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oxacillin

Trade name: pathocil

Small moleculeapproved

Approved

May 9, 1968

Oxacillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Oxacillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Oxacillin results from the inhibition of cell wall synthesis and is mediated through Oxacillin binding to penicillin binding proteins (PBPs). Oxacillin is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, Oxacillin inhibits 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 Oxacillin interferes with an autolysin inhibitor. Oxacillin is used in the treatment of resistant staphylococci infections. Oxacillin sodium was marketed under the trade name Bactocill. — NCATS

Clinical trial activity

11 trials · 12 clinical orgs · 23 marketing orgs

Phase 1
1
Phase 2
7
Phase 3
4
Phase 4
3

Earliest trial started Apr 1, 2002 (NCT00037050)

Timeline

1960s

  1. May 9, 1968

    American Home Products — Earliest FDA Approval

  2. May 9, 1968

    American Home Products — NDA Organization

1970s

  1. Apr 8, 1971

    Sandoz — Marketing Organization

  2. Jul 27, 1973

    GlaxoSmithKline — Marketing Organization

1980s

  1. Mar 10, 1980

    Ani Pharmaceuticals — Marketing Organization

  2. May 15, 1980

    Teva — Marketing Organization

  3. Sep 29, 1988

    Watson Pharmaceuticals — Marketing Organization

  4. Oct 26, 1989

    Baxalta — NDA Secondary Org

  5. Oct 26, 1989

    Baxter — NDA Secondary Org

1990s

  1. Dec 11, 1995

    Istituto Bio Ita Spa — Marketing Organization

2000s

  1. Jan 1, 2002

    Pfizer — Earliest Phase 3 Sponsor(trial)

  2. Jan 1, 2003

    Earliest Phase 2 Sponsor(trial)

2010s

  1. Mar 30, 2012

    Sagent Pharmaceuticals, Inc. — Marketing Organization

  2. Jan 18, 2013

    Aurobindo Pharma — Marketing Organization

  3. Jan 18, 2013

    Eugia Pharma — Marketing Organization

  4. Aug 25, 2014

    Mylan — Marketing Organization

  5. Aug 25, 2014

    STERISCIENCE — Marketing Organization

  6. Aug 25, 2014

    ONESOURCE SPECIALTY — Marketing Organization

  7. Dec 11, 2015

    Hospira — Marketing Organization

  8. Dec 11, 2015

    Pfizer — Marketing Organization

  9. Jul 31, 2017

    Wockhardt — Marketing Organization

  10. Sep 11, 2017

    Renaissance Pharma — Marketing Organization

  11. Sep 11, 2017

    Piramal — Marketing Organization

2020s

  1. Jul 20, 2020

    Fresenius — Marketing Organization

  2. Jan 1, 2023

    Earliest Phase 1 Sponsor(trial)

Indications

Approved for

Studied for

Mechanism of action

Approval history

  • approvedMay 9, 1968

Chemistry & pharmacology

Loading structure…

SMILES

Cc1onc(-c2ccccc2)c1C(=O)N[C@@H]1C(=O)N2[C@@H]1SC(C)(C)[C@@H]2C(=O)[O-].O.[Na+]
Mol. weight
441.44 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Single Stereoisomer
Inorganic
No
Polymer
No
Delivery
Oral, Parenteral
Availability
Prescription Only

