Norgestimate

Summary

Norgestimate (CHEMBL1200934) is an approved small-molecule contraceptive drug targeting TRPC3 and TRPC6; indicated across 8 conditions including acne and neural tube defect.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• Targets: 2 (TRPC3, TRPC6)
• Indications: 8 conditions
• Clinical trials: 7
• Chemistry: 369.5 Da · C23H31NO3

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL1200934
Name	Norgestimate
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	6540478
ChEBI	CHEBI:50815
Molecular formula	C23H31NO3
Molecular weight	369.5
InChIKey	KIQQMECNKUGGKA-NMYWJIRASA-N

SMILES: CC[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)OC(=O)C)CCC4=C/C(=N/O)/CC[C@H]34

IUPAC name: [(3E,8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-3-hydroxyimino-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate

Pharmacological roles (ChEBI): contraceptive drug, progestin, synthetic oral contraceptive.

Also known as: Dexnorgestrel acetime, Norgestimate, Norgestimate component of prefest, Norgestimate component of previfem, Norgestimate component of sprintec, Norgestimate component of tri-previfem, Norgestimate component of tri-sprintec, Norgestimato, NSC-759159, ORF 10131, ORF-10131, RWJ 10131

Patent coverage: 2,071 distinct patent families (7,839 SureChEMBL compound mentions), from 1 matched compound structure(s). 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
TRPC3	TRPC3		5.52	0.1%	Q13507
TRPC6	TRPC6		5.28	0.2%	Q9Y210

Broader ChEMBL bioactivity targets: 14 (assay-derived). Sample: Nuclear receptor ROR-gamma, 4’-phosphopantetheinyl transferase ffp, Glucocorticoid receptor, Progesterone receptor, Sodium-dependent noradrenaline transporter, Type-1 angiotensin II receptor, Sodium-dependent serotonin transporter, D(3) dopamine receptor, Sodium-dependent dopamine transporter, Adenosine receptor A3.

Bioactivity

ChEMBL activities: 7 potent at pChembl ≥ 5 of 15 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
PGR	7.7	AC50	20	nM	CHEMBL_ACT_25222977
NR3C1	7.39	AC50	41	nM	CHEMBL_ACT_25175775
P15207	5.44	AC50	3600	nM	CHEMBL_ACT_25232298
NR1I2	5.4	AC50	4000	nM	CHEMBL_ACT_25188122
P51450	5.3	Potency	5012	nM	CHEMBL_ACT_4790253
Q63921	5.11	AC50	7800	nM	CHEMBL_ACT_25174317
SLC6A3	5	AC50	10000	nM	CHEMBL_ACT_25123871

Target pathways

Aggregated over 2 target gene(s): TRPC3, TRPC6.

Top Reactome pathways

5 total, by targets touching each:

Pathway	Targets	Genes
Effects of PIP2 hydrolysis	2	TRPC3, TRPC6
Elevation of cytosolic Ca2+ levels	2	TRPC3, TRPC6
TRP channels	2	TRPC3, TRPC6
Role of second messengers in netrin-1 signaling	2	TRPC3, TRPC6
MECP2 regulates neuronal receptors and channels	1	TRPC3

Dominant GO biological processes

GO term	Targets
calcium ion transport	2
single fertilization	2
regulation of cytosolic calcium ion concentration	2
calcium ion transmembrane transport	2
monoatomic ion transport	2
monoatomic ion transmembrane transport	2
transmembrane transport	2
phototransduction	1
positive regulation of calcium ion transport into cytosol	1
response to ATP	1
response to calcium ion	1
positive regulation of cardiac muscle hypertrophy in response to stress	1
monoatomic cation transport	1
positive regulation of cytosolic calcium ion concentration	1
neuron differentiation	1

Indications & clinical

Indications

8 indications (1 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
acne	4	MONDO:0011438	EFO:0003894
neural tube defect	3	MONDO:0018075	MONDO:0018075
osteoporosis	2	MONDO:0005298	EFO:0003882
HIV infectious disease	1	MONDO:0005109	EFO:0000764
hepatitis C virus infection	1	MONDO:0005231	EFO:0003047
migraine disorder	1	MONDO:0005277	MONDO:0005277
cystic fibrosis	1	MONDO:0009061	MONDO:0009061

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

Clinical trials

Total trials: 7.

Phase distribution

Phase	Trials
PHASE1	3
PHASE2	2
PHASE4	1
Not specified	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00745901	PHASE4	COMPLETED	Study to Evaluate Cycle Control With Norgestimate/Ethinyl Estradiol and Drospirenone/Ethinyl Estradiol in Healthy Sexually Active Females
NCT00320567	PHASE2	COMPLETED	The Effect of Norgestimate/Ethinyl Estradiol on Bone Density in Pediatric Subjects With Anorexia Nervosa
NCT00344383	PHASE2	COMPLETED	An Open-Label Study Evaluating Breakthrough Bleeding and Spotting With Norgestimate/Ethinyl Estradiol Tablets Administered as an Extended Regimen
NCT00709189	PHASE1	COMPLETED	Bioequivalence Study of the Oral Contraceptive Tablet Containing Norgestimate (NGM)/Ethinyl Estradiol (EE) With or Without Folic Acid in Healthy Women.
NCT02127593	PHASE1	COMPLETED	A Bioequivalence Study of Norgestimate /Ethinyl Estradiol (NGM/EE) Tablets Manufactured at 2 Different Facilities
NCT02533427	PHASE1	COMPLETED	Study to Evaluate Effect of Sofosbuvir/Velpatasvir/GS-9857 Fixed-Dose Combination on the Pharmacokinetics of a Representative Hormonal Contraceptive Medication, Norgestimate/Ethinyl Estradiol
NCT00554632	Not specified	COMPLETED	Birth Control Pill vs Birth Control Patch Study

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.

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

Molecule	Source	Status	Shared targets
CLEMIZOLE	ChEMBL	Phase 2	TRPC3, TRPC6