Methylergonovine

Summary

Methylergonovine (CHEMBL1201356) is an approved small molecule (ATC G02AB01) targeting HTR1E, HTR1F, and HTR2A.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: G02AB01
• Targets: 5 (HTR1E, HTR1F, HTR2A…)
• Clinical trials: 3
• Chemistry: 339.4 Da · C20H25N3O2

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL1201356
Name	Methylergonovine
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	8226
ATC	G02AB01
Molecular formula	C20H25N3O2
Molecular weight	339.4
InChIKey	UNBRKDKAWYKMIV-QWQRMKEZSA-N

SMILES: CC[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-hydroxybutan-2-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide

Also known as: Ergotyl, Methylergometrine, Methylergonovine, Metilergometrina, SID26751766, SID90341291, SID104171343, SID50104453, methylergometrine, methyl ergonovine, SID144204360, METHYLERGOMETRINE

Parent form; salt/anhydrous children: CHEMBL1200843

Patent coverage: 848 distinct patent families (3,335 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 3,319 (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	Antagonist	7.2	0%	P28566
HTR1F	5-HT1F receptor	Antagonist	7.5	0.1%	P30939
HTR2A	5-HT2A receptor	Full agonist	9.4	0%	P28223
HTR2B	5-HT2B receptor	Partial agonist	9.3	0.4%	P41595
HTR2C	5-HT2C receptor	Full agonist	8.3	0%	P28335

Broader ChEMBL bioactivity targets: 27 (assay-derived). Sample: Microtubule-associated protein tau, Ubiquitin carboxyl-terminal hydrolase 2, Survival motor neuron protein, Prelamin-A/C, ATP-dependent DNA helicase Q1, 4’-phosphopantetheinyl transferase ffp, 5-hydroxytryptamine receptor 2B, Alpha-2A adrenergic receptor, Alpha-2C adrenergic receptor, Histamine H2 receptor.

Bioactivity

ChEMBL activities: 41 potent at pChembl ≥ 5 of 50 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
HTR2A	9.14	Ki	0.73	nM	CHEMBL_ACT_7770990
HTR2B	9.1	Ki	0.8	nM	CHEMBL_ACT_3555291
HTR2B	9.02	Ki	0.96	nM	CHEMBL_ACT_7770992
HTR6	8.93	Ki	1.18	nM	CHEMBL_ACT_7771000
HTR2B	8.82	IC50	1.5	nM	CHEMBL_ACT_7770991
P19327	8.63	Ki	2.33	nM	CHEMBL_ACT_7770986
HTR6	8.6	IC50	2.54	nM	CHEMBL_ACT_7770999
HTR2A	8.59	IC50	2.55	nM	CHEMBL_ACT_7770989
DRD1	8.51	AC50	3.1	nM	CHEMBL_ACT_25180973
HTR2B	8.43	AC50	3.7	nM	CHEMBL_ACT_25164233
P19327	8.39	IC50	4.07	nM	CHEMBL_ACT_7770985
HTR2B	8.27	AC50	5.4	nM	CHEMBL_ACT_25164299
HTR2C	8.18	Ki	6.56	nM	CHEMBL_ACT_7770994
HTR2A	8.14	AC50	7.2	nM	CHEMBL_ACT_25226781
P28564	8.03	Ki	9.26	nM	CHEMBL_ACT_7770988
HTR2C	7.89	IC50	13	nM	CHEMBL_ACT_7770993
HTR1A	7.84	AC50	14.4	nM	CHEMBL_ACT_25217464
P28564	7.82	IC50	15	nM	CHEMBL_ACT_7770987
ADRA1A	7.7	AC50	20	nM	CHEMBL_ACT_25230180
HTR2B	7.67	EC50	21.38	nM	CHEMBL_ACT_3555296
HTR2B	7.59	AC50	25.7	nM	CHEMBL_ACT_25229164
HRH2	7.24	AC50	58	nM	CHEMBL_ACT_25169765
DRD3	7.24	Ki	57	nM	CHEMBL_ACT_7768849
HTR2C	6.92	AC50	120	nM	CHEMBL_ACT_25132256
DRD3	6.78	IC50	167	nM	CHEMBL_ACT_7768848
CYP2D6	6.7	IC50	200	nM	CHEMBL_ACT_7768838
ADRA2B	6.68	Ki	210	nM	CHEMBL_ACT_7766765
DRD2	6.56	Ki	276	nM	CHEMBL_ACT_7768847
DRD3	6.54	AC50	290	nM	CHEMBL_ACT_25193987
ADRA2B	6.46	AC50	350	nM	CHEMBL_ACT_25144158

Target pathways

Aggregated over 5 target gene(s): HTR1E, HTR1F, HTR2A, HTR2B, HTR2C.

Top Reactome pathways

9 total, by targets touching each:

Pathway	Targets	Genes
Signal Transduction	5	HTR1E, HTR1F, HTR2A, HTR2B, HTR2C
Signaling by GPCR	5	HTR1E, HTR1F, HTR2A, HTR2B, HTR2C
Class A/1 (Rhodopsin-like receptors)	5	HTR1E, HTR1F, HTR2A, HTR2B, HTR2C
Amine ligand-binding receptors	5	HTR1E, HTR1F, HTR2A, HTR2B, HTR2C
GPCR downstream signalling	5	HTR1E, HTR1F, HTR2A, HTR2B, HTR2C
Serotonin receptors	5	HTR1E, HTR1F, HTR2A, HTR2B, HTR2C
GPCR ligand binding	5	HTR1E, HTR1F, HTR2A, HTR2B, HTR2C
G alpha (q) signalling events	3	HTR2A, HTR2B, HTR2C
G alpha (i) signalling events	2	HTR1E, HTR1F

