File:Amoxicillin_skeletal_formula_labelled.svg · Wikimedia Commons · See Wikimedia Commons
amoxicillin
Sign in to saveAlso known as amoxil, Amoxi-Tabs, BRL-2333, Larotid, Robamox, Amoxicilline, Sumox, Trimox
Amoxicillin is an antibiotic medication belonging to the aminopenicillin class of the penicillin family. The drug is used to treat bacterial infections such as middle ear infection, strep throat, pneumonia, skin infections, odontogenic infections, and urinary tract infections. It is taken orally (swallowed by mouth), or less commonly by either intramuscular injection or by an IV bolus injection, which is a relatively quick intravenous injection lasting from a couple of seconds to a few minutes.
OverviewAI-generated
Amoxicillin is a chemical compound with the formula C₁₆H₁₉N₃O₅S. Its mass is listed as 365.104542, while its weight is recorded as 365.4. The substance has a half-life of 61.3 and a defined daily dose of 1.
Chemical properties include an xlogp of -1.3 and a tpsa of 163. The molecule features 3 hydrogen bond donors and 6 hydrogen bond acceptors, with a charge of 0. It is referenced by 386 other encyclopedia articles.
Synthesized by Vinony from 20 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Key facts
- Drug.ChemSpiderID
- 31006
- Drug.UNII
- 9EM05410Q9
- Drug.KEGG
- D07452
- Drug.ChEBI
- 2676
- Drug.ChEMBL
- 1082
- Drug.S
- 1
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 455343638
- Drug.image
- Amoxicillin skeletal formula labelled.svg
- Drug.image_class
- skin-invert-image
- Drug.image2
- Amoxicillin-from-xtal-3D-bs-17.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Amoxil, Trimox, others
- Drug.MedlinePlus
- a685001
- Drug.DailyMedID
- Amoxicillin
- Drug.pregnancy_AU
- A
- Drug.routes_of_administration
- By mouth, intravenous (bolus), intramuscular
- Drug.class
- β-Lactam antibiotic; Aminopenicillin
via Wikipedia infobox
Chemical data
- Formula
- C16H19N3O5S
- Molecular weight
- 365.4 g/mol
- IUPAC name
- (2S,5R,6R)-6-[[(2R)-2-azaniumyl-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
- SMILES
- CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=C(C=C3)O)[NH3+])C(=O)[O-])C
- InChIKey
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N
- XLogP
- -1.3
- Polar surface area
- 163 Ų
- H-bond donors
- 3
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Research
28,197 papers- Oral amoxicillin and amoxicillin-clavulanic acid: properties, indications and usage.ReviewClinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases · 2020Huttner A, Bielicki J, Clements MN et al.DOI: 10.1016/j.cmi.2019.11.028
- Amoxicillin crystalluria and amoxicillin-induced crystal nephropathy: a narrative review.ReviewKidney international · 2025Vodovar D, Mousseaux C, Daudon M et al.DOI: 10.1016/j.kint.2024.09.019
- Amoxicillin-potassium clavulanate, a beta-lactamase-resistant antibiotic combination.ReviewClinical pharmacy · 1984Stein GE, Gurwith MJ
- Amoxicillin-Induced Aseptic Meningitis: 2 Case Reports and Appraisal of the Literature.ReviewJournal of investigational allergology & clinical immunology · 2019Alarcón E, Sansosti A, Navarro B et al.DOI: 10.18176/jiaci.0380
- Should testing be initiated prior to amoxicillin challenge in children?ReviewClinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology · 2019Abrams EM, Ben-Shoshan MDOI: 10.1111/cea.13443
- [Amoxicillin-clavulanic acid in late pregnancy].Gynecologie, obstetrique, fertilite & senologie · 2022Vauzelle CDOI: 10.1016/j.gofs.2021.12.008
- Amoxicillin and amoxicillin plus clavulanate: a safety review.ReviewExpert opinion on drug safety · 2009Salvo F, De Sarro A, Caputi AP et al.DOI: 10.1517/14740330802527984
- [Amoxicillin (AMPC)].ReviewNihon rinsho. Japanese journal of clinical medicine · 2002Sato K, Kato C
via PubMed
~18 min read
Encyclopedic overview
25 sectionsContents
- Medical uses
- Acute otitis media
- Respiratory infections
- ''H. pylori''
- Lyme borreliosis
- Odontogenic infections
- Skin infections
- Infections in infants in resource-limited settings
- Prevention of bacterial endocarditis
- Combination treatment
- Spectrum of activity
- Adverse effects
- Nonallergic rash
- Interactions
- Pharmacology
- Chemistry
- History
- Society and culture
- Economics
- Modes of delivery
- Names
- Veterinary uses
- References
- Further reading
- External links
{{Infobox drug | Watchedfields = changed | verifiedrevid = 455343638 | image = Amoxicillin skeletal formula labelled.svg | image_class = skin-invert-image | width = | alt = | caption = | image2 = Amoxicillin-from-xtal-3D-bs-17.png | image_class2 = bg-transparent | width2 = | alt2 =
| pronounce = | tradename = Amoxil, Trimox, others | Drugs.com = | MedlinePlus = a685001 | DailyMedID = Amoxicillin | pregnancy_AU = A | pregnancy_AU_comment = | pregnancy_category = | routes_of_administration = By mouth, intravenous (bolus), intramuscular | class = β-Lactam antibiotic; Aminopenicillin | ATC_prefix = J01 | ATC_suffix = CA04 | ATC_supplemental =
Excerpted from Wikipedia’s “amoxicillin” article, available under the CC BY-SA 4.0 licence.
Gallery (38)
Available in 72 languages
- Español
- Français
- Deutsch
- 中文
- 日本語
- Русский
- Português
- Italiano
- العربية
- हिन्दी
- Afrikaans
- Armenian
- Asturian
- azb
- Azerbaijani
- Bahasa Indonesia
- Bangla
- Basque
Show 53 more
- blk
- Bosnian
- Bulgarian
- Burmese
- Catalan
- Central Kurdish
- Czech
- dag
- Danish
- Esperanto
- Estonian
- Finnish
- Galician
- gpe
- Greek
- Haitian Creole
- Hausa
- Hebrew
- Hungarian
- Kashmiri
- Latin
- Lingala
- Macedonian
- Malagasy
- Malay
- Malayalam
- Minangkabau
- Nederlands
- Newari
- Odia
- Polski
- Punjabi
- Romanian
- Serbian
- Serbian (Latin)
- simple
- Slovak
- Slovenian
- Sundanese
- Svenska
- Tamil
- Telugu
- Tiếng Việt
- Türkçe
- Ukrainian
- Urdu
- Uzbek
- Walloon
- Welsh
- Wu Chinese
- فارسی
- ไทย
- 한국어
via Wikidata sitelinks · CC0