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
Dysgeusia 80.49 35.46 19 196 8440 2349430
Nasal discomfort 60.40 35.46 10 205 704 2357166
Epistaxis 57.71 35.46 15 200 9764 2348106
Ageusia 44.15 35.46 9 206 1989 2355881
Sneezing 42.48 35.46 9 206 2397 2355473
Drug hypersensitivity 38.06 35.46 16 199 46627 2311243

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

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
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
CHEBI has role CHEBI:37955 H1-receptor antagonist
CHEBI has role CHEBI:50857 anti-allergic agent
CHEBI has role CHEBI:49167 anti-asthmatic drug
CHEBI has role CHEBI:35523 bronchodilator agent
CHEBI has role CHEBI:50427 platelet aggregation inhibitor
FDA MoA N0000000190 Histamine H1 Receptor Antagonists
FDA EPC N0000175587 Histamine-1 Receptor Antagonist

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)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
EQ 0.125MG BASE/SPRAY DYMISTA MYLAN SPECIALITY LP N202236 May 1, 2012 RX SPRAY, METERED NASAL 9259428 June 13, 2023 TREATMENT OF SEASONAL ALLERGIC RHINITIS
EQ 0.125MG BASE/SPRAY DYMISTA MYLAN SPECIALITY LP N202236 May 1, 2012 RX SPRAY, METERED NASAL 8163723 Aug. 29, 2023 ALLERGIC RHINITIS
EQ 0.125MG BASE/SPRAY DYMISTA MYLAN SPECIALITY LP N202236 May 1, 2012 RX SPRAY, METERED NASAL 8163723 Aug. 29, 2023 RELIEF OF SYMPTOMS ASSOCIATED WITH SEASONAL ALLERGIC RHINITIS
EQ 0.125MG BASE/SPRAY DYMISTA MYLAN SPECIALITY LP N202236 May 1, 2012 RX SPRAY, METERED NASAL 8163723 Aug. 29, 2023 TREATMENT OF ALLERGIC RHINITIS, INCLUDING SEASONAL ALLERGIC RHINITIS
EQ 0.125MG BASE/SPRAY DYMISTA MYLAN SPECIALITY LP N202236 May 1, 2012 RX SPRAY, METERED NASAL 8163723 Aug. 29, 2023 TREATMENT OF SEASONAL ALLERGIC RHINITIS
EQ 0.125MG BASE/SPRAY DYMISTA MYLAN SPECIALITY LP N202236 May 1, 2012 RX SPRAY, METERED NASAL 8163723 Aug. 29, 2023 TREATMENT OF SYMPTOMS OF SEASONAL ALLERGIC RHINITIS
EQ 0.125MG BASE/SPRAY ASTEPRO MYLAN SPECIALITY LP N022203 Oct. 15, 2008 DISCN SPRAY, METERED NASAL 8518919 Nov. 22, 2025 TREATMENT OF ALLERGIC RHINITIS, INCLUDING SEASONAL AND PERENNIAL ALLERGIC RHINITIS
EQ 0.1876MG BASE/SPRAY ASTEPRO MYLAN SPECIALITY LP N022203 Aug. 31, 2009 RX SPRAY, METERED NASAL 8518919 Nov. 22, 2025 TREATMENT OF ALLERGIC RHINITIS, INCLUDING SEASONAL AND PERENNIAL ALLERGIC RHINITIS

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
EQ 0.125MG BASE/SPRAY AZELASTINE HYDROCHLORIDE AND FLUTICASONE PROPIONATE APOTEX A207712 April 28, 2017 RX SPRAY, METERED NASAL Aug. 29, 2020 PATENT CHALLENGE

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
4024042 VUID
N0000022047 NUI
C0052762 UMLSCUI
D00659 KEGG_DRUG
0L591QR10I UNII
79307-93-0 SECONDARY_CAS_RN
108644000 SNOMEDCT_US
18603 RXNORM
4024042 VANDF
372520005 SNOMEDCT_US
4237 MMSL
003931 NDDF
CHEMBL639 ChEMBL_ID
DB00972 DRUGBANK_ID
CHEMBL1200809 ChEMBL_ID
CHEBI:2950 CHEBI
4074 INN_ID
7121 IUPHAR_LIGAND_ID
2267 PUBCHEM_CID
C020976 MESH_SUPPLEMENTAL_RECORD_UI

