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Identification
NameMestranol
Accession NumberDB01357
TypeSmall Molecule
GroupsApproved
DescriptionThe 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 KeyIMSSROKUHAOUJS-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
Pharmacology
IndicationMestranol was used as one of the first oral contraceptives.
Structured Indications
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).
TargetKindPharmacological actionActionsOrganismUniProt ID
Estrogen receptorProteinyes
agonist
HumanP03372 details
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
Interactions
Drug Interactions
DrugInteractionDrug group
1,10-PhenanthrolineThe serum concentration of Mestranol can be decreased when it is combined with 1,10-Phenanthroline.Experimental
16-BromoepiandrosteroneThe serum concentration of 16-Bromoepiandrosterone can be increased when it is combined with Mestranol.Investigational
19-norandrostenedioneThe serum concentration of 19-norandrostenedione can be increased when it is combined with Mestranol.Experimental, Illicit
3,4-DichloroisocoumarinThe serum concentration of Mestranol can be decreased when it is combined with 3,4-Dichloroisocoumarin.Experimental
4-(2-AMINOETHYL)BENZENESULFONYL FLUORIDEThe serum concentration of Mestranol can be decreased when it is combined with 4-(2-AMINOETHYL)BENZENESULFONYL FLUORIDE.Experimental
4-AndrostenedioneThe serum concentration of 4-Androstenedione can be increased when it is combined with Mestranol.Experimental, Illicit
5-androstenedioneThe serum concentration of 5-androstenedione can be increased when it is combined with Mestranol.Experimental, Illicit
AbciximabMestranol may decrease the anticoagulant activities of Abciximab.Approved
AbirateroneThe metabolism of Mestranol can be decreased when combined with Abiraterone.Approved
AcarboseThe therapeutic efficacy of Acarbose can be decreased when used in combination with Mestranol.Approved, Investigational
AcenocoumarolMestranol may decrease the anticoagulant activities of Acenocoumarol.Approved
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Mestranol.Withdrawn
AcitretinThe therapeutic efficacy of Mestranol can be decreased when used in combination with Acitretin.Approved
AdapaleneThe therapeutic efficacy of Mestranol can be decreased when used in combination with Adapalene.Approved
AicarThe therapeutic efficacy of Aicar can be decreased when used in combination with Mestranol.Experimental
AlclometasoneThe serum concentration of Alclometasone can be increased when it is combined with Mestranol.Approved
AldosteroneThe serum concentration of Aldosterone can be increased when it is combined with Mestranol.Experimental
AlitretinoinThe therapeutic efficacy of Mestranol can be decreased when used in combination with Alitretinoin.Approved, Investigational
AlogliptinThe serum concentration of Mestranol can be decreased when it is combined with Alogliptin.Approved
Alpha-1-proteinase inhibitorThe serum concentration of Mestranol can be decreased when it is combined with Alpha-1-proteinase inhibitor.Approved
Ambroxol acefyllinateThe serum concentration of Ambroxol acefyllinate can be increased when it is combined with Mestranol.Experimental
AmcinonideThe serum concentration of Amcinonide can be increased when it is combined with Mestranol.Approved
AminophyllineThe serum concentration of Aminophylline can be increased when it is combined with Mestranol.Approved
AmiodaroneThe metabolism of Mestranol can be decreased when combined with Amiodarone.Approved, Investigational
AmobarbitalThe therapeutic efficacy of Mestranol can be decreased when used in combination with Amobarbital.Approved, Illicit
AmprenavirThe serum concentration of Mestranol can be decreased when it is combined with Amprenavir.Approved
AnastrozoleThe therapeutic efficacy of Anastrozole can be decreased when used in combination with Mestranol.Approved, Investigational
AncrodMestranol may decrease the anticoagulant activities of Ancrod.Investigational
AnecortaveThe serum concentration of Anecortave can be increased when it is combined with Mestranol.Investigational
Anthrax immune globulin humanMestranol may increase the thrombogenic activities of Anthrax immune globulin human.Approved
Antithrombin III humanThe serum concentration of Mestranol can be decreased when it is combined with Antithrombin III human.Approved
ApixabanThe serum concentration of Mestranol can be decreased when it is combined with Apixaban.Approved
AprepitantThe serum concentration of Mestranol can be decreased when it is combined with Aprepitant.Approved, Investigational
AprotininThe serum concentration of Mestranol can be decreased when it is combined with Aprotinin.Approved, Withdrawn
ArdeparinMestranol may decrease the anticoagulant activities of Ardeparin.Approved, Withdrawn
ArgatrobanThe serum concentration of Mestranol can be decreased when it is combined with Argatroban.Approved, Investigational
