azelaic acid 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
270 123-99-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • nonanedioic acid
  • azelaic acid dipotassium salt
  • azelaic acid
  • anchoic acid
  • finacea
  • lepargylic acid
  • n-Nonanedioic acid
  • Molecular weight: 188.22
  • Formula: C9H16O4
  • CLOGP: 1.56
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 2
  • TPSA: 74.60
  • ALOGS: -1.92
  • ROTB: 8
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

None

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 -3.651 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 0.284 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 71.945 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 18.113 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 82.820 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 82.520 % High 1
herg hERG pIC50 3.637 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 25.586 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 2.979 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 85.020 % High 1
kinase-safety-class ACVR2A,ACVR2B,ACVRL1,ALK,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK4,CDK5,CDK9,DDR1,DYRK1B,EGFR,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,GRK3,GSK3B,IKBKB,ITK,JAK1,JAK2,JAK3,KDR,MAP2K6,MAP3K14,MAP3K21,MAP3K7,MAP4K1,MAPK10,MAPK12,MAPK7,MAPK9,MAPKAPK2,MTOR,NTRK2,PDK1,PDK2,PDK4,PIK3CA,PIK3CB,PIK3CD,PIK3CG,PIM2,PRKCD,PRKDC,SIK2,SIK3,STK33,SYK,TEK,TGFBR1,TTK,ULK1,ZAP70 60
kinase-selectivity-class ACVR2B,AXL,BRAF,CDK4,CDK9,CSNK2A2,DDR1,DYRK1B,EIF2AK3,EPHB4,ERBB2,GRK2,JAK2,MAP2K6,MAP3K14,MAPK12,MAPK7,MAPK8,PIK3CB,PIK3CD,PLK1,PRKDC,SIK2,STK33,SYK,TEK,TGFBR1,TTK,UHMK1,ZAP70 30
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 1.862 High 1
mh-clint Mouse hepatocyte intrinsic clearance 63.680 High 1
mppb Mouse plasma protein binding (% unbound) 99.330 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 0.010 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 84.840 % High 1
rh-clint Rat hepatocyte intrinsic clearance 51.050 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 99.410 % High 1
rppb Rat plasma protein binding (% unbound) 66 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 822.243 uM High 1

Approvals:

