You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameMestranol
Accession NumberDB01357
TypeSmall Molecule
GroupsApproved
Description

The 3-methyl ether of ethinyl estradiol. It must be demethylated to be biologically active. It is used as the estrogen component of many combination ORAL contraceptives. [PubChem]

Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
NeconWatson Pharma, Inc.
NorinylActavis Pharma, Inc.
Norinyl 1/50 -(21-day Regimen)Pfizer Canada Inc
Norinyl 1/50 -(28-day Regimen)Pfizer Canada Inc
Norinyl 1/50 21 TabSyntex Inc.
Norinyl 1/50 28 TabSyntex Inc.
Ortho-novum 1/50 Tablets (21 Day)Janssen Inc
Ortho-novum 1/50 Tablets (28 Day)Janssen Inc
SaltsNot Available
Categories
UNIIB2V233XGE7
CAS number72-33-3
WeightAverage: 310.4299
Monoisotopic: 310.193280076
Chemical FormulaC21H26O2
InChI KeyInChIKey=IMSSROKUHAOUJS-ZTUUXWJNNA-N
InChI
InChI=1/C21H26O2/c1-4-21(22)12-10-19-18-7-5-14-13-15(23-3)6-8-16(14)17(18)9-11-20(19,21)2/h1,6,8,13,17-19,22H,5,7,9-12H2,2-3H3/t17-,18-,19+,20+,21+/s2
IUPAC Name
(1S,10R,11S,14R,15S)-14-ethynyl-5-methoxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-ol
SMILES
[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OC)C=C3
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrane steroids
Alternative Parents
Substituents
  • 17-hydroxysteroid
  • Hydroxysteroid
  • Estrane-skeleton
  • Phenanthrene
  • Tetralin
  • Anisole
  • Alkyl aryl ether
  • Benzenoid
  • Ynone
  • Tertiary alcohol
  • Cyclic alcohol
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Pharmacology
IndicationMestranol was used as one of the first oral contraceptives.
PharmacodynamicsNot Available
Mechanism of actionMestranol is the 3-methyl ether of ethinylestradiol. Ethinylestradiol, is a synthetic derivative of estradiol. Ethinylestradiol is orally bio-active and the estrogen used in almost all modern formulations of combined oral contraceptive pills. It binds to (and activates) the estrogen receptor. Mestranol is a biologically inactive prodrug of ethinylestradiol to which it is demethylated in the liver with a conversion efficiency of 70%. Estrogens diffuse into their target cells and interact with a protein receptor. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. The combination of an estrogen with a progestin suppresses the hypothalamic-pituitary system, decreasing the secretion of gonadotropin-releasing hormone (GnRH).
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
SubstrateEnzymesProduct
Mestranol
17β-ethinylestradiolDetails
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9929
Blood Brain Barrier+0.9465
Caco-2 permeable+0.8463
P-glycoprotein substrateSubstrate0.656
P-glycoprotein inhibitor INon-inhibitor0.6099
P-glycoprotein inhibitor IINon-inhibitor0.8382
Renal organic cation transporterNon-inhibitor0.8148
CYP450 2C9 substrateNon-substrate0.7521
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.7656
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9334
CYP450 2C19 inhibitorInhibitor0.7721
CYP450 3A4 inhibitorInhibitor0.5232
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7758
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.8714
BiodegradationNot ready biodegradable0.9829
Rat acute toxicity1.5234 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8958
hERG inhibition (predictor II)Inhibitor0.5679
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Kit
Tabletoral
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point150.5 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00377 mg/mLALOGPS
logP3.89ALOGPS
logP4.04ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)17.59ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity91.86 m3·mol-1ChemAxon
Polarizability36.7 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (9.65 KB)
Spectra
Spectrum TypeDescriptionSplash Key
MSMass Spectrum (Electron Ionization)splash10-01t9-1972000000-5e394201ba0e38e5391fView in MoNA
1D NMR13C NMR SpectrumNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AbciximabMestranol may decrease the anticoagulant activities of Abciximab.
AcenocoumarolMestranol may decrease the anticoagulant activities of Acenocoumarol.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Mestranol.
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Mestranol.
Anthrax immune globulinMestranol may increase the thrombogenic activities of Anthrax immune globulin.
BatimastatThe serum concentration of Mestranol can be decreased when it is combined with Batimastat.
BexaroteneThe serum concentration of Mestranol can be decreased when it is combined with Bexarotene.
ButabarbitalThe therapeutic efficacy of Mestranol can be decreased when used in combination with Butabarbital.
ButethalThe therapeutic efficacy of Mestranol can be decreased when used in combination with Butethal.
C1 Esterase Inhibitor (Human)Mestranol may increase the thrombogenic activities of C1 Esterase Inhibitor (Human).
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Mestranol.
CapromabMestranol may decrease effectiveness of Capromab as a diagnostic agent.
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Mestranol.
Citric AcidMestranol may decrease the anticoagulant activities of Citric Acid.
ColesevelamThe serum concentration of Mestranol can be decreased when it is combined with Colesevelam.
DalteparinMestranol may decrease the anticoagulant activities of Dalteparin.
