Ergonovine

Summary

Ergonovine (CHEMBL119443) is a phase-3 clinical-stage small-molecule diagnostic agent (ATC G02AB03) targeting HTR1E and HTR2A.

At a glance

• Status: Max clinical phase 3 (not approved)
• Modality: Small molecule
• ATC class: G02AB03
• Targets: 2 (HTR1E, HTR2A)
• Clinical trials: 7
• Chemistry: 325.4 Da · C19H23N3O2

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL119443
Name	Ergonovine
Type	Small molecule
Max phase	3
FDA approved	no
PubChem CID	443884
ChEBI	CHEBI:4822
ATC	G02AB03
Molecular formula	C19H23N3O2
Molecular weight	325.4
InChIKey	WVVSZNPYNCNODU-XTQGRXLLSA-N

SMILES: C[C@@H](CO)NC(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C

IUPAC name: (6aR,9R)-N-[(2S)-1-hydroxypropan-2-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide

ChEBI definition: A monocarboxylic acid amide that is lysergamide in which one of the hydrogens attached to the amide nitrogen is substituted by a 1-hydroxypropan-2-yl group (S-configuration). An ergot alkaloid that has a particularly powerful action on the uterus, its maleate (and formerly tartrate) salt is used in the active management of the third stage of labour, and to prevent or treat postpartum of postabortal haemorrhage caused by uterine atony: by maintaining uterine contraction and tone, blood vessels in the uterine wall are compressed and blood flow reduced.

Pharmacological roles (ChEBI): oxytocic, diagnostic agent, toxin.

Other ChEBI roles (chemical / environmental): fungal metabolite.

Also known as: Ergobasine, Ergometrina, Ergometrine, Ergostetrine, Ergotocine, SID26754288, SID124882895, Ergonovine, SID144205575, ERGONOVINE, ergonovine

Parent form; salt/anhydrous children: CHEMBL1213135

Patent coverage: 1,045 distinct patent families (3,432 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 3,424 (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
HTR1E	5-ht1e receptor	Full agonist	7.3	0%	P28566
HTR2A	5-HT2A receptor	Full agonist	8.5	0%	P28223

Broader ChEMBL bioactivity targets: 23 (assay-derived). Sample: Microtubule-associated protein tau, Lysine-specific demethylase 4E, Fructose-bisphosphate aldolase, ATP-dependent DNA helicase Q1, 15-hydroxyprostaglandin dehydrogenase [NAD(+)], 5-hydroxytryptamine receptor 2B, Alpha-2A adrenergic receptor, Alpha-2B adrenergic receptor, D(1A) dopamine receptor, Menin/Histone-lysine N-methyltransferase MLL.

Bioactivity

ChEMBL activities: 22 potent at pChembl ≥ 5 of 37 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
HTR2A	9.2	Ki	0.63	nM	CHEMBL_ACT_7669269
P28564	8.89	Ki	1.29	nM	CHEMBL_ACT_7669267
HTR6	8.82	Ki	1.5	nM	CHEMBL_ACT_7669279
HTR2A	8.66	IC50	2.21	nM	CHEMBL_ACT_7669268
HTR2B	8.58	Ki	2.63	nM	CHEMBL_ACT_7669271
P28564	8.55	IC50	2.85	nM	CHEMBL_ACT_7669266
HTR6	8.49	IC50	3.24	nM	CHEMBL_ACT_7669278
HTR2B	8.38	IC50	4.14	nM	CHEMBL_ACT_7669270
P19327	8.33	Ki	4.64	nM	CHEMBL_ACT_7669265
P19327	8.09	IC50	8.13	nM	CHEMBL_ACT_7669264
HTR2C	7.96	Ki	11	nM	CHEMBL_ACT_7669273
HTR2C	7.68	IC50	21	nM	CHEMBL_ACT_7669272
ADRA2B	6.88	Ki	132	nM	CHEMBL_ACT_7667038
DRD2	6.74	Ki	184	nM	CHEMBL_ACT_7667106
DRD3	6.71	Ki	193	nM	CHEMBL_ACT_7667108
ADRA2B	6.54	IC50	289	nM	CHEMBL_ACT_7667037
DRD2	6.26	IC50	552	nM	CHEMBL_ACT_7667105
DRD3	6.25	IC50	567	nM	CHEMBL_ACT_7667107
ADRA2A	6.2	Ki	630	nM	CHEMBL_ACT_7667036
ADRA2A	5.78	IC50	1680	nM	CHEMBL_ACT_7667035
DRD1	5.53	Ki	2950	nM	CHEMBL_ACT_7667104
DRD1	5.23	IC50	5901	nM	CHEMBL_ACT_7667103

