ChemFOnt: Showing chemical card for Amoxicillin (CFc000009487)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:38 UTC

Chemfont ID

CFc000009487

Molecule Identification

Common Name

Amoxicillin

Definition

Amoxicillin (International Nonproprietary Name), or amoxycillin (British Approved Name), is a moderate-spectrum, bacteriolytic, -lactam antibiotic used to treat bacterial infections caused by susceptible microorganisms. It is a broad-spectrum semisynthetic antibiotic similar to ampicillin except that its resistance to gastric acid permits higher serum levels with oral administration (PubChem). Amoxicillin is active against a wide range of Gram-positive and a limited range of Gram-negative organisms. It is susceptible to degradation by beta-lactamase-producing bacteria, and so may be given with clavulanic acid to increase its susceptibility. The incidence of beta-lactamase-producing resistant organisms, including E. coli, appears to be increasing. Amoxicillin binds to penicillin-binding protein 1A (PBP-1A) located inside the bacterial cell wall. Penicillins acylate the penicillin-sensitive transpeptidase C-terminal domain by opening the lactam ring. This inactivation of the enzyme prevents the formation of a cross-link of two linear peptidoglycan strands, inhibiting the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that amoxicillin interferes with an autolysin inhibitor. Amoxicillin is usually the drug of choice within the class because it is better absorbed, following oral administration, than other -lactam antibiotics. Amoxicillin in trihydrate form is available as capsules, chewable and dispersible tablets, syrup and pediatric suspension for oral use, and as the sodium salt for intravenous administration. It is one of the most common antibiotics prescribed for children, and the liquid forms are helpful in cases where the patient might find it difficult to take tablets or capsules. It has three ionizable groups. Amoxicillin as a once-daily dosing form (Moxatag) was approved by the American FDA in January 2008. Amoxicillin is one of the semi-synthetic penicillins discovered by Beecham scientists. The patent for amoxicillin has expired, thus amoxicillin is marketed under many trade names, including Actimoxi, Alphamox, AMK, Amoksibos, Amoxiclav Sandoz, Amoxidal, Amoxil, Amoxin, Amoksiklav, Amoxibiotic, Amoxicilina, Apo-Amoxi, Augmentin, Bactox, Betalaktam, Cilamox, Curam, Dedoxil, Dispermox, Duomox, E-Mox (250mg and 500 mg), Enhancin, Gimalxina, Geramox, Hiconcil, Isimoxin, Klavox, Lamoxy, Moxatag, Moxilen, Moxypen, Moxyvit, Nobactam, Novamoxin, Ospamox, Panklav, Pamoxicillin, Panamox, Polymox, Samthongcillin, Clamoxyl, Senox, Sinacilin, Trimox, Tolodina, Wymox, Yucla, Zerrsox, and Zimox. Amoxicillin is found in milk and milk products. It is a potential contaminant in cow's milk arising from its veterinary use.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(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	ChEBI
6-(p-Hydroxy-alpha-aminophenylacetamido)penicillanic acid	ChEBI
alpha-Amino-p-hydroxybenzylpenicillin	ChEBI
Amolin	ChEBI
Amopenixin	ChEBI
Amoxicilina	ChEBI
Amoxicillin anhydrous	ChEBI
Amoxicilline	ChEBI
Amoxicillinum	ChEBI
Amoxycilin	ChEBI
Amoxycillin	ChEBI
AMPC	ChEBI
AX	ChEBI
Clamoxyl	ChEBI
Moxal	ChEBI
p-Hydroxyampicillin	ChEBI
(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-carboxylate	Generator
6-(p-Hydroxy-a-aminophenylacetamido)penicillanate	Generator
6-(p-Hydroxy-a-aminophenylacetamido)penicillanic acid	Generator
6-(p-Hydroxy-alpha-aminophenylacetamido)penicillanate	Generator
6-(p-Hydroxy-α-aminophenylacetamido)penicillanate	Generator
6-(p-Hydroxy-α-aminophenylacetamido)penicillanic acid	Generator
a-Amino-p-hydroxybenzylpenicillin	Generator
Α-amino-p-hydroxybenzylpenicillin	Generator
Amoxicillin trihydrate	HMDB
Amoxycillin trihydrate	HMDB
D-Amoxicillin	HMDB
Actimoxi	HMDB
Amoxicillin monopotassium salt	HMDB
Amoxicillin monosodium salt	HMDB
Clariana brand OF amoxicillin	HMDB
Polymox	HMDB
Amoxicillin sodium	HMDB
Clamoxyl parenteral	HMDB
Trihydrate, amoxicillin	HMDB
Anhydrous, amoxicillin	HMDB
Clamoxyl g.a.	HMDB
Hydroxyampicillin	HMDB
Pfizer brand OF amoxicillin sodium salt	HMDB
Trimox	HMDB
Wymox	HMDB
Amoxicillin clariana brand	HMDB
Amoxicillin, (r*)-isomer	HMDB
Amoxil	HMDB
G.A., clamoxyl	HMDB
Penamox	HMDB
SmithKline beecham brand OF amoxicillin sodium salt	HMDB
Sodium, amoxicillin	HMDB
Parenteral, clamoxyl	HMDB
6-(a-Amino-4-hydroxyphenylacetamido)penicillanic acid	HMDB
6-(D-(-)-p-Hydroxy-alpha-aminobenzyl)penicillin	HMDB
6-[[Amino(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 9ci	HMDB
Almodan	HMDB
Amix	HMDB
Amoclen	HMDB
Amopen	HMDB
Amoram	HMDB
Amox 250 cap 250MG	HMDB
Amox 500 cap 500MG	HMDB
Amox S 125 sus 125mg/5ML	HMDB
Amox S 250 sus 250mg/5ML	HMDB
Amoxi	HMDB
Amoxi-mast	HMDB
Amoxicaps	HMDB
Amoxicillin (anhydrous)	HMDB
Amoxicillin and clavulanate potassium	HMDB
Amoxicillin pediatric	HMDB
Amoxicillin(usan)	HMDB
Amoxid	HMDB
Amoxiden	HMDB
Amoxivet	HMDB
Amoxycillin, ban	HMDB
Amoxymed	HMDB
Amrit	HMDB
Anemolin	HMDB
Apo-amoxi	HMDB
Apo-amoxi cap 250MG	HMDB
Apo-amoxi cap 500MG	HMDB
Apo-amoxi PWR for susp 125mg/5ML	HMDB
Apo-amoxi PWR for susp 250mg/5ML	HMDB
Apo-amoxi sugar free	HMDB
Aspenil	HMDB
AUGMENTIN '125'	HMDB
AUGMENTIN '200'	HMDB
AUGMENTIN '250'	HMDB
AUGMENTIN '400'	HMDB
AUGMENTIN '500'	HMDB
AUGMENTIN '875'	HMDB
AUGMENTIN es-600	HMDB
Biomox	HMDB
Bristamox	HMDB
BRL 2333	HMDB
Cemoxin	HMDB
Clamoxyl (SKB)	HMDB
D-(-)-alpha-Amino-p-hydroxybenzyl penicillin	HMDB
D-(-)-alpha-Amino-p-hydroxybenzylpenicillin	HMDB
D-(alpha-Amino-p-hydroxybenzyl)penicillin	HMDB
D-2-Amino-2-(4-hydroxyphenyl)acetamidopenicillanic acid	HMDB
Delacillin	HMDB
Dispermox	HMDB
Efpenix	HMDB
Flemoxin	HMDB
Galenamox	HMDB
Gen-amoxicillin 250MG	HMDB
Gen-amoxicillin 500MG	HMDB
Hiconcil	HMDB
Histocillin	HMDB
Ibiamox	HMDB
Imacillin	HMDB
Larotid	HMDB
Metafarma capsules	HMDB
Metifarma capsules	HMDB
Moxacin	HMDB
Moxatag	HMDB
Novamoxin cap 250MG	HMDB
Novamoxin cap 500MG	HMDB
Novamoxin sus 125mg/5ML	HMDB
Novamoxin sus 250mg/5ML	HMDB
Nu-amoxi cap 250MG	HMDB
Nu-amoxi cap 500MG	HMDB
Nu-amoxi sus 125/5ML	HMDB
Nu-amoxi sus 250mg/5ML	HMDB
Ospamox	HMDB
PHL-Amoxicillin	HMDB
Piramox	HMDB
PMS-Amoxicillin	HMDB
Prevpac	HMDB
Pro amox PWR for oral susp 125mg/5ML	HMDB
Pro amox-250 cap 250MG	HMDB
Pro amox-500 cap 500MG	HMDB
Pro-amox-250 orl sus 250mg/5ML	HMDB
R-Hydroxyampicillin	HMDB
Rimoxallin	HMDB
Robamox	HMDB
Sauracillin	HMDB
Sawamox PM	HMDB
Sumox	HMDB
Unicillin	HMDB
Utimox	HMDB
Vetramox	HMDB
Amoxicillin	HMDB

