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Identification
NameDrospirenone
Accession NumberDB01395
TypeSmall Molecule
GroupsApproved
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. It was shown in animal studies that drospirenone exhibits antiandrogenic activity judging from accessory sex gland growth in castrated, androgen-treated, juvenile rats.
Structure
Thumb
Synonyms
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
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
AngeliqBayer Health Care Pharmaceuticals Inc.
Drospirenone and Ethinyl EstradiolMylan Pharmaceuticals Inc.
Drospirenone and Ethinyl Estradiol Tablets 21Famy Care Ltd
Drospirenone and Ethinyl Estradiol Tablets 28Famy Care Ltd
Drospirenone and Ethinyl Estradiol Tablets USP (21-day Regimen)Glenmark Pharmaceuticals Canada Inc.
Drospirenone and Ethinyl Estradiol Tablets USP (28-day Regimen)Glenmark Pharmaceuticals Canada Inc.
GianviTeva Pharmaceuticals USA Inc
LorynaSandoz Inc
MyaApotex Inc
NikkiLupin Pharmaceuticals, Inc.
OcellaBarr Laboratories, Inc.
Qismette 21LUPIN LIMITED
Qismette 28LUPIN LIMITED
SyedaSandoz Inc
VesturaWatson Pharma, Inc.
YasminBayer Health Care Pharmaceuticals Inc.
Yasmin 21Bayer Inc
Yasmin 28Bayer Inc
Yasmin PlusBayer Inc
YazBayer Health Care Pharmaceuticals Inc.
Yaz PlusBayer Inc
Zamine 21Apotex Inc
Zamine 28Apotex Inc
ZarahWatson Pharma, Inc.
Zarah 21Cobalt Pharmaceuticals Company
Zarah 28Cobalt Pharmaceuticals Company
SaltsNot Available
Categories
UNIIN295J34A25
CAS number67392-87-4
WeightAverage: 366.4932
Monoisotopic: 366.219494826
Chemical FormulaC24H30O3
InChI KeyInChIKey=METQSPRSQINEEU-HXCATZOESA-N
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
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
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
Taxonomy
DescriptionThis compound 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
  • Gamma butyrolactone
  • Oxolane
  • Cyclic ketone
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the prevention of pregnancy in women who elect an oral contraceptive.
PharmacodynamicsDrospirenone 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.
Mechanism of actionProgestins 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.
Related Articles
AbsorptionOral bioavailability is approximately 76%.
Volume of distributionNot Available
Protein binding95-97%
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.

SubstrateEnzymesProduct
Drospirenone
Not Available
4,5-dihydro-drospirenone-3-sulfateDetails
Route of eliminationNot Available
Half life30 hours
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9383
Caco-2 permeable+0.6376
P-glycoprotein substrateSubstrate0.6524
P-glycoprotein inhibitor IInhibitor0.6171
P-glycoprotein inhibitor IINon-inhibitor0.6726
Renal organic cation transporterNon-inhibitor0.7005
CYP450 2C9 substrateNon-substrate0.796
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.6964
CYP450 1A2 substrateNon-inhibitor0.5534
CYP450 2C9 inhibitorNon-inhibitor0.8665
CYP450 2D6 inhibitorNon-inhibitor0.9336
CYP450 2C19 inhibitorNon-inhibitor0.7754
CYP450 3A4 inhibitorNon-inhibitor0.8355
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8541
Ames testNon AMES toxic0.9163
CarcinogenicityNon-carcinogens0.9505
BiodegradationNot ready biodegradable0.9757
Rat acute toxicity1.9430 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9393
hERG inhibition (predictor II)Non-inhibitor0.8215
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Tablet, film coatedoral
Kit
Tabletoral
Kitoral
PricesNot Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5798338 No1995-07-102015-07-10Us
US6441168 No2002-07-302022-07-30Us
US6787531 No2000-08-312020-08-31Us
US6933395 No1997-08-112017-08-11Us
US6958326 No2001-12-202021-12-20Us
US6987101 No1997-12-222017-12-22Us
US7163931 No2001-12-202021-12-20Us
US8617597 No2010-02-082030-02-08Us
US8906890 No2011-10-222031-10-22Us
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00225 mg/mLALOGPS
logP2.36ALOGPS
logP3.37ChemAxon
logS-5.2ALOGPS
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity101.68 m3·mol-1ChemAxon
Polarizability41.81 Å3ChemAxon
Number of Rings7ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (37.1 KB)
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

DOI: 10.1002/cjoc.201201147

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 ]
External Links
ATC CodesG03FA17G03AC10G03AA12
AHFS Codes
  • 68:12
PDB EntriesNot Available
FDA labelDownload (292 KB)
MSDSDownload (567 KB)
Interactions
Drug Interactions
Drug
AbciximabThe therapeutic efficacy of Abciximab can be decreased when used in combination with Drospirenone.
