General
Preferred name
NAPHAZOLINE
Synonyms
NAPHAZOLINE HYDROCHLORIDE ()
NAPHAZOLINE HCL ()
Albalon ()
Rhinantin ()
Naphazoline (nitrate) ()
Naphazoline (hydrochloride) ()
Naphthazoline (nitrate) ()
Naphthazoline (hydrochloride) ()
Vasocon ()
Naphazoline Nitrate ()
Antistin-Privine ()
Nafazair ()
Naphcon Forte ()
Gppe Nsl Soln ()
Opcon ()
NSC-35711 ()
Naphcon ()
Naphaz HCl ()
Nafazolin ()
Naphazoline-d4 (hydrochloride) ()
P&D ID
PD009276
CAS
550-99-2
35412-62-5
10061-11-7
835-31-4
5144-52-5
Tags
natural product
drug
available
Approved by
FDA
First approval
1971
Drug Status
investigational
approved
Drug indication
Hyperaemia
Itching
Adrenergic (vasoconstrictor)
Max Phase
Phase 4
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
ABSORPTION Absorption data for naphazoline are scarce but imidazoline compounds in general are weakly basic and lipophilic, with high bioavailability from the gastrointestinal tract[T530].
PHARMACODYNAMICS Naphazoline is a sympathomimetic alpha adrenergic agonist that acts to vasoconstrict nasal or ocular arterioles, resulting in reduced congestion at the site of administration[L5804,L5807].
HALF-LIFE Half life has not been determined but effects last for 4 to 8 hours[L5807]. Other imidazoline compounds have half lives varying from 2 to 12 hours[T530].
INDICATION Naphazoline is indicated for use as OTC eyedrops for ocular vasoconstriction or as a nasal preparation for nasal congestion[A176558,L5804,L5807].
ROE Imidazoline compounds undergo some hepatic metabolism but a large fraction of the dose may be excreted unchanged in the urine[T530]. Urinary excretion is higher with more acidic urine[T530].
METABOLISM Metabolism data for naphazoline are scarce. Imidazoline compounds undergo some hepatic metabolism but a large fraction of the dose may be excreted unchanged in the urine[T530].
DESCRIPTION Marketed formulations may contain naphazoline hydrochloride (PubChem CID 11079) or naphazoline nitrate (PubChem CID 16218420). (GtoPdb)
MOA Naphazoline is a vasoconstrictor that functions by stimulating alpha adrenergic receptors in arterioles leading to decreased congestion at the site of administration[L5804].; ; Naphazoline causes the release of norepinephrine in sympathetic nerves[A176567]. Norepinephrine binds to alpha adrenergic receptors and causes vasoconstriction[A176567]. Naphazoline is also a mild beta adrenergic receptor agonist, which can cause rebound vasodilation after the alpha adrenergic stimulation has ended[A176567]. Naphazoline's release of norepinephrine also triggers a negative feedback loop which decreases production of norepinephrine, which can lead to rhinitis medicamentosa after long term use when naphazoline is stopped[A176567].
TOXICITY In high doses or when ingested, naphazoline can lead to central nervous system depression (which can progress to coma and death), hypothermia, bradycardia, and death[A176558]. This effect is especially pronounced in children under 6 years[A176558,A176564].; ; Long term use of naphazoline can lead to rhinitis medicamentosa once naphazoline is stopped[A176567]. This condition is a result of norepinephrine release by naphazoline triggering a negative feedback loop[A176567].; ; Safety and effectiveness in children under 12 has not been established[F4214]. Studies in elderly patients have yet to be performed[F4214]. Risk in pregnancy, breast feeding, and on overall fertility have not been established, though pregnant and breast feeding patients should consider the risk and benefit before starting naphazoline treatment[F4214].
Cell lines
0
Organisms
1
Compound Sets
27
Cayman Chemical Bioactives
23774
34012
ChEMBL Approved Drugs
CHEMBL1706
CHEMBL761
ChEMBL Drugs
CHEMBL1706
CHEMBL761
Drug Repurposing Hub
DrugBank
DB06711
DrugBank Approved Drugs
DB06711
DrugCentral
3369
DrugCentral Approved Drugs
3369
DrugMAP
DMJFZDL
DrugMAP Approved Drugs
DMJFZDL
DrugMatrix
Enamine BioReference Compounds
EU-OPENSCREEN Bioactive Compound Library
EOS100008
Guide to Pharmacology
5509
Ki Database
Naphazoline
naphazoline
LSP-MoA library (Laboratory of Systems Pharmacology)
CHEMBL1706
CHEMBL761
Mcule NIBR MoA Box Subset
MCULE-9097339235
MedChem Express Bioactive Compound Library
HY-B0446
HY-111326A
NCATS Inxight Approved Drugs
H231GF11BV
NIH Clinical Collections (NCC)
Novartis Chemogenetic Library (NIBR MoA Box)
NPC Screening Collection
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
Naphazoline-hydrochloride-Naphcon
TargetMol Bioactive Compound Library
T0446
The Spectrum Collection
External IDs
74
Properties
(calculated by RDKit )
Molecular Weight
210.12
Hydrogen Bond Acceptors
2
Hydrogen Bond Donors
1
Rotatable Bonds
2
Ring Count
3
Aromatic Ring Count
2
cLogP
2.38
TPSA
24.39
Fraction CSP3
0.21
Chiral centers
0.0
Largest ring
6.0
QED
0.81
QED
0.81
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Pathway
Neuroscience
GPCR/G protein
Apoptosis
Immunology/Inflammation
Neuronal Signaling
Protein Tyrosine Kinase/RTK
Target
Adrenergic Receptor
ADRA1A, ADRA2A
Interleukin Related
TNF Receptor
VEGFR
Member status
virtual
MOA
alpha-Adrenoceptor Antagonists
Adrenergic Receptor agonist
Indication
eye irritation
Therapeutic Class
Anticancer Agents
Source data