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Astelin HUMAN PRESCRIPTION DRUG LABEL 1 0037-0241 SPRAY, METERED 137 ug NASAL NDA 17 sections
Astepro HUMAN PRESCRIPTION DRUG LABEL 1 0037-0243 SPRAY, METERED 205.50 ug NASAL NDA 17 sections
DYMISTA HUMAN PRESCRIPTION DRUG LABEL 2 0037-0245 SPRAY, METERED 137 ug NASAL NDA 17 sections
Azelastine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0054-0293 SPRAY, METERED 137 ug NASAL ANDA 17 sections
Azelastine Hydrochloride and Fluticasone Propionate HUMAN PRESCRIPTION DRUG LABEL 2 0378-3458 SPRAY, METERED 137 ug NASAL NDA authorized generic 17 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 42291-153 SPRAY, METERED 137 ug NASAL ANDA 19 sections
azelastine hcl nasal HUMAN PRESCRIPTION DRUG LABEL 1 45802-026 SPRAY 205.50 ug NASAL ANDA 18 sections
Azelastine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 47335-779 SPRAY, METERED 137 ug NASAL ANDA 17 sections
Azelastine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 47335-938 SOLUTION/ DROPS 0.50 mg INTRAOCULAR ANDA 11 sections
Azelastine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50090-2330 SPRAY, METERED 137 ug NASAL ANDA 18 sections
Azelastine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50090-3833 SPRAY, METERED 1 mg NASAL ANDA 18 sections
Azelastine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50383-738 SPRAY, METERED 1 mg NASAL ANDA 16 sections
Azelastine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50383-942 SPRAY, METERED 1.50 mg NASAL ANDA 16 sections
Azelastine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51525-0234 SPRAY, METERED 205.50 ug NASAL NDA authorized generic 16 sections
Azelastine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51525-0294 SPRAY, METERED 137 ug NASAL NDA 18 sections
AZELASTINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 51991-814 SPRAY, METERED 137 ug NASAL ANDA 19 sections
Astelin HUMAN PRESCRIPTION DRUG LABEL 1 54868-5072 SPRAY, METERED 137 ug NASAL NDA 11 sections
Azelastine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 54868-6131 SPRAY, METERED 137 ug NASAL ANDA 11 sections
AZELASTINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 60505-0578 SOLUTION/ DROPS 0.50 mg INTRAOCULAR ANDA 10 sections
Azelastine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 60505-0833 SPRAY, METERED 137 ug NASAL ANDA 18 sections
Azelastine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 60505-0848 SPRAY, METERED 205.50 ug NASAL ANDA 17 sections
Azelastine hydrochloride and Fluticasone propionate HUMAN PRESCRIPTION DRUG LABEL 2 60505-0953 SPRAY, METERED 137 ug NASAL ANDA 17 sections
Azelastine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 61314-308 SOLUTION/ DROPS 0.50 mg INTRAOCULAR ANDA 10 sections
Azelastine Hydrochloride Ophthalmic Solution 0.05% HUMAN PRESCRIPTION DRUG LABEL 1 62332-506 SOLUTION/ DROPS 0.50 mg OPHTHALMIC ANDA 10 sections
Azelastine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 65162-676 SPRAY, METERED 1 mg NASAL ANDA 18 sections
Azelastine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 65162-706 SPRAY, METERED 205.50 ug NASAL ANDA 18 sections
Azelastine HUMAN PRESCRIPTION DRUG LABEL 1 67877-477 SPRAY, METERED 137 ug NASAL ANDA 17 sections
Azelastine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 68071-4359 SOLUTION/ DROPS 0.50 mg INTRAOCULAR ANDA 11 sections
Azelastine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 68083-287 SOLUTION/ DROPS 0.50 mg INTRAOCULAR ANDA 10 sections