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

Stem definitionDrug idCAS RN
antihistaminics or local vasoconstrictors, antazoline derivatives 3369 835-31-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • naphazoline nitrate
  • naphazoline
  • naphthazoline
  • naphthizine
  • nephazoline
  • rhinazine
  • naphazoline hydrochloride
  • naphazoline HCl
An adrenergic vasoconstrictor agent used as a decongestant.
  • Molecular weight: 210.28
  • Formula: C14H14N2
  • CLOGP: 3.83
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 1
  • TPSA: 24.39
  • ALOGS: -3.74
  • ROTB: 2
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.40 mg N

ADMET properties:

None

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 0.230 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 0.815 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 15.885 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 4.140 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 48.100 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 70.860 % High 1
herg hERG pIC50 5.088 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 2.748 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 6.607 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 57.880 % High 1
kinase-safety-class ACVR2A,ACVR2B,AXL,BRAF,CAMK2D,CDK5,CDK9,DYRK1B,EIF2AK3,ERBB2,GRK2,ITK,MAP3K7,MAPK10,MAPK7,NTRK2,PDK4,PIK3CB,PRKDC,SIK2,STK33,TEK,TTK 23
kinase-selectivity-class AXL,PIK3CB,PIK3CD 3
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 1.622 High 1
mh-clint Mouse hepatocyte intrinsic clearance 66.834 High 1
mppb Mouse plasma protein binding (% unbound) 47.640 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 3.273 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 61.640 % High 1
rh-clint Rat hepatocyte intrinsic clearance 84.723 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 85.020 % High 1
rppb Rat plasma protein binding (% unbound) 56.020 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 924.698 uM High 1

Approvals:

DateAgencyCompanyOrphan
June 7, 1971 FDA NOVARTIS

FDA Adverse Event Reporting System (Female)

None

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
Catarrh 193.95 167.98 50 2703 5936 42612646
Burns second degree 193.05 167.98 50 2703 6046 42612536
Steroid dependence 188.20 167.98 50 2703 6672 42611910
Parosmia 181.53 167.98 50 2703 7641 42610941
Gingival pain 181.15 167.98 51 2702 8443 42610139
Hypopnoea 180.31 167.98 50 2703 7832 42610750
Alcohol poisoning 173.04 167.98 48 2705 7526 42611056
Systemic lupus erythematosus 172.00 167.98 50 2703 9274 42609308

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
Catarrh 234.78 74.47 52 3143 7283 110578821
Burns second degree 232.04 74.47 52 3143 7681 110578423
Steroid dependence 227.34 74.47 52 3143 8417 110577687
Alcohol poisoning 213.49 74.47 50 3145 8970 110577134
Hypopnoea 212.06 74.47 52 3143 11328 110574776
Parosmia 204.47 74.47 52 3143 13128 110572976
Gingival pain 195.33 74.47 52 3143 15684 110570420
Rhinitis 176.83 74.47 52 3143 22493 110563611
Cardiac murmur 172.29 74.47 52 3143 24576 110561528
Impaired work ability 151.90 74.47 48 3147 26371 110559733
Nightmare 148.97 74.47 52 3143 38811 110547293
Bronchiectasis 148.27 74.47 51 3144 36442 110549662
Impaired quality of life 137.86 74.47 46 3149 29971 110556133
Swollen tongue 137.01 74.47 55 3140 60307 110525797
Tinnitus 136.85 74.47 55 3140 60485 110525619
Tubulointerstitial nephritis 135.56 74.47 53 3142 54231 110531873
Frequent bowel movements 128.09 74.47 55 3140 71335 110514769
Accidental overdose 127.28 74.47 50 3145 51784 110534320
Eczema 124.15 74.47 54 3141 72239 110513865
Dysgeusia 119.27 74.47 52 3143 69933 110516171
Colitis ulcerative 117.44 74.47 53 3142 77310 110508794
Vertigo 114.64 74.47 54 3141 86816 110499288
Stress 101.87 74.47 53 3142 105295 110480809
Haematochezia 100.06 74.47 54 3141 115470 110470634
Medication error 96.16 74.47 51 3144 105315 110480789
Rectal haemorrhage 95.46 74.47 53 3142 119780 110466324
Palpitations 86.47 74.47 55 3140 159157 110426947
Deep vein thrombosis 82.69 74.47 51 3144 139836 110446268
Cerebrovascular accident 82.34 74.47 56 3139 181228 110404876
Migraine 80.28 74.47 54 3141 171598 110414506
Loss of personal independence in daily activities 79.41 74.47 51 3144 149969 110436135