AcarboseThe therapeutic efficacy of Acarbose can be decreased when used in combination with Drospirenone.
AceclofenacAceclofenac may increase the hyperkalemic activities of Drospirenone.
AcenocoumarolThe therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Drospirenone.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Drospirenone.
Acetylsalicylic acidAcetylsalicylic acid may increase the hyperkalemic activities of Drospirenone.
AdapaleneAdapalene may increase the hyperkalemic activities of Drospirenone.
AicarThe therapeutic efficacy of Aicar can be decreased when used in combination with Drospirenone.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Drospirenone.
AliskirenDrospirenone may increase the hyperkalemic activities of Aliskiren.
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Drospirenone.
AlphacetylmethadolThe risk or severity of adverse effects can be increased when Alphacetylmethadol is combined with Drospirenone.
AmilorideDrospirenone may increase the hyperkalemic activities of Amiloride.
AmiodaroneThe serum concentration of Drospirenone can be increased when it is combined with Amiodarone.
AncrodThe therapeutic efficacy of Ancrod can be decreased when used in combination with Drospirenone.
AntipyrineAntipyrine may increase the hyperkalemic activities of Drospirenone.
Antithrombin III humanThe therapeutic efficacy of Antithrombin III human can be decreased when used in combination with Drospirenone.
ApixabanThe therapeutic efficacy of Apixaban can be decreased when used in combination with Drospirenone.
ApremilastApremilast may increase the hyperkalemic activities of Drospirenone.
ArdeparinThe therapeutic efficacy of Ardeparin can be decreased when used in combination with Drospirenone.
ArgatrobanThe therapeutic efficacy of Argatroban can be decreased when used in combination with Drospirenone.
AtazanavirThe serum concentration of Drospirenone can be increased when it is combined with Atazanavir.
AzapropazoneAzapropazone may increase the hyperkalemic activities of Drospirenone.
AzelastineAzelastine may increase the hyperkalemic activities of Drospirenone.
Azilsartan medoxomilAzilsartan medoxomil may increase the hyperkalemic activities of Drospirenone.
BalsalazideBalsalazide may increase the hyperkalemic activities of Drospirenone.
BecaplerminThe therapeutic efficacy of Becaplermin can be decreased when used in combination with Drospirenone.
BenazeprilBenazepril may increase the hyperkalemic activities of Drospirenone.
BenoxaprofenBenoxaprofen may increase the hyperkalemic activities of Drospirenone.
BezitramideThe risk or severity of adverse effects can be increased when Bezitramide is combined with Drospirenone.
BivalirudinThe therapeutic efficacy of Bivalirudin can be decreased when used in combination with Drospirenone.
BoceprevirThe serum concentration of Drospirenone can be increased when it is combined with Boceprevir.
BromfenacBromfenac may increase the hyperkalemic activities of Drospirenone.
BuforminThe therapeutic efficacy of Buformin can be decreased when used in combination with Drospirenone.
BuprenorphineThe risk or severity of adverse effects can be increased when Buprenorphine is combined with Drospirenone.
ButorphanolThe risk or severity of adverse effects can be increased when Butorphanol is combined with Drospirenone.
