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amoxicillin

Small moleculeapproved

Approved

Jan 18, 1974

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. — NCATS

Clinical trial activity

366 trials · 373 clinical orgs · 30 marketing orgs

Phase 1
36
Phase 2
75
Phase 3
55
Phase 4
161

Earliest trial started Apr 1, 1996 (NCT00539149)

Timeline

1970s

  1. Jan 18, 1974

    GlaxoSmithKline — Earliest FDA Approval

  2. Jan 18, 1974

    GlaxoSmithKline — Marketing Organization

  3. Jan 18, 1974

    GlaxoSmithKline — NDA Secondary Org

  4. Jan 18, 1974

    GlaxoSmithKline — NDA Organization

  5. Dec 9, 1974

    Apothecon — Marketing Organization

  6. Feb 9, 1976

    Teva — Marketing Organization

  7. Aug 3, 1978

    Belcher Pharmaceuticals — Marketing Organization

  8. Aug 3, 1978

    Chartwell Pharmaceuticals — Marketing Organization

  9. Aug 2, 1979

    Neopharma — NDA Secondary Org

  10. Aug 2, 1979

    US Antibiotics — NDA Secondary Org

  11. Aug 2, 1979

    US Antibiotics — Marketing Organization

1980s

  1. Aug 7, 1985

    Atral — Marketing Organization

  2. Feb 25, 1988

    Strides Pharma Science — Marketing Organization

  3. Feb 25, 1988

    DAVA Pharmaceuticals — Marketing Organization

1990s

  1. Sep 30, 1994

    Sandoz — Marketing Organization

  2. Dec 2, 1997

    Takeda — NDA Secondary Org

  3. Apr 8, 1999

    Sun Pharmaceuticals — Marketing Organization

2000s

  1. Mar 14, 2002

    Novartis — Marketing Organization

  2. Aug 11, 2003

    Ranbaxy — Marketing Organization

  3. Nov 9, 2005

    Aurobindo Pharma — Marketing Organization

  4. Mar 29, 2006

    Hikma — Marketing Organization

  5. Jun 18, 2007

    Wockhardt — Marketing Organization

  6. Jan 1, 2008

    Earliest Phase 1 Sponsor(trial)

  7. Jan 23, 2008

    Pragma Therapeutics — Marketing Organization

  8. Jan 23, 2008

    Pragma Therapeutics — NDA Secondary Org

  9. Oct 20, 2008

    Apotex — Marketing Organization

2010s

  1. Feb 8, 2011

    Cumberland Pharmaceuticals — NDA Secondary Org

  2. Jan 1, 2013

    Earliest Phase 3 Sponsor(trial)

  3. Aug 30, 2013

    Ani Pharmaceuticals — Marketing Organization

  4. Oct 7, 2016

    Rising Pharmaceuticals — Marketing Organization

  5. Dec 30, 2016

    Micro Labs Ltd India — Marketing Organization

  6. Jan 1, 2017

    Earliest Phase 2 Sponsor(trial)

  7. Nov 1, 2019

    RedHill Biopharma — NDA Secondary Org

2020s

  1. May 3, 2022

    Phathom Pharmaceuticals, Inc. — NDA Secondary Org

  2. Sep 13, 2023

    Deva Holding A.S. — Marketing Organization

Indications

Approved for

Studied for

Mechanism of action

Combination products

  • augmentin '500'

    with clavulanate

    Also known as augmentin '125', augmentin '200', augmentin '250', augmentin '400', augmentin '875', augmentin es, augmentin xr

  • omeclamox-pak

    with clarithromycin, omeprazole

  • prevpac (copackaged)

    with clarithromycin, lansoprazole

    Also known as lansoprazole, amoxicillin and clarithromycin (copackaged)

  • talicia

    with rifabutin, omeprazole

    Also known as omeprazole magnesium, amoxicillin, rifabutin

  • voquezna dual pak

    with vonoprazan

  • voquezna triple pak

    with vonoprazan, clarithromycin

    Also known as vonoprazan, amoxicillin, and clarithromycin, vonoprazan+amoxicillin+clarithromycin 14 days, vonoprazan+amoxicillin+clarithromycin 7 days

Approval history

  • approvedPriority reviewJan 18, 1974

Chemistry & pharmacology

Loading structure…

SMILES

CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccc(O)cc3)C(=O)N2[C@H]1C(=O)O
Mol. weight
365.41 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Single Stereoisomer
Inorganic
No
Polymer
No
Delivery
Oral
Availability
Prescription Only