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC R01AA08 RESPIRATORY SYSTEM
NASAL PREPARATIONS
DECONGESTANTS AND OTHER NASAL PREPARATIONS FOR TOPICAL USE
Sympathomimetics, plain
ATC R01AB02 RESPIRATORY SYSTEM
NASAL PREPARATIONS
DECONGESTANTS AND OTHER NASAL PREPARATIONS FOR TOPICAL USE
Sympathomimetics, combinations excl. corticosteroids
ATC S01GA01 SENSORY ORGANS
OPHTHALMOLOGICALS
DECONGESTANTS AND ANTIALLERGICS
Sympathomimetics used as decongestants
ATC S01GA51 SENSORY ORGANS
OPHTHALMOLOGICALS
DECONGESTANTS AND ANTIALLERGICS
Sympathomimetics used as decongestants
MeSH PA D000316 Adrenergic alpha-Agonists
MeSH PA D002317 Cardiovascular Agents
MeSH PA D014662 Vasoconstrictor Agents
MeSH PA D014663 Nasal Decongestants
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018663 Adrenergic Agents
MeSH PA D019141 Respiratory System Agents
CHEBI has role CHEBI:22587 antiviral agent
CHEBI has role CHEBI:67079 anti-inflammatory agent
CHEBI has role CHEBI:77715 nasal decongestant

Related Drugs by ATC class:

R01AA Sympathomimetics, plain 13 drugs
cyclopentamineephedrineepinephrinefenoxazolineindanazolinemetizolineoxymetazolinephenylephrinetetryzolinetramazolinetuaminoheptanetymazoline show all 13 →
R01AB Sympathomimetics, combinations excl. corticosteroids 6 drugs
ephedrineoxymetazolinephenylephrinetetryzolinetuaminoheptanexylometazoline
S01GA Sympathomimetics used as decongestants 6 drugs
brimonidineoxedrineoxymetazolinephenylephrinetetryzolinexylometazoline

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

DiseaseRelationSNOMED_IDDOID
Red eye indication 75705005
Ocular Itching indication
Hyperthyroidism contraindication 34486009 DOID:7998
Hypertensive disorder contraindication 38341003 DOID:10763
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Diabetes mellitus contraindication 73211009 DOID:9351
Hyperglycemia contraindication 80394007 DOID:4195
Eye infection contraindication 128351009
Injury of eye region contraindication 282752000
Angle-closure glaucoma contraindication 392291006 DOID:13550




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 10.3 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
Alpha-2B adrenergic receptor GPCR AGONIST Ki 6.39 PDSP CHEMBL
Alpha-2C adrenergic receptor GPCR AGONIST Ki 6.39 PDSP CHEMBL
Alpha-2A adrenergic receptor GPCR AGONIST Ki 7.68 PDSP CHEMBL
Alpha-1A adrenergic receptor GPCR AGONIST EC50 8.90 IUPHAR
Nischarin Membrane receptor Ki 6.92 CHEMBL
Nischarin Membrane receptor Ki 6.61 CHEMBL
Adrenergic receptor alpha-2 GPCR Ki 8.24 CHEMBL
Adrenergic receptor alpha-1 GPCR EC50 7.92 CHEMBL
Adrenergic receptor alpha GPCR Ki 8.24 CHEMBL

External reference:

