Norethindrone Acetate

Summary

Norethindrone Acetate (CHEMBL1201146) is an approved small-molecule synthetic oral contraceptive; indicated across 10 conditions including endometriosis and acne.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• Indications: 10 conditions
• Clinical trials: 34
• Chemistry: 340.5 Da · C22H28O3

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL1201146
Name	Norethindrone Acetate
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	5832
ChEBI	CHEBI:7628
Molecular formula	C22H28O3
Molecular weight	340.5
InChIKey	IMONTRJLAWHYGT-ZCPXKWAGSA-N

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

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

ChEBI definition: A 3-oxo Δ4-steroid that is norethisterone in which the hydroxy group has been converted to its acetate ester.

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

Also known as: Aygestin, Norethidrone acetate, Norethindrone acetate, Norethisteron acetate, Norethisterone acetate, Norethisteroni acetas, Norethynyltestosterone, Norlutate, Norlutin acetate, NSC-22844, SH-420, SID29215468

Patent coverage: 2,598 distinct patent families (9,144 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

Broader ChEMBL bioactivity targets: 14 (assay-derived). Sample: Microtubule-associated protein tau, Nuclear receptor ROR-gamma, Ferritin light chain, Androgen receptor, Glucocorticoid receptor, Thromboxane A2 receptor, Progesterone receptor, Muscarinic acetylcholine receptor M2, Muscarinic acetylcholine receptor M1, Sodium-dependent noradrenaline transporter, Alpha-1A adrenergic receptor, Adenosine receptor A3, Androgen receptor, Cytochrome P450 2C19.

Bioactivity

ChEMBL activities: 13 potent at pChembl ≥ 5 of 17 total. Top 100 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
PGR	7.48	AC50	33	nM	CHEMBL_ACT_25204205
P15207	7.15	Ki	71	nM	CHEMBL_ACT_7729387
P15207	6.97	IC50	106	nM	CHEMBL_ACT_7729386
AR	6.9	AC50	124.6	nM	CHEMBL_ACT_25203272
NR3C1	6.53	Ki	293	nM	CHEMBL_ACT_7727235
NR3C1	6.19	IC50	646	nM	CHEMBL_ACT_7727234
CYP2C19	6.1	IC50	800	nM	CHEMBL_ACT_7727202
ADORA3	6.08	AC50	837.9	nM	CHEMBL_ACT_25198651
CHRM1	5.51	AC50	3101	nM	CHEMBL_ACT_25210139
ADRA1A	5.23	AC50	5915	nM	CHEMBL_ACT_25218778
P51450	5.1	Potency	7943	nM	CHEMBL_ACT_4984115
CHRM2	5.03	AC50	9438	nM	CHEMBL_ACT_25195650
TBXA2R	5.01	AC50	9739	nM	CHEMBL_ACT_25197773

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

3 approved indications. FDA phase 4, plus an anticancer drug’s labelled cancer uses (which ChEMBL often logs at phase 3).

Indication	Phase	MONDO	EFO
endometriosis	4	MONDO:0005133	EFO:0001065
acne	4	MONDO:0011438	EFO:0003894
hypogonadism	4	MONDO:0002146	MONDO:0002146

2 diseases in clinical trials (phase 1–3, investigational — not approved indications). Highest ChEMBL trial phase per disease; a non-cancer approved use is occasionally logged at phase 3 here.

Disease (in trials)	Phase	MONDO	EFO
breast neoplasm	3	MONDO:0021100	MONDO:0007254
lymphoma	2	MONDO:0005062	EFO:0000574

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

Clinical trials

Total trials: 34.

