Nomegestrol acetate

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

Identification

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Name
Nomegestrol acetate
Accession Number
DB13981
Type
Small Molecule
Groups
Investigational
Description

Nomegestrol acetate, abbreviated as NOMAC and sold under the brand names Lutenyl and Zoely among others, is a progestin medication which is used in birth control pills, menopausal hormone therapy, and for the treatment of gynecological disorders.

Structure
Thumb
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
Categories
UNII
83J78V5W05
CAS number
58652-20-3
Weight
Average: 370.489
Monoisotopic: 370.214409446
Chemical Formula
C23H30O4
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]

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Additional Data Available
Adverse Effects

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

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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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinNomegestrol acetate may decrease the anticoagulant activities of (R)-warfarin.
(S)-WarfarinNomegestrol acetate may decrease the anticoagulant activities of (S)-Warfarin.
3,5-diiodothyropropionic acidThe metabolism of Nomegestrol acetate can be decreased when combined with 3,5-diiodothyropropionic acid.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Nomegestrol acetate.
4-OxoretinolThe therapeutic efficacy of Nomegestrol acetate can be decreased when used in combination with 4-Oxoretinol.
5-androstenedioneThe metabolism of Nomegestrol acetate can be decreased when combined with 5-androstenedione.
6-Deoxyerythronolide BThe metabolism of Nomegestrol acetate can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of Nomegestrol acetate can be decreased when combined with 6-O-benzylguanine.
7-ethyl-10-hydroxycamptothecinThe metabolism of Nomegestrol acetate can be decreased when combined with 7-ethyl-10-hydroxycamptothecin.
9-aminocamptothecinThe metabolism of Nomegestrol acetate can be decreased when combined with 9-aminocamptothecin.
Additional Data Available
  • Extended Description
    Extended Description

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  • Severity
    Severity

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  • Evidence Level
    Evidence Level

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  • Action
    Evidence Level

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Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Drug
D08281
ChemSpider
82771
ChEBI
135564
ChEMBL
CHEMBL1476022
Wikipedia
Nomegestrol_acetate

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentContraception1
3CompletedPreventionContraception1
3TerminatedPreventionContraception1
3Unknown StatusTreatmentDisseminated Sclerosis1
3WithdrawnTreatmentContraception1
4TerminatedScreeningContraception / Hypercoagulability1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00415 mg/mLALOGPS
logP3.46ALOGPS
logP3.42ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)17.72ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area60.44 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity104.18 m3·mol-1ChemAxon
Polarizability41.78 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Classification
Not classified

Enzymes

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
  1. 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]

Drug created on January 20, 2018 08:25 / Updated on April 10, 2019 22:40