ArmodafinilThe serum concentration of Mestranol can be decreased when it is combined with Armodafinil.Approved, Investigational
ArtemetherThe serum concentration of Mestranol can be decreased when it is combined with Artemether.Approved
AsunaprevirThe serum concentration of Mestranol can be decreased when it is combined with Asunaprevir.Approved, Investigational
AtazanavirThe serum concentration of Mestranol can be decreased when it is combined with Atazanavir.Approved, Investigational
BalaglitazoneThe therapeutic efficacy of Balaglitazone can be decreased when used in combination with Mestranol.Investigational
BarbexacloneThe therapeutic efficacy of Mestranol can be decreased when used in combination with Barbexaclone.Experimental
BarbitalThe therapeutic efficacy of Mestranol can be decreased when used in combination with Barbital.Illicit
BatimastatThe serum concentration of Mestranol can be decreased when it is combined with Batimastat.Experimental
BecaplerminMestranol may decrease the anticoagulant activities of Becaplermin.Approved, Investigational
BeclomethasoneThe serum concentration of Beclomethasone can be increased when it is combined with Mestranol.Investigational
Beclomethasone dipropionateThe serum concentration of Beclomethasone dipropionate can be increased when it is combined with Mestranol.Approved, Investigational
BenazeprilThe serum concentration of Mestranol can be decreased when it is combined with Benazepril.Approved, Investigational
BenzamidineThe serum concentration of Mestranol can be decreased when it is combined with Benzamidine.Experimental
BetamethasoneThe serum concentration of Betamethasone can be increased when it is combined with Mestranol.Approved, Vet Approved
BexaroteneThe serum concentration of Mestranol can be decreased when it is combined with Bexarotene.Approved, Investigational
BexaroteneThe therapeutic efficacy of Mestranol can be decreased when used in combination with Bexarotene.Approved, Investigational
Bi201335The serum concentration of Mestranol can be decreased when it is combined with Bi201335.Investigational
BivalirudinThe serum concentration of Mestranol can be decreased when it is combined with Bivalirudin.Approved, Investigational
BoceprevirThe serum concentration of Mestranol can be decreased when it is combined with Boceprevir.Approved
BosentanThe serum concentration of Mestranol can be decreased when it is combined with Bosentan.Approved, Investigational
BudesonideThe serum concentration of Budesonide can be increased when it is combined with Mestranol.Approved
BuforminThe therapeutic efficacy of Buformin can be decreased when used in combination with Mestranol.Withdrawn
C1 Esterase Inhibitor (Human)Mestranol may increase the thrombogenic activities of C1 Esterase Inhibitor (Human).Approved
C1 Esterase Inhibitor (Recombinant)Mestranol may increase the thrombogenic activities of C1 Esterase Inhibitor (Recombinant).Approved
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Mestranol.Approved
CandoxatrilThe serum concentration of Mestranol can be decreased when it is combined with Candoxatril.Experimental
CandoxatrilatThe serum concentration of Mestranol can be decreased when it is combined with Candoxatrilat.Experimental
CapecitabineThe metabolism of Mestranol can be decreased when combined with Capecitabine.Approved, Investigational
CaptoprilThe serum concentration of Mestranol can be decreased when it is combined with Captopril.Approved
CarbamazepineThe therapeutic efficacy of Mestranol can be decreased when used in combination with Carbamazepine.Approved, Investigational
CastanospermineThe therapeutic efficacy of Castanospermine can be decreased when used in combination with Mestranol.Experimental
CelecoxibCelecoxib may increase the thrombogenic activities of Mestranol.Approved, Investigational
CeritinibThe serum concentration of Mestranol can be increased when it is combined with Ceritinib.Approved
CertoparinMestranol may decrease the anticoagulant activities of Certoparin.Approved
Chenodeoxycholic acidThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Mestranol.Approved
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Mestranol.Approved
CholecalciferolThe metabolism of Mestranol can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CholestyramineThe serum concentration of Mestranol can be decreased when it is combined with Cholestyramine.Approved
ChymostatinThe serum concentration of Mestranol can be decreased when it is combined with Chymostatin.Experimental
CiclesonideThe serum concentration of Ciclesonide can be increased when it is combined with Mestranol.Approved, Investigational
CiglitazoneThe therapeutic efficacy of Ciglitazone can be decreased when used in combination with Mestranol.Experimental
CilastatinThe serum concentration of Mestranol can be decreased when it is combined with Cilastatin.Approved
CilazaprilThe serum concentration of Mestranol can be decreased when it is combined with Cilazapril.Approved
Citric AcidMestranol may decrease the anticoagulant activities of Citric Acid.Nutraceutical, Vet Approved
ClobazamThe serum concentration of Mestranol can be decreased when it is combined with Clobazam.Approved, Illicit
ClobetasolThe serum concentration of Clobetasol can be increased when it is combined with Mestranol.Investigational
Clobetasol propionateThe serum concentration of Clobetasol propionate can be increased when it is combined with Mestranol.Approved
ClocortoloneThe serum concentration of Clocortolone can be increased when it is combined with Mestranol.Approved
ClotrimazoleThe metabolism of Mestranol can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe serum concentration of Mestranol can be decreased when it is combined with Cobicistat.Approved
ColesevelamThe serum concentration of Mestranol can be decreased when it is combined with Colesevelam.Approved
ColestipolThe serum concentration of Mestranol can be decreased when it is combined with Colestipol.Approved
Cortisone acetateThe serum concentration of Cortisone acetate can be increased when it is combined with Mestranol.Approved
CyclosporineThe metabolism of Mestranol can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
Dabigatran etexilateThe serum concentration of Mestranol can be decreased when it is combined with Dabigatran etexilate.Approved
DabrafenibThe serum concentration of Mestranol can be decreased when it is combined with Dabrafenib.Approved
DalteparinMestranol may decrease the anticoagulant activities of Dalteparin.Approved
DanaparoidMestranol may decrease the anticoagulant activities of Danaparoid.Approved, Withdrawn
DarunavirThe serum concentration of Mestranol can be decreased when it is combined with Darunavir.Approved
dehydroepiandrosterone sulfateThe serum concentration of dehydroepiandrosterone sulfate can be increased when it is combined with Mestranol.Investigational
DelavirdineThe metabolism of Mestranol can be decreased when combined with Delavirdine.Approved
DeoxyspergualinThe therapeutic efficacy of Deoxyspergualin can be decreased when used in combination with Mestranol.Investigational
DesirudinMestranol may decrease the anticoagulant activities of Desirudin.Approved
DesoximetasoneThe serum concentration of Desoximetasone can be increased when it is combined with Mestranol.Approved
Desoxycorticosterone acetateThe serum concentration of Desoxycorticosterone acetate can be increased when it is combined with Mestranol.Approved
Desoxycorticosterone PivalateThe serum concentration of Desoxycorticosterone Pivalate can be increased when it is combined with Mestranol.Experimental, Vet Approved
DexamethasoneThe serum concentration of Dexamethasone can be increased when it is combined with Mestranol.Approved, Investigational, Vet Approved
Dexamethasone isonicotinateThe serum concentration of Dexamethasone isonicotinate can be increased when it is combined with Mestranol.Vet Approved
DextranMestranol may decrease the anticoagulant activities of Dextran.Approved, Vet Approved
Dextran 40Mestranol may decrease the anticoagulant activities of Dextran 40.Approved
Dextran 70Mestranol may decrease the anticoagulant activities of Dextran 70.Approved
Dextran 75Mestranol may decrease the anticoagulant activities of Dextran 75.Approved
DicoumarolMestranol may decrease the anticoagulant activities of Dicoumarol.Approved
DiflorasoneThe serum concentration of Diflorasone can be increased when it is combined with Mestranol.Approved
DifluocortoloneThe serum concentration of Difluocortolone can be increased when it is combined with Mestranol.Approved
DifluprednateThe serum concentration of Difluprednate can be increased when it is combined with Mestranol.Approved
DulaglutideThe therapeutic efficacy of Dulaglutide can be decreased when used in combination with Mestranol.Approved
DyphyllineThe serum concentration of Dyphylline can be increased when it is combined with Mestranol.Approved
EcabetThe serum concentration of Mestranol can be decreased when it is combined with Ecabet.Approved, Investigational
Edetic AcidMestranol may decrease the anticoagulant activities of Edetic Acid.Approved, Vet Approved
EdoxabanThe serum concentration of Mestranol can be decreased when it is combined with Edoxaban.Approved
EfavirenzThe metabolism of Mestranol can be decreased when combined with Efavirenz.Approved, Investigational
ElafinThe serum concentration of Mestranol can be decreased when it is combined with Elafin.Investigational
ElvitegravirThe serum concentration of Mestranol can be decreased when it is combined with Elvitegravir.Approved
EmpagliflozinThe therapeutic efficacy of Empagliflozin can be decreased when used in combination with Mestranol.Approved
EnalaprilThe serum concentration of Mestranol can be decreased when it is combined with Enalapril.Approved, Vet Approved
EnalaprilatThe serum concentration of Mestranol can be decreased when it is combined with Enalaprilat.Approved
EnalkirenThe serum concentration of Mestranol can be decreased when it is combined with Enalkiren.Experimental
EnoxaparinMestranol may decrease the anticoagulant activities of Enoxaparin.Approved
EquileninThe serum concentration of Equilenin can be increased when it is combined with Mestranol.Experimental
EquilinThe serum concentration of Equilin can be increased when it is combined with Mestranol.Approved
Eslicarbazepine acetateThe serum concentration of Mestranol can be decreased when it is combined with Eslicarbazepine acetate.Approved
EstroneThe serum concentration of Estrone can be increased when it is combined with Mestranol.Approved
Estrone sulfateThe serum concentration of Estrone sulfate can be increased when it is combined with Mestranol.Approved
Ethyl biscoumacetateMestranol may decrease the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
EtodolacEtodolac may increase the thrombogenic activities of Mestranol.Approved, Investigational, Vet Approved
EtoricoxibEtoricoxib may increase the thrombogenic activities of Mestranol.Approved, Investigational
EtravirineThe metabolism of Mestranol can be decreased when combined with Etravirine.Approved
ExemestaneThe therapeutic efficacy of Exemestane can be decreased when used in combination with Mestranol.Approved, Investigational
ExenatideThe serum concentration of Mestranol can be decreased when it is combined with Exenatide.Approved, Investigational
FelbamateThe serum concentration of Mestranol can be decreased when it is combined with Felbamate.Approved
FlibanserinThe serum concentration of Flibanserin can be increased when it is combined with Mestranol.Approved
FloxuridineThe metabolism of Mestranol can be decreased when combined with Floxuridine.Approved
fluasteroneThe serum concentration of fluasterone can be increased when it is combined with Mestranol.Investigational
FluconazoleThe metabolism of Mestranol can be decreased when combined with Fluconazole.Approved
FludrocortisoneThe serum concentration of Fludrocortisone can be increased when it is combined with Mestranol.Approved
FluindioneMestranol may decrease the anticoagulant activities of Fluindione.Investigational
FlumethasoneThe serum concentration of Flumethasone can be increased when it is combined with Mestranol.Approved, Vet Approved
FlunisolideThe serum concentration of Flunisolide can be increased when it is combined with Mestranol.Approved, Investigational
Fluocinolone AcetonideThe serum concentration of Fluocinolone Acetonide can be increased when it is combined with Mestranol.Approved, Investigational, Vet Approved
FluocinonideThe serum concentration of Fluocinonide can be increased when it is combined with Mestranol.Approved, Investigational
FluocortoloneThe serum concentration of Fluocortolone can be increased when it is combined with Mestranol.Approved, Withdrawn
FluorometholoneThe serum concentration of Fluorometholone can be increased when it is combined with Mestranol.Approved
FluorouracilThe metabolism of Mestranol can be decreased when combined with Fluorouracil.Approved
FluprednideneThe serum concentration of Fluprednidene can be increased when it is combined with Mestranol.Approved, Withdrawn
FluprednisoloneThe serum concentration of Fluprednisolone can be increased when it is combined with Mestranol.Approved
FlurandrenolideThe serum concentration of Flurandrenolide can be increased when it is combined with Mestranol.Approved
Fluticasone furoateThe serum concentration of Fluticasone furoate can be increased when it is combined with Mestranol.Approved
Fluticasone PropionateThe serum concentration of Fluticasone Propionate can be increased when it is combined with Mestranol.Approved
FluvastatinThe metabolism of Mestranol can be decreased when combined with Fluvastatin.Approved
FluvoxamineThe metabolism of Mestranol can be decreased when combined with Fluvoxamine.Approved, Investigational
FondaparinuxMestranol may decrease the anticoagulant activities of Fondaparinux.Investigational
Fondaparinux sodiumMestranol may decrease the anticoagulant activities of Fondaparinux sodium.Approved, Investigational
FormestaneThe serum concentration of Formestane can be increased when it is combined with Mestranol.Approved, Investigational, Withdrawn
FosamprenavirThe serum concentration of Mestranol can be decreased when it is combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Mestranol can be decreased when it is combined with Fosaprepitant.Approved
FosinoprilThe serum concentration of Mestranol can be decreased when it is combined with Fosinopril.Approved
FosphenytoinThe therapeutic efficacy of Mestranol can be decreased when used in combination with Fosphenytoin.Approved
GabexateThe serum concentration of Mestranol can be decreased when it is combined with Gabexate.Investigational
GeldanamycinThe serum concentration of Mestranol can be decreased when it is combined with Geldanamycin.Experimental
GemfibrozilThe metabolism of Mestranol can be decreased when combined with Gemfibrozil.Approved
GlibornurideThe therapeutic efficacy of Glibornuride can be decreased when used in combination with Mestranol.Withdrawn
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Mestranol.Approved
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Mestranol.Approved
GlipizideThe therapeutic efficacy of Glipizide can be decreased when used in combination with Mestranol.Approved
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Mestranol.Approved
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Mestranol.Approved
GM6001The serum concentration of Mestranol can be decreased when it is combined with GM6001.Experimental
GriseofulvinThe metabolism of Mestranol can be increased when combined with Griseofulvin.Approved, Vet Approved
GusperimusThe therapeutic efficacy of Gusperimus can be decreased when used in combination with Mestranol.Investigational
HE3286The serum concentration of HE3286 can be increased when it is combined with Mestranol.Investigational
HeparinMestranol may decrease the anticoagulant activities of Heparin.Approved, Investigational
HexobarbitalThe therapeutic efficacy of Mestranol can be decreased when used in combination with Hexobarbital.Approved
HirulogThe serum concentration of Mestranol can be decreased when it is combined with Hirulog.Experimental
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Mestranol.Approved, Investigational
HydrocortisoneThe serum concentration of Hydrocortisone can be increased when it is combined with Mestranol.Approved, Vet Approved
idraparinuxThe serum concentration of Mestranol can be decreased when it is combined with idraparinux.Investigational
ImidaprilThe serum concentration of Mestranol can be decreased when it is combined with Imidapril.Investigational
IndinavirThe serum concentration of Mestranol can be decreased when it is combined with Indinavir.Approved
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Mestranol.Approved
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Mestranol.Approved
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Mestranol.Approved
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Mestranol.Approved
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Mestranol.Approved
Insulin PorkThe therapeutic efficacy of Insulin Pork can be decreased when used in combination with Mestranol.Approved
IrbesartanThe metabolism of Mestranol can be decreased when combined with Irbesartan.Approved, Investigational
IsoflurophateThe serum concentration of Mestranol can be decreased when it is combined with Isoflurophate.Approved, Withdrawn
IsotretinoinThe therapeutic efficacy of Mestranol can be decreased when used in combination with Isotretinoin.Approved
IstaroximeThe serum concentration of Istaroxime can be increased when it is combined with Mestranol.Investigational
IxazomibThe serum concentration of Mestranol can be decreased when it is combined with Ixazomib.Approved
KetoconazoleThe metabolism of Mestranol can be decreased when combined with Ketoconazole.Approved, Investigational
LamotrigineThe serum concentration of Lamotrigine can be decreased when it is combined with Mestranol.Approved, Investigational
LeflunomideThe metabolism of Mestranol can be decreased when combined with Leflunomide.Approved, Investigational
LenalidomideMestranol may increase the thrombogenic activities of Lenalidomide.Approved
LepirudinThe serum concentration of Mestranol can be decreased when it is combined with Lepirudin.Approved
LevothyroxineThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Mestranol.Approved
LinagliptinThe serum concentration of Mestranol can be decreased when it is combined with Linagliptin.Approved
LiothyronineThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Mestranol.Approved, Vet Approved
LiotrixThe therapeutic efficacy of Liotrix can be decreased when used in combination with Mestranol.Approved
LiraglutideThe therapeutic efficacy of Liraglutide can be decreased when used in combination with Mestranol.Approved
LisinoprilThe serum concentration of Mestranol can be decreased when it is combined with Lisinopril.Approved, Investigational
LopinavirThe serum concentration of Mestranol can be decreased when it is combined with Lopinavir.Approved
LosartanThe metabolism of Mestranol can be decreased when combined with Losartan.Approved
LovastatinThe metabolism of Mestranol can be decreased when combined with Lovastatin.Approved, Investigational
LumacaftorThe serum concentration of Mestranol can be decreased when it is combined with Lumacaftor.Approved
LumiracoxibLumiracoxib may increase the thrombogenic activities of Mestranol.Approved, Investigational
ME-609The serum concentration of ME-609 can be increased when it is combined with Mestranol.Investigational
