azelastine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antihistaminics 271 58581-89-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • azelastine
  • azelastine hydrochloride
  • azelastine HCl
Azelastine hydrochloride, a phthalazinone derivative, exhibits histamine H1-receptor antagonist activity in isolated tissues, animal models, and humans. Azelastine Hydrochloride is administered as a racemic mixture with no difference in pharmacologic activity noted between the enantiomers in in vitro studies. The major metabolite, desmethylazelastine, also possesses H1-receptor antagonist activity.
  • Molecular weight: 381.90
  • Formula: C22H24ClN3O
  • CLOGP: 4.01
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 0
  • TPSA: 35.91
  • ALOGS: -4.62
  • ROTB: 3

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.56 mg N
4 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 2 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.30 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 99 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 15 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 9 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.17 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 22 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Nov. 1, 1996 FDA MEDA PHARMS

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
Treatment failure 403.68 15.17 252 10017 92835 46582958
Sinusitis 157.50 15.17 167 10102 129601 46546192
Asthma 82.33 15.17 101 10168 91441 46584352
Headache 45.91 15.17 217 10052 478135 46197658
Product dose omission issue 36.51 15.17 100 10169 168420 46507373
Toxicity to various agents 35.45 15.17 3 10266 211763 46464030
Nasal discomfort 35.33 15.17 17 10252 3721 46672072
Infusion site swelling 33.92 15.17 19 10250 5680 46670113
Bronchitis 33.76 15.17 73 10196 105906 46569887
Infusion site erythema 31.23 15.17 20 10249 7622 46668171
Nasal congestion 29.34 15.17 44 10225 48069 46627724
Cough 28.52 15.17 113 10156 230136 46445657
Sinus disorder 26.82 15.17 25 10244 16538 46659255
Upper-airway cough syndrome 25.94 15.17 18 10251 7829 46667964
Ear infection 24.98 15.17 28 10241 22985 46652808
Ear discomfort 23.51 15.17 16 10253 6745 46669048
Sneezing 20.18 15.17 19 10250 12722 46663071
Pre-existing condition improved 19.17 15.17 14 10255 6598 46669195
Wheezing 18.40 15.17 38 10231 53348 46622445
Drug interaction 16.95 15.17 12 10257 203082 46472711
Rheumatoid arthritis 16.62 15.17 17 10252 240198 46435595
General physical health deterioration 16.07 15.17 3 10266 115766 46560027
Sleep apnoea syndrome 16.01 15.17 22 10247 22179 46653614
Product taste abnormal 15.79 15.17 8 10261 1955 46673838
Multiple allergies 15.69 15.17 13 10256 7358 46668435
Fatigue 15.61 15.17 203 10066 608494 46067299

FDA Adverse Event Reporting System (Male)

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
Treatment failure 262.43 18.23 116 3933 34563 29913866
Sinusitis 51.99 18.23 40 4009 33305 29915124
Transferrin increased 36.08 18.23 5 4044 5 29948424
Chorioretinopathy 33.50 18.23 11 4038 1441 29946988
Oesophageal injury 31.12 18.23 5 4044 22 29948407
Amaurosis fugax 24.61 18.23 7 4042 566 29947863
Headache 19.10 18.23 61 3988 182245 29766184
Merycism 18.90 18.23 3 4046 12 29948417
Eosinophilic granulomatosis with polyangiitis 18.90 18.23 7 4042 1308 29947121
Oesophageal ulcer 18.56 18.23 9 4040 3268 29945161

Pharmacologic Action:

SourceCodeDescription
ATC R01AC03 RESPIRATORY SYSTEM
NASAL PREPARATIONS
DECONGESTANTS AND OTHER NASAL PREPARATIONS FOR TOPICAL USE
Antiallergic agents, excl. corticosteroids
ATC R06AX19 RESPIRATORY SYSTEM
ANTIHISTAMINES FOR SYSTEMIC USE
ANTIHISTAMINES FOR SYSTEMIC USE
Other antihistamines for systemic use
ATC S01GX07 SENSORY ORGANS
OPHTHALMOLOGICALS
DECONGESTANTS AND ANTIALLERGICS
Other antiallergics
FDA MoA N0000000190 Histamine H1 Receptor Antagonists
FDA EPC N0000175587 Histamine-1 Receptor Antagonist
CHEBI has role CHEBI:35523 bronchodilator agents
CHEBI has role CHEBI:37955 h1-receptor blockers
CHEBI has role CHEBI:49167 anti-asthmatic agents
CHEBI has role CHEBI:50427 platelet aggregation inhibitors
CHEBI has role CHEBI:50857 anti-allergic agents
CHEBI has role CHEBI:64964 5-lipoxygenase inhibitor
MeSH PA D018926 Anti-Allergic Agents
MeSH PA D018927 Anti-Asthmatic Agents
MeSH PA D001993 Bronchodilator Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D018494 Histamine Agents
MeSH PA D006633 Histamine Antagonists
MeSH PA D006634 Histamine H1 Antagonists
MeSH PA D039563 Histamine H1 Antagonists, Non-Sedating
MeSH PA D016859 Lipoxygenase Inhibitors
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D019141 Respiratory System Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Vasomotor rhinitis indication 8229003 DOID:4730
Allergic rhinitis indication 61582004
Seasonal allergic rhinitis indication 367498001
Allergic conjunctivitis indication 473460002 DOID:11204
Kidney disease contraindication 90708001 DOID:557
Drowsy contraindication 271782001
Ocular Irritation contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.91 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Histamine H1 receptor GPCR ANTAGONIST Ki 8.17 WOMBAT-PK CHEMBL
Multidrug resistance protein 1 Transporter WOMBAT-PK
Alpha-1A adrenergic receptor GPCR Ki 7.30 CHEMBL
Alpha-1B adrenergic receptor GPCR Ki 7.30 CHEMBL
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 7 CHEMBL
Histamine H3 receptor GPCR Ki 6.83 CHEMBL

