AMOXICILLIN ANHYDROUS

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 Search

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

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 221	Inhibitor 6625	Duodenal Ulcer

Conditions

Condition	Modality	Targets	Highest Phase	Product
Gonorrhea 51	Primary	Bacterial penicillin-binding protein	Approved 7892	AMOXIL
Urinary Tract Infections 221	Primary	Bacterial penicillin-binding protein	Approved 7892	AMOXIL
Duodenal Ulcer 48	Primary	Bacterial penicillin-binding protein	Approved 7892	AMOXIL
Staphylococcal Skin Infections 86	Primary	Bacterial penicillin-binding protein	Approved 7892	AMOXIL
Infections of the ear, nose, and throat 3	Primary	Bacterial penicillin-binding protein	Approved 7892	AMOXIL
[Chlamydial Infection (in pregnant women), Lyme Disease] 3			Approved (off-label) 8

PubMed

Title	Date	PubMed
Amoxicillin plus metronidazole in the treatment of adult periodontitis patients. A double-blind placebo-controlled study.	2001 Apr	11314884
Simultaneous determination of five beta-lactam antibiotics in bovine milk using liquid chromatography coupled with electrospray ionization tandem mass spectrometry.	2001 Apr 1	11321318
[Eradication therapy of Helicobacter pylori infection].	2001 Feb	11307304
[The history of Helicobacter pylori].	2001 Feb	11307300
[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
Antibiotic resistance and antibiotic sensitivity based treatment in Helicobacter pylori infection: advantages and outcome.	2001 May	11316688
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

Name

Type

Language

AMOXICILLIN ANHYDROUS

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