C1 Esterase Inhibitor (Human)Drospirenone may increase the thrombogenic activities of C1 Esterase Inhibitor (Human).
C1 Esterase Inhibitor (Recombinant)Drospirenone may increase the thrombogenic activities of C1 Esterase Inhibitor (Recombinant).
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Drospirenone.
CandesartanCandesartan may increase the hyperkalemic activities of Drospirenone.
CandoxatrilCandoxatril may increase the hyperkalemic activities of Drospirenone.
CaptoprilCaptopril may increase the hyperkalemic activities of Drospirenone.
CarfentanilThe risk or severity of adverse effects can be increased when Carfentanil is combined with Drospirenone.
CarprofenCarprofen may increase the hyperkalemic activities of Drospirenone.
CastanospermineCastanospermine may increase the hyperkalemic activities of Drospirenone.
CastanospermineThe therapeutic efficacy of Castanospermine can be decreased when used in combination with Drospirenone.
CelecoxibCelecoxib may increase the hyperkalemic activities of Drospirenone.
CeritinibThe serum concentration of Drospirenone can be increased when it is combined with Ceritinib.
CertoparinThe therapeutic efficacy of Certoparin can be decreased when used in combination with Drospirenone.
ChloroquineChloroquine may increase the hyperkalemic activities of Drospirenone.
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Drospirenone.
CiglitazoneThe therapeutic efficacy of Ciglitazone can be decreased when used in combination with Drospirenone.
CilazaprilCilazapril may increase the hyperkalemic activities of Drospirenone.
Citric AcidThe therapeutic efficacy of Citric Acid can be decreased when used in combination with Drospirenone.
ClarithromycinThe serum concentration of Drospirenone can be increased when it is combined with Clarithromycin.
ClonixinClonixin may increase the hyperkalemic activities of Drospirenone.
CobicistatThe serum concentration of Drospirenone can be increased when it is combined with Cobicistat.
CodeineThe risk or severity of adverse effects can be increased when Codeine is combined with Drospirenone.
D-LimoneneD-Limonene may increase the hyperkalemic activities of Drospirenone.
Dabigatran etexilateThe therapeutic efficacy of Dabigatran etexilate can be decreased when used in combination with Drospirenone.
DalteparinThe therapeutic efficacy of Dalteparin can be decreased when used in combination with Drospirenone.
DanaparoidThe therapeutic efficacy of Danaparoid can be decreased when used in combination with Drospirenone.
DarunavirThe serum concentration of Drospirenone can be increased when it is combined with Darunavir.
DesirudinThe therapeutic efficacy of Desirudin can be decreased when used in combination with Drospirenone.
DextranThe therapeutic efficacy of Dextran can be decreased when used in combination with Drospirenone.
Dextran 40The therapeutic efficacy of Dextran 40 can be decreased when used in combination with Drospirenone.
Dextran 70The therapeutic efficacy of Dextran 70 can be decreased when used in combination with Drospirenone.
Dextran 75The therapeutic efficacy of Dextran 75 can be decreased when used in combination with Drospirenone.
DextromoramideThe risk or severity of adverse effects can be increased when Dextromoramide is combined with Drospirenone.
DextropropoxypheneThe risk or severity of adverse effects can be increased when Dextropropoxyphene is combined with Drospirenone.
DezocineThe risk or severity of adverse effects can be increased when Dezocine is combined with Drospirenone.
DiclofenacDiclofenac may increase the hyperkalemic activities of Drospirenone.
DicoumarolThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Drospirenone.
DiflunisalDiflunisal may increase the hyperkalemic activities of Drospirenone.
DihydrocodeineThe risk or severity of adverse effects can be increased when Dihydrocodeine is combined with Drospirenone.
DihydroetorphineThe risk or severity of adverse effects can be increased when Dihydroetorphine is combined with Drospirenone.
DihydromorphineThe risk or severity of adverse effects can be increased when Dihydromorphine is combined with Drospirenone.
