drospirenone   Click here for help

GtoPdb Ligand ID: 2874

Synonyms: dihydrospirorenone | Slynd® | Yasmin® | ZK30595
Approved drug
drospirenone is an approved drug
Compound class: Synthetic organic
Comment: Drospirenone is a synthetic analogue of spironolactone, that has a similar pharmacological profile to endogenous progesterone. As a contraceptive agent it is used for its progestin-like activity, but it also has anti-androgen and anti-mineralocorticoid properties.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 0
Topological polar surface area 43.37
Molecular weight 366.22
XLogP 4.35
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES O=C1CCC2(C(=C1)C1CC1C1C2CCC2(C1C1CC1C12CCC(=O)O1)C)C
Isomeric SMILES O=C1CC[C@]2(C(=C1)[C@@H]1C[C@@H]1[C@@H]1[C@@H]2CC[C@]2([C@H]1[C@@H]1C[C@@H]1[C@]12CCC(=O)O1)C)C
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 METQSPRSQINEEU-HXCATZOESA-N
No information available.
Summary of Clinical Use Click here for help
Drospirenone is used in combination with estrogens (such as ethinylestradiol or estradiol) in many female contraceptive and hormone replacement therapy medications. Drospirenone may also be used to treat acne and severe forms of premenstrual syndrome. In June 2019, drospirenone (Slynd®) received FDA approval as the first progestin-only oral contraceptive pill with a 24 active/4 inactive tablet dosing regimen, and which provides a 24-hour missed pill window. The anti-mineralocorticoid activity of drospirenone means that it is contrindicated in women with conditions that predispose to hyperkalemia (e.g. renal or hepatic impairment, or adrenal insufficiency).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Binding of drospirenone to the progesterone receptor reduces the frequency of gonadotropin releasing hormone (GnRH) pulses from the hypothalamus and blunts the pre-ovulatory LH surge, thereby reducing the likelihood of effective ovulation.