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

Identification

Name
Demegestone
Accession Number
DB13857
Type
Small Molecule
Groups
Experimental
Description

Demegestone is a progesterone receptor agonist that was previously used to treat luteal insufficiency. It was previously marketed in France as Lutionex, but has since been discontinued.

Structure
Thumb
Synonyms
Not Available
External IDs
R 2453
International/Other Brands
Lutionex
Categories
UNII
6E89AM91SZ
CAS number
10116-22-0
Weight
Average: 312.4458
Monoisotopic: 312.20893014
Chemical Formula
C21H28O2
InChI Key
JWAHBTQSSMYISL-MHTWAQMVSA-N
InChI
InChI=1S/C21H28O2/c1-13(22)20(2)11-9-19-18-6-4-14-12-15(23)5-7-16(14)17(18)8-10-21(19,20)3/h12,18-19H,4-11H2,1-3H3/t18-,19+,20-,21+/m1/s1
IUPAC Name
(1S,3aS,3bS,11aS)-1-acetyl-1,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,10H,11H,11aH-cyclopenta[a]phenanthren-7-one
SMILES
[H][C@@]12CC[C@](C)(C(C)=O)[C@@]1(C)CCC1=C3CCC(=O)C=C3CC[C@@]21[H]

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
AProgesterone receptor
agonist
Human
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)-warfarinDemegestone may decrease the anticoagulant activities of (R)-warfarin.
(S)-WarfarinDemegestone may decrease the anticoagulant activities of (S)-Warfarin.
3,5-diiodothyropropionic acidThe metabolism of Demegestone can be decreased when combined with 3,5-diiodothyropropionic acid.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Demegestone.
5-androstenedioneThe metabolism of Demegestone can be decreased when combined with 5-androstenedione.
6-Deoxyerythronolide BThe metabolism of Demegestone can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of Demegestone can be decreased when combined with 6-O-benzylguanine.
AbciximabDemegestone may decrease the anticoagulant activities of Abciximab.
AbemaciclibThe metabolism of Demegestone can be decreased when combined with Abemaciclib.
AbirateroneThe metabolism of Demegestone can be decreased when combined with Abiraterone.
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Drug
D07223
ChemSpider
84009
ChEBI
135339
ChEMBL
CHEMBL2104231
Wikipedia
Demegestone
ATC Codes
G03DB05 — Demegestone

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

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

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0111 mg/mLALOGPS
logP3.7ALOGPS
logP3.96ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)18.42ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity93.31 m3·mol-1ChemAxon
Polarizability36.71 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as 20-oxosteroids. These are steroid derivatives carrying a C=O group at the 20-position of the steroid skeleton.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Oxosteroids
Direct Parent
20-oxosteroids
Alternative Parents
3-oxosteroids / Cyclohexenones / Organic oxides / Hydrocarbon derivatives
Substituents
20-oxosteroid / 3-oxosteroid / Cyclohexenone / Cyclic ketone / Ketone / Organic oxygen compound / Organic oxide / Hydrocarbon derivative / Organooxygen compound / Carbonyl group
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor ...
Gene Name
PGR
Uniprot ID
P06401
Uniprot Name
Progesterone receptor
Molecular Weight
98979.96 Da
References
  1. Pharmacology of estrogens and progestogens: influence of different routes of administration [File]

Enzymes

Kind
Protein
Organism
Human
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. Simmons KB, Haddad LB, Nanda K, Curtis KM: Drug interactions between rifamycin antibiotics and hormonal contraception: a systematic review. BJOG. 2018 Jun;125(7):804-811. doi: 10.1111/1471-0528.15027. Epub 2017 Dec 15. [PubMed:29130574]

Drug created on June 23, 2017 14:50 / Updated on November 02, 2018 07:47