DiphenoxylateThe risk or severity of adverse effects can be increased when Diphenoxylate is combined with Drospirenone.
DPDPEThe risk or severity of adverse effects can be increased when DPDPE is combined with Drospirenone.
DroxicamDroxicam may increase the hyperkalemic activities of Drospirenone.
DulaglutideThe therapeutic efficacy of Dulaglutide can be decreased when used in combination with Drospirenone.
Edetic AcidThe therapeutic efficacy of Edetic Acid can be decreased when used in combination with Drospirenone.
EdoxabanThe therapeutic efficacy of Edoxaban can be decreased when used in combination with Drospirenone.
EmpagliflozinThe therapeutic efficacy of Empagliflozin can be decreased when used in combination with Drospirenone.
EnalaprilEnalapril may increase the hyperkalemic activities of Drospirenone.
EnalaprilatEnalaprilat may increase the hyperkalemic activities of Drospirenone.
EnoxaparinThe therapeutic efficacy of Enoxaparin can be decreased when used in combination with Drospirenone.
EpirizoleEpirizole may increase the hyperkalemic activities of Drospirenone.
EplerenoneDrospirenone may increase the hyperkalemic activities of Eplerenone.
EprosartanEprosartan may increase the hyperkalemic activities of Drospirenone.
EtanerceptEtanercept may increase the hyperkalemic activities of Drospirenone.
Ethyl biscoumacetateThe therapeutic efficacy of Ethyl biscoumacetate can be decreased when used in combination with Drospirenone.
EthylmorphineThe risk or severity of adverse effects can be increased when Ethylmorphine is combined with Drospirenone.
EtodolacEtodolac may increase the hyperkalemic activities of Drospirenone.
EtofenamateEtofenamate may increase the hyperkalemic activities of Drospirenone.
EtoricoxibEtoricoxib may increase the hyperkalemic activities of Drospirenone.
EtorphineThe risk or severity of adverse effects can be increased when Etorphine is combined with Drospirenone.
Evening primrose oilEvening primrose oil may increase the hyperkalemic activities of Drospirenone.
ExenatideThe therapeutic efficacy of Exenatide can be decreased when used in combination with Drospirenone.
exisulindexisulind may increase the hyperkalemic activities of Drospirenone.
FenbufenFenbufen may increase the hyperkalemic activities of Drospirenone.
FenoprofenFenoprofen may increase the hyperkalemic activities of Drospirenone.
FentanylThe risk or severity of adverse effects can be increased when Fentanyl is combined with Drospirenone.
FloctafenineFloctafenine may increase the hyperkalemic activities of Drospirenone.
FlunixinFlunixin may increase the hyperkalemic activities of Drospirenone.
FlurbiprofenFlurbiprofen may increase the hyperkalemic activities of Drospirenone.
Fondaparinux sodiumThe therapeutic efficacy of Fondaparinux sodium can be decreased when used in combination with Drospirenone.
ForasartanForasartan may increase the hyperkalemic activities of Drospirenone.
FosinoprilFosinopril may increase the hyperkalemic activities of Drospirenone.
GlibornurideThe therapeutic efficacy of Glibornuride can be decreased when used in combination with Drospirenone.
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Drospirenone.
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Drospirenone.
GlipizideThe therapeutic efficacy of Glipizide can be decreased when used in combination with Drospirenone.
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Drospirenone.
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Drospirenone.
HeparinThe therapeutic efficacy of Heparin can be decreased when used in combination with Drospirenone.
HeroinThe risk or severity of adverse effects can be increased when Heroin is combined with Drospirenone.
HirulogThe therapeutic efficacy of Hirulog can be decreased when used in combination with Drospirenone.
HMPL-004HMPL-004 may increase the hyperkalemic activities of Drospirenone.
HydrocodoneThe serum concentration of Hydrocodone can be decreased when it is combined with Drospirenone.
HydrocodoneThe risk or severity of adverse effects can be increased when Hydrocodone is combined with Drospirenone.
HydromorphoneThe risk or severity of adverse effects can be increased when Hydromorphone is combined with Drospirenone.