Oral

Yes

Parenteral

No

Topical

No

Sources

Also known as

  • amix 125
  • amix 250
  • amix 500
  • amocillin
  • amocilline
  • amopen
  • amopen
  • amopen
  • amoram
  • amoram
  • amox
  • amox
  • amoxacillin
  • amoxacillin
  • amoxcillin
  • amoxcillin
  • amoxcillin
  • amoxicilina
  • amoxicilina
  • amoxicilina
  • amoxicillin
  • amoxicillin
  • amoxicillin
  • amoxicillin
  • amoxicillin
  • amoxicillin
  • amoxicillin
  • amoxicillin
  • amoxicillin
  • amoxicillin anhydrous
  • amoxicillin anhydrous
  • amoxicillin anhydrous
  • amoxicillin anhydrous
  • amoxicillin (anhydrous)
  • amoxicillin (anhydrous)
  • amoxicillin - ascorbic acid - niacinamide - riboflavin - thiamine
  • amoxicillin, ascorbic acid, niacinamide, riboflavin, thiamine drug combination
  • amoxicilline
  • amoxicilline
  • amoxicilline
  • amoxicillin hydrate
  • amoxicillin pediatric
  • amoxicillin pediatric
  • amoxicillin sodium
  • amoxicillin sodium
  • amoxicillin sodium
  • amoxicillin trihydrate
  • amoxicillin trihydrate
  • amoxicillin trihydrate
  • amoxicillin trihydrate
  • amoxicillin trihydrate
  • amoxicillin trihydrate
  • amoxicillin trihydrate
  • amoxicillinum
  • amoxicillinum
  • amoxicllin
  • amoxident 250
  • amoxident 500
  • amoxi-inject
  • amoxi-inject
  • amoxil
  • amoxil
  • amoxil
  • amoxil
  • amoxil fiztab
  • amoxil sf
  • amoxi-tabs
  • amoxi-tabs
  • amoxycillin
  • amoxycillin
  • amoxycillin
  • amoxycillin
  • amoxycillin
  • amoxymed
  • amoxymed
  • amrit
  • amrit
  • aquacil
  • biomox
  • biomox
  • brl-2333
  • brl-2333
  • brl-2333ab-b
  • brl-2333ab-b
  • co-amoxiclav
  • combination of fosfomycin, metronidazole and rhgm-csf (administered together intraperitoneally) and three days of antibiotics p.o.
  • dedoxil
  • dedoxil
  • dispermox
  • dispermox
  • flemoxin solutab
  • galenamox
  • galenamox
  • iramox
  • larotid
  • larotid
  • moxacin
  • moxacin
  • moxatag
  • moxatag
  • polymox
  • polymox
  • respillin
  • robamox
  • robamox
  • sumox
  • sumox
  • trimox
  • trimox
  • utimox
  • utimox
  • vetremox
  • wymox
  • wymox
  • zoxycil 250
  • zoxycil 500

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT07296302N/AFeb 28, 2026Universidade Estadual de Montes Claros
NCT07295353N/AJan 31, 2026Free University of Amsterdam, THE AKKERMANSIA COMPANY, University of Amsterdam, ZonMw: The Netherlands Organisation for Health Research and Development
NCT07275580Phase 4Jan 10, 2026Fundação de Amparo à Pesquisa do Estado de São Paulo, University of Sao Paulo
NCT07104552Phase 4Jan 1, 2026Assistance Publique - Hôpitaux de Paris
NCT07293910Phase 2Dec 20, 2025Tanta University
NCT07115173Phase 4Dec 1, 2025Sungkyunkwan University
NCT07242443Phase 4Nov 20, 2025First People's Hospital of Hangzhou
NCT06921213Phase 2Oct 1, 2025Chiangmai University, Medical Research Council, Murdoch University, National University of Ireland, Stellenbosch University, University of London, University of Sydney, Wellcome Trust
NCT06906757N/ASep 30, 2025University of Melbourne
NCT07183462Phase 4Sep 10, 2025Tel Aviv University
NCT07179159N/ASep 9, 2025Qilu Hospital of Shandong University, Shandong University, Shandong University of Traditional Chinese Medicine, Zibo Maternal and Child Health Hospital
NCT07294846Phase 1Sep 8, 2025Sinorda Biomedicine
NCT07159412N/AAug 31, 2025Nanjing Medical University
NCT07040839Phase 4Jul 31, 2025Rehman Medical Institute - RMI
NCT07012785N/AJun 30, 2025Southeast University
NCT07015736Phase 4Jun 10, 2025Eskisehir Osmangazi University
NCT06977841N/AJun 10, 2025Fudan University
NCT06964334Phase 3Jun 1, 2025Assiut University
NCT06895135N/AMay 31, 2025University of Health Sciences Lahore
NCT06901375Early Phase 1 (Phase 1)May 31, 2025Nanjing Medical University
Showing 20 of 366 trials
Page 1 / 19