DateAgencyCompanyOrphan
Sept. 13, 1995 FDA ALLERGAN

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Blepharospasm 579.77 38.73 284 23167 55161 90549835
Taste disorder 491.74 38.73 263 23188 61283 90543713
Epilepsy 418.39 38.73 262 23189 81944 90523052
Infusion site reaction 395.37 38.73 158 23293 18881 90586115
Gastrooesophageal reflux disease 324.99 38.73 299 23152 166038 90438958
Back injury 311.06 38.73 177 23274 46445 90558551
Peripheral venous disease 218.71 38.73 178 23273 83743 90521253
Breast cancer stage III 213.53 38.73 176 23275 84271 90520725
Product quality issue 206.17 38.73 168 23283 79157 90525839
Hypercholesterolaemia 196.09 38.73 181 23270 100711 90504285
Onychomadesis 190.61 38.73 129 23322 45869 90559127
Paraesthesia 181.11 38.73 270 23181 250056 90354940
Facet joint syndrome 176.79 38.73 169 23282 98220 90506776
Memory impairment 172.55 38.73 233 23218 197011 90407985
Wound infection 154.80 38.73 163 23288 106239 90498757
Abdominal pain upper 151.66 38.73 292 23159 332382 90272614
Hypoaesthesia 144.68 38.73 277 23174 313933 90291063
Live birth 144.20 38.73 137 23314 78970 90526026
Bursitis 142.60 38.73 173 23278 131481 90473515
Liver function test increased 134.24 38.73 136 23315 84719 90520277
Overlap syndrome 133.74 38.73 58 23393 8490 90596506
Night sweats 132.66 38.73 165 23286 128601 90476395
Neck pain 120.54 38.73 148 23303 113815 90491181
Dry mouth 118.18 38.73 188 23263 183871 90421125
C-reactive protein increased 114.71 38.73 184 23267 181205 90423791
Gait inability 114.50 38.73 164 23287 146292 90458704
Migraine 112.11 38.73 187 23264 190205 90414791
Obesity 108.33 38.73 135 23316 105372 90499624
Joint range of motion decreased 107.65 38.73 153 23298 135490 90469506
Lung disorder 107.27 38.73 161 23290 149722 90455274
Irritable bowel syndrome 102.97 38.73 189 23262 207259 90397737
Fatigue 100.41 38.73 91 23360 1153932 89451064
Folliculitis 98.68 38.73 184 23267 204169 90400827
Nail disorder 92.17 38.73 94 23357 58973 90546023
Impaired healing 89.23 38.73 191 23260 234008 90370988
Psoriatic arthropathy 85.58 38.73 185 23266 228150 90376846
Sleep disorder 85.41 38.73 170 23281 197860 90407136
Inflammation 83.95 38.73 159 23292 178433 90426563
Lip dry 80.25 38.73 114 23337 100841 90504155
Type 2 diabetes mellitus 79.99 38.73 168 23283 203076 90401920
Musculoskeletal pain 79.92 38.73 152 23299 171099 90433897
Anaemia 78.21 38.73 3 23448 352799 90252197
Maternal exposure during pregnancy 77.89 38.73 237 23214 359826 90245170
Fibromyalgia 74.86 38.73 165 23286 206104 90398892
Osteoarthritis 73.80 38.73 159 23292 195571 90409425
Helicobacter infection 72.97 38.73 173 23278 226677 90378319
Rheumatic fever 72.79 38.73 137 23314 152984 90452012
Anti-cyclic citrullinated peptide antibody positive 71.44 38.73 176 23275 236257 90368739
Stomatitis 71.18 38.73 193 23258 274505 90330491
Duodenal ulcer perforation 70.35 38.73 168 23283 221120 90383876
Product use in unapproved indication 69.61 38.73 218 23233 336018 90268978
Muscle injury 69.47 38.73 146 23305 176508 90428488
Dyspnoea 67.87 38.73 77 23374 880878 89724118
Fall 66.50 38.73 21 23430 481789 90123207
Muscle spasms 65.28 38.73 177 23274 251706 90353290
Hypotension 65.22 38.73 5 23446 325392 90279604
Blister 64.90 38.73 178 23273 254820 90350176
Drug intolerance 62.49 38.73 255 23196 447336 90157660
Muscular weakness 59.42 38.73 151 23300 206515 90398481
Exostosis 59.38 38.73 71 23380 53063 90551933
Cough 56.70 38.73 13 23438 368949 90236047
Nausea 56.36 38.73 128 23323 1110188 89494808
Urinary tract infection 52.87 38.73 8 23443 305624 90299372
Blood cholesterol increased 52.70 38.73 145 23306 207867 90397129
Hypocholesterolaemia 52.65 38.73 28 23423 6421 90598575
Depression 52.45 38.73 184 23267 300417 90304579
Glossodynia 51.93 38.73 192 23259 321587 90283409
Intentional product use issue 50.84 38.73 147 23304 216745 90388251
Back pain 49.07 38.73 11 23440 317164 90287832
Red blood cell sedimentation rate increased 47.04 38.73 80 23371 82515 90522481
Laryngitis 45.86 38.73 61 23390 50692 90554304
Urticaria 45.84 38.73 181 23270 312553 90292443
Injury 45.52 38.73 133 23318 197216 90407780
Therapeutic product effect decreased 45.08 38.73 166 23285 277405 90327591
Synovitis 44.49 38.73 186 23265 329566 90275430
Hepatic enzyme increased 44.47 38.73 198 23253 360538 90244458
Breast cancer stage II 44.13 38.73 50 23401 35284 90569712
Rheumatoid arthritis 43.18 38.73 197 23254 362417 90242579
Drug tolerance 42.45 38.73 36 23415 17880 90587116
General physical health deterioration 42.34 38.73 193 23258 354922 90250074
Wheezing 41.74 38.73 146 23305 237934 90367062
Headache 40.11 38.73 104 23347 862642 89742354
Thrombocytopenia 39.65 38.73 4 23447 208721 90396275
Constipation 39.04 38.73 12 23439 280383 90324613

FDA Adverse Event Reporting System (Male)