IbuprofenIbuprofen may increase the hyperkalemic activities of Drospirenone.
IbuproxamIbuproxam may increase the hyperkalemic activities of Drospirenone.
IcatibantIcatibant may increase the hyperkalemic activities of Drospirenone.
IdelalisibThe serum concentration of Drospirenone can be increased when it is combined with Idelalisib.
IndinavirThe serum concentration of Drospirenone can be increased when it is combined with Indinavir.
IndomethacinIndomethacin may increase the hyperkalemic activities of Drospirenone.
IndoprofenIndoprofen may increase the hyperkalemic activities of Drospirenone.
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Drospirenone.
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Drospirenone.
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Drospirenone.
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Drospirenone.
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Drospirenone.
Insulin PorkThe therapeutic efficacy of Insulin Pork can be decreased when used in combination with Drospirenone.
IrbesartanIrbesartan may increase the hyperkalemic activities of Drospirenone.
IsoxicamIsoxicam may increase the hyperkalemic activities of Drospirenone.
ItraconazoleThe serum concentration of Drospirenone can be increased when it is combined with Itraconazole.
KebuzoneKebuzone may increase the hyperkalemic activities of Drospirenone.
KetobemidoneThe risk or severity of adverse effects can be increased when Ketobemidone is combined with Drospirenone.
KetoconazoleThe serum concentration of Drospirenone can be increased when it is combined with Ketoconazole.
KetoprofenKetoprofen may increase the hyperkalemic activities of Drospirenone.
KetorolacKetorolac may increase the hyperkalemic activities of Drospirenone.
LeflunomideLeflunomide may increase the hyperkalemic activities of Drospirenone.
LepirudinThe therapeutic efficacy of Lepirudin can be decreased when used in combination with Drospirenone.
Levomethadyl AcetateThe risk or severity of adverse effects can be increased when Levomethadyl Acetate is combined with Drospirenone.
LevorphanolThe risk or severity of adverse effects can be increased when Levorphanol is combined with Drospirenone.
LinagliptinThe therapeutic efficacy of Linagliptin can be decreased when used in combination with Drospirenone.
LiraglutideThe therapeutic efficacy of Liraglutide can be decreased when used in combination with Drospirenone.
LisinoprilLisinopril may increase the hyperkalemic activities of Drospirenone.
LofentanilThe risk or severity of adverse effects can be increased when Lofentanil is combined with Drospirenone.
LopinavirThe serum concentration of Drospirenone can be increased when it is combined with Lopinavir.
LornoxicamLornoxicam may increase the hyperkalemic activities of Drospirenone.
LosartanLosartan may increase the hyperkalemic activities of Drospirenone.
LoxoprofenLoxoprofen may increase the hyperkalemic activities of Drospirenone.
LumiracoxibLumiracoxib may increase the hyperkalemic activities of Drospirenone.
Magnesium salicylateMagnesium salicylate may increase the hyperkalemic activities of Drospirenone.
MasoprocolMasoprocol may increase the hyperkalemic activities of Drospirenone.
Meclofenamic acidMeclofenamic acid may increase the hyperkalemic activities of Drospirenone.
Mefenamic acidMefenamic acid may increase the hyperkalemic activities of Drospirenone.
MeloxicamMeloxicam may increase the hyperkalemic activities of Drospirenone.
MesalazineMesalazine may increase the hyperkalemic activities of Drospirenone.
MetamizoleMetamizole may increase the hyperkalemic activities of Drospirenone.
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Drospirenone.
MethadoneThe risk or severity of adverse effects can be increased when Methadone is combined with Drospirenone.
Methadyl AcetateThe risk or severity of adverse effects can be increased when Methadyl Acetate is combined with Drospirenone.
MiglitolThe therapeutic efficacy of Miglitol can be decreased when used in combination with Drospirenone.
MiglustatThe therapeutic efficacy of Miglustat can be decreased when used in combination with Drospirenone.
MitiglinideThe therapeutic efficacy of Mitiglinide can be decreased when used in combination with Drospirenone.