Organizations

Research & Development (373)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
Shandong UniversityAcademic/Hospital181822017
People's Liberation Army of ChinaGovernment171522017
Nanjing Medical UniversityAcademic/Hospital151342019
Kaohsiung Medical UniversityAcademic/Hospital11832016
Jiao Tong UniversityAcademic/Hospital10912018
Zhejiang UniversityAcademic/Hospital9622017
Fudan UniversityAcademic/Hospital8822017
GlaxoSmithKlineFor profit5332011
Mackay Medical CollegeAcademic/Hospital5512017
Sun Yat-Sen UniversityAcademic/Hospital5532022
Alexandria UniversityAcademic/Hospital4432019
Central South UniversityAcademic/Hospital4422017
Chang Gung UniversityAcademic/Hospital4422016
Monash UniversityAcademic/Hospital4322023
University of California, San FranciscoAcademic/Hospital4422017
University of CampinasAcademic/Hospital4322006
University of LondonAcademic/Hospital4322018
University of TorontoAcademic/Hospital4342018
University of WashingtonAcademic/Hospital4022021
Washington University in St. LouisAcademic/Hospital4422017
373 organizations
Page 1 / 19

Marketing (42)

OrganizationOrg typeRelationshipDate
American Home ProductsFor profitMKTG—
Ani PharmaceuticalsFor profitMKTGAug 30, 2013
Ani PharmaceuticalsFor profitMKTGAug 30, 2013
ApotexFor profitMKTGOct 20, 2008
ApotheconFor profitMKTGDec 9, 1974
AtralFor profitMKTGAug 7, 1985
Aurobindo PharmaFor profitMKTGNov 9, 2005
Aurobindo PharmaFor profitSYNJan 17, 2007
Aurobindo PharmaFor profitSYNApr 19, 2019
Belcher PharmaceuticalsFor profitMKTGAug 3, 1978
Chartwell PharmaceuticalsFor profitMKTGAug 3, 1978
Chartwell PharmaceuticalsFor profitSYNDec 8, 1978
Cumberland PharmaceuticalsFor profitNDA2Feb 8, 2011
DAVA PharmaceuticalsFor profitMKTGFeb 25, 1988
Deva Holding A.S.For profitMKTGSep 13, 2023
GlaxoSmithKlineFor profitMKTGJan 18, 1974
GlaxoSmithKlineFor profitNDA2Jan 18, 1974
GlaxoSmithKlineFor profitNDAJan 18, 1974
HikmaFor profitMKTGMar 29, 2006
HikmaFor profitSYNJan 25, 2005
Micro Labs Ltd IndiaFor profitMKTGDec 30, 2016
Micro Labs Ltd IndiaFor profitSYNJun 24, 2022
MylanFor profitMKTG—
NeopharmaFor profitNDA2Aug 2, 1979
NovartisFor profitMKTGMar 14, 2002
Parke-DavisFor profitMKTG—
Phathom Pharmaceuticals, Inc.For profitNDA2May 3, 2022
Pragma TherapeuticsFor profitMKTGJan 23, 2008
Pragma TherapeuticsFor profitNDA2Jan 23, 2008
RanbaxyFor profitMKTGAug 11, 2003
RedHill BiopharmaFor profitNDA2Nov 1, 2019
Rising PharmaceuticalsFor profitMKTGOct 7, 2016
SandozFor profitMKTGSep 30, 1994
SandozFor profitSYNNov 21, 2002
Strides Pharma ScienceFor profitMKTGFeb 25, 1988
Sun PharmaceuticalsFor profitMKTGApr 8, 1999
TakedaFor profitNDA2Dec 2, 1997
TevaFor profitMKTGFeb 9, 1976
TevaFor profitSYNOct 29, 2002
US AntibioticsFor profitNDA2Aug 2, 1979
US AntibioticsFor profitMKTGAug 2, 1979
WockhardtFor profitMKTGJun 18, 2007