None

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Blepharospasm 554.37 52.29 250 20921 54601 110513527
Taste disorder 441.51 52.29 226 20945 65161 110502967
Infusion site reaction 381.22 52.29 139 21032 17543 110550585
Epilepsy 354.10 52.29 227 20944 99982 110468146
Back injury 329.07 52.29 167 21004 47232 110520896
Gastrooesophageal reflux disease 323.72 52.29 271 20900 179705 110388423
Hypercholesterolaemia 256.35 52.29 179 20992 90658 110477470
Breast cancer stage III 249.54 52.29 167 21004 78950 110489178
Product quality issue 229.07 52.29 157 21014 77142 110490986
Peripheral venous disease 221.68 52.29 159 21012 83958 110484170
Onychomadesis 211.27 52.29 123 21048 45540 110522588
Facet joint syndrome 201.72 52.29 159 21012 96669 110471459
Wound infection 189.41 52.29 153 21018 96312 110471816
Paraesthesia 181.12 52.29 243 20928 276278 110291850
Bursitis 170.66 52.29 164 21007 129754 110438374
Memory impairment 168.70 52.29 198 20973 196746 110371382
Maternal exposure during pregnancy 165.38 52.29 223 20948 254660 110313468
Night sweats 160.82 52.29 161 21010 133822 110434306
Abdominal pain upper 158.20 52.29 258 20913 348853 110219275
Impaired healing 152.47 52.29 188 20983 196529 110371599
Folliculitis 151.00 52.29 173 20998 167480 110400648
Live birth 150.95 52.29 117 21054 69367 110498761
Overlap syndrome 150.90 52.29 59 21112 9000 110559128
Irritable bowel syndrome 148.82 52.29 170 21001 164045 110404083
Liver function test increased 146.00 52.29 127 21044 88421 110479707
Gait inability 145.80 52.29 154 21017 136222 110431906
Hypoaesthesia 143.38 52.29 233 20938 313990 110254138
Neck pain 142.34 52.29 145 21026 122985 110445143
Helicobacter infection 136.41 52.29 171 21000 181706 110386422
Glossodynia 134.55 52.29 188 20983 221816 110346312
Dry mouth 132.77 52.29 177 20994 199771 110368357
Anti-cyclic citrullinated peptide antibody positive 128.42 52.29 166 21005 181818 110386310
Obesity 126.51 52.29 131 21040 113220 110454908
Joint range of motion decreased 120.41 52.29 132 21039 121700 110446428
Psoriatic arthropathy 119.76 52.29 167 21004 196594 110371534
Duodenal ulcer perforation 119.02 52.29 158 21013 177542 110390586
C-reactive protein increased 118.06 52.29 175 20996 217744 110350384
Type 2 diabetes mellitus 117.81 52.29 157 21014 177075 110391053
Fibromyalgia 117.62 52.29 154 21017 170755 110397373
Muscle injury 112.98 52.29 137 21034 140670 110427458
Osteoarthritis 109.64 52.29 154 21017 182469 110385659
Lung disorder 108.34 52.29 152 21019 179895 110388233
Migraine 107.91 52.29 148 21023 171504 110396624
Rheumatic fever 106.13 52.29 124 21047 122455 110445673
Nail disorder 105.50 52.29 88 21083 57847 110510281
Blister 104.15 52.29 169 21002 227207 110340921
Sleep disorder 103.98 52.29 157 21014 198487 110369641
Musculoskeletal pain 102.03 52.29 149 21022 182874 110385254
Stomatitis 101.61 52.29 184 20987 270058 110298070
Drug intolerance 95.44 52.29 228 20943 406284 110161844
Hepatic enzyme increased 90.94 52.29 194 20977 320698 110247430
Synovitis 87.41 52.29 174 20997 273918 110294210
Pemphigus 84.34 52.29 149 21022 214421 110353707
Hypotension 83.62 52.29 4 21167 523845 110044283
Anaemia 81.81 52.29 6 21165 547080 110021048
Rheumatoid arthritis 81.29 52.29 178 20993 299435 110268693
Inflammation 79.60 52.29 137 21034 193101 110375027
Blood cholesterol increased 78.74 52.29 133 21038 184652 110383476
Therapeutic product effect decreased 77.76 52.29 155 21016 244161 110323967
Muscle spasms 77.44 52.29 167 21004 277990 110290138
Contraindicated product administered 77.22 52.29 156 21015 248111 110320017
Depression 74.43 52.29 178 20993 317157 110250971
Lip dry 73.21 52.29 93 21078 99990 110468138
Systemic lupus erythematosus 72.28 52.29 154 21017 254184 110313944
Treatment failure 72.13 52.29 162 21009 277072 110291056
Dyspnoea 69.42 52.29 66 21105 1106806 109461322
Fatigue 67.89 52.29 80 21091 1215878 109352250
Muscular weakness 66.66 52.29 147 21024 248321 110319807
Pericarditis 64.95 52.29 135 21036 218979 110349149
Urticaria 64.42 52.29 169 21002 318688 110249440
Fall 64.29 52.29 18 21153 603464 109964664
Exostosis 62.14 52.29 59 21112 45897 110522231
Hand deformity 61.72 52.29 132 21039 218374 110349754
Hypocholesterolaemia 60.77 52.29 28 21143 6393 110561735
Intentional product use issue 60.20 52.29 141 21030 247765 110320363
Neutropenia 59.31 52.29 3 21168 374617 110193511
Injury 55.81 52.29 112 21059 177153 110390975
Product use in unapproved indication 54.73 52.29 199 20972 447178 110120950
Cough 54.60 52.29 11 21160 461630 110106498
Wound 54.38 52.29 131 21040 234306 110333822
General physical health deterioration 53.57 52.29 191 20980 425104 110143024
Death 53.45 52.29 34 21137 698835 109869293