Target pathways

Aggregated over 2 target gene(s): HTR1E, HTR2A.

Top Reactome pathways

9 total, by targets touching each:

Pathway	Targets	Genes
Signal Transduction	2	HTR1E, HTR2A
Signaling by GPCR	2	HTR1E, HTR2A
Class A/1 (Rhodopsin-like receptors)	2	HTR1E, HTR2A
Amine ligand-binding receptors	2	HTR1E, HTR2A
GPCR downstream signalling	2	HTR1E, HTR2A
Serotonin receptors	2	HTR1E, HTR2A
GPCR ligand binding	2	HTR1E, HTR2A
G alpha (q) signalling events	1	HTR2A
G alpha (i) signalling events	1	HTR1E

Dominant GO biological processes

GO term	Targets
G protein-coupled receptor signaling pathway	2
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger	2
chemical synaptic transmission	2
signal transduction	2
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathway	1
adenylate cyclase-inhibiting serotonin receptor signaling pathway	1
adenylate cyclase-activating G protein-coupled receptor signaling pathway	1
temperature homeostasis	1
positive regulation of cytokine production involved in immune response	1
glycolytic process	1
intracellular calcium ion homeostasis	1
positive regulation of cytosolic calcium ion concentration	1
phospholipase C-activating serotonin receptor signaling pathway	1
serotonin receptor signaling pathway	1
memory	1

Indications & clinical

Indications

0 indications (0 at ChEMBL trial phase 4).

Clinical trials

Total trials: 7.

Phase distribution

Phase	Trials
Not specified	5
PHASE3	2

Top trials by phase / activity

NCT	Phase	Status	Title
NCT02306733	PHASE3	UNKNOWN	Ergometrine Versus Oxytocin in the Management of Atonic Post-partum Haemorrhage (PPH) in Women Delivered Vaginally
NCT02410759	PHASE3	UNKNOWN	Carbetocin Versus Ergometrine in the Management of Atonic Post Partum Haemorrhage (PPH) in Women Delivered Vaginally
NCT06285409	Not specified	RECRUITING	Comparing the Dose-response Profiles of Uterotonics After Initial Carbetocin Administration - an Ex-vivo Study in Desensitized Human Myometrium
NCT00989027	Not specified	COMPLETED	Impact of Uterotonic Agents on Isolated Human Myometrium
NCT01689311	Not specified	COMPLETED	In Vitro Myometrial Contractions in Laboring and Non-laboring Women
NCT02046499	Not specified	COMPLETED	A Randomized Trial Comparing Oxytocin and Oxytocin + Ergometrine for Prevention of Postpartum Haemorrhage at Caesarean Section
NCT03578263	Not specified	COMPLETED	Carbetocin Versus Oxytocin and Ergometrine for the Prevention of Postpartum Hemorrhage

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.