Oral

Yes

Parenteral

Yes

Topical

No

Sources

Also known as

  • (2s,5r,6r)-3,3-dimethyl-6-{[(5-methyl-3-phenylisoxazol-4-yl)carbonyl]amino}-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • (2s,5r,6r)-3,3-dimethyl-6-{[(5-methyl-3-phenylisoxazol-4-yl)carbonyl]amino}-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • (5-methyl-3-phenyl-4-isoxazolyl)penicillin
  • (5-methyl-3-phenyl-4-isoxazolyl)penicillin
  • 5-methyl-3-phenyl-4-isoxazolyl-penicillin
  • 5-methyl-3-phenyl-4-isoxazolyl-penicillin
  • 6beta-(5-methyl-3-phenylisoxazol-4-yl)penicillanic acid
  • 6beta-(5-methyl-3-phenylisoxazol-4-yl)penicillanic acid
  • bactocill
  • bactocill
  • cryptocillin
  • cryptocillin
  • oxacilina
  • oxacilina
  • oxacillin
  • oxacillin
  • oxacillin
  • oxacillin
  • oxacillin
  • oxacillin
  • oxacillin
  • oxacillin
  • oxacilline
  • oxacilline
  • oxacillin sodium
  • oxacillin sodium
  • oxacillin sodium
  • oxacillin sodium
  • oxacillin sodium hydrate
  • oxacillin sodium hydrate
  • oxacillin sodium hydrate
  • oxacillin sodium hydrate
  • oxacillin sodium hydrate
  • oxacillin sodium hydrate
  • oxacillinum
  • oxacillinum
  • oxazocillin
  • oxazocillin
  • oxazocillin
  • oxazocilline
  • oxazocilline
  • oxazocilline
  • p-12
  • p-12
  • prostaphlin
  • prostaphlin
  • prostaphlin
  • so 16423
  • so 16423
  • sq-16423
  • sq-16423

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT06616168Phase 1Sep 1, 2023Lviv National Medical University
NCT05156437Phase 4Dec 20, 2021West Virginia University
NCT04775953Phase 2Apr 22, 2021National Institute of Allergy and Infectious Diseases (NIAID)
NCT02344511Phase 3Mar 1, 2016Actavis, Allergan
NCT02701595Phase 3Mar 1, 2016François Rabelais University, University of Toulouse
NCT02701608Phase 3Mar 1, 2016François Rabelais University, University of Toulouse
NCT01104662Phase 4Apr 1, 2010Cubist
NCT00428844Phase 2Jan 1, 2007Cubist
NCT01166932Phase 4Apr 1, 2005Sao Paulo State University
NCT00062647Phase 2Aug 1, 2003Duke University, Theravance
NCT00037050Phase 3Apr 1, 2002Pfizer
Showing 11 of 11 trials
Page 1 / 1

Organizations

Research & Development (12)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
CubistFor profit2222007
François Rabelais UniversityAcademic/Hospital2012016
University of ToulouseAcademic/Hospital2212016
ActavisFor profit1112016
AllerganFor profit1012016
Duke UniversityAcademic/Hospital1012003
Lviv National Medical UniversityAcademic/Hospital1112023
National Institute of Allergy and Infectious Diseases (NIAID)Government1112021
PfizerFor profit1112002
Sao Paulo State UniversityAcademic/Hospital1112005
TheravanceFor profit1112003
West Virginia UniversityAcademic/Hospital1112021
12 organizations
Page 1 / 1

Marketing (27)

OrganizationOrg typeRelationshipDate
American Home ProductsFor profitNDAMay 9, 1968
Ani PharmaceuticalsFor profitMKTGMar 10, 1980
Ani PharmaceuticalsFor profitSYNMar 10, 1980
ApotheconFor profitNDA2—
ApotheconFor profitMKTG—
Aurobindo PharmaFor profitMKTGJan 18, 2013
BaxaltaFor profitNDA2Oct 26, 1989
BaxterFor profitNDA2Oct 26, 1989
Elkins SinnFor profitMKTG—
Eugia PharmaFor profitMKTGJan 18, 2013
FreseniusFor profitMKTGJul 20, 2020
GlaxoSmithKlineFor profitMKTGJul 27, 1973
HospiraFor profitMKTGDec 11, 2015
HospiraFor profitSYNDec 11, 2015
Istituto Bio Ita SpaFor profitMKTGDec 11, 1995
MylanFor profitMKTGAug 25, 2014
ONESOURCE SPECIALTYFor profitMKTGAug 25, 2014
PfizerFor profitMKTGDec 11, 2015
PiramalFor profitMKTGSep 11, 2017
Renaissance PharmaFor profitMKTGSep 11, 2017
STERISCIENCEFor profitMKTGAug 25, 2014
STERISCIENCEFor profitSYNAug 25, 2014
Sagent Pharmaceuticals, Inc.For profitMKTGMar 30, 2012
SandozFor profitMKTGApr 8, 1971
TevaFor profitMKTGMay 15, 1980
Watson PharmaceuticalsFor profitMKTGSep 29, 1988
WockhardtFor profitMKTGJul 31, 2017