FDA Adverse Event Reporting System (Pediatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Transposition of the great vessels 31.04 23.83 5 10 29 113909

Pharmacologic Action:

SourceCodeDescription
ATC D10AX03 DERMATOLOGICALS
ANTI-ACNE PREPARATIONS
ANTI-ACNE PREPARATIONS FOR TOPICAL USE
Other anti-acne preparations for topical use
FDA PE N0000008841 Decreased Protein Synthesis
FDA PE N0000009982 Decreased Sebaceous Gland Activity
MeSH PA D000970 Antineoplastic Agents
MeSH PA D003879 Dermatologic Agents
CHEBI has role CHEBI:33282 antibacterial agent
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:50177 dermatologic drug
CHEBI has role CHEBI:76924 plant metabolite

Related Drugs by ATC class:

D10AX Other anti-acne preparations for topical use 5 drugs
aluminium chloridealuminium oxideclascoteronedapsoneresorcinol

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Acne vulgaris indication 88616000
Rosacea indication 398909004 DOID:8881
Skin hypopigmented contraindication 23006000
Wilson's disease contraindication 88518009
Skin irritation contraindication 367466007




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 4.46 acidic
pKa2 5.06 acidic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
15% FINACEA LEO PHARMA AS N207071 July 29, 2015 RX AEROSOL, FOAM TOPICAL 10117812 Oct. 18, 2027 TOPICAL TREATMENT OF INFLAMMATORY PAPULES AND PUSTULES OF MILD TO MODERATE ROSACEA
15% FINACEA LEO PHARMA AS N207071 July 29, 2015 RX AEROSOL, FOAM TOPICAL 9211259 Feb. 28, 2029 TOPICAL TREATMENT OF INFLAMMATORY PAPULES AND PUSTULES OF MILD TO MODERATE ROSACEA

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])		Mechanism
action		Bioact sourceMoA source
3-oxo-5-alpha-steroid 4-dehydrogenase 2 Enzyme WOMBAT-PK

External reference:

