Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:51:59 UTC
HMDB IDHMDB0015467
Secondary Accession Numbers
  • HMDB15467
Metabolite Identification
Common NameDrospirenone
DescriptionDrospirenone 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.
Structure
Data?1582753300
Synonyms
ValueSource
1,2-DihydrospirorenoneChEBI
6beta,7Beta;15beta,16beta-dimethylene-3-oxo-17alpha-pregn-4-ene-21,17-carbolactoneChEBI
DehydrospirorenoneChEBI
DrospirenonaChEBI
DrospirenonumChEBI
SlyndKegg
6b,7Beta;15b,16b-dimethylene-3-oxo-17a-pregn-4-ene-21,17-carbolactoneGenerator
6Β,7beta;15β,16β-dimethylene-3-oxo-17α-pregn-4-ene-21,17-carbolactoneGenerator
6Β,7β,15β,16β-dimethylene-3-oxo-17α-pregn-4-ene-21,17 carbolactoneHMDB
DRSPHMDB
1,2-Dihydro-spirorenoneHMDB
DihydrospirorenoneHMDB
6beta,7beta,15beta,16beta-Dimethylen-3-oxo-17alpha-pregn-4-en-21,17-carbolactonHMDB
Chemical FormulaC24H30O3
Average Molecular Weight366.4932
Monoisotopic Molecular Weight366.219494826
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]nonadecane-15,2'-oxolan]-5-ene-5',7-dione
Traditional Nameyasmin
CAS Registry Number67392-87-4
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
InChI Identifier
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 KeyMETQSPRSQINEEU-HXCATZOESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as spironolactones and derivatives. These are steroid lactones with a structure based on the spironolactone skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid lactones
Direct ParentSpironolactones and derivatives
Alternative Parents
Substituents
  • Spironolactone
  • Cyclohexenone
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Cyclic ketone
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Organic oxide
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0022 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0022 g/LALOGPS
logP2.36ALOGPS
logP3.37ChemAxon
logS-5.2ALOGPS
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity101.68 m³·mol⁻¹ChemAxon
Polarizability41.81 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+187.05331661259
DarkChem[M-H]-182.91731661259
DeepCCS[M-2H]-222.14630932474
DeepCCS[M+Na]+196.16330932474
AllCCS[M+H]+191.032859911
AllCCS[M+H-H2O]+188.632859911
AllCCS[M+NH4]+193.332859911
AllCCS[M+Na]+193.932859911
AllCCS[M-H]-197.932859911
AllCCS[M+Na-2H]-198.032859911
AllCCS[M+HCOO]-198.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Drospirenone[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=C213984.7Standard polar33892256
Drospirenone[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=C213100.1Standard non polar33892256
Drospirenone[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=C213604.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Drospirenone,1TMS,isomer #1C[C@]12CC[C@H]3[C@H]([C@@H]1[C@@H]1C[C@@H]1[C@@]21CCC(=O)O1)[C@H]1C[C@H]1C1=CC(O[Si](C)(C)C)=CC[C@@]13C3167.8Semi standard non polar33892256
Drospirenone,1TMS,isomer #1C[C@]12CC[C@H]3[C@H]([C@@H]1[C@@H]1C[C@@H]1[C@@]21CCC(=O)O1)[C@H]1C[C@H]1C1=CC(O[Si](C)(C)C)=CC[C@@]13C3136.1Standard non polar33892256
Drospirenone,1TMS,isomer #1C[C@]12CC[C@H]3[C@H]([C@@H]1[C@@H]1C[C@@H]1[C@@]21CCC(=O)O1)[C@H]1C[C@H]1C1=CC(O[Si](C)(C)C)=CC[C@@]13C3626.8Standard polar33892256
Drospirenone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)[C@@H]1C[C@@H]1[C@H]1[C@@H]3[C@@H]4C[C@@H]4[C@@]4(CCC(=O)O4)[C@@]3(C)CC[C@@H]123419.3Semi standard non polar33892256
Drospirenone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)[C@@H]1C[C@@H]1[C@H]1[C@@H]3[C@@H]4C[C@@H]4[C@@]4(CCC(=O)O4)[C@@]3(C)CC[C@@H]123380.5Standard non polar33892256
Drospirenone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)[C@@H]1C[C@@H]1[C@H]1[C@@H]3[C@@H]4C[C@@H]4[C@@]4(CCC(=O)O4)[C@@]3(C)CC[C@@H]123761.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Drospirenone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0w9c-0169000000-37155c35a2dfebdf38362017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Drospirenone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Drospirenone 50V, Positive-QTOFsplash10-055f-0900000000-772901ee1c9dba98a43f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Drospirenone 20V, Positive-QTOFsplash10-014i-0009000000-300e8223fa42b1134cab2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Drospirenone 10V, Positive-QTOFsplash10-014i-0009000000-53df13fe7fdac47824102021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Drospirenone 30V, Positive-QTOFsplash10-00r2-0941000000-98ac83e1ebad8a375bf22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Drospirenone 50V, Positive-QTOFsplash10-055f-0900000000-da66174427c7e2f2c7ac2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Drospirenone 40V, Positive-QTOFsplash10-0532-0910000000-364eccbcf5d287156d5d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Drospirenone 40V, Positive-QTOFsplash10-0532-0910000000-da3aa3811e9eaf4b9c182021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Drospirenone 30V, Positive-QTOFsplash10-00r2-0941000000-7a161e31078b8238f5582021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Drospirenone 10V, Positive-QTOFsplash10-014i-0019000000-1287f5a96f64146a88cf2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Drospirenone 20V, Positive-QTOFsplash10-066v-0059000000-42514644851cc67da7762016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Drospirenone 40V, Positive-QTOFsplash10-0cdi-2490000000-ad1a0e6e02a199b656092016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Drospirenone 10V, Negative-QTOFsplash10-014i-0009000000-a9189466642bfd0f55d52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Drospirenone 20V, Negative-QTOFsplash10-01b9-0009000000-bf5682f6dc8a5a63079b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Drospirenone 40V, Negative-QTOFsplash10-00kf-7059000000-fc557f2b38e64b366f1c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Drospirenone 10V, Positive-QTOFsplash10-014i-0009000000-fdfa94d563b812aaf6222021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Drospirenone 20V, Positive-QTOFsplash10-014i-0329000000-e846c7e35c919773fa042021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Drospirenone 40V, Positive-QTOFsplash10-000l-0942000000-43df2f2243fbd4d876e62021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Drospirenone 10V, Negative-QTOFsplash10-014i-0009000000-174ae70c06846ef08cd22021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Drospirenone 20V, Negative-QTOFsplash10-014i-0009000000-bfcf28dede045890094d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Drospirenone 40V, Negative-QTOFsplash10-0296-1039000000-7d134b564b09ff7dfdb92021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01395 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01395 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01395
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID62105
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDrospirenone
METLIN IDNot Available
PubChem Compound68873
PDB IDNot Available
ChEBI ID50838
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Krattenmacher R: Drospirenone: pharmacology and pharmacokinetics of a unique progestogen. Contraception. 2000 Jul;62(1):29-38. [PubMed:11024226 ]
  2. Wichianpitaya J, Taneepanichskul S: A comparative efficacy of low-dose combined oral contraceptives containing desogestrel and drospirenone in premenstrual symptoms. Obstet Gynecol Int. 2013;2013:487143. doi: 10.1155/2013/487143. Epub 2013 Feb 20. [PubMed:23577032 ]
  3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  4. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  5. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  6. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in carboxylesterase activity
Specific function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular weight:
68417.575
References