Chemical Formula

C₁₆H₁₉N₃O₅S

Average Molecular Weight

365.404

Monoisotopic Molecular Weight

365.104541423

IUPAC Name

(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

Traditional Name

amoxicillin

CAS Registry Number

26787-78-0

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=C(O)C=C1)C(O)=O

InChI Identifier

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

InChI Key

LSQZJLSUYDQPKJ-NJBDSQKTSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1].

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactams

Sub Class

Beta lactams

Direct Parent

Penicillins

Alternative Parents

Substituents

Penicillin
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
Phenylacetamide
Phenol
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Benzenoid
Monocyclic benzene moiety
Thiazolidine
Tertiary carboxylic acid amide
Azetidine
Amino acid or derivatives
Secondary carboxylic acid amide
Carboxamide group
Amino acid
Azacycle
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Dialkylthioether
Hemithioaminal
Thioether
Primary aliphatic amine
Amine
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

penicillin (CHEBI:2676 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0015193)

Source

Exogenous

Exogenous (HMDB: HMDB0015193)

Food

Food (HMDB: HMDB0015193)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Milk and milk products (FooDB: FOOD00863)

Endogenous

Endogenous (HMDB: HMDB0015193)

Animal

Animal (HMDB: HMDB0015193)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Antimicrobial agent (HMDB: HMDB0015193)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.96 g/L	ALOGPS
logP	0.75	ALOGPS
logP	-2.3	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	3.23	ChemAxon
pKa (Strongest Basic)	7.22	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.96 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	89.5 m³·mol⁻¹	ChemAxon
Polarizability	35.52 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon