Mestranol

Thuốc Gốc

Small Molecule

CAS: 72-33-3

CTHH: C₂₁H₂₆O₂

PTK: 310.4299

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]

Nhận Dạng Quốc Tế & Đặc Tính Hóa Học

Công thức hóa học

C₂₁H₂₆O₂

Phân tử khối

310.4299

Monoisotopic mass

310.193280076

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

InChI Key

InChIKey=IMSSROKUHAOUJS-ZTUUXWJNNA-N

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

Traditional IUPAC Name

mestranol

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

Độ tan chảy

150.5 °C

Độ hòa tan

3.77e-03 g/l

logP

4.04

logS

-4.9

pKa (strongest acidic)

17.59

pKa (Strongest Basic)

-1.7

PSA

29.46 Å²

Refractivity

91.86 m³·mol^-1

Polarizability

36.7 Å³

Rotatable Bond Count

H Bond Acceptor Count

H Bond Donor Count

Physiological Charge

Number of Rings

Bioavailability

Rule of Five

true

Ghose Filter

true

Cơ Chế Tác Dụng : 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] 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).

Chỉ Định : Mestranol was used as one of the first oral contraceptives.

Tương Tác Thuốc :

Aminophylline The contraceptive increases the effect and toxicity of theophylline
Amoxicillin This anti-infectious agent could decrease the effect of the oral contraceptive
Ampicillin This anti-infectious agent could decrease the effect of the oral contraceptive
Amprenavir Ritonavir could decrease the contraceptive efficacy
Aprepitant Aprepitant could decrease the effect of the oral contraceptive
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.
Benzylpenicillin This anti-infectious agent could decreases the effect of the oral contraceptive
Bosentan Decreases the effect of contraceptive
Carbamazepine This product may cause a slight decrease of contraceptive effect
Carbenicillin This anti-infectious agent could decreases the effect of the oral contraceptive
Clavulanate This anti-infectious agent could decrease the effect of the oral contraceptive
Cloxacillin 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
Demeclocycline 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
Doxycycline This anti-infectious agent could decrease the effect of the oral contraceptive
Flucloxacillin This anti-infectious agent could decrease the effect of the oral contraceptive
Fosphenytoin This product may cause a slight decrease of contraceptive effect
Griseofulvin This product may cause a slight decrease of contraceptive effect
Itraconazole This anti-infectious agent could decrease the effect of the oral contraceptive
Ketoconazole This anti-infectious agent could decrease the effect of the oral contraceptive
Lamotrigine The oral contraceptive decreases the effect of lamotrigine
Minocycline This anti-infectious agent could decrease the effect of the oral contraceptive
Modafinil Modafinil decreases the effect of the contraceptive
Nelfinavir Ritonavir could decrease the contraceptive efficacy
Oxcarbazepine Oxcarbazepine decreases the effect of the contraceptive
Oxtriphylline The contraceptive increases the effect and toxicity of theophylline
Penicillin V This anti-infectious agent could decrease the effect of the oral contraceptive
Phenobarbital This product may cause a slight decrease of contraceptive effect
Phenytoin This product may cause a slight decrease of contraceptive effect
Pioglitazone Possible loss of contraceptive effect
Piperacillin 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
Prednisolone The estrogenic agent, mestranol, may increase the effect of the corticosteroid, prednisolone.
Prednisone The estrogenic agent, mestranol, may increase the effect of corticosteroid, prednisone.
Primidone This product may cause a slight decrease of contraceptive effect
Raloxifene Association not recommended
Rifabutin This product may cause a slight decrease of the contraceptive effect
Rifampicin This product may cause a slight decrease of contraceptive effect
Tetracycline This anti-infectious agent could decrease the effect of the oral contraceptive
Theophylline The contraceptive increases the effect and toxicity of theophylline
Thiopental Thiopental may decrease the effect of Mestranol. Contraceptive failure may occur. Alternative nonhomomonal contraception should be used during concomitant therapy.
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.
Tizanidine Oral contraceptives decrease the clearance of Tizanidine.
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.
Topiramate Topiramate may decrease the effect of the oral contraceptive, Mestranol. An alternate form of contraception should be used during concomitant therapy.
Tretinoin Oral Tretinoin may decrease the effect of oral contraceptive, Mestranol. An alternate form of contraception should be used during concomitant therapy.
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.

Tài Liệu Tham Khảo Thêm

drugbank

http://www.drugbank.ca/drugs/DB01357

KEGG Compound

http://www.genome.jp/dbget-bin/www_bget?cpd:C07618

KEGG Drug

http://www.genome.jp/dbget-bin/www_bget?drug:D00575

PharmGKB

http://www.pharmgkb.org/drug/PA450388

Wikipedia

http://en.wikipedia.org/wiki/Mestranol

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