DicoumarolMestranol may decrease the anticoagulant activities of Dicoumarol.
Edetic AcidMestranol may decrease the anticoagulant activities of Edetic Acid.
EnoxaparinMestranol may decrease the anticoagulant activities of Enoxaparin.
Eslicarbazepine acetateThe serum concentration of Mestranol can be decreased when it is combined with Eslicarbazepine acetate.
Ethyl biscoumacetateMestranol may decrease the anticoagulant activities of Ethyl biscoumacetate.
FloxuridineThe metabolism of Mestranol can be decreased when combined with Floxuridine.
FluconazoleThe metabolism of Mestranol can be decreased when combined with Fluconazole.
FludrocortisoneThe serum concentration of Fludrocortisone can be increased when it is combined with Mestranol.
Fondaparinux sodiumMestranol may decrease the anticoagulant activities of Fondaparinux sodium.
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Mestranol.
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Mestranol.
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Mestranol.
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Mestranol.
HeparinMestranol may decrease the anticoagulant activities of Heparin.
HeptabarbitalThe therapeutic efficacy of Mestranol can be decreased when used in combination with Heptabarbital.
HexobarbitalThe therapeutic efficacy of Mestranol can be decreased when used in combination with Hexobarbital.
IcosapentIcosapent may increase the thrombogenic activities of Mestranol.
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Mestranol.
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Mestranol.
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Mestranol.
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Mestranol.
Insulin HumanThe therapeutic efficacy of Insulin Regular can be decreased when used in combination with Mestranol.
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Mestranol.
IsoflurophateThe serum concentration of Mestranol can be decreased when it is combined with Isoflurophate.
LinagliptinThe therapeutic efficacy of Linagliptin can be decreased when used in combination with Mestranol.
LiothyronineThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Mestranol.
LumacaftorThe serum concentration of Mestranol can be decreased when it is combined with Lumacaftor.
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Mestranol.
MethohexitalThe therapeutic efficacy of Mestranol can be decreased when used in combination with Methohexital.
PentobarbitalThe therapeutic efficacy of Mestranol can be decreased when used in combination with Pentobarbital.
PhenindioneMestranol may decrease the anticoagulant activities of Phenindione.
PhenprocoumonMestranol may decrease the anticoagulant activities of Phenprocoumon.
PhenytoinThe metabolism of Mestranol can be increased when combined with Phenytoin.
PrimidoneThe therapeutic efficacy of Mestranol can be decreased when used in combination with Primidone.
RepaglinideThe therapeutic efficacy of Repaglinide can be decreased when used in combination with Mestranol.
RifabutinThe serum concentration of Mestranol can be decreased when it is combined with Rifabutin.
SaxagliptinThe therapeutic efficacy of Saxagliptin can be decreased when used in combination with Mestranol.
SecobarbitalThe therapeutic efficacy of Mestranol can be decreased when used in combination with Secobarbital.
SimeprevirThe serum concentration of Mestranol can be decreased when it is combined with Simeprevir.
St. John's WortThe therapeutic efficacy of Mestranol can be decreased when used in combination with St. John's Wort.
SulfisoxazoleThe metabolism of Mestranol can be decreased when combined with Sulfisoxazole.
SulodexideMestranol may decrease the anticoagulant activities of Sulodexide.
TheophyllineThe serum concentration of Theophylline can be increased when it is combined with Mestranol.
TolbutamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Mestranol.
TreprostinilMestranol may decrease the anticoagulant activities of Treprostinil.
VildagliptinThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Mestranol.
Vitamin CThe serum concentration of Mestranol can be increased when it is combined with Vitamin C.
WarfarinMestranol may decrease the anticoagulant activities of Warfarin.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
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 tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription fact...
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
References
  1. Dulos J, Vijn P, van Doorn C, Hofstra CL, Veening-Griffioen D, de Graaf J, Dijcks FA, Boots AM: Suppression of the inflammatory response in experimental arthritis is mediated via estrogen receptor alpha but not estrogen receptor beta. Arthritis Res Ther. 2010;12(3):R101. doi: 10.1186/ar3032. Epub 2010 May 24. [PubMed:20497523 ]
  2. Cleuren AC, Van der Linden IK, De Visser YP, Wagenaar GT, Reitsma PH, Van Vlijmen BJ: 17alpha-Ethinylestradiol rapidly alters transcript levels of murine coagulation genes via estrogen receptor alpha. J Thromb Haemost. 2010 Aug;8(8):1838-46. doi: 10.1111/j.1538-7836.2010.03930.x. Epub 2010 May 27. [PubMed:20524981 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid 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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Schmider J, Greenblatt DJ, von Moltke LL, Karsov D, Vena R, Friedman HL, Shader RI: Biotransformation of mestranol to ethinyl estradiol in vitro: the role of cytochrome P-450 2C9 and metabolic inhibitors. J Clin Pharmacol. 1997 Mar;37(3):193-200. [PubMed:9089421 ]
Comments
comments powered by Disqus
Drug created on July 06, 2007 13:51 / Updated on October 29, 2013 15:24