General
Preferred name
RESORCINOL
Synonyms
Resorcinol disodium salt ()
1,3-Benzenediol ()
m-dihydroxybenzene ()
3-hydroxyphenol ()
NSC-1571 ()
Resorcinum ()
C.i. oxidation base 31 ()
Resorcin ()
D.D.D. ()
C.I.-76505 ()
FEMA NO. 3589 ()
Tilloderm ()
Benzene-1,3-diol ()
P&D ID
PD001765
CAS
108-46-3
26982-54-7
Tags
natural product
drug
available
Approved by
FDA
Drug Status
approved
Drug indication
Keratolytic
Discovery agent
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)
PHARMACODYNAMICS In vitro and in vivo studies have demonstrated that resorcinol can inhibit peroxidases in the thyroid and subsequently block the synthesis of thyroid hormones and cause goiter [F61, L2747]. Resorcinol interferes with the iodination of tyrosine and the oxidation of iodide [F61, L2747]. In an in vitro study involving lactoperoxidase (LPO) and thyroid peroxidase (TPO), it was shown that the mechanism of these two enzymes can become irreversibly inhibited by way of a suicide inactivation by resorcinol [F61, L2747].; ; It is believed that the Fe3+ of the porphyrin residue of the peroxidase to is oxidised to Fe4+ by hydrogen peroxide with the transfer of an oxygen radical [F61, L2747]. In LPO and TPO, the resulting π-cation radical of the porphyrin can isomerize to a radical cation with the radical in an aromatic side chain of the enzyme [F61, L2747]. The latter radical can bind, in a pH-dependent reaction, covalently and irreversibly to the resorcinol radical formed during regular oxidation of resorcinol and this reduces the activity of the enzyme greatly [F61, L2747]. While the inactivation of the enzyme and the binding of resorcinol to the enzyme may be largely increased by the presence of 0.1 nM iodide, increasing the iodide concentration to 5 mM reduced the resorcinol binding to the enzyme by one quarter but increased the enzyme activity, determined as the rate of iodination of tyrosine, more than proportionally from 6.2% to 44.7% [F61, L2747]. Nevertheless, the role played by iodide ions in the irreversible inactivation of the enzymes is not yet fully elucidated [F61, L2747].; ; Ultimately, such in vitro and in vivo data propose that the anti-thyroidal activity of resorcinol is caused by inhibition of thyroid peroxidase enzymes, resulting in decreased thyroid hormone production and increased proliferation due to an increase in the secretion of TSH (thyroid stimulating hormone) [F61, L2747]. The iodination process is catalyzed by a haem-containing enzyme, and resorcinol is known to form covalent bonds with haem [F61, L2747].; ; Despite the legitimacy of this pharmacodynamic profile in resorcinol, the therapeutic uses for which it may be formally indicated for at this time do not actually rely upon any of these mechanisms or dynamics, which are primarily elicited only upon systemic exposure to resorcinol or particularly high overdosage of the agent. This is especially true, considering resorcinol is most commonly available as topical applications to the public.
Cell lines
1
Organisms
0
Compound Sets
12
ChEMBL Approved Drugs
CHEMBL24147
ChEMBL Drugs
CHEMBL24147
Drug Repurposing Hub
DrugBank
DB11085
DrugBank Approved Drugs
DB11085
DrugCentral
3524
DrugCentral Approved Drugs
3524
DrugMAP
DMM37C0
DrugMatrix
NCATS Inxight Approved Drugs
YUL4LO94HK
NPC Screening Collection
The Spectrum Collection
External IDs
43
Properties
(calculated by RDKit )
Molecular Weight
110.04
Hydrogen Bond Acceptors
2
Hydrogen Bond Donors
2
Rotatable Bonds
0
Ring Count
1
Aromatic Ring Count
1
cLogP
1.1
TPSA
40.46
Fraction CSP3
0.0
Chiral centers
0.0
Largest ring
6.0
QED
0.52
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Pathway
Microbiology&virology
Target
Antibacterial
CA12, CA14, CA2, PTGS1
Indication
acne vulgaris (AV), eczema, psoriasis, seborrheic dermatitis
MOA
phosphodiesterase inhibitor
Source data