  1. Koitka M, Hochel J, Gieschen H, Borchert HH: Improving the ex vivo stability of drug ester compounds in rat and dog serum: inhibition of the specific esterases and implications on their identity. J Pharm Biomed Anal. 2010 Feb 5;51(3):664-78. doi: 10.1016/j.jpba.2009.09.023. Epub 2009 Sep 23. [PubMed:19850433 ]
General function:
Involved in peroxidase activity
Specific function:
Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular weight:
68995.625
References
  1. Maia H Jr, Casoy J, Athayde C, Valente Filho J, Coutinho EM: The effect of a continuous regimen of drospirenone 3 mg/ethinylestradiol 30 microg on Cox-2 and Ki-67 expression in the endometrium. Eur J Contracept Reprod Health Care. 2010 Feb;15(1):35-40. doi: 10.3109/13625180903383928. [PubMed:20063991 ]
General function:
Involved in DNA binding
Specific function:
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3
Gene Name:
AR
Uniprot ID:
P10275
Molecular weight:
98987.9
References
  1. Krattenmacher R: Drospirenone: pharmacology and pharmacokinetics of a unique progestogen. Contraception. 2000 Jul;62(1):29-38. [PubMed:11024226 ]
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Isoform A is inactive in stimulating c-Src/MAPK signaling on hormone stimulation
Gene Name:
PGR
Uniprot ID:
P06401
Molecular weight:
98980.0
References
  1. Krattenmacher R: Drospirenone: pharmacology and pharmacokinetics of a unique progestogen. Contraception. 2000 Jul;62(1):29-38. [PubMed:11024226 ]
  2. Bray JD, Jelinsky S, Ghatge R, Bray JA, Tunkey C, Saraf K, Jacobsen BM, Richer JK, Brown EL, Winneker RC, Horwitz KB, Lyttle CR: Quantitative analysis of gene regulation by seven clinically relevant progestins suggests a highly similar mechanism of action through progesterone receptors in T47D breast cancer cells. J Steroid Biochem Mol Biol. 2005 Dec;97(4):328-41. Epub 2005 Sep 12. [PubMed:16157482 ]
  3. Fuhrmann U, Krattenmacher R, Slater EP, Fritzemeier KH: The novel progestin drospirenone and its natural counterpart progesterone: biochemical profile and antiandrogenic potential. Contraception. 1996 Oct;54(4):243-51. [PubMed:8922878 ]
  4. Arias-Loza PA, Hu K, Schafer A, Bauersachs J, Quaschning T, Galle J, Jazbutyte V, Neyses L, Ertl G, Fritzemeier KH, Hegele-Hartung C, Pelzer T: Medroxyprogesterone acetate but not drospirenone ablates the protective function of 17 beta-estradiol in aldosterone salt-treated rats. Hypertension. 2006 Nov;48(5):994-1001. Epub 2006 Sep 25. [PubMed:17000933 ]
  5. Sitruk-Ware R: New progestagens for contraceptive use. Hum Reprod Update. 2006 Mar-Apr;12(2):169-78. Epub 2005 Nov 16. [PubMed:16291771 ]
  6. Sitruk-Ware R: New progestogens: a review of their effects in perimenopausal and postmenopausal women. Drugs Aging. 2004;21(13):865-83. [PubMed:15493951 ]
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Receptor for both mineralocorticoids (MC) such as aldosterone and glucocorticoids (GC) such as corticosterone or cortisol. Binds to mineralocorticoid response elements (MRE) and transactivates target genes. The effect of MC is to increase ion and water transport and thus raise extracellular fluid volume and blood pressure and lower potassium levels
Gene Name:
NR3C2
Uniprot ID:
P08235
Molecular weight:
107066.6
References
  1. Krattenmacher R: Drospirenone: pharmacology and pharmacokinetics of a unique progestogen. Contraception. 2000 Jul;62(1):29-38. [PubMed:11024226 ]
  2. Fuhrmann U, Krattenmacher R, Slater EP, Fritzemeier KH: The novel progestin drospirenone and its natural counterpart progesterone: biochemical profile and antiandrogenic potential. Contraception. 1996 Oct;54(4):243-51. [PubMed:8922878 ]
  3. Muhn P, Fuhrmann U, Fritzemeier KH, Krattenmacher R, Schillinger E: Drospirenone: a novel progestogen with antimineralocorticoid and antiandrogenic activity. Ann N Y Acad Sci. 1995 Jun 12;761:311-35. [PubMed:7625729 ]
  4. Oelkers WK: Effects of estrogens and progestogens on the renin-aldosterone system and blood pressure. Steroids. 1996 Apr;61(4):166-71. [PubMed:8732994 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]