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

Identification

Name
Norethynodrel
Accession Number
DB09371
Type
Small Molecule
Groups
Approved
Description

A synthetic progestational hormone with actions and uses similar to those of PROGESTERONE. It has been used in the treatment of functional uterine bleeding and endometriosis. As a contraceptive, it has usually been administered in combination with MESTRANOL.

Structure
Thumb
Synonyms
  • Noretynodrel
  • Noretynodrelum
External IDs
CB 8023 / NSC-15432 / SC-4642
Categories
UNII
88181ACA0M
CAS number
68-23-5
Weight
Average: 298.426
Monoisotopic: 298.193280077
Chemical Formula
C20H26O2
InChI Key
ICTXHFFSOAJUMG-SLHNCBLASA-N
InChI
InChI=1S/C20H26O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,16-18,22H,4-12H2,2H3/t16-,17-,18+,19+,20+/m1/s1
IUPAC Name
(1R,3aS,3bR,9bS,11aS)-1-ethynyl-1-hydroxy-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,6H,7H,8H,9H,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one
SMILES
[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])CC(=O)CC3

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UEstrogen receptor alphaNot AvailableHuman
UAndrogen receptorNot AvailableHuman
USex hormone-binding globulinNot AvailableHuman
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)-warfarinNorethynodrel may decrease the anticoagulant activities of (R)-warfarin.
(S)-WarfarinNorethynodrel may decrease the anticoagulant activities of (S)-Warfarin.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Norethynodrel.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Norethynodrel.
5-androstenedioneThe metabolism of Norethynodrel can be decreased when combined with 5-androstenedione.
6-Deoxyerythronolide BThe metabolism of Norethynodrel can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Norethynodrel.
AbciximabNorethynodrel may decrease the anticoagulant activities of Abciximab.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Norethynodrel.
AbirateroneThe metabolism of Norethynodrel can be decreased when combined with Abiraterone.
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Drug
D05207
KEGG Compound
C14249
ChemSpider
5995
BindingDB
50410507
ChEBI
34895
ChEMBL
CHEMBL1387
Wikipedia
Norethynodrel
ATC Codes
G03FA09 — Noretynodrel and estrogen

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 Solubility0.00982 mg/mLALOGPS
logP2.6ALOGPS
logP2.81ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)16.21ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity87.18 m3·mol-1ChemAxon
Polarizability34.79 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
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0ar0-2920000000-a5153b3c1dec94ce1a96

Taxonomy

Description
This compound belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Oxosteroids
Direct Parent
Oxosteroids
Alternative Parents
3-oxosteroids / 17-hydroxysteroids / Cyclohexenones / Ynones / Tertiary alcohols / Cyclic alcohols and derivatives / Acetylides / Organic oxides / Hydrocarbon derivatives
Substituents
3-oxosteroid / Hydroxysteroid / Oxosteroid / 17-hydroxysteroid / Cyclohexenone / Ynone / Cyclic alcohol / Tertiary alcohol / Ketone / Cyclic ketone
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
oxo steroid (CHEBI:34895) / Pregnane and derivatives [Fig] (C14249)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
Molecular Weight
66215.45 Da
References
  1. Witters H, Freyberger A, Smits K, Vangenechten C, Lofink W, Weimer M, Bremer S, Ahr PH, Berckmans P: The assessment of estrogenic or anti-estrogenic activity of chemicals by the human stably transfected estrogen sensitive MELN cell line: results of test performance and transferability. Reprod Toxicol. 2010 Aug;30(1):60-72. doi: 10.1016/j.reprotox.2010.02.008. Epub 2010 Mar 31. [PubMed:20362049]
  2. van der Burg B, Winter R, Weimer M, Berckmans P, Suzuki G, Gijsbers L, Jonas A, van der Linden S, Witters H, Aarts J, Legler J, Kopp-Schneider A, Bremer S: Optimization and prevalidation of the in vitro ERalpha CALUX method to test estrogenic and antiestrogenic activity of compounds. Reprod Toxicol. 2010 Aug;30(1):73-80. doi: 10.1016/j.reprotox.2010.04.007. Epub 2010 May 8. [PubMed:20435135]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
Gene Name
AR
Uniprot ID
P10275
Uniprot Name
Androgen receptor
Molecular Weight
98987.9 Da
References
  1. van der Burg B, Winter R, Man HY, Vangenechten C, Berckmans P, Weimer M, Witters H, van der Linden S: Optimization and prevalidation of the in vitro AR CALUX method to test androgenic and antiandrogenic activity of compounds. Reprod Toxicol. 2010 Aug;30(1):18-24. doi: 10.1016/j.reprotox.2010.04.012. Epub 2010 May 10. [PubMed:20438827]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Androgen binding
Specific Function
Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone...
Gene Name
SHBG
Uniprot ID
P04278
Uniprot Name
Sex hormone-binding globulin
Molecular Weight
43778.755 Da
References
  1. Hong H, Branham WS, Ng HW, Moland CL, Dial SL, Fang H, Perkins R, Sheehan D, Tong W: Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and alpha-fetoprotein. Toxicol Sci. 2015 Feb;143(2):333-48. doi: 10.1093/toxsci/kfu231. Epub 2014 Oct 27. [PubMed:25349334]

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. Reimers A, Brodtkorb E, Sabers A: Interactions between hormonal contraception and antiepileptic drugs: Clinical and mechanistic considerations. Seizure. 2015 May;28:66-70. doi: 10.1016/j.seizure.2015.03.006. Epub 2015 Mar 20. [PubMed:25843765]

Drug created on November 30, 2015 12:10 / Updated on November 02, 2018 07:02