QuickView for Mestranol (compound)

Summary
General Info

PubChem

PubChem Compound 4080

Name:	Mestranol
PubChem Compound ID:	4080
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.
Molecular formula:	C₂₁H₂₆O₂
Molecular weight:	310.43 g/mol
Synonyms:	SC 4725; 17.alpha.-Ethinylestradiol 3-methyl ether; Ethynyloestradiol 3-methyl ether; EE3ME; Inostral; 3-Methoxy-17.alpha.-ethynyl-1,3,5(10)-oestratrien-17.beta.-ol; Ethinyloestradiol 3-methyl ether; 3-Methoxy-17.alpha.-ethynyl-1,3,5(10)-estratrien-17.beta.-ol; 17.alpha.-Ethynyl-3-methoxy-17.beta.-hydroxy-.delta.-1,3, 5(10)-estratriene; Component of Enovid. show more » SC 4725; 17.alpha.-Ethinylestradiol 3-methyl ether; Ethynyloestradiol 3-methyl ether; EE3ME; Inostral; 3-Methoxy-17.alpha.-ethynyl-1,3,5(10)-oestratrien-17.beta.-ol; Ethinyloestradiol 3-methyl ether; 3-Methoxy-17.alpha.-ethynyl-1,3,5(10)-estratrien-17.beta.-ol; 17.alpha.-Ethynyl-3-methoxy-17.beta.-hydroxy-.delta.-1,3, 5(10)-estratriene; Component of Enovid; Component of Ovulen; 17.alpha.-Ethinyl estradiol 3-methyl ether; 3-Methoxy-17.alpha.-ethynyloestradiol; NSC98536; 17.alpha.-Ethinyl oestradiol 3-methyl ether; .delta.-MVE; 19-Norpregna-1,3,5(10)-trien-20-yn-17-ol, 3-methoxy-, (17.alpha.)-; 17.alpha.-Ethynylestradiol methyl ether; (+ )-17.Alpha.-Ethynyl-17.beta.-hydroxy-3-methoxy-1,3, 5(10)-oestratriene; 19-Nor-17.alpha.-pregna-1,3, 5 (10)-trien-20-yn-17-ol, 3-methoxy-; NCIOpen2_009561; Component of Norquen; 3-Methylethynylestradiol; Estra-1,3,5(10)-trien-17.beta.-ol, 17-ethynyl-3-methoxy-; 17-Ethynyl-3-methoxy-1,3,5(10)-oestratien-17.beta.-ol; 3-Methoxy-19-nor-17.alpha.-pregna-1,3,5(10)-trien-20-yn-17-ol; (+)-17.Alpha.-Ethynyl-17.beta.-hydroxy-3-methoxy-1,3, 5(10)-estratriene; Compound 33355; 19-Norpregna-1,3, 5 (10)-trien-20-yn-17-ol, 3-methoxy-, (17.alpha.)-; 17.beta.-Estradiol, 17-ethynyl-, 3- (methyl ether); 8027 C. B.; Ovastol; 3-Methoxy-17.alpha.-ethinylestradiol; 3-Methoxy-17.alpha.-ethynylestradiol; 17.alpha.-Ethynyl-3-methoxy-17.beta.-hydroxy-.delta.-1,3, 5(10)-oestratriene; EE(sub3)ME; Ethinylestradiol 3-methyl ether; Ethynylestradiol 3-methyl ether; Component of Ortho-Novum; Devocin; Component of Norinyl; 17-Ethynylestradiol 3-methyl ether; 72-33-3; 17.alpha.-Ethynylestradiol 3-methyl ether; Ethynylestradiol methyl ether; 17.alpha.-19-Norpregna-1,3,5(10)-trien-20-yn-17-ol, 3-methoxy-; 17.alpha.-Ethynyloestradiol 3-methyl ether; 3-O-Methylethynylestradiol; 17-Ethynyl-3-methoxy-1,3,5(10)-estratrien-17.beta.-ol; Norquen; NSC84032; Component of C-Quens; 3-Methoxy-17.alpha.-ethinyloestradiol; Mestranol; 3-Methoxyethynylestradiol show less «

DrugBank

Identification

Name:	Mestranol
Name (isomeric):	DB01357
Drug Type:	small molecule
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.
Category:	Estrogens
CAS number:	72-33-3

Pharmacology

Indication:	Mestranol was used as one of the first oral contraceptives.
Mechanism of Action:	Mestranol 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 ethinyl... show more » Mestranol 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). show less «

Indication:

Mestranol was used as one of the first oral contraceptives.

