General
Preferred name
MEQUINOL
Synonyms
Leucodinine b ()
Leucobasal ()
4-Hydroxyanisole ()
4-Methoxyphenol ()
p-Hydroxyanisole ()
Novo-Dermoquinona ()
HQMME; Hydroxyquinone Methyl Ether ()
Mechinolum ()
p-Guaiacol ()
Leucodine B ()
BMS-181158 ()
NSC-4960 ()
Menthyl Anthranilate ()
4HA ()
P&D ID
PD002118
CAS
150-76-5
Tags
natural product
drug
available
Approved by
FDA
First approval
1999
Drug Status
approved
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)
MOA Solar lentigines and related hyperpigmented lesions are localized, pigmented, macular lesions of the skin, usually on the areas of the body which have been chronically exposed to sunlight [FDA Label]. These lesions are characterized by increased numbers of active melanocytes and increased melanin production [FDA Label].; ; Although the mechanism of action of mequinol is not fully elucidated [FDA Label], when employed as an active ingredient in combination with other agents like tretinoin in skin depigmentation products, a synergy between a number of potential mechanisms is proposed.; ; Firstly, mequinol is in fact considered a melanocytotoxic chemical which when oxidized in melanocytes results in the formation of toxic compounds like quinones [L993]. Such cytotoxic agents are subsequently capable of damaging and destroying pigment cells, which results in skin depigmentation [L993] of solar lentigines or other related hyperpigmented lesions. Nevertheless, skin cells are naturally capable of protecting themselves against such cytotoxic entities by endogenous intracellular glutathione (GSH) [L993]. This protection is elicited through the enzymatic action of glutathione S-transferase (GST), which is responsible for the conjugation of agents toxic to glutathione [L993]. Conversely, tretinoin has been observed to serve as a potent inhibitor of mammalian GSTs and to be capable of reducing the level of intracellular GSH in various cells [L993]. As a result, the combination of mequinol with tretinoin seemingly allows for a synergistic enhancement of a melanocytotoxic effect that involves the inhibition and impairment of GSH and GST cytoprotection [L993].; ; Secondly, even though mequinol is a substrate for the enzyme tyrosinase and therefore acts as a competitive inhibitor of the formation of melanin precursors by way of tyrosinase facilitated reactions, the clinical significance of this action is unknown [FDA Label].
DESCRIPTION A tyrosinase inhibitor (GtoPdb)
TOXICITY If a mequinol and tretinoin combination topical product is applied excessively, some potential adverse effects like marked redness, peeling of skin, discomfort, discoloration, or hypopigmentation may occur [FDA Label]. Such products are not indicated for oral ingestion [FDA Label].; ; MSDS data reports that chronic exposure to a dose of 25 UMOL/L in humans can result in mutagenic effects like DNA inhibition in lymphocytes [MSDS].
Compound Sets
15
ChEMBL Approved Drugs
CHEMBL544
ChEMBL Drugs
CHEMBL544
Drug Repurposing Hub
DrugBank
DB09516
DrugBank Approved Drugs
DB09516
DrugCentral
4221
DrugCentral Approved Drugs
4221
Guide to Pharmacology
6827
MedChem Express Bioactive Compound Library
HY-30270
NIH Mechanistic Set
NPC Screening Collection
ReFrame library
Selleckchem Bioactive Compound Library
mequinol
TargetMol Bioactive Compound Library
T0501
The Spectrum Collection
External IDs
44
Properties
(calculated by RDKit )
Molecular Weight
124.05
Hydrogen Bond Acceptors
2
Hydrogen Bond Donors
1
Rotatable Bonds
1
Ring Count
1
Aromatic Ring Count
1
cLogP
1.4
TPSA
29.46
Fraction CSP3
0.14
Chiral centers
0.0
Largest ring
6.0
QED
0.61
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Target
radical polymerization
TYR
Indication
skin depigmentation
Source data