External reference:

IDSource
ZQI909440X UNII
4024042 VUID
N0000022047 NUI
D00659 KEGG_DRUG
79307-93-0 SECONDARY_CAS_RN
4021001 VANDF
4024042 VANDF
C0052762 UMLSCUI
CHEBI:2951 CHEBI
CHEMBL639 ChEMBL_ID
CHEMBL1200809 ChEMBL_ID
DB00972 DRUGBANK_ID
2267 PUBCHEM_CID
4074 INN_ID
C020976 MESH_SUPPLEMENTAL_RECORD_UI
7121 IUPHAR_LIGAND_ID
18603 RXNORM
169403 MMSL
4237 MMSL
8899 MMSL
003931 NDDF
003932 NDDF
108644000 SNOMEDCT_US
108646003 SNOMEDCT_US
372520005 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
DYMISTA HUMAN PRESCRIPTION DRUG LABEL 2 0037-0245 SPRAY, METERED 137 ug NULLSAL NDA 28 sections
Azelastine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0054-0293 SPRAY, METERED 137 ug NULLSAL ANDA 27 sections
Azelastine Hydrochloride and Fluticasone Propionate HUMAN PRESCRIPTION DRUG LABEL 2 0378-3458 SPRAY, METERED 137 ug NULLSAL NDA authorized generic 29 sections
Azelastine Hydrochloride Human Prescription Drug Label 1 17478-718 SOLUTION/ DROPS 0.50 mg OPHTHALMIC ANDA 10 sections
Azelastine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42291-094 SPRAY, METERED 1 mg NULLSAL ANDA 27 sections
azelastine hcl nasal HUMAN PRESCRIPTION DRUG LABEL 1 45802-026 SPRAY 205.50 ug NULLSAL ANDA 27 sections
AZELASTINE HYDROCHLORIDE AND FLUTICASONE PROPIONULLTE HUMAN PRESCRIPTION DRUG LABEL 2 45802-066 SPRAY, METERED 137 ug NULLSAL ANDA 26 sections
Azelastine Hydrochloride Human Prescription Drug Label 1 47335-779 SPRAY, METERED 137 ug NULLSAL ANDA 25 sections
Azelastine Hydrochloride Human Prescription Drug Label 1 47335-938 SOLUTION/ DROPS 0.50 mg INTRAOCULAR ANDA 17 sections
Azelastine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50090-2330 SPRAY, METERED 137 ug NULLSAL ANDA 19 sections
Azelastine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50090-3833 SPRAY, METERED 1 mg NULLSAL ANDA 27 sections
Azelastine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50383-738 SPRAY, METERED 1 mg NULLSAL ANDA 25 sections
Azelastine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50383-942 SPRAY, METERED 1.50 mg NULLSAL ANDA 25 sections
AZELASTINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 51991-814 SPRAY, METERED 137 ug NULLSAL ANDA 28 sections
Azelastine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 53002-1279 SPRAY, METERED 137 ug NULLSAL ANDA 19 sections
Astelin HUMAN PRESCRIPTION DRUG LABEL 1 54868-5072 SPRAY, METERED 137 ug NULLSAL NDA 22 sections
Azelastine Hydrochloride Human prescription drug label 1 54868-6131 SPRAY, METERED 137 ug NULLSAL ANDA 19 sections
AZELASTINE HYDROCHLORIDE Human Prescription Drug Label 1 59651-214 SPRAY, METERED 137 ug NULLSAL ANDA 26 sections
AZELASTINE HYDROCHLORIDE Human Prescription Drug Label 1 59651-215 SPRAY, METERED 205.50 ug NULLSAL ANDA 26 sections
AZELASTINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 60505-0578 SOLUTION/ DROPS 0.50 mg INTRAOCULAR ANDA 17 sections
Azelastine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 60505-0833 SPRAY, METERED 137 ug NULLSAL ANDA 19 sections
Azelastine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 60505-0848 SPRAY, METERED 205.50 ug NULLSAL ANDA 26 sections
Azelastine hydrochloride and Fluticasone propionate HUMAN PRESCRIPTION DRUG LABEL 2 60505-0953 SPRAY, METERED 137 ug NULLSAL ANDA 27 sections
Azelastine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 61314-308 SOLUTION/ DROPS 0.50 mg INTRAOCULAR ANDA 16 sections
Azelastine Hydrochloride Ophthalmic Solution 0.05% Human Prescription Drug Label 1 62332-506 SOLUTION/ DROPS 0.50 mg OPHTHALMIC ANDA 16 sections
AZELASTINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 63629-2057 SPRAY, METERED 137 ug NULLSAL ANDA 27 sections
azelastine hcl nasal HUMAN PRESCRIPTION DRUG LABEL 1 63629-2519 SPRAY 205.50 ug NULLSAL ANDA 27 sections
Azelastine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 65162-676 SPRAY, METERED 1 mg NULLSAL ANDA 27 sections
Azelastine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 65162-706 SPRAY, METERED 205.50 ug NULLSAL ANDA 19 sections
Azelastine Human Prescription Drug Label 1 67877-477 SPRAY, METERED 137 ug NULLSAL ANDA 25 sections