Dominant GO biological processes

GO term	Targets
G protein-coupled receptor signaling pathway	5
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger	5
chemical synaptic transmission	5
signal transduction	5
intracellular calcium ion homeostasis	3
phospholipase C-activating serotonin receptor signaling pathway	3
serotonin receptor signaling pathway	3
positive regulation of phosphatidylinositol biosynthetic process	3
release of sequestered calcium ion into cytosol	3
positive regulation of ERK1 and ERK2 cascade	3
G protein-coupled serotonin receptor signaling pathway	3
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathway	2
adenylate cyclase-inhibiting serotonin receptor signaling pathway	2
adenylate cyclase-activating G protein-coupled receptor signaling pathway	2
positive regulation of cell population proliferation	2

Indications & clinical

Indications

0 indications (0 at ChEMBL trial phase 4).

Clinical trials

Total trials: 3.

Phase distribution

Phase	Trials
PHASE4	2
EARLY_PHASE1	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT03904446	PHASE4	COMPLETED	Multimodal Uterotonics at the Time of Cesarean Section in Laboring Patients
NCT05772156	PHASE4	COMPLETED	Prophylactic Methylergonovine for Twin Cesarean
NCT03303235	EARLY_PHASE1	WITHDRAWN	Intravenous Versus Intramuscular Administration of Methylergonovine for Uterine Contraction in Cesarean Sections

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.

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

Molecule	Source	Status	Shared targets
CLOZAPINE	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR1F, HTR2A, HTR2B, HTR2C
Cyproheptadine	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR1F, HTR2A, HTR2B, HTR2C
Dihydroergotamine	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR1F, HTR2A, HTR2B, HTR2C
Ergotamine	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR1F, HTR2A, HTR2B, HTR2C
IMIPRAMINE	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR1F, HTR2A, HTR2B, HTR2C
Olanzapine	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR1F, HTR2A, HTR2B, HTR2C
Quetiapine	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR1F, HTR2A, HTR2B, HTR2C
Risperidone	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR1F, HTR2A, HTR2B, HTR2C
Rizatriptan	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR1F, HTR2A, HTR2B, HTR2C
Sorafenib	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR1F, HTR2A, HTR2B, HTR2C
SUMATRIPTAN	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR1F, HTR2A, HTR2B, HTR2C
SEROTONIN	ChEMBL + PubChem	Phase 3 (approved)	HTR1E, HTR1F, HTR2A, HTR2B, HTR2C
MEBUFOTENIN	ChEMBL	Phase 2	HTR1E, HTR1F, HTR2A, HTR2B, HTR2C
Asenapine	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR2A, HTR2B, HTR2C
Cannabidiol	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR2A, HTR2B, HTR2C
Ziprasidone	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR2A, HTR2B, HTR2C
AZELASTINE	ChEMBL	Phase 4 (approved)	HTR1E, HTR2A, HTR2B, HTR2C
BREXPIPRAZOLE	ChEMBL	Phase 4 (approved)	HTR1E, HTR2A, HTR2B, HTR2C
Yohimbine	ChEMBL + PubChem	Phase 3 (approved)	HTR1E, HTR1F, HTR2A, HTR2B
LATREPIRDINE	ChEMBL	Phase 3	HTR1E, HTR2A, HTR2B, HTR2C
LYSERGIDE	ChEMBL	Phase 2	HTR1E, HTR2A, HTR2B, HTR2C
PSILOCIN	ChEMBL	Phase 2	HTR1E, HTR2A, HTR2B, HTR2C
FIDAXOMICIN	ChEMBL + PubChem	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
LASMIDITAN	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR1F, HTR2B
PIMAVANSERIN	ChEMBL + PubChem	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
Pramipexole	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR2A, HTR2B
PROPOXYPHENE	ChEMBL + PubChem	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
Zolmitriptan	ChEMBL + PubChem	Phase 4 (approved)	HTR1E, HTR1F, HTR2A
ALOSETRON	ChEMBL	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
AMIODARONE	ChEMBL	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
AMITRIPTYLINE	ChEMBL	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
AMLODIPINE	ChEMBL	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
AMOXAPINE	ChEMBL	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
APOMORPHINE	ChEMBL	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
ARIPIPRAZOLE	ChEMBL	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
ASTEMIZOLE	ChEMBL	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
ATOMOXETINE	ChEMBL	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
AZATADINE	ChEMBL	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
BENFLUOREX	ChEMBL	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
BENPERIDOL	ChEMBL	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
BENZQUINAMIDE	ChEMBL	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
BENZTROPINE	ChEMBL	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
BROMOCRIPTINE	ChEMBL	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
BUSPIRONE	ChEMBL	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
CARIPRAZINE	ChEMBL	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
CARVEDILOL	ChEMBL	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
CHLORHEXIDINE	ChEMBL	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
CHLORPROMAZINE	ChEMBL	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
CINACALCET	ChEMBL	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
CISAPRIDE	ChEMBL	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
CITALOPRAM	ChEMBL	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
CLEMASTINE	ChEMBL	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
CLOMIPRAMINE	ChEMBL	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
CLOTRIMAZOLE	ChEMBL	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
CYCLIZINE	ChEMBL	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
CYCLOBENZAPRINE	ChEMBL	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
DAPIPRAZOLE	ChEMBL	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
DASATINIB	ChEMBL	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
DESIPRAMINE	ChEMBL	Phase 4 (approved)	HTR2A, HTR2B, HTR2C
DESLORATADINE	ChEMBL	Phase 4 (approved)	HTR2A, HTR2B, HTR2C