Compound: Drospirenone
SMILES: O=C1C=C2[C@]([C@@H]3[C@H]([C@H]4[C@]([C@@]5(OC(=O)CC5)[C@@H]6[C@H]4C6)(C)CC3)[C@@H]7[C@H]2C7)(C)CC1
InChIKey: METQSPRSQINEEU-HXCATZOESA-N
Synonyms: Drospirenone, 67392-87-4, Dihydrospirorenone, Dehydrospirorenone, Drospirenona, 1,2-Dihydrospirorenone, DRSP, Drospirenonum, ZK 30595, Slynd, ZK-30595, DTXSID7046465, ZK30595, N295J34A25, NSC-760103, (6R,7R,8R,9S,10R,13S,14S,15S,16S,17S)-1,3',4',6,6a,7,8,9,10,11,12,13,14,15,15a,16-Hexadecahydro-10,13-dimethylspiro-(17H-dicyclopropa(6,7:15,16)cyclopenta(a)phenanthrene-17,2'(5'H)-furan)-3,5'(2H)-dione, DTXCID5026465, CHEBI:50838, NEXTSTELLIS COMPONENT DROSPIRENONE, 1,2-dihydro-spirorenone, 6beta,7beta;15beta,16beta-Dimethylene-3-oxo-17alpha-pregn-4-ene-21,17-carbolactone, (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, (1R,2R,4R,10R,11S,14S,15S,16S,18S,19S)-10,14-dimethylspiro[hexacyclo[9.8.0.02,4.05,10.014,19.016,18]nonadec-5-ene-15,5'-oxolane]-2',7-dione, (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, (1R,2R,4R,10R,11S,14S,15S,16S,18S,19S)-10,14-dimethylspiro(hexacyclo(9.8.0.02,4.05,10.014,19.016,18)nonadec-5-ene-15,5'-oxolane)-2',7-dione, 6beta,7beta,15beta,16beta-dimethylen-3-oxo-17alpha-pregn-4-en-21,17-carbolacton, RefChem:55077, G03AC10, 6-beta,7-beta:15-beta,16-beta-Dimethylene-3-oxo-17-alpha-pregn-4-ene-21,17-carbolactone, Drospirenonum [INN-Latin], Drospirenona [INN-Spanish], MFCD00867350, 17-Hydroxy-6beta,7beta:15beta,16beta-dimethylene-3-oxo-17alpha-pregn-4-ene-21-carboxylic acid, gamma-lactone, Drospirenone [INN], CAS-67392-87-4, CCRIS 6523, EINECS 266-679-2, BRN 4765500, UNII-N295J34A25, Drospirenone CRS, HSDB 7896, NCGC00164590-01, Drospirenone [USAN:USP:INN:BAN], SH-470, Slinda (TN), Slynd (TN), Drospirenone (Standard), 1, 2-Dihydrospirorenone, DROSPIRENONE [MI], DROSPIRENONE [JAN], DROSPIRENONE [USAN], 6-beta,7-beta;15-beta,16-beta-Dimethylene-3-oxo-17-alpha-pregn-4-ene-21,17-carbolactone, CHEMBL1509, DROSPIRENONE [VANDF], DROSPIRENONE [MART.], Spiro(17H-dicyclopropa(6,7:15,16)cyclopenta(a)phenanthrene-17,2'(5'H)-furan)-3,5'(2H)-dione, 1,3',4',6,7,8,9,10,11,12,13,14,15,16,20,21-hexadecahydro-10,13-dimethyl-, (6R-(6alpha,7alpha,8beta,9alpha,10beta,13beta,14alpha,15alpha,16alpha,17beta))-, DROSPIRENONE [USP-RS], DROSPIRENONE [WHO-DD], SCHEMBL153316, Drospirenone (JAN/USP/INN), GTPL2874, orb1308263, Drospirenone - Bio-X trade mark, HY-B0111R, YAZ COMPONENT DROSPIRENONE, Drospirenone, >=98% (HPLC), BDBM150275, DROSPIRENONE [ORANGE BOOK], BEYAZ COMPONENT DROSPIRENONE, DROSPIRENONE [EP MONOGRAPH], Drospirenone for peak identification, EX-A3153, HY-B0111, YASMIN COMPONENT DROSPIRENONE, DROSPIRENONE [USP MONOGRAPH], Tox21_112216, ANGELIQ COMPONENT DROSPIRENONE, EBC-11181, MSK011116, s1377, SAFYRAL COMPONENT DROSPIRENONE, AKOS015895237, Tox21_112216_1, CCG-268245, CS-1863, DB01395, FD22620, MSK011116-100A, NSC 760103, 6beta,7beta,15beta,16beta-dimethylene-3-oxo-17alpha-pregn-4-ene-21,17 carbolactone, Drospirenone for peak identification CRS, NCGC00164590-02, NCGC00164590-04, NCGC00164590-07, AS-13025, BD166530, SY106001, US8987239, A, D4209, NS00002775, D03917, AB01274783-01, AB01274783_02, Drospirenone Solution in Acetonitrile, 100ug/mL, AR-270/43507886, EN300-19767634, Q419646, SR-01000942231, SR-01000942231-1, BRD-K04394237-001-03-7, BRD-K04394237-001-04-5, BRD-K04394237-001-06-0, Drospirenone, European Pharmacopoeia (EP) Reference Standard, Drospirenone, United States Pharmacopeia (USP) Reference Standard, 6?,7?,15?,16?