Nomegestrol acetate

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name

Nomegestrol acetate

Accession Number

DB13981

Description

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

Similar Structures

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

External IDs

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

Pharmacology

Indication

Not Available

Associated Conditions

Associated Therapies

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

Affected organisms

Not Available

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

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.

Drug	Interaction
Unlock Additional Data
Abametapir	The serum concentration of Nomegestrol acetate can be increased when it is combined with Abametapir.
Abciximab	Nomegestrol acetate may decrease the anticoagulant activities of Abciximab.
Acenocoumarol	The therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Nomegestrol acetate.
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.
Acetohexamide	The therapeutic efficacy of Acetohexamide can be decreased when used in combination with Nomegestrol acetate.
Acetylsalicylic acid	Nomegestrol acetate may decrease the anticoagulant activities of Acetylsalicylic acid.
Acitretin	The therapeutic efficacy of Nomegestrol acetate can be decreased when used in combination with Acitretin.
Alitretinoin	The therapeutic efficacy of Nomegestrol acetate can be decreased when used in combination with Alitretinoin.
Alpelisib	The metabolism of Nomegestrol acetate can be increased when combined with Alpelisib.

Additional Data Available

Extended Description

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Extended description of the mechanism of action and particular properties of each drug interaction.

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Severity

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A severity rating for each drug interaction, from minor to major.

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Evidence Level

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Action

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An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions

Not Available

Products

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Zoely	Nomegestrol acetate (2.5 mg) + Estradiol hemihydrate (1.5 mg)	Tablet, film coated	Oral	Theramex Ireland Limited	2011-07-26	Not applicable
Zoely	Nomegestrol acetate (2.5 mg) + Estradiol hemihydrate (1.5 mg)	Tablet, film coated	Oral	Theramex Ireland Limited	2011-07-26	Not applicable
Zoely	Nomegestrol acetate (2.5 mg) + Estradiol hemihydrate (1.5 mg)	Tablet, film coated	Oral	Theramex Ireland Limited	2011-07-26	Not applicable
Zoely	Nomegestrol acetate (2.5 mg) + Estradiol hemihydrate (1.5 mg)	Tablet, film coated	Oral	Theramex Ireland Limited	2011-07-26	Not applicable

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

EMC Summary of Product Characteristics: Zoely (nomegestrol acetate/estradiol) oral tablets [Link]
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

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	1
3	Unknown Status	Treatment	Disseminated Sclerosis	1
3	Withdrawn	Treatment	Contraception	1
2	Completed	Treatment	Contraception	1
2	Completed	Treatment	Menstrual Cramps	1
1	Completed	Not Available	Contraception	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Tablet	Oral	5 MG
Tablet	Oral	1.5 MG
Tablet, coated	Oral	2.5 mg
Tablet, coated	Oral	1.5 mg
Tablet, film coated	Oral
Tablet, film coated	Oral	1.5 MG
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: Not Available

Enzymes

Details1. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Substrate

General Function: Vitamin d3 25-hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name: CYP3A4
Uniprot ID: P08684
Uniprot Name: Cytochrome P450 3A4
Molecular Weight: 57342.67 Da

References

Binkowska M, Woron J: Progestogens in menopausal hormone therapy. Prz Menopauzalny. 2015 Jun;14(2):134-43. doi: 10.5114/pm.2015.52154. Epub 2015 Jun 22. [PubMed:26327902]