Icillin

Summary

Icillin (CHEMBL258405) is a phase-3 clinical-stage small molecule targeting TRPA1 and TRPM8.

At a glance

• Status: Max clinical phase 3 (not approved)
• Modality: Small molecule
• Targets: 2 (TRPA1, TRPM8)
• Chemistry: 311.29 Da · C16H13N3O4

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL258405
Name	Icillin
Type	Small molecule
Max phase	3
FDA approved	no
PubChem CID	161930
Molecular formula	C16H13N3O4
Molecular weight	311.29
InChIKey	RCEFMOGVOYEGJN-UHFFFAOYSA-N

SMILES: C1C=C(NC(=O)N1C2=CC=CC=C2O)C3=CC(=CC=C3)[N+](=O)[O-]

IUPAC name: 3-(2-hydroxyphenyl)-6-(3-nitrophenyl)-1,4-dihydropyrimidin-2-one

Also known as: Icillin, Icilin, icilin, SID11111340, SID11114126, SID24787011, SID50104889, SID85231095, SID90341669, SID124880477, ICILLIN, ICILIN

Patent coverage: 403 distinct patent families (1,025 SureChEMBL compound mentions), from 3 matched compound structure(s). One matched structure accounts for 876 (85%) 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
TRPA1	TRPA1	Agonist		0.1%	O75762
TRPM8	TRPM8	Agonist	6.9	0.5%	Q7Z2W7

Broader ChEMBL bioactivity targets: 15 (assay-derived). Sample: Tyrosyl-DNA phosphodiesterase 1, Transient receptor potential cation channel subfamily M member 8, Microtubule-associated protein tau, Prelamin-A/C, Ferritin light chain, 15-hydroxyprostaglandin dehydrogenase [NAD(+)], Thyrotropin receptor, Cytochrome P450 2D6, Nuclear factor NF-kappa-B p105 subunit, Cytochrome P450 1A2.

Bioactivity

ChEMBL activities: 14 potent at pChembl ≥ 5 of 25 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
TRPM8	8.3	EC50	5	nM	CHEMBL_ACT_29154312
TDP1	7.3	Potency	50.1	nM	CHEMBL_ACT_3933938
Q8R455	7.24	IC50	58	nM	CHEMBL_ACT_15240587
TRPM8	7.22	EC50	60	nM	CHEMBL_ACT_3301118
Q8R455	6.96	EC50	110	nM	CHEMBL_ACT_15239992
Q8R455	6.72	EC50	190	nM	CHEMBL_ACT_2604890
TRPM8	6.52	EC50	300	nM	CHEMBL_ACT_13512225
TRPM8	6.52	EC50	300	nM	CHEMBL_ACT_25073049
CYP2C9	6	Potency	1000	nM	CHEMBL_ACT_5033547
CYP2C9	6	AC50	1000	nM	CHEMBL_ACT_6010595
TSHR	5.4	Potency	3981	nM	CHEMBL_ACT_3937279
LMNA	5.2	Potency	6310	nM	CHEMBL_ACT_3652540
CYP2C19	5.2	Potency	6310	nM	CHEMBL_ACT_4006387
CYP2C19	5.2	AC50	6310	nM	CHEMBL_ACT_6008657

Target pathways

Aggregated over 2 target gene(s): TRPA1, TRPM8.

Top Reactome pathways

1 total, by targets touching each:

Pathway	Targets	Genes
TRP channels	2	TRPA1, TRPM8

Dominant GO biological processes

GO term	Targets
monoatomic ion transport	2
intracellular calcium ion homeostasis	2
response to cold	2
thermoception	2
calcium ion transmembrane transport	2
calcium ion transport	2
calcium-mediated signaling	2
monoatomic ion transmembrane transport	2
transmembrane transport	2
cell surface receptor signaling pathway	1
response to xenobiotic stimulus	1
urinary bladder smooth muscle contraction	1
sensory perception of pain	1
cellular response to heat	1
positive regulation of insulin secretion involved in cellular response to glucose stimulus	1

Indications & clinical

Indications

0 indications (0 at ChEMBL trial phase 4).

Clinical trials

Total trials: 0.

Clinical evidence (CIViC)

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

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

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.

35 molecules share ≥1 primary target. Top 35 by shared-target count:

Molecule	Source	Status	Shared targets
dronabinol	ChEMBL + PubChem	Phase 4 (approved)	TRPA1, TRPM8
MENTHOL	ChEMBL	Phase 4 (approved)	TRPA1, TRPM8
LEVOMENTHOL	ChEMBL	Phase 3	TRPA1, TRPM8
CANNABIDIVARIN	ChEMBL	Phase 2	TRPA1, TRPM8
CANNABIGEROL	ChEMBL	Phase 2	TRPA1, TRPM8
TETRAHYDROCANNABIVARIN	ChEMBL	Phase 2	TRPA1, TRPM8
Eugenol	PubChem	Approved	TRPA1, TRPM8
menthol, unspecified form	PubChem	Approved	TRPA1, TRPM8
CANNABIDIOL	ChEMBL + PubChem	Phase 4 (approved)	TRPM8
CAPSAICIN	ChEMBL + PubChem	Phase 4 (approved)	TRPM8
CLOTRIMAZOLE	ChEMBL + PubChem	Phase 4 (approved)	TRPM8
DICLOFENAC	ChEMBL + PubChem	Phase 4 (approved)	TRPA1
DISULFIRAM	ChEMBL + PubChem	Phase 4 (approved)	TRPA1
ECONAZOLE	ChEMBL + PubChem	Phase 4 (approved)	TRPM8
MEFENAMIC ACID	ChEMBL + PubChem	Phase 4 (approved)	TRPA1
NICOTINE	ChEMBL	Phase 4 (approved)	TRPA1
RESVERATROL	ChEMBL + PubChem	Phase 3 (approved)	TRPA1
CANNABINOL	ChEMBL	Phase 3	TRPA1
ACOLTREMON	ChEMBL	Phase 2	TRPM8
ALLICIN	ChEMBL	Phase 2	TRPA1
CARVACROL	ChEMBL	Phase 2	TRPA1
CHLORDANTOIN	ChEMBL	Phase 2	TRPA1
ELISMETREP	ChEMBL	Phase 2	TRPM8
FLUFENAMIC ACID	ChEMBL	Phase 2	TRPA1
RG6341	ChEMBL	Phase 2	TRPA1
SALIRASIB	ChEMBL	Phase 2	TRPA1
SANGUINARIUM	ChEMBL	Phase 2	TRPA1
SB-705498	ChEMBL	Phase 2	TRPM8
THYMOL	ChEMBL	Phase 2	TRPA1
Acetaldehyde	PubChem	Approved	TRPA1
Caffeine	PubChem	Approved	TRPA1
camphor (synthetic)	PubChem	Approved	TRPA1
eucalyptol	PubChem	Approved	TRPM8
Propylene Glycol	PubChem	Approved	TRPA1
Serotonin	PubChem	Approved	TRPM8