Mechanism of Action:

Mestranol 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 ethinyl...
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Interactions

Drug interaction:

Dicloxacillin	This anti-infectious agent could decrease the effect of the oral contraceptive
Carbamazepine	This product may cause a slight decrease of contraceptive effect
Tolbutamide	Tolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Mestranol. Consider alternate therapy or monitor for changes in Mestranol therapeutic and adverse effects if Tolbutamide is initiated, discontinued or dose changed.
Penicillin V	This anti-infectious agent could decrease the effect of the oral contraceptive
Minocycline	This anti-infectious agent could decrease the effect of the oral contraceptive

Dicloxacillin	This anti-infectious agent could decrease the effect of the oral contraceptive
Carbamazepine	This product may cause a slight decrease of contraceptive effect
Tolbutamide	Tolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Mestranol. Consider alternate therapy or monitor for changes in Mestranol therapeutic and adverse effects if Tolbutamide is initiated, discontinued or dose changed.
Penicillin V	This anti-infectious agent could decrease the effect of the oral contraceptive
Minocycline	This anti-infectious agent could decrease the effect of the oral contraceptive
Carbenicillin	This anti-infectious agent could decreases the effect of the oral contraceptive
Phenytoin	This product may cause a slight decrease of contraceptive effect
Artemether	Artemether may decrease the effectiveness of mestranol by increasing its metabolism via CYP3A4. Consider an alternate non-hormonal means of contraception during artemether therapy.
Prednisone	The estrogenic agent, mestranol, may increase the effect of corticosteroid, prednisone.
Fosphenytoin	This product may cause a slight decrease of contraceptive effect
Aprepitant	Aprepitant could decrease the effect of the oral contraceptive
Ampicillin	This anti-infectious agent could decrease the effect of the oral contraceptive
Topiramate	Topiramate may decrease the effect of the oral contraceptive, Mestranol. An alternate form of contraception should be used during concomitant therapy.
Cloxacillin	This anti-infectious agent could decrease the effect of the oral contraceptive
Clavulanate	This anti-infectious agent could decrease the effect of the oral contraceptive
Tizanidine	Oral contraceptives decrease the clearance of Tizanidine.
Amprenavir	Ritonavir could decrease the contraceptive efficacy
Ketoconazole	This anti-infectious agent could decrease the effect of the oral contraceptive
Warfarin	Mestranol may alter the anticoagulant effect of warfarin. Concomitant therapy should be avoided. Monitor for changes in coagulation status if mestranol is initiated, discontinued or dose changed.
Tipranavir	Mestranol may increase the adverse dermatological effects (i.e. skin rash) of Tipranavir. Tipranavir may decrease the serum concentration Mestranol. Use an alternate form of contraception or monitor for estrogen deficiency if Mestranol is used for hormone replacement therapy.
Oxtriphylline	The contraceptive increases the effect and toxicity of theophylline
Rifampin	This product may cause a slight decrease of contraceptive effect
Amoxicillin	This anti-infectious agent could decrease the effect of the oral contraceptive
Bosentan	Decreases the effect of contraceptive
Oxcarbazepine	Oxcarbazepine decreases the effect of the contraceptive
Doxycycline	This anti-infectious agent could decrease the effect of the oral contraceptive
Theophylline	The contraceptive increases the effect and toxicity of theophylline
Griseofulvin	This product may cause a slight decrease of contraceptive effect
Phenobarbital	This product may cause a slight decrease of contraceptive effect
Nelfinavir	Ritonavir could decrease the contraceptive efficacy
Piperacillin	This anti-infectious agent could decrease the effect of the oral contraceptive
Rifabutin	This product may cause a slight decrease of the contraceptive effect
Itraconazole	This anti-infectious agent could decrease the effect of the oral contraceptive
Colesevelam	Bile Acid Sequestrants may decrease the serum concentration of Contraceptives (Estrogens). Administer estrogen-based oral contraceptives at least 1-4 hours prior to or 4-6 hours after administration of a bile acid sequestrant. Consider alternatives in order to avoid this combination when possible, due to the risk for impaired contraceptive effectiveness. Ethinyl estradiol patches and vaginal rings may also be somewhat impacted by this interaction, though the extent and significance of such an interaction is uncertain.
Cyclosporine	The contraceptive increases the effect and toxicity of cyclosporine
Lamotrigine	The oral contraceptive decreases the effect of lamotrigine
Penicillin G	This anti-infectious agent could decreases the effect of the oral contraceptive
Demeclocycline	This anti-infectious agent could decrease the effect of the oral contraceptive
Aminophylline	The contraceptive increases the effect and toxicity of theophylline
Modafinil	Modafinil decreases the effect of the contraceptive
Flucloxacillin	This anti-infectious agent could decrease the effect of the oral contraceptive
Pivampicillin	This anti-infectious agent could decrease the effect of the oral contraceptive
Primidone	This product may cause a slight decrease of contraceptive effect
Raloxifene	Association not recommended
Thiopental	Thiopental may decrease the effect of Mestranol. Contraceptive failure may occur. Alternative nonhomomonal contraception should be used during concomitant therapy.
Prednisolone	The estrogenic agent, mestranol, may increase the effect of the corticosteroid, prednisolone.
Tretinoin	Oral Tretinoin may decrease the effect of oral contraceptive, Mestranol. An alternate form of contraception should be used during concomitant therapy.
Pioglitazone	Possible loss of contraceptive effect
Tetracycline	This anti-infectious agent could decrease the effect of the oral contraceptive

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Targets

Estrogen receptor

Enzymes

Cytochrome P450 2C9