MedrysoneThe serum concentration of Medrysone can be increased when it is combined with Mestranol.Approved
MelengestrolThe serum concentration of Melengestrol can be increased when it is combined with Mestranol.Vet Approved
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Mestranol.Approved
MethohexitalThe therapeutic efficacy of Mestranol can be decreased when used in combination with Methohexital.Approved
MethylphenobarbitalThe therapeutic efficacy of Mestranol can be decreased when used in combination with Methylphenobarbital.Approved
MethylprednisoloneThe serum concentration of Methylprednisolone can be increased when it is combined with Mestranol.Approved, Vet Approved
MetreleptinThe serum concentration of Mestranol can be decreased when it is combined with Metreleptin.Approved
MifepristoneThe serum concentration of Mestranol can be increased when it is combined with Mifepristone.Approved, Investigational
MiglitolThe therapeutic efficacy of Miglitol can be decreased when used in combination with Mestranol.Approved
MiglustatThe therapeutic efficacy of Miglustat can be decreased when used in combination with Mestranol.Approved
MitiglinideThe therapeutic efficacy of Mitiglinide can be decreased when used in combination with Mestranol.Approved, Investigational
ModafinilThe serum concentration of Mestranol can be decreased when it is combined with Modafinil.Approved, Investigational
MoexiprilThe serum concentration of Mestranol can be decreased when it is combined with Moexipril.Approved
MometasoneThe serum concentration of Mometasone can be increased when it is combined with Mestranol.Approved, Vet Approved
Mycophenolic acidThe serum concentration of Mestranol can be decreased when it is combined with Mycophenolic acid.Approved
N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-ProlineThe serum concentration of Mestranol can be decreased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Experimental
NabumetoneNabumetone may increase the thrombogenic activities of Mestranol.Approved
NadroparinMestranol may decrease the anticoagulant activities of Nadroparin.Approved
NafamostatThe serum concentration of Mestranol can be decreased when it is combined with Nafamostat.Investigational
NafcillinThe metabolism of Mestranol can be increased when combined with Nafcillin.Approved
NateglinideThe therapeutic efficacy of Nateglinide can be decreased when used in combination with Mestranol.Approved, Investigational
NCX 1022The serum concentration of NCX 1022 can be increased when it is combined with Mestranol.Investigational
NCX 4016The serum concentration of Mestranol can be decreased when it is combined with NCX 4016.Investigational
NelfinavirThe serum concentration of Mestranol can be decreased when it is combined with Nelfinavir.Approved
NevirapineThe serum concentration of Mestranol can be decreased when it is combined with Nevirapine.Approved
NicardipineThe metabolism of Mestranol can be decreased when combined with Nicardipine.Approved
NitroaspirinThe serum concentration of Mestranol can be decreased when it is combined with Nitroaspirin.Investigational
Oleoyl estroneThe serum concentration of Oleoyl estrone can be increased when it is combined with Mestranol.Investigational
OmapatrilatThe serum concentration of Mestranol can be decreased when it is combined with Omapatrilat.Investigational
OmeprazoleThe metabolism of Mestranol can be decreased when combined with Omeprazole.Approved, Investigational, Vet Approved
OspemifeneThe risk or severity of adverse effects can be increased when Mestranol is combined with Ospemifene.Approved
OtamixabanThe serum concentration of Mestranol can be decreased when it is combined with Otamixaban.Investigational
OxcarbazepineThe serum concentration of Mestranol can be decreased when it is combined with Oxcarbazepine.Approved
ParamethasoneThe serum concentration of Paramethasone can be increased when it is combined with Mestranol.Approved
ParecoxibParecoxib may increase the thrombogenic activities of Mestranol.Approved
PentobarbitalThe therapeutic efficacy of Mestranol can be decreased when used in combination with Pentobarbital.Approved, Vet Approved
Pentosan PolysulfateMestranol may decrease the anticoagulant activities of Pentosan Polysulfate.Approved
PerindoprilThe serum concentration of Mestranol can be decreased when it is combined with Perindopril.Approved
PhenforminThe therapeutic efficacy of Phenformin can be decreased when used in combination with Mestranol.Approved, Withdrawn
PhenindioneMestranol may decrease the anticoagulant activities of Phenindione.Approved
PhenobarbitalThe metabolism of Mestranol can be increased when combined with Phenobarbital.Approved
PhenprocoumonMestranol may decrease the anticoagulant activities of Phenprocoumon.Approved
PhenytoinThe therapeutic efficacy of Mestranol can be decreased when used in combination with Phenytoin.Approved, Vet Approved
