Drospirenone

Các tên gọi khác (7 ) :

1,2-Dihydrospirorenone
6beta,7Beta;15beta,16beta-dimethylene-3-oxo-17alpha-pregn-4-ene-21,17-carbolactone
6β,7β,15β,16β-dimethylene-3-oxo-17α-pregn-4-ene-21,17 carbolactone
Dehydrospirorenone
Drospirenona
Drospirenonum
DRSP

mineralocorticoid receptor antagonists

Thuốc Gốc

Small Molecule

CAS: 67392-87-4

CTHH: C₂₄H₃₀O₃

PTK: 366.4932

Drospirenone is a synthetic progestin that is an analog to spironolactone. It is found in a number of birth control formulations. Drospirenone differs from other synthetic progestins in that its pharmacological profile in preclinical studies shows it to be closer to the natural progesterone. As such it has anti-mineralocorticoid properties, counteracts the estrogen-stimulated activity of the renin-angiotensin-aldosterone system, and is not androgenic. It was shown in animal studies that drospirenone exhibits antiandrogenic activity judging from accessory sex gland growth in castrated, androgen-treated, juvenile rats.

Nhận Dạng Quốc Tế & Đặc Tính Hóa Học

Công thức hóa học

C₂₄H₃₀O₃

Phân tử khối

366.4932

Monoisotopic mass

366.219494826

InChI

InChI=1S/C24H30O3/c1-22-6-3-12(25)9-17(22)13-10-14(13)20-16(22)4-7-23(2)21(20)15-11-18(15)24(23)8-5-19(26)27-24/h9,13-16,18,20-21H,3-8,10-11H2,1-2H3/t13-,14+,15-,16+,18+,20-,21+,22-,23+,24+/m1/s1

InChI Key

InChIKey=METQSPRSQINEEU-HXCATZOESA-N

IUPAC Name

(1R,2R,4R,10R,11S,14S,15S,16S,18S,19S)-10,14-dimethylspiro[hexacyclo[9.8.0.0^{2,4}.0^{5,10}.0^{14,19}.0^{16,18}]nonadecane-15,2'-oxolan]-5-ene-5',7-dione

Traditional IUPAC Name

drospirenone

SMILES

[H][C@@]12C[C@]1([H])[C@@]1([H])[C@]3([H])[C@]4([H])C[C@]4([H])[C@@]4(CCC(=O)O4)[C@@]3(C)CC[C@]1([H])[C@@]1(C)CCC(=O)C=C21

Độ hòa tan

2.25e-03 g/l

logP

3.37

logS

-5.2

pKa (Strongest Basic)

-5

PSA

43.37 Å²

Refractivity

101.68 m³·mol^-1

Polarizability

41.81 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

Dược Lực Học : Drospirenone differs from other synthetic progestins in that its pharmacological profile in preclinical studies shows it to be closer to the natural progesterone. As such it has anti-mineralocorticoid properties, counteracts the estrogen-stimulated activity of the renin-angiotensin-aldosterone system, and is not androgenic.

Cơ Chế Tác Dụng : Drospirenone is a synthetic progestin that is an analog to spironolactone. It is found in a number of birth control formulations. Drospirenone differs from other synthetic progestins in that its pharmacological profile in preclinical studies shows it to be closer to the natural progesterone. As such it has anti-mineralocorticoid properties, counteracts the estrogen-stimulated activity of the renin-angiotensin-aldosterone system, and is not androgenic. It was shown in animal studies that drospirenone exhibits antiandrogenic activity judging from accessory sex gland growth in castrated, androgen-treated, juvenile rats. Progestins such as drospirenone diffuse freely into target cells in the female reproductive tract, mammary gland, hypothalamus, and the pituitary and bind to the progesterone receptor. Once bound to the receptor, progestins slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH surge.

Dược Động Học :

▧ Absorption :
Oral bioavailability is approximately 76%.
▧ Protein binding :
95-97%
▧ Metabolism :
Extensively metabolized following oral or intravenous administration. The two major metabolites are inactive and are formed independent of the CYP450 enzyme system. The metabolites are the acid form of drospirenone formed by opening of the lactone ring and the 4,5-dihydro-drospirenone-3-sulfate.
▧ Half Life :
30 hours

Chỉ Định : For the prevention of pregnancy in women who elect an oral contraceptive.

Tương Tác Thuốc :

Artemether Artemether may decrease the effectiveness of drospirinone by increasing its metabolism via CYP3A4. Consider an alternate non-hormonal means of contraception during artemether therapy.
Benazepril Increased risk of hyperkalemia
Bexarotene Bexarotene may decrease the serum concentration of Contraceptives (Progestins). Since bexarotene is teratogenic and can lower serum concentrations of drospirenone, it is advised that women of childbearing potential use two forms of contraception (including at least one non-hormonal form).
Boceprevir Boceprevir increases levels by affecting CYP3A4 metabolism. Concomitant therapy is contraindicated.
Candesartan Increased risk of hyperkalemia
Captopril Increased risk of hyperkalemia
Cilazapril Increased risk of hyperkalemia
Colesevelam Bile Acid Sequestrants may decrease the serum concentration of Contraceptives (Progestins). Administer oral progestin-containing 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.
Enalapril Increased risk of hyperkalemia
Eprosartan Increased risk of hyperkalemia
Fosinopril Increased risk of hyperkalemia
Heparin Heparin can increase risk of hyperkalemia for patients on drospirenone
Irbesartan Increased risk of hyperkalemia
Lisinopril Increased risk of hyperkalemia
Losartan Increased risk of hyperkalemia
Olmesartan Increased risk of hyperkalemia
Perindopril Increased risk of hyperkalemia
Potassium Increased risk of hyperkalemia
Quinapril Increased risk of hyperkalemia
Ramipril Increased risk of hyperkalemia
Telmisartan Telmisartan may increase the hyperkalemic effect of Drospirenone. Monitor for increased serum potassium concentrations during concomitant therapy.
Thiopental Thiopental may decrease the effect of Drospirenone. Contraceptive failure may occur. Alternative nonhomomonal contraception should be used during concomitant therapy.
Trandolapril Increased risk of hyperkalemia. Monitor serum potassium levels.
Treprostinil Additive hypotensive effect. Monitor antihypertensive therapy during concomitant use.
Tretinoin Oral Tretinoin may decrease the effect of oral contraceptive, Drospirenone. An alternate form of contraception should be used during concomitant therapy.
Triamterene Increased risk of hyperkalemia
Warfarin Drospirenone may alter the anticoagulant effect of warfarin. Concomitant therapy should be avoided. Monitor for changes in coagulation status if drospirenone is initiated, discontinued or dose changed.

Liều Lượng & Cách Dùng : Tablet - Oral - 0.451 mg levomefolate calcium
Tablet - Oral - 3 mg drospirenone (DRSP), 0.03 mg ethinyl estradiol (EE) as betadex clathrate and 0.451 mg levomefol

Dữ Kiện Thương Mại

Nhà Sản Xuất

Công ty : Bayer HealthCare Pharmaceuticals Inc.

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

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

Sản phẩm biệt dược : Yaz

Tài Liệu Tham Khảo Thêm

drugbank

http://www.drugbank.ca/drugs/DB01395

PubChem Compound

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=68873

PubChem Substance

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46507653

KEGG Drug

http://www.genome.jp/dbget-bin/www_bget?drug:D03917

ChemSpider

http://www.chemspider.com/Chemical-Structure.62105.html

National Drug Code Directory

http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/50419-405-03

PharmGKB

http://www.pharmgkb.org/drug/PA164749409

Wikipedia

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

RxList

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

Drugs.com

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

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