azelaic acid
Trade name: azelex
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
Earliest trial started Jan 1, 2002 (NCT00031096)
Timeline
1990s
- Sep 13, 1995
Almirall — Earliest FDA Approval
- Sep 13, 1995
Aqua Pharmaceuticals — NDA Secondary Org
- Sep 13, 1995
Almirall — NDA Secondary Org
- Sep 13, 1995
Almirall — NDA Organization
2000s
- Jan 1, 2002
Earliest Phase 3 Sponsor(trial)
- Dec 24, 2002
Leo Pharma — NDA Secondary Org
- Jan 1, 2006
Earliest Phase 2 Sponsor(trial)
2010s
- Jan 1, 2011
Earliest Phase 1 Sponsor(trial)
- Nov 19, 2018
Actavis — Marketing Organization
- Nov 19, 2018
Glenmark Pharmaceuticals — Marketing Organization
- Nov 19, 2018
Tolmar Inc. — Marketing Organization
- Nov 19, 2018
Encube Ethicals Pvt. Ltd. — Marketing Organization
- Nov 19, 2018
Allergan PLC (2015) — Marketing Organization
- Aug 23, 2019
Taro Pharmaceuticals — Marketing Organization
- Aug 23, 2019
Sun Pharmaceuticals — Marketing Organization
2020s
- Oct 7, 2020
Teva — Marketing Organization
Indications
Approved for
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
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
- WikipediaAzelaic acid ↗
- NCATSF2VW3D43YT ↗
- ChEMBLCHEMBL1238 ↗
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 ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT06966388 | Phase 1 | Aug 13, 2025 | Virginia Commonwealth University |
| NCT06090071 | Phase 4 | Dec 31, 2023 | Austin Institute for Clinical Research, SkinCeuticals |
| NCT05416333 | Early Phase 1 (Phase 1) | Jan 31, 2023 | Wake Forest University |
| NCT05887219 | Phase 1 | Nov 1, 2022 | Government of Pakistan |
| NCT03826277 | N/A | Feb 28, 2019 | Higher School of Applied Sciences (VIST) |
| NCT03689010 | Phase 3 | Dec 12, 2017 | Taro Pharmaceuticals |
| NCT03418610 | Phase 4 | Dec 6, 2017 | Bayer, Clinical Research Center of the Carolinas |
| NCT02800148 | Phase 3 | Nov 1, 2016 | DPT Laboratories, Perrigo |
| NCT03287791 | Phase 3 | Jul 19, 2016 | Actavis |
| NCT03094403 | Phase 1 | Jul 1, 2016 | Catawba Clinical Research, Taro Pharmaceuticals |
| NCT03071549 | Phase 3 | Apr 1, 2016 | Cairo University |
| NCT02147691 | Phase 4 | May 1, 2014 | Bayer, Derm Research, PLLC |
| NCT02058628 | Phase 4 | Feb 1, 2014 | GlaxoSmithKline |
| NCT02120924 | Phase 3 | Jul 1, 2013 | Actavis, Akesis, LLC |
| NCT01555463 | Phase 3 | Sep 1, 2012 | Bayer |
| NCT01659853 | Phase 3 | Sep 1, 2012 | Galderma |
| NCT01850095 | N/A | Mar 1, 2012 | Associacao Fundo de Incentivo a Psicofarmcologia, Bayer, Federal University of São Paulo, Sao Paulo State University, University of Sao Paulo |
| NCT01494467 | Phase 3 | Dec 1, 2011 | Galderma |
| NCT01493687 | Phase 3 | Dec 1, 2011 | Galderma |
| NCT01430312 | Phase 1 | Sep 1, 2011 | Bayer |
Organizations
Research & Development (29)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Bayer | For profit | 17 | 11 | 5 | 2002 |
| Galderma | For profit | 5 | 5 | 2 | 2010 |
| Wake Forest University | Academic/Hospital | 3 | 3 | 3 | 2010 |
| Actavis | For profit | 2 | 2 | 1 | 2013 |
| Derm Research, PLLC | For profit | 2 | 2 | 1 | 2009 |
| Taro Pharmaceuticals | For profit | 2 | 2 | 2 | 2016 |
| Akesis, LLC | For profit | 1 | 0 | 1 | 2013 |
| Associacao Fundo de Incentivo a Psicofarmcologia | Academic/Hospital | 1 | 0 | 1 | 2012 |
| Astion Pharma A/S | For profit | 1 | 1 | 1 | 2007 |
| Austin Institute for Clinical Research | For profit | 1 | 1 | 1 | 2023 |
| Cairo University | Academic/Hospital | 1 | 1 | 1 | 2016 |
| Callender Center for Clinical Research | Academic/Hospital | 1 | 1 | 1 | 2009 |
| Catawba Clinical Research | For profit | 1 | 0 | 1 | 2016 |
| Clinical Research Center of the Carolinas | For profit | 1 | 1 | 1 | 2017 |
| Dermatology Specialists | Academic/Hospital | 1 | 0 | 1 | 2010 |
| Dermatology Specialists Research | Academic/Hospital | 1 | 1 | 1 | 2010 |
| DPT Laboratories | For profit | 1 | 0 | 1 | 2016 |
| Federal University of São Paulo | Academic/Hospital | 1 | 1 | 1 | 2012 |
| GlaxoSmithKline | For profit | 1 | 1 | 1 | 2014 |
| Government of Pakistan | Government | 1 | 1 | 1 | 2022 |
Marketing (14)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Actavis | For profit | MKTG | Nov 19, 2018 |
| Allergan PLC (2015) | For profit | MKTG | Nov 19, 2018 |
| Almirall | For profit | NDA2 | Sep 13, 1995 |
| Almirall | For profit | NDA | Sep 13, 1995 |
| Aqua Pharmaceuticals | For profit | NDA2 | Sep 13, 1995 |
| Encube Ethicals Pvt. Ltd. | For profit | MKTG | Nov 19, 2018 |
| Glenmark Pharmaceuticals | For profit | MKTG | Nov 19, 2018 |
| Glenmark Pharmaceuticals | For profit | SYN | Nov 19, 2018 |
| Leo Pharma | For profit | NDA2 | Dec 24, 2002 |
| Sun Pharmaceuticals | For profit | MKTG | Aug 23, 2019 |
| Taro Pharmaceuticals | For profit | SYN | Apr 19, 2021 |
| Taro Pharmaceuticals | For profit | MKTG | Aug 23, 2019 |
| Teva | For profit | MKTG | Oct 7, 2020 |
| Tolmar Inc. | For profit | MKTG | Nov 19, 2018 |