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ketoconazole

Trade name: nizoral

Small moleculeapproved

Approved

Jun 12, 1981

2S,4R ketoconazole or levoketoconazole is the 2S,4R enantiomer of ketoconazole, purified from racemic ketoconazole. Both enantiomers exerts antifungal activity. Ketoconazole activates AhR in gene reporter cell line and dose-dependently induces CYP1A1 mRNA and CYP1A1 protein in HepG2 cells, with enantiospecific pattern, i.e. 2R,4S ketoconazole was much more active as compared to 2S,4R ketoconazole. Levoketoconazole was shown to be a more potent inhibitor than the 2R,4S enantiomer of several enzymes in the steroidogenic pathway (CYP11B1, CYP17 and CYP21). Levoketoconazole was tested for the treatment of endogenous Cushing’s syndrome (Phase III) and type 2 diabetes mellitus (Phase II). — NCATS

Clinical trial activity

181 trials · 145 clinical orgs · 25 marketing orgs

Phase 1
113
Phase 2
55
Phase 3
25
Phase 4
6

Earliest trial started Sep 1, 1994 (NCT00000579)

Timeline

1980s

  1. Jun 12, 1981

    Janssen Pharmaceutica NV — Earliest FDA Approval

  2. Jun 12, 1981

    Janssen Pharmaceutica NV — NDA Organization

  3. Dec 31, 1985

    Johnson and Johnson — NDA Secondary Org

1990s

  1. Jan 1, 1994

    Earliest Phase 3 Sponsor(trial)

  2. Jan 1, 1997

    Earliest Phase 2 Sponsor(trial)

  3. Oct 10, 1997

    Kramer — NDA Secondary Org

  4. Jan 1, 1998

    Earliest Phase 1 Sponsor(trial)

  5. Jun 15, 1999

    Heritage Pharma — Marketing Organization

  6. Jun 15, 1999

    Chartwell Pharmaceuticals — Marketing Organization

  7. Jun 15, 1999

    Pliva — Marketing Organization

  8. Jun 15, 1999

    Sun Pharmaceuticals — Marketing Organization

  9. Jun 15, 1999

    Taro Pharmaceuticals — Marketing Organization

  10. Jun 15, 1999

    Teva — Marketing Organization

  11. Jul 27, 1999

    AAIPharma — Marketing Organization

  12. Dec 23, 1999

    Aurobindo Pharma — Marketing Organization

  13. Dec 23, 1999

    Mylan — Marketing Organization

2000s

  1. Jan 10, 2002

    Aavis Pharma — Marketing Organization

  2. Jan 10, 2002

    Apotex — Marketing Organization

  3. Jan 10, 2002

    Senores Pharms — Marketing Organization

  4. Jan 10, 2002

    RISE PHARMA — Marketing Organization

  5. Jan 7, 2004

    Padagis Us — Marketing Organization

  6. Apr 28, 2004

    Fougera — Marketing Organization

  7. Apr 11, 2005

    Tolmar Inc. — Marketing Organization

  8. Jul 28, 2006

    Almirall — NDA Secondary Org

  9. Jun 12, 2007

    Mylan — NDA Secondary Org

2010s

  1. Aug 25, 2011

    Perrigo — Marketing Organization

  2. Jun 18, 2018

    Strides Pharma Science — Marketing Organization

2020s

  1. May 20, 2021

    Encube Ethicals Pvt. Ltd. — Marketing Organization

  2. May 21, 2021

    Exeltis — Marketing Organization

  3. Nov 17, 2021

    Tasman Pharma — Marketing Organization

Indications

Approved for

Studied for

Mechanism of action

Approval history

  • approvedPriority reviewJun 12, 1981

Chemistry & pharmacology

Loading structure…

SMILES

CC(=O)N1CCN(c2ccc(OCC3COC(Cn4ccnc4)(c4ccc(Cl)cc4Cl)O3)cc2)CC1
Mol. weight
531.44 g/mol
Lipinski Ro5
1 violation(s)
Rule of 3
No
Chirality
Racemic Mixture
Inorganic
No
Polymer
No
Delivery
Oral, Topical
Availability
Over the Counter

Oral

Yes

Parenteral

No

Topical

Yes

Black box warning

Sources

Also known as

  • 2s, 4r ketoconazole
  • 2s, 4r ketoconazole
  • brizoral
  • cor-003
  • cor-003
  • cor-003
  • daktarin gold
  • daktarin intensiv
  • dandrazol
  • dandrid
  • dio-902
  • dio-902
  • extina
  • extina
  • fungarest
  • fungoral
  • ketaconazole
  • ketaconazole
  • ketoconazol
  • ketoconazol
  • ketoconazol
  • ketoconazole
  • ketoconazole
  • ketoconazole
  • ketoconazole
  • ketoconazole
  • ketoconazole
  • ketoconazole
  • ketoconazole
  • ketoconazole
  • ketoconazole
  • ketoconazole
  • ketoconazole
  • ketoconazole
  • (+/-)-ketoconazole
  • ketoconazolum
  • ketoconazolum
  • ketoderm
  • ketoisdin
  • ketokonazole
  • ketopine
  • ketosidin
  • ketozole
  • ketozole
  • ketozole
  • ketozoral
  • levoketoconazole
  • levoketoconazole
  • nizoral
  • nizoral
  • nizoral
  • nizoral
  • nizoral a-d
  • nizoral a-d
  • nizorelle
  • nizral
  • panfungol
  • panfungol
  • panfungol
  • r-41400
  • r-41400
  • r-41400
  • xolegel
  • xolegel

