Drospirenone

Details

• Internal ID: afcb45fe-429e-469a-9da1-9a41b059edbf
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Spironolactones and derivatives
• IUPAC Name: (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
• SMILES (Canonical): CC12CCC(=O)C=C1C3CC3C4C2CCC5(C4C6CC6C57CCC(=O)O7)C
• SMILES (Isomeric): C[C@]12CCC(=O)C=C1[C@@H]3C[C@@H]3[C@@H]4[C@@H]2CC[C@]5([C@H]4[C@@H]6C[C@@H]6[C@@]57CCC(=O)O7)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
• Popularity: 742 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₀O₃
• Molecular Weight: 366.50 g/mol
• Exact Mass: 366.21949481 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 4.31
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• 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
• 392D874
• 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)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9970	99.70%
Caco-2	+	0.6058	60.58%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.8714	87.14%
Subcellular localzation	Mitochondria	0.6873	68.73%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8299	82.99%
OATP1B3 inhibitior	+	0.9770	97.70%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	+	0.7000	70.00%
BSEP inhibitior	+	0.8535	85.35%
P-glycoprotein inhibitior	+	0.7522	75.22%
P-glycoprotein substrate	-	0.7068	70.68%
CYP3A4 substrate	+	0.7979	79.79%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8978	89.78%
CYP3A4 inhibition	-	0.8355	83.55%
CYP2C9 inhibition	-	0.8665	86.65%
CYP2C19 inhibition	-	0.7754	77.54%
CYP2D6 inhibition	-	0.9336	93.36%
CYP1A2 inhibition	-	0.5534	55.34%
CYP2C8 inhibition	+	0.7271	72.71%
CYP inhibitory promiscuity	-	0.8541	85.41%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5409	54.09%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9832	98.32%
Skin irritation	-	0.5691	56.91%
Skin corrosion	-	0.9025	90.25%
Ames mutagenesis	-	0.9900	99.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6713	67.13%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	-	0.5223	52.23%
skin sensitisation	-	0.6388	63.88%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.4547	45.47%
Acute Oral Toxicity (c)	III	0.7290	72.90%
Estrogen receptor binding	+	0.6133	61.33%
Androgen receptor binding	+	0.8696	86.96%
Thyroid receptor binding	+	0.6771	67.71%
Glucocorticoid receptor binding	+	0.9179	91.79%
Aromatase binding	+	0.8882	88.82%
PPAR gamma	+	0.6143	61.43%
Honey bee toxicity	-	0.7675	76.75%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6600	66.00%
Fish aquatic toxicity	+	0.9939	99.39%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1871	P10275	Androgen Receptor	27 nM; 630 nM	IC50; IC50	via Super-PRED; via Super-PRED
CHEMBL1994	P08235	Mineralocorticoid receptor	3.3 nM	IC50	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	707.9 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.50%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.89%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.07%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.46%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.97%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.48%	94.45%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	87.40%	94.78%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	86.81%	86.00%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	85.65%	89.05%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.10%	97.14%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	84.21%	93.40%
CHEMBL2581	P07339	Cathepsin D	83.54%	98.95%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.96%	90.71%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.94%	94.80%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.24%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.63%	99.23%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.51%	92.94%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.25%	94.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 68873
• LOTUS: LTS0157281
• wikiData: Q419646