Nomegestrol acetate

Identification

Generic Name

Nomegestrol acetate

DrugBank Accession Number

DB13981

Background

Nomegestrol acetate, also known as NOMAC, is a progestin used in oral contraceptives, menopausal hormone therapy, and for the treatment of gynecological disorders.

Type

Small Molecule

Groups

Approved, Investigational

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Nomegestrol acetate (DB13981)

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Weight

Average: 370.489
Monoisotopic: 370.214409446

Chemical Formula

C₂₃H₃₀O₄

Synonyms

• 17-alpha-Acetoxy-6-methyl-19-nor-4,6-pregnadiene-3,20-dione
• 17-alpha-Hydroxy-6-methyl-19-norpregna-4,6-diene-3,20-dione acetate
• Nomegestrol acetate

External IDs

• ORG 10486-0
• ORG-10486-0
• TX 066
• TX-066

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Pharmacology

Indication

Not Available

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Symptomatic treatment of	Luteal insufficiency		••••••••••••			••••••
Used in combination for therapy	Menopausal symptoms	Combination Product in combination with: Estradiol (DB00783)	••••••••••••			••••••
Symptomatic treatment of	Menopausal symptoms		••••••••••••			••••••

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Associated Therapies

• Hormone Replacement Therapy
• Oral Contraceptives

Contraindications & Blackbox Warnings

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Pharmacodynamics

Not Available

Mechanism of action

Not Available

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects

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Toxicity

Not Available

Pathways

Not Available

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abametapir	The serum concentration of Nomegestrol acetate can be increased when it is combined with Abametapir.
Abciximab	The risk or severity of adverse effects can be increased when Nomegestrol acetate is combined with Abciximab.
Acenocoumarol	The risk or severity of adverse effects can be increased when Nomegestrol acetate is combined with Acenocoumarol.
Acetaminophen	The metabolism of Nomegestrol acetate can be increased when combined with Acetaminophen.
Acetazolamide	The metabolism of Nomegestrol acetate can be increased when combined with Acetazolamide.

Food Interactions

Not Available

Products

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Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
FEMIDEN® 1.5 MG/2.5MG TABLETAS RECUBIERTAS	Nomegestrol acetate (2.5 mg) + Estradiol hemihydrate (1.5 mg)	Tablet, coated	Oral	GADOR S.A.	2019-02-27	Not applicable
NAEMIS	Nomegestrol acetate (3.75 mg) + Estradiol (1.5 MG)	Tablet	Oral	Theramex Ireland Limited	2014-07-08	Not applicable
OBLAISE ®	Nomegestrol acetate (2.5 mg) + Estradiol hemihydrate (1.5 mg)	Tablet, coated	Oral	ASOCIACION PROBIENESTAR DE LA FAMILIA COLOMBIANA PROFAMILIA	2016-12-28	2022-02-03
Zoely	Nomegestrol acetate (2.5 mg) + Estradiol hemihydrate (1.5 mg)	Tablet, film coated	Oral	Theramex Ireland Limited	2016-09-08	Not applicable
Zoely	Nomegestrol acetate (2.5 mg) + Estradiol hemihydrate (1.5 mg)	Tablet, film coated	Oral	Theramex Ireland Limited	2016-09-08	Not applicable

Categories

Drug Categories

• Adrenal Cortex Hormones
• Combination Contraceptives (with Estrogen and derivatives)
• Contraceptive Agents, Female
• Contraceptives, Oral
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A4 Substrates
• Cytochrome P-450 Substrates
• Fused-Ring Compounds
• Hormonal Contraceptives for Systemic Use
• Norpregnanes
• Norsteroids
• Pregnadienes
• Pregnanes
• Progesterone Congeners
• Progestin Contraceptives
• Progestins
• Steroids

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Steroid esters / 20-oxosteroids / 3-oxosteroids / Cyclohexenones / Alpha-acyloxy ketones / Carboxylic acid esters / Monocarboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives

Substituents

20-oxosteroid / 3-oxosteroid / Aliphatic homopolycyclic compound / Alpha-acyloxy ketone / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cyclic ketone / Cyclohexenone / Hydrocarbon derivative

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Affected organisms

Not Available

Chemical Identifiers

UNII

83J78V5W05

CAS number

58652-20-3

InChI Key

IIVBFTNIGYRNQY-YQLZSBIMSA-N

InChI

InChI=1S/C23H30O4/c1-13-11-20-18(17-6-5-16(26)12-19(13)17)7-9-22(4)21(20)8-10-23(22,14(2)24)27-15(3)25/h11-12,17-18,20-21H,5-10H2,1-4H3/t17-,18-,20-,21+,22+,23+/m1/s1

IUPAC Name

(1R,3aS,3bS,9aR,9bS,11aS)-1-acetyl-5,11a-dimethyl-7-oxo-1H,2H,3H,3aH,3bH,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl acetate

SMILES

[H][C@@]12CC[C@](OC(C)=O)(C(C)=O)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3C(C)=C[C@@]21[H]

References

General References

1. EMC Summary of Product Characteristics: Zoely (nomegestrol acetate/estradiol) oral tablets [Link]
2. AIFA Product Information: Lutenyl (nomegestrol acetate) oral tablets [Link]

External Links

KEGG Drug

D08281

ChemSpider

82771

RxNav

53744

ChEBI

135564

ChEMBL

CHEMBL1476022

ZINC

ZINC000003938628

Wikipedia

Nomegestrol_acetate

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Other	Ovulation Inhibition	1
4	Terminated	Screening	Contraception / Hypercoagulability	1
4	Unknown Status	Treatment	Hypermenorrhea	1
3	Completed	Prevention	Contraception	1
3	Terminated	Prevention	Contraception	2

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Tablet	Oral
Tablet	Oral	5 MG
Tablet, coated	Oral
Tablet, film coated	Oral	5 Mg
Tablet	Oral
Tablet, film coated	Oral
Tablet, film coated	Oral	2.5 mg

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00415 mg/mL	ALOGPS
logP	3.46	ALOGPS
logP	3.42	Chemaxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	17.72	Chemaxon
pKa (Strongest Basic)	-4.8	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	3	Chemaxon
Hydrogen Donor Count	0	Chemaxon
Polar Surface Area	60.44 Å2	Chemaxon
Rotatable Bond Count	3	Chemaxon
Refractivity	104.18 m3·mol-1	Chemaxon
Polarizability	41.78 Å3	Chemaxon
Number of Rings	4	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0udl-0049000000-ffed205be8215a92a1f3
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-066r-2009000000-d960dd20d99fecd63f8a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4i-4039000000-8ce653eb373657f42dcc
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-004u-0194000000-a97ac129533b6eba7925
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4i-9010000000-33e016dfecad56827ef9
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-00dr-2932000000-c32eec93775da410d8d1
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	200.8049353	predicted	DarkChem Lite v0.1.0
[M+H]+	201.6837353	predicted	DarkChem Lite v0.1.0
[M+Na]+	201.0782353	predicted	DarkChem Lite v0.1.0

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Drug created at January 20, 2018 15:25 / Updated at February 21, 2021 18:54