IDSource
D00743 KEGG_DRUG
5144-52-5 SECONDARY_CAS_RN
550-99-2 SECONDARY_CAS_RN
4018585 VANDF
4019855 VANDF
C0027373 UMLSCUI
CHEMBL761 ChEMBL_ID
DB06711 DRUGBANK_ID
CHEMBL1706 ChEMBL_ID
D009278 MESH_DESCRIPTOR_UI
4436 PUBCHEM_CID
5509 IUPHAR_LIGAND_ID
4153 INN_ID
H231GF11BV UNII
235810 RXNORM
2098 MMSL
5154 MMSL
72185 MMSL
001802 NDDF
003876 NDDF
003877 NDDF
372803000 SNOMEDCT_US
57583000 SNOMEDCT_US
6232005 SNOMEDCT_US
734561005 SNOMEDCT_US
CHEBI:7471 CHEBI
H231GF11BV INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Naphcon A HUMAN OTC DRUG LABEL 2 0065-0085 SOLUTION/ DROPS 0.25 mg OPHTHALMIC NDA 14 sections
Eye Allergy Relief HUMAN OTC DRUG LABEL 2 0363-0430 SOLUTION/ DROPS 0.27 mg OPHTHALMIC NDA 14 sections
WALGREENS MAXIMUM REDNESS RELIEF HUMAN OTC DRUG LABEL 2 0363-1465 SOLUTION 0 mg OPHTHALMIC OTC monograph final 13 sections
Walgreens Eye Drops Maximum Redness Relief 15mL HUMAN OTC DRUG LABEL 2 0363-4546 SOLUTION/ DROPS 0.03 g OPHTHALMIC OTC Monograph Drug 13 sections
Walgreens Redness Relief Eye Drops 15mL HUMAN OTC DRUG LABEL 2 0363-4548 SOLUTION/ DROPS 0.01 g OPHTHALMIC OTC Monograph Drug 14 sections
7 Select Redness Relief HUMAN OTC DRUG LABEL 2 10202-850 SOLUTION/ DROPS 0 mg OPHTHALMIC OTC Monograph Drug 14 sections
RohtoCool Relief HUMAN OTC DRUG LABEL 2 10742-8141 LIQUID 0.12 mg OPHTHALMIC OTC Monograph Drug 12 sections
RohtoCool HUMAN OTC DRUG LABEL 2 10742-8142 LIQUID 0.12 mg OPHTHALMIC OTC Monograph Drug 12 sections
RohtoMax Strength HUMAN OTC DRUG LABEL 2 10742-8158 LIQUID 0.30 mg OPHTHALMIC OTC Monograph Drug 12 sections
Rohto Optic Glow HUMAN OTC DRUG LABEL 3 10742-8160 LIQUID 0.30 mg OPHTHALMIC OTC Monograph Drug 13 sections
Target Eye Drops Maximum Redness Relief Eye HUMAN OTC DRUG LABEL 2 11673-100 SOLUTION/ DROPS 30 mg OPHTHALMIC OTC Monograph Drug 12 sections
Eye Allergy Relief HUMAN OTC DRUG LABEL 2 11673-430 SOLUTION/ DROPS 0.27 mg OPHTHALMIC NDA 14 sections
Red Eye Relief HUMAN OTC DRUG LABEL 2 11673-578 SOLUTION/ DROPS 30 mg OPHTHALMIC OTC monograph final 13 sections
Eye Allergy Relief HUMAN OTC DRUG LABEL 2 11822-0552 SOLUTION/ DROPS 0.27 mg OPHTHALMIC NDA 14 sections
NAFASOLINA HUMAN OTC DRUG LABEL 1 12539-146 SOLUTION/ DROPS 50 mg NASAL OTC Monograph Drug 10 sections
FLORIL REDNESS RELIEF HUMAN OTC DRUG LABEL 2 16995-001 SOLUTION/ DROPS 3 mg OPHTHALMIC OTC monograph final 10 sections
Pure Eyes Sterile Eyes HUMAN OTC DRUG LABEL 2 20146-7000 SOLUTION/ DROPS 0.10 mg OPHTHALMIC OTC monograph drug 14 sections
Signature Care Eye Drops Redness and Dry Eye Relief HUMAN OTC DRUG LABEL 2 21130-703 SOLUTION/ DROPS 0.01 g OPHTHALMIC OTC Monograph Drug 14 sections
AK-Con HUMAN PRESCRIPTION DRUG LABEL 1 21695-915 SOLUTION 1 mg OPHTHALMIC ANDA 16 sections
Opcon-A HUMAN OTC DRUG LABEL 2 24208-430 SOLUTION/ DROPS 0.27 mg OPHTHALMIC NDA 14 sections
Opcon-A HUMAN OTC DRUG LABEL 2 24208-431 SOLUTION/ DROPS 0.27 mg OPHTHALMIC NDA 14 sections
Advanced Eye Relief/ Redness Maximum Relief HUMAN OTC DRUG LABEL 2 24208-450 SOLUTION/ DROPS 0.30 mg OPHTHALMIC OTC Monograph Drug 14 sections
CLEAR EYES REDNESS RELIEF HANDY POCKET PAL HUMAN OTC DRUG LABEL 2 29485-1139 SOLUTION/ DROPS 0 mg OPHTHALMIC OTC MONOGRAPH FINAL 15 sections
Kroger Eye Drops Redness Relief HUMAN OTC DRUG LABEL 2 30142-573 SOLUTION/ DROPS 0.01 g OPHTHALMIC OTC Monograph Drug 13 sections
Topcare Maximum Redness Relief Eye Drops HUMAN OTC DRUG LABEL 2 36800-975 SOLUTION 0.03 g OPHTHALMIC OTC Monograph Drug 12 sections
Meijer Maximum Redness Relief and Lubricant HUMAN OTC DRUG LABEL 2 41250-715 SOLUTION/ DROPS 0.03 g OPHTHALMIC OTC Monograph Drug 14 sections
Meijer Redness Relief HUMAN OTC DRUG LABEL 2 41250-846 SOLUTION/ DROPS 0.01 g OPHTHALMIC OTC Monograph Drug 14 sections
Xpect Industrial Eye Relief HUMAN OTC DRUG LABEL 2 42961-255 SOLUTION/ DROPS 0.01 g OPHTHALMIC OTC Monograph Drug 14 sections
GNP Eye Drops Redness and Dry Eye Relief HUMAN OTC DRUG LABEL 2 46122-606 SOLUTION 0.01 g OPHTHALMIC OTC Monograph Drug 13 sections
Colirio Ojo De Aguila Eye Drops HUMAN OTC DRUG LABEL 2 48201-106 SOLUTION/ DROPS 0.01 g OPHTHALMIC OTC Monograph Drug 14 sections