Phase distribution

Phase	Trials
PHASE3	19
Not specified	8
PHASE4	2
PHASE2	2
PHASE1	2
PHASE2/PHASE3	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT02693002	PHASE4	TERMINATED	Estrogen Diastolic Heart Failure
NCT05293574	PHASE4	UNKNOWN	A Trial of Norethisterone Acetate and Expectant Management in Treatment of Simple Ovarian Cysts
NCT00003771	PHASE3	COMPLETED	Hormone Replacement Therapy and the Risk of Breast Cancer Recurrence in Women With Previous Early Stage Breast Cancer
NCT00391807	PHASE3	COMPLETED	Study of Safety and Efficacy of an Oral Contraceptive
NCT00932321	PHASE3	COMPLETED	Study of Safety and Efficacy of an Oral Contraceptive
NCT01140217	PHASE3	COMPLETED	Efficacy and Safety Study of Norethindrone Acetate Transdermal Delivery System in Contraception
NCT01160315	PHASE2/PHASE3	COMPLETED	Efficiency of Gonadotropin-releasing Hormone (GnRH) Agonist in Preventing Chemotherapy Induced Ovarian Failure
NCT02654054	PHASE3	COMPLETED	Efficacy and Safety of Elagolix in Combination With Estradiol/Norethindrone Acetate for the Management of Heavy Menstrual Bleeding Associated With Uterine Fibroids in Premenopausal Women
NCT02691494	PHASE3	COMPLETED	Efficacy and Safety of Elagolix in Combination With Estradiol/Norethindrone Acetate for the Management of Heavy Menstrual Bleeding Associated With Uterine Fibroids in Premenopausal Women (Replicate Study)
NCT02925494	PHASE3	COMPLETED	An Extension Study to Evaluate the Efficacy and Safety of Elagolix in Premenopausal Women With Heavy Menstrual Bleeding Associated With Uterine Fibroids
NCT03049735	PHASE3	COMPLETED	LIBERTY 1: Efficacy & Safety Study of Relugolix in Women With Heavy Menstrual Bleeding Associated With Uterine Fibroids
NCT03103087	PHASE3	COMPLETED	LIBERTY 2: Efficacy & Safety Study of Relugolix in Women With Heavy Menstrual Bleeding Associated With Uterine Fibroids
NCT03106454	PHASE3	COMPLETED	Ovulation Incidence in Oral Contraceptive Users
NCT03204318	PHASE3	COMPLETED	SPIRIT 1: Efficacy and Safety Study of Relugolix in Women With Endometriosis-Associated Pain
NCT03204331	PHASE3	COMPLETED	SPIRIT 2: Efficacy and Safety Study of Relugolix in Women With Endometriosis-Associated Pain
NCT03213457	PHASE3	COMPLETED	A Clinical Study to Evaluate the Safety and Efficacy of Elagolix in Participants With Moderate to Severe Endometriosis-Associated Pain
NCT03412890	PHASE3	COMPLETED	LIBERTY EXTENSION: Efficacy and Safety Extension Study of Relugolix in Women With Heavy Menstrual Bleeding Associated With Uterine Fibroids
NCT03654274	PHASE3	COMPLETED	SPIRIT EXTENSION: Efficacy and Safety Extension Study of Relugolix in Women With Endometriosis-Associated Pain
NCT03751124	PHASE3	COMPLETED	Study of Relugolix With Estradiol and Norethindrone Acetate in Women With Heavy Menstrual Bleeding Associated With Uterine Fibroids
NCT03970330	PHASE3	TERMINATED	Low-Dose Naltrexone in Combination With Standard Treatment in Women With Endometriosis
NCT04290013	PHASE3	UNKNOWN	Effects of Tranexemic Acid Versus Norethisterone Acetate on Endometrial Vasculature .
NCT04527003	PHASE3	TERMINATED	Cannabidiol and Management of Endometriosis Pain
NCT00453960	PHASE2	COMPLETED	Genistein and Endometrial Hyperplasia
NCT02542410	PHASE2	COMPLETED	Dopamine Receptor Agonist Therapy for Pain Relief in Women Suffering From Endometriosis: A Pilot Study
NCT01157182	PHASE1	COMPLETED	Estradiol/Norethindrone Acetate Tablets, 1/0.5 mg Under Fasting Conditions
NCT01181726	PHASE1	COMPLETED	Estradiol/Norethindrone Acetate Tablets, 1/0.5 mg Under Fed Conditions
NCT05739136	Not specified	ACTIVE_NOT_RECRUITING	MYFEMBREE®: A Retrospective Cohort Study Using an Administrative Healthcare Database to Assess Pregnancy Outcomes in Women Treated With Relugolix Combination Therapy
NCT05916469	Not specified	RECRUITING	Heavy Menstrual Bleeding Progestin Treatment in Bleeding Disorders Study
NCT06953076	Not specified	RECRUITING	Ultrasound Transformation of Myomas During Relugolix-Estradiol-Norethisterone Treatment: The MySaturn Study
NCT01499602	Not specified	COMPLETED	Efficacy of LNG-IUS for Treatment of Non-atypical Endometrial Hyperplasia in Perimenopausal Women
NCT01667978	Not specified	COMPLETED	The Effect of Protease Inhibitors on the Pharmacokinetics of Oral Norethindrone Contraception
NCT02353247	Not specified	COMPLETED	Use of Norethindrone Acetate for Management of Bleeding Associated With the Etonogestrel Contraceptive Implant
NCT05153928	Not specified	UNKNOWN	Management of Uterine Leiomyomata and Adenomyosis
NCT05476172	Not specified	COMPLETED	The Effect of Dienogest vs. Norethindrone Acetate Treatment in Endometriosis

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

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).