NAV

Norethynodrel

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

Identification

Generic Name
Norethynodrel
DrugBank Accession Number
DB09371
Background

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.

Type
Small Molecule
Groups
Approved
Structure
3D
Similar Structures
Weight
Average: 298.426
Monoisotopic: 298.193280077
Chemical Formula
C20H26O2
Synonyms
  • Norethynodrel
  • Noretynodrel
  • Noretynodrelum
External IDs
  • CB 8023
  • NSC-15432
  • SC-4642
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UEstrogen receptor alphaNot AvailableHumans
UAndrogen receptorNot AvailableHumans
USex hormone-binding globulinNot AvailableHumans
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.
DrugInteraction
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AbametapirThe serum concentration of Norethynodrel can be increased when it is combined with Abametapir.
AbciximabThe risk or severity of adverse effects can be increased when Norethynodrel is combined with Abciximab.
AcenocoumarolThe risk or severity of adverse effects can be increased when Norethynodrel is combined with Acenocoumarol.
AcetaminophenThe metabolism of Norethynodrel can be increased when combined with Acetaminophen.
AcetazolamideThe metabolism of Norethynodrel can be increased when combined with Acetazolamide.
Food Interactions
Not Available

Categories

ATC Codes
G03FA09 — Noretynodrel and estrogen
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
17-hydroxysteroid / 3-oxosteroid / Acetylide / Alcohol / Aliphatic homopolycyclic compound / Carbonyl group / Cyclic alcohol / Cyclic ketone / Cyclohexenone / Hydrocarbon derivative
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
oxo steroid (CHEBI:34895) / Pregnane and derivatives [Fig] (C14249)
Affected organisms
Not Available

Chemical Identifiers

UNII
88181ACA0M
CAS number
68-23-5
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

References

General References
Not Available
KEGG Drug
D05207
KEGG Compound
C14249
ChemSpider
5995
BindingDB
50410507
RxNav
7515
ChEBI
34895
ChEMBL
CHEMBL1387
ZINC
ZINC000118913164
Wikipedia
Norethynodrel

Clinical Trials

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

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
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0006-4901000000-ccaeb7005f3f1f68e10a
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0ar0-2920000000-a5153b3c1dec94ce1a96
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-bae628d6aa710c001321
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-833867c2579583d501b8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-25ad08ac79cac4b824a2
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01q9-0290000000-46393b4132af8168ffa0
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00xr-0390000000-ef9edda710df22c58996
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0930000000-c866866347f7a186d1e9
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-182.2111433
predicted
DarkChem Lite v0.1.0
[M-H]-178.08022
predicted
DeepCCS 1.0 (2019)
[M+H]+182.2302433
predicted
DarkChem Lite v0.1.0
[M+H]+180.43808
predicted
DeepCCS 1.0 (2019)
[M+Na]+182.3489433
predicted
DarkChem Lite v0.1.0
[M+Na]+186.3506
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Estrogen receptor alpha
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
Details2. Androgen receptor
Kind
Protein
Organism
Humans
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. [Article]
Details3. Sex hormone-binding globulin
Kind
Protein
Organism
Humans
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. [Article]

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
  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. [Article]

Drug created at November 30, 2015 19:10 / Updated at February 21, 2021 18:52