation of the impact of amoxicillin, clarithromycin and their combination on human gastrointestinal colonization by Candida species.
2001 May-Jun
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
Name Type Language
AMOXICILLIN ANHYDROUS
HSDB  
Common Name English
AMOXICILLIN [INN]
Common Name English
AMOXYCILLIN
Common Name English
AMOXICILLINE
Common Name English
AMOXICILLIN [MART.]
Common Name English
AMOXICILLIN (ANHYDROUS)
Common Name English
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*)))-
Systematic Name English
AMOXICILLIN ANHYDROUS [HSDB]
Common Name English
NSC-277174
Code English
AMOXICILLIN [MI]
Common Name English
(2S,5R,6R)-6-((R)-(-)-2-AMINO-2-(P-HYDROXYPHENYL)ACETAMIDO)-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID
Systematic Name English
AMOXICILLIN [WHO-DD]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175497
Created by admin on Mon Oct 21 22:11:50 UTC 2019 , Edited by admin on Mon Oct 21 22:11:50 UTC 2019
NCI_THESAURUS C1500
Created by admin on Mon Oct 21 22:11:50 UTC 2019 , Edited by admin on Mon Oct 21 22:11:50 UTC 2019
WHO-ATC J01CA04
Created by admin on Mon Oct 21 22:11:50 UTC 2019 , Edited by admin on Mon Oct 21 22:11:50 UTC 2019
Code System Code Type Description
DRUG BANK
DB01060
Created by admin on Mon Oct 21 22:11:50 UTC 2019 , Edited by admin on Mon Oct 21 22:11:50 UTC 2019
PRIMARY
CAS
26787-78-0
Created by admin on Mon Oct 21 22:11:50 UTC 2019 , Edited by admin on Mon Oct 21 22:11:50 UTC 2019
PRIMARY
EPA CompTox
26787-78-0
Created by admin on Mon Oct 21 22:11:50 UTC 2019 , Edited by admin on Mon Oct 21 22:11:50 UTC 2019
PRIMARY
ChEMBL
CHEMBL1082
Created by admin on Mon Oct 21 22:11:50 UTC 2019 , Edited by admin on Mon Oct 21 22:11:50 UTC 2019
PRIMARY
INN
3230
Created by admin on Mon Oct 21 22:11:50 UTC 2019 , Edited by admin on Mon Oct 21 22:11:50 UTC 2019
PRIMARY
HSDB
26787-78-0
Created by admin on Mon Oct 21 22:11:50 UTC 2019 , Edited by admin on Mon Oct 21 22:11:50 UTC 2019
PRIMARY
EVMPD
SUB05481MIG
Created by admin on Mon Oct 21 22:11:50 UTC 2019 , Edited by admin on Mon Oct 21 22:11:50 UTC 2019
PRIMARY
NCI_THESAURUS
C87367
Created by admin on Mon Oct 21 22:11:50 UTC 2019 , Edited by admin on Mon Oct 21 22:11:50 UTC 2019
PRIMARY
PUBCHEM
33613
Created by admin on Mon Oct 21 22:11:50 UTC 2019 , Edited by admin on Mon Oct 21 22:11:50 UTC 2019
PRIMARY
MERCK INDEX
M1844
Created by admin on Mon Oct 21 22:11:50 UTC 2019 , Edited by admin on Mon Oct 21 22:11:50 UTC 2019
PRIMARY Merck Index
RXCUI
1297882
Created by admin on Mon Oct 21 22:11:50 UTC 2019 , Edited by admin on Mon Oct 21 22:11:50 UTC 2019
PRIMARY RxNorm
LactMed
26787-78-0
Created by admin on Mon Oct 21 22:11:50 UTC 2019 , Edited by admin on Mon Oct 21 22:11:50 UTC 2019
PRIMARY
ECHA (EC/EINECS)
248-003-8
Created by admin on Mon Oct 21 22:11:50 UTC 2019 , Edited by admin on Mon Oct 21 22:11:50 UTC 2019
PRIMARY