-Dimethylene-3-oxo-4-androstene-[17(?-1')-spiro-5']perhydrofuran-2'-one, Drospirenone for peak identification, European Pharmacopoeia (EP) Reference Standard, (1aR,2'S,5aR,5bS,7aS,8aS,9aS,9bS,9cR,9dR)-5a,7a-Dimethyl-1,1a,5,5a,5b,6,7,7a,8a,9,9a,9b,9c,9d-tetradecahydrospiro[cyclopropa[4,5]cyclopenta[1,2-a]cyclopropa[l]phenanthrene-8,2'-oxolane]-3,5'(4H)-dione, 3-oxo-6alpha,7alpha,15alpha,16alpha-tetrahydro-7'H,16'H-dicyclopropa[6,7;15,16]-17alpha-pregn-4-ene-21,17-carbolactone, 5a,7a-dimethyl-1,1a,3,3',4,4',5,5a,5b,6,7,7a,8a,9,9a,9b,9c,9d-octaadecahydrospiro(cyclopropa[4,5]cyclopenta[1,2-a]cyclopropa[l]phenanthren-8,5'-furan)-2',3-dione, 6beta,7beta:15beta,16beta -Dimethylene-3-oxo-17alpha-pregn-4-ene-21,17-carbolactone, Dihydrospirorenone, Spiro[8H-cyclopropa[4,5]cyclopenta[1,2-a]cyclopropa[l]phenanthrene-8,2'(5'H)-furan]-3,5'(4H)-dione, 1,1a,3',4',5,5a,5b,6,7,7a,8a,9,9a,9b,9c,9d-hexadecahydro-5a,7a-dimethyl-, (1aR,5aR,5bS,7aS,8S,8aS,9a R,9bS,9cR,9dR)-
Theoretical properties:
molecular_formula: C24H30O3
molecular_weight: 366.5 g/mol
exact_mass: 366.21949481 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 0
heavy_atom_count: 27
topological_polar_surface_area: 43.4 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 196-200
solubility: 2.25e-03 g/L
Descriptions:
pubchem: Drospirenone is a steroid lactone and a 3-oxo-Delta(4) steroid. It has a role as a contraceptive drug, an aldosterone antagonist and a progestin.
chembl: DROSPIRENONE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Drospirenone is a progestin and antiandrogen medication which is used in birth control pills to prevent pregnancy and in menopausal hormone therapy, among other uses. It is available both alone under the brand name Slynd and in combination with an estrogen under the brand name Yasmin among others. The medication is an analog of the drug spironolactone. Drospirenone is taken by mouth.
Common side effects include acne, headache, breast tenderness, weight increase, and menstrual changes. Rare side effects may include high potassium levels and blood clots (when taken as a combined oestrogen-progestogen pill), among others. Drospirenone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It has additional antimineralocorticoid and antiandrogenic activity and no other important hormonal activity. Because of its antimineralocorticoid activity and lack of undesirable off-target activity, drospirenone is said to more closely resemble bioidentical progesterone than other progestins.
Drospirenone was patented in 1976 and introduced for medical use in 2000. It is available widely throughout the world. The medication is sometimes referred to as a "fourth-generation" progestin. It is available as a generic medication. In 2020, a formulation of drospirenone with ethinylestradiol was the 145th most commonly prescribed medication in the United States, with more than 4 million prescriptions.