Amoxicillin

Title: Amoxicillin
CAS Registry Number: 26787-78-0
CAS Name: (2S,5R,6R)-6-[[(2R)-Amino(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Additional Names: (-)-6-[2-amino-2-(p-hydroxyphenyl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 6-[D(-)-a-amino-p-hydroxyphenylacetamido]penicillanic acid; a-amino-p-hydroxybenzylpenicillin; 6-(p-hydroxy-a-aminophenylacetamido)penicillanic acid; p-hydroxyampicillin; amoxycillin; AMPC
Trademarks: Helvamox (Helvepharm); Pasetocin (Kyowa); Penimox (IBSA); Supramox (Grenthal); Zamocilline (Inpharzam)
Molecular Formula: C16H19N3O5S
Molecular Weight: 365.40
Percent Composition: C 52.59%, H 5.24%, N 11.50%, O 21.89%, S 8.78%
Literature References: Semi-synthetic antibiotic related to penicillin. Prepn: Nayler, Smith, GB 978178 (1964 to Beecham); eidem, US 3192198 (1965); Long, Nayler, DE 1942693 and GB 1241844 (1970 and 1971 to Beecham), C.A. 72, 90447q (1970). Resolution of isomers: Long et al., J. Chem. Soc. C 1971, 1920. Series of articles on activity, pharmacology, absorption and excretion: Antimicrob. Agents Chemother. 1970, 407-430. Review of antibacterial activity, pharmacokinetics and therapeutic use: R. N. Brogden et al., Drugs 18, 169-184 (1979). Comprehensive description: A. E. Bird, Anal. Profiles Drug Subs. Excip. 23, 1-52 (1994).
Derivative Type: Trihydrate
CAS Registry Number: 61336-70-7
Manufacturers' Codes: BRL-2333
Trademarks: Agram (Fabre); Alfamox (Teofarma); Amocilline (Inpharzam); Amodex (Bouchara); Amoram (Eastern); Amoxidin (Lagap); Amoxil (GSK); Amoxillat (Novartis); Amoxypen (Grenthal); Ardine (Antibioticos); Bactox (Innotech); Betamox (Norbrook); Bristamox (BMS); Cuxacillin (TAD); Flemoxine (Yamanouchi); Gramidil (Dexo); Hiconcil (BMS); Larotid (Roche); Ospamox (Novartis); Polymox (BMS); Robamox (Wyeth); Sigamopen (Alpharma); Trimox (BMS); Velamox (GSK); Widecillin (Meiji); Wymox (Wyeth); Zimox (Pfizer)
Properties: Off-white crystalline powder. [a]D20 +246° (c = 0.1). uv max (ethanol): 230, 274 nm (e 10850, 1400); (0.1N HCl): 229, 272 nm (e 9500, 1080); (0.1N KOH): 248, 291 (e 2200, 3000). Solubility (mg/ml): water 4.0; methanol 7.5; abs ethanol 3.4. Insol in hexane, benzene, ethyl acetate, acetonitrile.
Optical Rotation: [a]D20 +246° (c = 0.1)
Absorption maximum: uv max (ethanol): 230, 274 nm (e 10850, 1400); (0.1N HCl): 229, 272 nm (e 9500, 1080); (0.1N KOH): 248, 291 (e 2200, 3000)
Derivative Type: Sodium salt
CAS Registry Number: 34642-77-8
Trademarks: Clamoxyl (GSK); Ibiamox (IBI)
Molecular Formula: C16H18N3NaO5S
Molecular Weight: 387.39
Percent Composition: C 49.61%, H 4.68%, N 10.85%, Na 5.93%, O 20.65%, S 8.28%
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Penicillins.
AMPA Ampelopsin Amperozide Amphecloral Amphenidone

Amoxicillin
Amoxicillin.svg
Amoxicillin-3D-balls.png
Systematic (IUPAC) name
(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
Clinical data
Trade names Actimoxi, Alphamox, Amocla,Tycil, Amoxil, Trimox, among others
AHFS/Drugs.com monograph
MedlinePlus a685001
Pregnancy cat. A (AU) B (US)
Legal status POM (UK) -only (US)
Routes Oral, intravenous
Pharmacokinetic data
Bioavailability 95% oral
Metabolism less than 30% biotransformed in liver
Half-life 61.3 minutes
Excretion renal
Identifiers
CAS number 26787-78-0 YesY
ATC code J01CA04 QG51AA03
PubChem CID 33613
DrugBank DB01060
ChemSpider 31006 YesY
UNII 9EM05410Q9 YesY
KEGG D07452 YesY
ChEBI CHEBI:2676 YesY
ChEMBL CHEMBL1082 YesY
Chemical data
Formula C16H19N3O5S 
Mol. mass 365.4 g/mol
 YesY (what is this?)  (verify)
Amoxicillin BP

Amoxicillin (INN), formerly amoxycillin (BAN), and abbreviated amox, is a moderate-spectrum, bacteriolytic, β-lactam antibiotic in the aminopenicillin family 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 β-lactam antibiotics. Amoxicillin is one of the most common antibiotics prescribed for children. The drug first became available in 1972.

Amoxicillin is susceptible to degradation by β-lactamase-producing bacteria, which are resistant to a narrow spectrum of β-lactam antibiotics, such as penicillin. For this reason, it is often combined with clavulanic acid, a β-lactamase inhibitor. This increases effectiveness by reducing its susceptibility to β-lactamase resistance.[1]