Estradiol valerate/Dienogest

Các tên gọi khác (4 ) :

17-hydroxy-3-oxo-19-nor-17α-pregna-4,9-diene-21-nitrile
17α-cyanomethyl-17β-hydroxy-estra-4,9(10)-dien-3-one
17β-Estradiol-17-valerate
pentanoate d'estra-1,3,5(10)-triène-3-ol-17β-yle

Thuốc Gốc

Small Molecule

CAS: 65928-58-7

CTHH: C₄₃H₅₇NO₅

PTK: 667.9164

Estradiol valerate/Dienogest is a Combined oral contraceptive (COC) indicated for use by women to prevent pregnancy. It is also indicated for the treatment of heavy menstrual bleeding in women. The efficacy of Estradiol valerate/Dienogest in women with a body mass index of >30 kg/m2 has not been evaluated.

Nhận Dạng Quốc Tế & Đặc Tính Hóa Học

Công thức hóa học

C₄₃H₅₇NO₅

Phân tử khối

667.9164

Monoisotopic mass

667.423673939

InChI

InChI=1S/C23H32O3.C20H25NO2/c1-3-4-5-22(25)26-21-11-10-20-19-8-6-15-14-16(24)7-9-17(15)18(19)12-13-23(20,21)2;1-19-8-6-16-15-5-3-14(22)12-13(15)2-4-17(16)18(19)7-9-20(19,23)10-11-21/h7,9,14,18-21,24H,3-6,8,10-13H2,1-2H3;12,17-18,23H,2-10H2,1H3/t18-,19-,20+,21+,23+;17-,18+,19+,20-/m11/s1

InChI Key

InChIKey=LRHSUZNWLAJWRT-GAJBHWORSA-N

IUPAC Name

2-[(10S,11S,14R,15S)-14-hydroxy-15-methyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1,6-dien-14-yl]acetonitrile (1S,10R,11S,14S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-yl pentanoate

Traditional IUPAC Name

dienogest estradiol valerate

SMILES

[H][C@@]12CC[C@@](O)(CC#N)[C@@]1(C)CCC1=C3CCC(=O)C=C3CC[C@@]21[H].[H][C@@]12CC[C@H](OC(=O)CCCC)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3

Độ tan chảy

144-145

Độ hòa tan

<1 mg/mL

logP

5.78

logS

-5.8

pKa (strongest acidic)

10.33

pKa (Strongest Basic)

-5.4

PSA

46.53 Å²

Refractivity

102.89 m³·mol^-1

Polarizability

42.76 Å³

Rotatable Bond Count

H Bond Acceptor Count

H Bond Donor Count

Physiological Charge

Number of Rings

Bioavailability

MDDR-Like Rule

true

Dược Lực Học : Estradiol valerate is a synthetic prodrug of 17ß-estradiol, while dienogest (DNG) is a progestin. DNG displays properties of 19-nortestosterone derivatives as well as properties associated with progesterone derivatives.

Cơ Chế Tác Dụng : Estradiol valerate/Dienogest is a Combined oral contraceptive (COC) indicated for use by women to prevent pregnancy. It is also indicated for the treatment of heavy menstrual bleeding in women. The efficacy of Estradiol valerate/Dienogest in women with a body mass index of >30 kg/m2 has not been evaluated. Estradiol valerate/Dienogest lower the risk of becoming pregnant primarily by suppressing ovulation. Additionally, cervical mucus changes that inhibit sperm penetration and endometrial changes that reduce the likelihood of implantation are other possible mechanisms.

