azelaic acid

Trade name: azelex

Small moleculeapproved

Approved

Sep 13, 1995

Azelaic acid, a naturally occurring saturated dicarboxylic acid found in wheat, rye, and barley, possesses antimicrobial activity, affects keratin production, and reduces inflammation. One of the brand name for azelaic acid is FINACEA,Gel, 15% is indicated for topical treatment of the inflammatory papules and pustules of mild to moderate rosacea. Although some reduction of erythema, which was present in patients with papules, and pustules of rosacea occurred in clinical studies, efficacy for treatment of erythema in rosacea in the absence of papules and pustules has not been evaluated. Rosacea is a common skin condition thought to be primarily an inflammatory disorder. Neutrophils, in particular, have been implicated in the inflammation associated with rosacea and mediate many of their effects through the release of reactive oxygen species. Many effective agents for rosacea, including topical azelaic acid have anti-inflammatory properties. Azelaic acid per se has multiple modes of action in rosacea, but an anti-inflammatory effect achieved by reducing reactive oxygen species appears to be the main pharmacological action. A possible mechanism of action for azelaic acid in the human epidermis includes its possibility to inhibit tyrosinase and of membrane-associated thioredoxin reductase enzymes, this enzyme is shown to regulate tyrosinase through a feedback mechanism involving electron transfer to intracellular thioredoxin, followed by a specific interaction between reduced thioredoxin and tyrosinase. — NCATS

Clinical trial activity

39 trials · 29 clinical orgs · 11 marketing orgs

Phase 1
7
Phase 2
15
Phase 3
13
Phase 4
12

Earliest trial started Jan 1, 2002 (NCT00031096)

Timeline

1990s

  1. Sep 13, 1995

    Almirall — Earliest FDA Approval

  2. Sep 13, 1995

    Aqua Pharmaceuticals — NDA Secondary Org

  3. Sep 13, 1995

    Almirall — NDA Secondary Org

  4. Sep 13, 1995

    Almirall — NDA Organization

2000s

  1. Jan 1, 2002

    Earliest Phase 3 Sponsor(trial)

  2. Dec 24, 2002

    Leo Pharma — NDA Secondary Org

  3. Jan 1, 2006

    Earliest Phase 2 Sponsor(trial)

2010s

  1. Jan 1, 2011

    Earliest Phase 1 Sponsor(trial)

  2. Nov 19, 2018

    Actavis — Marketing Organization

  3. Nov 19, 2018

    Glenmark Pharmaceuticals — Marketing Organization

  4. Nov 19, 2018

    Tolmar Inc. — Marketing Organization

  5. Nov 19, 2018

    Encube Ethicals Pvt. Ltd. — Marketing Organization

  6. Nov 19, 2018

    Allergan PLC (2015) — Marketing Organization

  7. Aug 23, 2019

    Taro Pharmaceuticals — Marketing Organization

  8. Aug 23, 2019

    Sun Pharmaceuticals — Marketing Organization

2020s

  1. Oct 7, 2020

    Teva — Marketing Organization

Indications

Mechanism of action

  • Unspecified targetOTHER

    Unknown

    May act through thioredoxin reductase of acne causing bacteria (e.g., Staphylococcus epidermidis and Propionibacterium acnes)

Approval history

  • approvedSep 13, 1995

Chemistry & pharmacology

Loading structure…

SMILES

OC(=O)CCCCCCCC(O)=O
Mol. weight
188.2209 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Achiral Molecule
Inorganic
No
Polymer
No
Delivery
Topical
Availability
Prescription Only

Oral

No

Parenteral

No

Topical

Yes

Sources

Also known as

  • 1,7-dicarboxyheptane
  • 1,7-dicarboxyheptane
  • 1,7-heptanedicarboxylic acid
  • 1,7-heptanedicarboxylic acid
  • 1,9-nonanedioic acid
  • 1,9-nonanedioic acid
  • acide azélaïque
  • acide azélaïque
  • ácido azelaico
  • ácido azelaico
  • acidum acelaicum
  • acidum acelaicum
  • acidum azelaicum
  • acidum azelaicum
  • anchoic acid
  • anchoic acid
  • anchoic acid
  • asf1057
  • azaleic acid
  • azelaic acid
  • azelaic acid
  • azelaic acid
  • azelaic acid
  • azelaic acid
  • azelaic acid
  • azelaic acid
  • azelaic acid
  • azelaic acid
  • azelaic acid
  • azelaic acid, dilithium salt
  • azelaic acid dipotassium salt
  • azelaic acid, dipotassium salt
  • azelaic acid, disodium salt
  • azelaic acid, monosodium salt
  • azelaic acid, potassium salt
  • azelaic acid, sodium salt
  • azelainsaeure
  • azelainsaeure
  • azelainsäure
  • azelainsäure
  • azelex
  • azelex
  • azelex
  • azelex
  • finacea
  • finacea
  • finacea
  • finacea
  • lepargylic acid
  • lepargylic acid
  • lepargylic acid
  • monosodium azelate
  • n-nonanedioic acid
  • n-nonanedioic acid
  • n-nonanedioic acid
  • nonandisaeure
  • nonandisaeure
  • nonandisäure
  • nonandisäure
  • nonanedioic acid
  • nonanedioic acid
  • nonanedioic acid
  • nonanedioic acid
  • nonanedioic acid
  • nonanedioic acid
  • skinoren
  • skinoren
  • skinoren
  • skinoren
  • zk-62498
  • zk-62498