IDSource
4020935 VUID
N0000148416 NUI
D03034 KEGG_DRUG
18602 RXNORM
C0052761 UMLSCUI
CHEBI:48131 CHEBI
AZ1 PDB_CHEM_ID
CHEMBL1238 ChEMBL_ID
DB00548 DRUGBANK_ID
2266 PUBCHEM_CID
C010038 MESH_SUPPLEMENTAL_RECORD_UI
7484 IUPHAR_LIGAND_ID
5883 INN_ID
F2VW3D43YT UNII
4236 MMSL
46056 MMSL
72313 MMSL
4020935 VANDF
003930 NDDF
108908008 SNOMEDCT_US
386936005 SNOMEDCT_US
F2VW3D43YT INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
azelaic acid HUMAN PRESCRIPTION DRUG LABEL 1 0591-2131 GEL 0.15 g TOPICAL ANDA 16 sections
Azelaic Acid Gel HUMAN PRESCRIPTION DRUG LABEL 1 0781-7172 GEL 0.15 g TOPICAL NDA AUTHORIZED GENERIC 26 sections
Finacea HUMAN PRESCRIPTION DRUG LABEL 1 10922-825 GEL 0.15 g TOPICAL NDA 21 sections
AZELEX HUMAN PRESCRIPTION DRUG LABEL 1 16110-869 CREAM 0.20 g CUTANEOUS NDA 20 sections
Azelaic Acid Gel HUMAN PRESCRIPTION DRUG LABEL 1 21922-038 GEL 0.15 g TOPICAL ANDA 23 sections
Finacea HUMAN PRESCRIPTION DRUG LABEL 1 50090-3032 GEL 0.15 g TOPICAL NDA 23 sections
FINACEA FOAM HUMAN PRESCRIPTION DRUG LABEL 1 50222-303 AEROSOL, FOAM 0.15 g TOPICAL NDA 26 sections
Azelaic Acid HUMAN PRESCRIPTION DRUG LABEL 1 51672-1389 GEL 0.15 g TOPICAL ANDA 26 sections
AZELEX HUMAN PRESCRIPTION DRUG LABEL 1 54868-4442 CREAM 0.20 g CUTANEOUS NDA 20 sections
Finacea HUMAN PRESCRIPTION DRUG LABEL 1 54868-5236 GEL 0.15 g TOPICAL NDA 13 sections
azelaic acid HUMAN PRESCRIPTION DRUG LABEL 1 68462-626 GEL 0.15 g TOPICAL ANDA 23 sections
Azelaic Acid Gel HUMAN PRESCRIPTION DRUG LABEL 1 72162-2297 GEL 0.15 g TOPICAL ANDA 23 sections
AZELAIC ACID 15% / NIACINAMIDE 4% HUMAN PRESCRIPTION DRUG LABEL 2 72934-2008 CREAM 15 g TOPICAL unapproved drug other 4 sections
Rosacea TherapyMoisturizing HUMAN OTC DRUG LABEL 2 73503-009 CREAM 5 g TOPICAL OTC Monograph Drug 17 sections
AnubisMed HUMAN OTC DRUG LABEL 7 83021-402 LIQUID 7 g TOPICAL OTC monograph final 9 sections
10% azelaic acid acne cream HUMAN OTC DRUG LABEL 9 84148-009 CREAM 10 g CUTANEOUS unapproved drug other 12 sections
15% azelaic acid acne cream HUMAN OTC DRUG LABEL 9 84148-010 CREAM 15 g CUTANEOUS unapproved drug other 12 sections
whitening HUMAN OTC DRUG LABEL 3 84356-002 SOAP 10 g TOPICAL OTC Monograph Drug 12 sections
BIBOYA Azelaic Acid Tea Tree Acne Cream HUMAN OTC DRUG LABEL 4 84507-005 CREAM 0.20 mg TOPICAL OTC Monograph Drug 8 sections
KOITE 12% Azelaie Acid Balancing Face Cream HUMAN OTC DRUG LABEL 1 84507-037 CREAM 12 mg TOPICAL OTC Monograph Drug 7 sections
RIGBOO 12% Gel Azelaic Acid Acne HUMAN OTC DRUG LABEL 4 84507-045 GEL 0.00 mg TOPICAL OTC Monograph Drug 7 sections
Acne Buster Salicylic Acid Drying Serum HUMAN OTC DRUG LABEL 5 84509-102 LIQUID 0.02 mg TOPICAL OTC Monograph Drug 11 sections
PEGO Acne Buster Salicylic Acid Drying Serum HUMAN OTC DRUG LABEL 5 84509-108 LIQUID 0.02 mg TOPICAL OTC Monograph Drug 10 sections
AOAO Acne Buster Salicylic Acid Drying Serum HUMAN OTC DRUG LABEL 5 84509-109 LIQUID 0.02 mg TOPICAL OTC Monograph Drug 10 sections
14% Azelaic Acid Acne HUMAN OTC DRUG LABEL 1 84753-056 CREAM 14 g TOPICAL OTC Monograph Drug 8 sections
Bloomellee 14%Gel Azelaic Acid Cream HUMAN OTC DRUG LABEL 1 87386-002 CREAM 0.14 g TOPICAL OTC Monograph Drug 9 sections
Bloomellee 12%Gel Azelaic Acid Acne HUMAN OTC DRUG LABEL 1 87386-003 CREAM 0.12 g TOPICAL OTC Monograph Drug 9 sections
10% Azelaic Acid HUMAN OTC DRUG LABEL 1 87815-002 CREAM 10 g TOPICAL OTC Monograph Drug 14 sections
14% Azelaic Acid HUMAN OTC DRUG LABEL 1 87815-003 CREAM 14 g TOPICAL OTC Monograph Drug 14 sections