391 molecules share ≥1 primary target. Top 60 by shared-target count:

Molecule	Source	Status	Shared targets
Asenapine	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR2A
Cannabidiol	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR2A
CLOZAPINE	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR2A
Cyproheptadine	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR2A
Dihydroergotamine	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR2A
Ergotamine	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR2A
IMIPRAMINE	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR2A
methylergonovine	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR2A
Olanzapine	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR2A
Pramipexole	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR2A
Quetiapine	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR2A
Risperidone	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR2A
Rizatriptan	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR2A
Sorafenib	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR2A
SUMATRIPTAN	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR2A
Ziprasidone	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR2A
Zolmitriptan	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR2A
AZELASTINE	ChEMBL	Phase 4 (approved)	HTR1E, HTR2A
BREXPIPRAZOLE	ChEMBL	Phase 4 (approved)	HTR1E, HTR2A
SEROTONIN	ChEMBL + PubChem	Phase 3 (approved)	HTR1E, HTR2A
Yohimbine	ChEMBL + PubChem	Phase 3 (approved)	HTR1E, HTR2A
LATREPIRDINE	ChEMBL	Phase 3	HTR1E, HTR2A
LYSERGIDE	ChEMBL	Phase 2	HTR1E, HTR2A
MEBUFOTENIN	ChEMBL	Phase 2	HTR1E, HTR2A
PSILOCIN	ChEMBL	Phase 2	HTR1E, HTR2A
RITANSERIN	ChEMBL	Phase 2	HTR1E, HTR2A
FIDAXOMICIN	ChEMBL + PubChem	Phase 4 (approved)	HTR2A
PIMAVANSERIN	ChEMBL + PubChem	Phase 4 (approved)	HTR2A
PROPOXYPHENE	ChEMBL + PubChem	Phase 4 (approved)	HTR2A
ABEMACICLIB	ChEMBL	Phase 4 (approved)	HTR2A
ACETOPHENAZINE	ChEMBL	Phase 4 (approved)	HTR2A
ACYCLOVIR	ChEMBL	Phase 4 (approved)	HTR2A
ALMOTRIPTAN	ChEMBL	Phase 4 (approved)	HTR2A
ALOSETRON	ChEMBL	Phase 4 (approved)	HTR2A
AMIODARONE	ChEMBL	Phase 4 (approved)	HTR2A
AMISULPRIDE	ChEMBL	Phase 4 (approved)	HTR2A
AMITRIPTYLINE	ChEMBL	Phase 4 (approved)	HTR2A
AMLODIPINE	ChEMBL	Phase 4 (approved)	HTR2A
AMOXAPINE	ChEMBL	Phase 4 (approved)	HTR2A
APOMORPHINE	ChEMBL	Phase 4 (approved)	HTR2A
ARIPIPRAZOLE	ChEMBL	Phase 4 (approved)	HTR2A
ASTEMIZOLE	ChEMBL	Phase 4 (approved)	HTR2A
ATOMOXETINE	ChEMBL	Phase 4 (approved)	HTR2A
AZATADINE	ChEMBL	Phase 4 (approved)	HTR2A
BAZEDOXIFENE	ChEMBL	Phase 4 (approved)	HTR2A
BEDAQUILINE	ChEMBL	Phase 4 (approved)	HTR2A
BENFLUOREX	ChEMBL	Phase 4 (approved)	HTR2A
BENPERIDOL	ChEMBL	Phase 4 (approved)	HTR2A
BENZBROMARONE	ChEMBL	Phase 4 (approved)	HTR2A
BENZPHETAMINE	ChEMBL	Phase 4 (approved)	HTR2A
BENZQUINAMIDE	ChEMBL	Phase 4 (approved)	HTR2A
BENZTROPINE	ChEMBL	Phase 4 (approved)	HTR2A
BEPRIDIL	ChEMBL	Phase 4 (approved)	HTR2A
BIFONAZOLE	ChEMBL	Phase 4 (approved)	HTR2A
BLONANSERIN	ChEMBL	Phase 4 (approved)	HTR2A
BOSUTINIB	ChEMBL	Phase 4 (approved)	HTR2A
BROMOCRIPTINE	ChEMBL	Phase 4 (approved)	HTR2A
BROMPERIDOL	ChEMBL	Phase 4 (approved)	HTR2A
BUSPIRONE	ChEMBL	Phase 4 (approved)	HTR2A
BUTENAFINE	ChEMBL	Phase 4 (approved)	HTR2A