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT05638763Phase 2Nov 30, 2024Universidad Autonoma de Nuevo Leon
NCT06577077Phase 3Sep 30, 2024Ache Laboratorios Farmaceuticos S.A.
NCT07237763N/AJan 15, 2024Cairo University
NCT06305637Phase 1Dec 4, 2023Taro Pharmaceuticals
NCT04869449Early Phase 1 (Phase 1)Jan 31, 2022Pennsylvania State University
NCT04886323N/AJun 1, 2021Anhui Medical University, Hefei CAS Ion Medical and Technical Devices Co.,Ltd
NCT04246190Phase 1Feb 24, 2020Chong Kun Dang Pharmaceutical, Yonsei University
NCT04203342Phase 1Jan 6, 2020ACM Global Laboratories, Douglas Pharmaceuticals, Novum Pharmaceutical Research Services
NCT04212000Phase 1Dec 16, 2019Cortendo AB
NCT04037605Early Phase 1 (Phase 1)Jul 24, 2019Los Angeles Biomedical Research Institute
NCT03763396Early Phase 1 (Phase 1)May 31, 2019University of Toronto
NCT03845348Phase 3Apr 1, 2019Big Leap Clinical Research Joint Stock Company, Sunstar Joint Stock Company
NCT03880825Phase 1Mar 28, 2019Cortendo AB
NCT03796273Early Phase 1 (Phase 1)Mar 13, 2019National Cancer Institute (NCI), Wake Forest University
NCT05054023Phase 2/Phase 3 (Phase 3)Jan 21, 2019University of Monastir
NCT03768388Phase 1Nov 30, 2018Cortendo AB
NCT03688971Phase 2Oct 31, 2018Cutanea Life Sciences, Inc.
NCT04007237Phase 4Sep 1, 2018University of Indonesia
NCT03824912Phase 3Aug 23, 2018ACM Global Laboratories, Encube Ethicals Pvt. Ltd., Novum Pharmaceutical Research Services
NCT03471364Early Phase 1 (Phase 1)Aug 22, 2018Mayo Clinic, National Cancer Institute (NCI)
Showing 20 of 181 trials
Page 1 / 10

Organizations

Research & Development (145)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
National Cancer Institute (NCI)Government20541996
GlaxoSmithKlineFor profit181532006
Boehringer IngelheimFor profit7712008
Johnson and JohnsonFor profit7732007
PfizerFor profit7721999
AstraZenecaFor profit6522006
Cortendo ABFor profit6622014
University of Texas at HoustonAcademic/Hospital6521996
National Institutes of Health (NIH)Government5141995
The University of Texas, DallasAcademic/Hospital5031994
AbbottFor profit4412008
Harvard UniversityAcademic/Hospital4231994
RocheFor profit4412010
University of California, San FranciscoAcademic/Hospital4221994
AstellasFor profit3312006
BayerFor profit3222006
Biolab Sanus FarmaceuticaFor profit3222014
Bristol-Myers SquibbFor profit3312005
CelgeneFor profit3312011
Cornell UniversityAcademic/Hospital3312000
145 organizations
Page 1 / 8

Marketing (29)

OrganizationOrg typeRelationshipDate
AAIPharmaFor profitMKTGJul 27, 1999
Aavis PharmaFor profitMKTGJan 10, 2002
AlmirallFor profitNDA2Jul 28, 2006
ApotexFor profitMKTGJan 10, 2002
Aurobindo PharmaFor profitMKTGDec 23, 1999
Chartwell PharmaceuticalsFor profitMKTGJun 15, 1999
Encube Ethicals Pvt. Ltd.For profitMKTGMay 20, 2021
ExeltisFor profitMKTGMay 21, 2021
FougeraFor profitMKTGApr 28, 2004
Heritage PharmaFor profitMKTGJun 15, 1999
Janssen Pharmaceutica NVFor profitNDAJun 12, 1981
Johnson and JohnsonFor profitNDA2Dec 31, 1985
Johnson and JohnsonFor profitSYNJun 12, 1981
Johnson and JohnsonFor profitMKTG—
KramerFor profitNDA2Oct 10, 1997
MylanFor profitNDA2Jun 12, 2007
MylanFor profitMKTGDec 23, 1999
Padagis UsFor profitMKTGJan 7, 2004
PerrigoFor profitMKTGAug 25, 2011
PerrigoFor profitSYNJan 7, 2004
PlivaFor profitMKTGJun 15, 1999
RISE PHARMAFor profitMKTGJan 10, 2002
Senores PharmsFor profitMKTGJan 10, 2002
Strides Pharma ScienceFor profitMKTGJun 18, 2018
Sun PharmaceuticalsFor profitMKTGJun 15, 1999
Taro PharmaceuticalsFor profitMKTGJun 15, 1999
Tasman PharmaFor profitMKTGNov 17, 2021
TevaFor profitMKTGJun 15, 1999
Tolmar Inc.For profitMKTGApr 11, 2005