PhosphoramidonThe serum concentration of Mestranol can be decreased when it is combined with Phosphoramidon.Experimental
PioglitazoneThe therapeutic efficacy of Pioglitazone can be decreased when used in combination with Mestranol.Approved, Investigational
PramlintideThe therapeutic efficacy of Pramlintide can be decreased when used in combination with Mestranol.Approved, Investigational
PrasteroneThe risk or severity of adverse effects can be increased when Prasterone is combined with Mestranol.Approved, Nutraceutical
PrednicarbateThe serum concentration of Prednicarbate can be increased when it is combined with Mestranol.Approved
PrednisoloneThe serum concentration of Prednisolone can be increased when it is combined with Mestranol.Approved, Vet Approved
PrednisoneThe serum concentration of Prednisone can be increased when it is combined with Mestranol.Approved, Vet Approved
PregnenoloneThe serum concentration of Pregnenolone can be increased when it is combined with Mestranol.Experimental
PrimidoneThe metabolism of Mestranol can be increased when combined with Primidone.Approved, Vet Approved
PrinomastatThe serum concentration of Mestranol can be decreased when it is combined with Prinomastat.Investigational
Protein CMestranol may decrease the anticoagulant activities of Protein C.Approved
Protein S humanMestranol may decrease the anticoagulant activities of Protein S human.Approved
ProtocatechualdehydeMestranol may decrease the anticoagulant activities of Protocatechualdehyde.Approved
PrucaloprideThe serum concentration of Mestranol can be decreased when it is combined with Prucalopride.Approved
PyrimethamineThe metabolism of Mestranol can be decreased when combined with Pyrimethamine.Approved, Vet Approved
QuinaprilThe serum concentration of Mestranol can be decreased when it is combined with Quinapril.Approved, Investigational
QuinineThe metabolism of Mestranol can be decreased when combined with Quinine.Approved
RacecadotrilThe serum concentration of Mestranol can be decreased when it is combined with Racecadotril.Investigational
RamiprilThe serum concentration of Mestranol can be decreased when it is combined with Ramipril.Approved
RemikirenThe serum concentration of Mestranol can be decreased when it is combined with Remikiren.Approved
RepaglinideThe therapeutic efficacy of Repaglinide can be decreased when used in combination with Mestranol.Approved, Investigational
ReviparinMestranol may decrease the anticoagulant activities of Reviparin.Approved
RifabutinThe serum concentration of Mestranol can be decreased when it is combined with Rifabutin.Approved
RifampicinThe metabolism of Mestranol can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Mestranol can be increased when combined with Rifapentine.Approved
RimexoloneThe serum concentration of Rimexolone can be increased when it is combined with Mestranol.Approved
RitonavirThe serum concentration of Mestranol can be decreased when it is combined with Ritonavir.Approved, Investigational
RivaroxabanThe serum concentration of Mestranol can be decreased when it is combined with Rivaroxaban.Approved
RofecoxibRofecoxib may increase the thrombogenic activities of Mestranol.Investigational, Withdrawn
RopiniroleThe serum concentration of Ropinirole can be increased when it is combined with Mestranol.Approved, Investigational
RosiglitazoneThe therapeutic efficacy of Rosiglitazone can be decreased when used in combination with Mestranol.Approved, Investigational
SaquinavirThe serum concentration of Mestranol can be decreased when it is combined with Saquinavir.Approved, Investigational
SaxagliptinThe serum concentration of Mestranol can be decreased when it is combined with Saxagliptin.Approved
SecobarbitalThe metabolism of Mestranol can be increased when combined with Secobarbital.Approved, Vet Approved
SelegilineThe serum concentration of Selegiline can be increased when it is combined with Mestranol.Approved, Investigational, Vet Approved
SildenafilThe metabolism of Mestranol can be decreased when combined with Sildenafil.Approved, Investigational
SimeprevirThe serum concentration of Mestranol can be decreased when it is combined with Simeprevir.Approved
SitagliptinThe serum concentration of Mestranol can be decreased when it is combined with Sitagliptin.Approved, Investigational
Somatropin recombinantThe therapeutic efficacy of Somatropin recombinant can be decreased when used in combination with Mestranol.Approved, Investigational
SorafenibThe metabolism of Mestranol can be decreased when combined with Sorafenib.Approved, Investigational
SpiraprilThe serum concentration of Mestranol can be decreased when it is combined with Spirapril.Approved
St. John's WortThe therapeutic efficacy of Mestranol can be decreased when used in combination with St. John's Wort.Nutraceutical
