ChemFOnt: Showing chemical card for Amoxycillin (CFc000011711)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:59:33 UTC

Chemfont ID

CFc000011711

Molecule Identification

Common Name

Amoxycillin

Definition

Amoxycillin is found in milk and milk products. Potential contaminant in cow's milk arising from its veterinary use Amoxicillin (International Nonproprietary Name), formerly amoxycillin (British Approved Name), is a moderate-spectrum, bacteriolytic, -lactam antibiotic used to treat bacterial infections caused by susceptible microorganisms. It 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 dispersable tablets plus 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 where the patient might find it difficult to take tablets or capsules. It has three ionizable groups. Amoxycillin is a once daily dosing form (Moxatag) was approved by the American FDA in January 2008. Amoxicillin is a moderate-spectrum antibiotic active against a wide range of Gram-positive, and a limited range of Gram-negative organisms. It is usually the drug of choice within the class because it is better absorbed, following oral administration, than other beta-lactam antibiotics. Amoxicillin is susceptible to degradation by β-lactamase-producing bacteria, and so may be given with clavulanic acid to increase its susceptability. The incidence of β-lactamase-producing resistant organisms, including E. coli, appears to be increasing. Amoxicillin is sometimes combined with clavulanic acid, a β-lactamase inhibitor, to increase the spectrum of action against Gram-negative organisms, and to overcome bacterial antibiotic resistance mediated through β-lactamase production. 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

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
6-(a-amino-4-hydroxyphenylacetamido)Penicillanic acid	HMDB
6-(D-(-)-P-Hydroxy-alpha-aminobenzyl)penicillin	HMDB
6-(P-Hydroxy-alpha-aminophenylacetamido)penicillanic acid	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
alpha-amino-P-Hydroxybenzylpenicillin	HMDB
Amix	HMDB
Amoclen	HMDB
Amolin	HMDB
Amopen	HMDB
Amopenixin	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
Amoxicilina	HMDB
Amoxicillin (anhydrous)	HMDB
Amoxicillin	HMDB
Amoxicillin and clavulanate potassium	HMDB
Amoxicillin anhydrous	HMDB
Amoxicillin pediatric	HMDB
Amoxicillin trihydrate	HMDB
Amoxicillin(usan)	HMDB
Amoxicilline	HMDB
Amoxicillinum	HMDB
Amoxid	HMDB
Amoxiden	HMDB
Amoxil	HMDB
Amoxivet	HMDB
Amoxycillin trihydrate	HMDB
Amoxycillin, ban	HMDB
Amoxymed	HMDB
AMPC	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	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
D-Amoxicillin	HMDB
Delacillin	HMDB
Dispermox	HMDB
Efpenix	HMDB
Flemoxin	HMDB
Galenamox	HMDB
Gen-amoxicillin 250MG	HMDB
Gen-amoxicillin 500MG	HMDB
Hiconcil	HMDB
Histocillin	HMDB
Hydroxyampicillin	HMDB
Ibiamox	HMDB
Imacillin	HMDB
Larotid	HMDB
Metafarma capsules	HMDB
Metifarma capsules	HMDB
Moxacin	HMDB
Moxal	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
P-Hydroxyampicillin	HMDB
PHL-Amoxicillin	HMDB
Piramox	HMDB
PMS-Amoxicillin	HMDB
Polymox	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
Trimox	HMDB
Unicillin	HMDB
Utimox	HMDB
Vetramox	HMDB
Wymox	HMDB

Chemical Formula

C₁₆H₁₉N₃O₅S

Average Molecular Weight

365.404

Monoisotopic Molecular Weight

365.104541423

IUPAC Name

6-[2-amino-2-(4-hydroxyphenyl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Traditional Name

amoxil

CAS Registry Number

26787-78-0

SMILES

CC1(C)SC2C(NC(=O)C(N)C3=CC=C(O)C=C3)C(=O)N2C1C(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)

InChI Key

LSQZJLSUYDQPKJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as heteroaromatic compounds. Heteroaromatic compounds are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Heteroaromatic compounds

Sub Class

Not Available

Direct Parent

Heteroaromatic compounds

Alternative Parents

Substituents

Heteroaromatic compound
Furan
Organic disulfide
Oxacycle
Sulfenyl compound
Organic oxygen compound
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030500)
Cytoplasm (HMDB: HMDB0030500)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030500)

Source

Exogenous

Exogenous (HMDB: HMDB0030500)

Food

Food (HMDB: HMDB0030500)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Milk and milk products (FooDB: FOOD00863)

Endogenous

Endogenous (HMDB: HMDB0030500)

Animal

Animal (HMDB: HMDB0030500)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Antimicrobial agent (HMDB: HMDB0030500)

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)	7.43	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	35.22 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

External Links

HMDB ID

HMDB0030500

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002369

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Amoxicillin

METLIN ID

Not Available

PubChem Compound

2171

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Amoxycillin (CFc000011711)

MOL for CFc000011711 (Amoxycillin)

3D MOL for CFc000011711 (Amoxycillin)

3D SDF for CFc000011711 (Amoxycillin)

3D-SDF for CFc000011711 (Amoxycillin)

PDB for CFc000011711 (Amoxycillin)

3D PDB for CFc000011711 (Amoxycillin)

SMILES for CFc000011711 (Amoxycillin)

INCHI for CFc000011711 (Amoxycillin)

Structure for CFc000011711 (Amoxycillin)

3D Structure for CFc000011711 (Amoxycillin)