Phenol

Summary

Phenol (CHEMBL14060) is an approved small-molecule antiseptic drug (ATC R02AA19) targeting EPHX2; indicated across 8 conditions including varicose disease and herpes labialis.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: R02AA19 (+3 more)
• Targets: 1 (EPHX2)
• Indications: 8 conditions
• Clinical trials: 17
• Chemistry: 94.11 Da · C6H6O

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL14060
Name	Phenol
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	996
ChEBI	CHEBI:15882
ATC	R02AA19, C05BB05, N01BX03, D08AE03
Molecular formula	C6H6O
Molecular weight	94.11
InChIKey	ISWSIDIOOBJBQZ-UHFFFAOYSA-N

SMILES: C1=CC=C(C=C1)O

IUPAC name: phenol

ChEBI definition: An organic hydroxy compound that consists of benzene bearing a single hydroxy substituent. The parent of the class of phenols.

Pharmacological roles (ChEBI): disinfectant, antiseptic drug.

Other ChEBI roles (chemical / environmental): human xenobiotic metabolite, mouse metabolite.

Also known as: Carbolicum acidum, Chloraseptic, ENT-1814, Liquefied phenol, Liquified phenol, NSC-36808, Phenic acid, Phenol, liquified, Phenylic alcohol, S.b. ward, Salicylic acid related compound c

Parent form; salt/anhydrous children: CHEMBL2107497

Patent coverage: 763,084 distinct patent families (1,871,332 SureChEMBL compound mentions), from 3 matched compound structure(s). One matched structure accounts for 1,871,322 (100%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

Gene	Target	Action	pAffinity	Cancer dependency	UniProt
EPHX2	epoxide hydrolase 2	Inhibition		0%	P34913

Broader ChEMBL bioactivity targets: 13 (assay-derived). Sample: Tyrosyl-DNA phosphodiesterase 1, Carbonic anhydrase 2, Alpha-galactosidase A, Carbonic anhydrase 1, Carbonic anhydrase 3, Carbonic anhydrase 12, Carbonic anhydrase 14, Carbonic anhydrase 9, Carbonic anhydrase 4, Endolysin.

Bioactivity

ChEMBL activities: 36 potent at pChembl ≥ 5 of 57 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
CA3	5.57	Ki	2700	nM	CHEMBL_ACT_12667986
CA3	5.57	Ki	2700	nM	CHEMBL_ACT_3116813
CA3	5.57	Ki	2700	nM	CHEMBL_ACT_3395194
CA3	5.57	Ki	2700	nM	CHEMBL_ACT_3426866
CA2	5.26	Ki	5500	nM	CHEMBL_ACT_12662915
CA2	5.26	Ki	5500	nM	CHEMBL_ACT_12662983
CA2	5.26	Ki	5500	nM	CHEMBL_ACT_12667987
CA2	5.26	Ki	5500	nM	CHEMBL_ACT_13855450
CA2	5.26	Ki	5500	nM	CHEMBL_ACT_15670691
CA2	5.26	Ki	5500	nM	CHEMBL_ACT_15774631
CA2	5.26	Ki	5500	nM	CHEMBL_ACT_3116814
CA2	5.26	Ki	5500	nM	CHEMBL_ACT_3395193
CA2	5.26	Ki	5500	nM	CHEMBL_ACT_3426859
CA2	5.26	Ki	5500	nM	CHEMBL_ACT_5197943
CA2	5.26	Ki	5500	nM	CHEMBL_ACT_5307590
CA9	5.06	Ki	8800	nM	CHEMBL_ACT_12662910
CA9	5.06	Ki	8800	nM	CHEMBL_ACT_12667980
CA9	5.06	Ki	8800	nM	CHEMBL_ACT_13855434
CA9	5.06	Ki	8800	nM	CHEMBL_ACT_15774614
CA9	5.06	Ki	8800	nM	CHEMBL_ACT_3116807
CA9	5.06	Ki	8800	nM	CHEMBL_ACT_3395200
CA9	5.06	Ki	8800	nM	CHEMBL_ACT_3426908
CA9	5.06	Ki	8800	nM	CHEMBL_ACT_5197955
CA12	5.04	Ki	9200	nM	CHEMBL_ACT_12662905
CA12	5.04	Ki	9200	nM	CHEMBL_ACT_12667979
CA12	5.04	Ki	9200	nM	CHEMBL_ACT_13855418
CA12	5.04	Ki	9200	nM	CHEMBL_ACT_3116806
CA12	5.04	Ki	9200	nM	CHEMBL_ACT_3395201
CA12	5.04	Ki	9200	nM	CHEMBL_ACT_3426915
CA12	5.04	Ki	9200	nM	CHEMBL_ACT_5197967

Target pathways

Aggregated over 1 target gene(s): EPHX2.