Dược Động Học :

▧ Volume of Distribution :
In serum, 38% of estradiol is bound to sex hormone-binding globulin (SHBG), 60% to albumin and 2–3% circulates in free form. An apparent volume of distribution of approximately 1.2 L/kg was determined after intravenous (IV) administration.
▧ Protein binding :
~90%
▧ Metabolism :
Estradiol undergoes an extensive first-pass effect and a considerable part of the dose administered is already metabolized in the gastrointestinal mucosa. The CYP 3A family is known to play the most important role in human estradiol metabolism. The main metabolites are estrone and its sulfate or glucuronide conjugates. Dienogest is extensively metabolized by the known pathways of steroid metabolism (hydroxylation, conjugation), with the formation of mostly inactive metabolites. CYP3A4 was identified as a predominant enzyme catalyzing the metabolism of dienogest.
▧ Route of Elimination :
Estradiol and its metabolites are mainly excreted in urine, with about 10% being excreted in the feces. Dienogest is primarily excreted renally in the form of metabolites and unchanged dienogest is the dominating fraction in plasma.
▧ Half Life :
The terminal half-life of estradiol is approximately 14 hours. The terminal half-life of dienogest is approximately 11 hours.

Chỉ Định : Indicated for use by women for pregnancy prevention. Also indicated for the treatment of heavy menstrual bleeding in women without organic pathology who choose to use an oral contraceptive as their method of birth control.

Tương Tác Thuốc :

Bosentan Affects CYP3A4 metabolism, decreases or effects levels of Estradiol valerate/Dienogest.
Carbamazepine Affects CYP3A4 metabolism, decreases or effects levels of Estradiol valerate/Dienogest.
Dexamethasone Affects CYP3A4 metabolism, decreases or effects levels of Estradiol valerate/Dienogest.
Efavirenz Affects CYP3A4 metabolism, decreases or effects levels of Estradiol valerate/Dienogest.
Fosphenytoin Affects CYP3A4 metabolism, decreases or effects levels of Estradiol valerate/Dienogest.
Nafcillin Affects CYP3A4 metabolism, decreases or effects levels of Estradiol valerate/Dienogest.
Nevirapine Affects CYP3A4 metabolism, decreases or effects levels of Estradiol valerate/Dienogest.
Ospemifene Pharmacodynamic synergist; contraindicated.
Pentobarbital Affects CYP3A4 metabolism, decreases or effects levels of Estradiol valerate/Dienogest.
Phenobarbital Affects CYP3A4 metabolism, decreases or effects levels of Estradiol valerate/Dienogest.
Phenytoin Affects CYP3A4 metabolism, decreases or effects levels of Estradiol valerate/Dienogest.
Primidone Affects CYP3A4 metabolism, decreases or effects levels of Estradiol valerate/Dienogest.
Rifabutin Affects CYP3A4 metabolism, decreases or effects levels of Estradiol valerate/Dienogest.
Rifapentine Affects CYP3A4 metabolism, decreases or effects levels of Estradiol valerate/Dienogest.
St. John's Wort Affects CYP3A4 metabolism, decreases or effects levels of Estradiol valerate/Dienogest.

Liều Lượng & Cách Dùng : Tablet, film coated - Oral - (dark red) 1 mg estradiol valerate
Tablet, film coated - Oral - (dark yellow) 3 mg estradiol valerate
Tablet, film coated - Oral - (light yellow) 2 mg estradiol valerate and 3 mg dienogest
Tablet, film coated - Oral - (medium red) 2 mg estradiol valerate and 2 mg dienogest
Tablet, film coated - Oral - white tablets (inert), with an embossed “DT” in a regular hexagon on one side

Dữ Kiện Thương Mại

Nhà Sản Xuất

Công ty : Bristol Myers-Squibb

Sản phẩm biệt dược : Delestrogen
Công ty : Bayer HealthCare Pharmaceuticals Inc.

Sản phẩm biệt dược : Natazia
Công ty : Bayer HealthCare Pharmaceuticals Inc.

Sản phẩm biệt dược : Qlaira

Tài Liệu Tham Khảo Thêm

drugbank

http://www.drugbank.ca/drugs/DB08866

KEGG Drug

http://www.genome.jp/dbget-bin/www_bget?drug:D01413

National Drug Code Directory

http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/50419-409-03

RxList

http://www.rxlist.com/natazia-drug.htm

Drugs.com

http://www.drugs.com/natazia.html

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