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT06966388Phase 1Aug 13, 2025Virginia Commonwealth University
NCT06090071Phase 4Dec 31, 2023Austin Institute for Clinical Research, SkinCeuticals
NCT05416333Early Phase 1 (Phase 1)Jan 31, 2023Wake Forest University
NCT05887219Phase 1Nov 1, 2022Government of Pakistan
NCT03826277N/AFeb 28, 2019Higher School of Applied Sciences (VIST)
NCT03689010Phase 3Dec 12, 2017Taro Pharmaceuticals
NCT03418610Phase 4Dec 6, 2017Bayer, Clinical Research Center of the Carolinas
NCT02800148Phase 3Nov 1, 2016DPT Laboratories, Perrigo
NCT03287791Phase 3Jul 19, 2016Actavis
NCT03094403Phase 1Jul 1, 2016Catawba Clinical Research, Taro Pharmaceuticals
NCT03071549Phase 3Apr 1, 2016Cairo University
NCT02147691Phase 4May 1, 2014Bayer, Derm Research, PLLC
NCT02058628Phase 4Feb 1, 2014GlaxoSmithKline
NCT02120924Phase 3Jul 1, 2013Actavis, Akesis, LLC
NCT01555463Phase 3Sep 1, 2012Bayer
NCT01659853Phase 3Sep 1, 2012Galderma
NCT01850095N/AMar 1, 2012Associacao Fundo de Incentivo a Psicofarmcologia, Bayer, Federal University of São Paulo, Sao Paulo State University, University of Sao Paulo
NCT01494467Phase 3Dec 1, 2011Galderma
NCT01493687Phase 3Dec 1, 2011Galderma
NCT01430312Phase 1Sep 1, 2011Bayer
Showing 20 of 39 trials
Page 1 / 2

Organizations

Research & Development (29)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
BayerFor profit171152002
GaldermaFor profit5522010
Wake Forest UniversityAcademic/Hospital3332010
ActavisFor profit2212013
Derm Research, PLLCFor profit2212009
Taro PharmaceuticalsFor profit2222016
Akesis, LLCFor profit1012013
Associacao Fundo de Incentivo a PsicofarmcologiaAcademic/Hospital1012012
Astion Pharma A/SFor profit1112007
Austin Institute for Clinical ResearchFor profit1112023
Cairo UniversityAcademic/Hospital1112016
Callender Center for Clinical ResearchAcademic/Hospital1112009
Catawba Clinical ResearchFor profit1012016
Clinical Research Center of the CarolinasFor profit1112017
Dermatology SpecialistsAcademic/Hospital1012010
Dermatology Specialists ResearchAcademic/Hospital1112010
DPT LaboratoriesFor profit1012016
Federal University of São PauloAcademic/Hospital1112012
GlaxoSmithKlineFor profit1112014
Government of PakistanGovernment1112022
29 organizations
Page 1 / 2

Marketing (14)

OrganizationOrg typeRelationshipDate
ActavisFor profitMKTGNov 19, 2018
Allergan PLC (2015)For profitMKTGNov 19, 2018
AlmirallFor profitNDA2Sep 13, 1995
AlmirallFor profitNDASep 13, 1995
Aqua PharmaceuticalsFor profitNDA2Sep 13, 1995
Encube Ethicals Pvt. Ltd.For profitMKTGNov 19, 2018
Glenmark PharmaceuticalsFor profitMKTGNov 19, 2018
Glenmark PharmaceuticalsFor profitSYNNov 19, 2018
Leo PharmaFor profitNDA2Dec 24, 2002
Sun PharmaceuticalsFor profitMKTGAug 23, 2019
Taro PharmaceuticalsFor profitSYNApr 19, 2021
Taro PharmaceuticalsFor profitMKTGAug 23, 2019
TevaFor profitMKTGOct 7, 2020
Tolmar Inc.For profitMKTGNov 19, 2018