SulfadiazineThe metabolism of Mestranol can be decreased when combined with Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleThe metabolism of Mestranol can be decreased when combined with Sulfamethoxazole.Approved
SulfisoxazoleThe metabolism of Mestranol can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
SulodexideMestranol may decrease the anticoagulant activities of Sulodexide.Approved, Investigational
TelaprevirThe serum concentration of Mestranol can be decreased when it is combined with Telaprevir.Approved
TemocaprilThe serum concentration of Mestranol can be decreased when it is combined with Temocapril.Experimental, Investigational
ThalidomideMestranol may increase the thrombogenic activities of Thalidomide.Approved, Investigational, Withdrawn
TheophyllineThe serum concentration of Theophylline can be increased when it is combined with Mestranol.Approved
ThiamylalThe therapeutic efficacy of Mestranol can be decreased when used in combination with Thiamylal.Approved, Vet Approved
ThiazolidinedioneThe therapeutic efficacy of Thiazolidinedione can be decreased when used in combination with Mestranol.Investigational
ThiopentalThe therapeutic efficacy of Mestranol can be decreased when used in combination with Thiopental.Approved, Vet Approved
ThiorphanThe serum concentration of Mestranol can be decreased when it is combined with Thiorphan.Experimental
Thyroid, porcineThe therapeutic efficacy of Thyroid, porcine can be decreased when used in combination with Mestranol.Approved
TicagrelorThe metabolism of Mestranol can be decreased when combined with Ticagrelor.Approved
TiclopidineThe metabolism of Mestranol can be decreased when combined with Ticlopidine.Approved
TipranavirMestranol may increase the dermatologic adverse activities of Tipranavir.Approved, Investigational
TixocortolThe serum concentration of Tixocortol can be increased when it is combined with Mestranol.Approved
TizanidineThe serum concentration of Tizanidine can be increased when it is combined with Mestranol.Approved
TolazamideThe therapeutic efficacy of Tolazamide can be decreased when used in combination with Mestranol.Approved
TolbutamideThe metabolism of Mestranol can be decreased when combined with Tolbutamide.Approved
TopiramateThe serum concentration of Mestranol can be decreased when it is combined with Topiramate.Approved
TrandolaprilThe serum concentration of Mestranol can be decreased when it is combined with Trandolapril.Approved
Tranexamic AcidMestranol may increase the thrombogenic activities of Tranexamic Acid.Approved
TretinoinThe therapeutic efficacy of Mestranol can be decreased when used in combination with Tretinoin.Approved, Investigational, Nutraceutical
TriamcinoloneThe serum concentration of Triamcinolone can be increased when it is combined with Mestranol.Approved, Vet Approved
TrimethoprimThe metabolism of Mestranol can be decreased when combined with Trimethoprim.Approved, Vet Approved
TroglitazoneThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Mestranol.Withdrawn
UbenimexThe serum concentration of Mestranol can be decreased when it is combined with Ubenimex.Experimental
UlinastatinThe serum concentration of Mestranol can be decreased when it is combined with Ulinastatin.Investigational
Ursodeoxycholic acidThe therapeutic efficacy of Ursodeoxycholic acid can be decreased when used in combination with Mestranol.Approved, Investigational
ValdecoxibValdecoxib may increase the thrombogenic activities of Mestranol.Investigational, Withdrawn
Valproic AcidThe metabolism of Mestranol can be decreased when combined with Valproic Acid.Approved, Investigational
ValsartanThe metabolism of Mestranol can be decreased when combined with Valsartan.Approved, Investigational
VildagliptinThe serum concentration of Mestranol can be decreased when it is combined with Vildagliptin.Approved, Investigational
Vitamin CThe serum concentration of Mestranol can be increased when it is combined with Vitamin C.Approved, Nutraceutical
VogliboseThe therapeutic efficacy of Voglibose can be decreased when used in combination with Mestranol.Approved, Investigational
VoriconazoleThe metabolism of Mestranol can be decreased when combined with Voriconazole.Approved, Investigational
WarfarinMestranol may decrease the anticoagulant activities of Warfarin.Approved
XimelagatranThe serum concentration of Mestranol can be decreased when it is combined with Ximelagatran.Approved, Investigational, Withdrawn
Ym150The serum concentration of Mestranol can be decreased when it is combined with Ym150.Investigational
ZafirlukastThe metabolism of Mestranol can be decreased when combined with Zafirlukast.Approved, Investigational
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot 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
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

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 ]
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Drug created on July 06, 2007 13:51 / Updated on August 17, 2016 12:23