Top Reactome pathways

3 total, by targets touching each:

Pathway	Targets	Genes
Synthesis of epoxy (EET) and dihydroxyeicosatrienoic acids (DHET)	1	EPHX2
Biosynthesis of maresins	1	EPHX2
Peroxisomal protein import	1	EPHX2

Dominant GO biological processes

GO term	Targets
regulation of cell growth	1
response to toxic substance	1
positive regulation of gene expression	1
dephosphorylation	1
cholesterol homeostasis	1
stilbene catabolic process	1
phospholipid dephosphorylation	1
regulation of cholesterol metabolic process	1
epoxide metabolic process	1
lipid metabolic process	1

Indications & clinical

Indications

8 indications (4 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
varicose disease	4	MONDO:0008638	HP:0002619
herpes labialis	4	MONDO:0043653	EFO:1001347
allergic disease	4	MONDO:0005271	MONDO:0005271
cytomegalovirus infection	3	MONDO:0005132	EFO:0001062
nephrotic syndrome	3	MONDO:0005377	EFO:0004255
allergic rhinitis	1	MONDO:0011786	EFO:0005854

2 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 17.

Phase distribution

Phase	Trials
Not specified	11
PHASE4	3
PHASE1	2
EARLY_PHASE1	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT07440173	PHASE4	NOT_YET_RECRUITING	Phenol and Botulinum Toxin vs Botulinum Toxin Alone for Post-Stroke Upper-Limb Spasticity
NCT03973177	PHASE4	WITHDRAWN	Phenol Neurolysis of Genicular Nerves for Chronic Knee Pain
NCT04560049	PHASE4	COMPLETED	Phenol and Silver Nitrate Application in Pilonidal Sinus
NCT06798038	PHASE1	NOT_YET_RECRUITING	Comparison of the Efficacy of Chemical Genicular Nerve Neurolysis Using Alcohol or Phenol Versus Radiofrequency Ablation Under Ultrasound Guidance for Pain Management in Patients With Knee Osteoarthritis
NCT01468415	PHASE1	UNKNOWN	Efficiency Comparison Between Methylprednisolone and Phenol 8% Treatment Using a Trans Sacral Approach - on Lower Back Pain and Limbs
NCT04794842	EARLY_PHASE1	UNKNOWN	Comparing Topical Tetracaine Drops to Topical Focal Phenol for Local Anesthesia During Intratympanic Steroid Injection
NCT06324656	Not specified	RECRUITING	The Efficacy of Combining Platelet-rich Plasma With Crystallized Phenol in Pilonidal Sinus Disease
NCT06391307	Not specified	RECRUITING	The Role of Mesenchymal Stem Cell and Exosome in Treating Pilonidal Sinus Disease in Children
NCT07021365	Not specified	NOT_YET_RECRUITING	Comparison of Ganglion Impar Radiofrequency Ablation and Phenol Neurolysis Techniques for Chronic Coccydynia Treatment
NCT07023952	Not specified	RECRUITING	Effect of Phenol Addition to Laser Treatment on Epithelialization and Healing Process in Pilonidal Sinus
NCT07267039	Not specified	ACTIVE_NOT_RECRUITING	Phenol Neurolysis Versus Local Anesthetic Plus Steroid Genicular Nerve Block in Knee Osteoarthritis
NCT07420452	Not specified	NOT_YET_RECRUITING	Silac Versus Phenol for the Treatment of Pilonidal Sinus Disease: A Randomized Controlled Trial
NCT01792557	Not specified	UNKNOWN	Crystallized Phenol Versus Transposition Flaps for Treatment of Pilonidal Disease: A Prospective Study
NCT02848209	Not specified	COMPLETED	Histological Skin Changes of Different Peeling Agents in Surgically Subcutaneous Undermined Skin
NCT03070028	Not specified	COMPLETED	Minimally Invasive Treatment Methods for Pilonidal Disease
NCT03601533	Not specified	UNKNOWN	Ultrasound-guided Genicular Nerve Block With Phenol for the Treatment of Chronic Pain Due to Knee Osteoarthritis
NCT06265675	Not specified	UNKNOWN	Comparison of the Efficacy of Phenol Block and Corticosteroid-Local Anesthetic Block Applied to the Genicular Nerve

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Related molecules

Related molecules

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

18 molecules share ≥1 primary target. Top 18 by shared-target count:

Molecule	Source	Status	Shared targets
FULVESTRANT	ChEMBL + PubChem	Phase 4 (approved)	EPHX2
REGORAFENIB	ChEMBL + PubChem	Phase 4 (approved)	EPHX2
OXAPROZIN	ChEMBL	Phase 4 (approved)	EPHX2
SORAFENIB	ChEMBL	Phase 4 (approved)	EPHX2
ZAFIRLUKAST	ChEMBL	Phase 4 (approved)	EPHX2
ZILEUTON	ChEMBL	Phase 4 (approved)	EPHX2
EBSELEN	ChEMBL	Phase 3	EPHX2
QUERCETIN	ChEMBL	Phase 3	EPHX2
RUTIN	ChEMBL	Phase 3	EPHX2
SODIUM LAURYL	ChEMBL	Phase 3	EPHX2
AR9281	ChEMBL	Phase 2	EPHX2
ATRELEUTON	ChEMBL	Phase 2	EPHX2
ELLAGIC ACID	ChEMBL	Phase 2	EPHX2
GSK2256294	ChEMBL	Phase 2	EPHX2
ISOQUERCETIN	ChEMBL	Phase 2	EPHX2
TALINOLOL	ChEMBL	Phase 2	EPHX2
TRICLOCARBAN	ChEMBL	Phase 2	EPHX2
URSOLIC ACID	ChEMBL	Phase 2	EPHX2