MoexiprilMoexipril may increase the hyperkalemic activities of Drospirenone.
MorphineThe risk or severity of adverse effects can be increased when Morphine is combined with Drospirenone.
Mycophenolate mofetilMycophenolate mofetil may increase the hyperkalemic activities of Drospirenone.
Mycophenolic acidMycophenolic acid may increase the hyperkalemic activities of Drospirenone.
NabumetoneNabumetone may increase the hyperkalemic activities of Drospirenone.
NadroparinThe therapeutic efficacy of Nadroparin can be decreased when used in combination with Drospirenone.
NaftifineNaftifine may increase the hyperkalemic activities of Drospirenone.
NalbuphineThe risk or severity of adverse effects can be increased when Nalbuphine is combined with Drospirenone.
NaproxenNaproxen may increase the hyperkalemic activities of Drospirenone.
NateglinideThe therapeutic efficacy of Nateglinide can be decreased when used in combination with Drospirenone.
NCX 4016NCX 4016 may increase the hyperkalemic activities of Drospirenone.
NefazodoneThe serum concentration of Drospirenone can be increased when it is combined with Nefazodone.
NelfinavirThe serum concentration of Drospirenone can be increased when it is combined with Nelfinavir.
NepafenacNepafenac may increase the hyperkalemic activities of Drospirenone.
Niflumic AcidNiflumic Acid may increase the hyperkalemic activities of Drospirenone.
NimesulideNimesulide may increase the hyperkalemic activities of Drospirenone.
NimodipineThe serum concentration of Nimodipine can be decreased when it is combined with Drospirenone.
NormethadoneThe risk or severity of adverse effects can be increased when Normethadone is combined with Drospirenone.
OlmesartanOlmesartan may increase the hyperkalemic activities of Drospirenone.
OlopatadineOlopatadine may increase the hyperkalemic activities of Drospirenone.
OlsalazineOlsalazine may increase the hyperkalemic activities of Drospirenone.
OmapatrilatOmapatrilat may increase the hyperkalemic activities of Drospirenone.
OpiumThe risk or severity of adverse effects can be increased when Opium is combined with Drospirenone.
OrgoteinOrgotein may increase the hyperkalemic activities of Drospirenone.
OtamixabanThe therapeutic efficacy of Otamixaban can be decreased when used in combination with Drospirenone.
OxaprozinOxaprozin may increase the hyperkalemic activities of Drospirenone.
OxycodoneThe risk or severity of adverse effects can be increased when Oxycodone is combined with Drospirenone.
OxymorphoneThe risk or severity of adverse effects can be increased when Oxymorphone is combined with Drospirenone.
OxyphenbutazoneOxyphenbutazone may increase the hyperkalemic activities of Drospirenone.
ParecoxibParecoxib may increase the hyperkalemic activities of Drospirenone.
PentazocineThe risk or severity of adverse effects can be increased when Pentazocine is combined with Drospirenone.
Pentosan PolysulfateThe therapeutic efficacy of Pentosan Polysulfate can be decreased when used in combination with Drospirenone.
PerindoprilPerindopril may increase the hyperkalemic activities of Drospirenone.
PethidineThe risk or severity of adverse effects can be increased when Pethidine is combined with Drospirenone.
PhenforminThe therapeutic efficacy of Phenformin can be decreased when used in combination with Drospirenone.
PhenindioneThe therapeutic efficacy of Phenindione can be decreased when used in combination with Drospirenone.
PhenprocoumonThe therapeutic efficacy of Phenprocoumon can be decreased when used in combination with Drospirenone.
PhenylbutazonePhenylbutazone may increase the hyperkalemic activities of Drospirenone.
PimecrolimusPimecrolimus may increase the hyperkalemic activities of Drospirenone.
PioglitazoneThe therapeutic efficacy of Pioglitazone can be decreased when used in combination with Drospirenone.
PirfenidonePirfenidone may increase the hyperkalemic activities of Drospirenone.
PiroxicamPiroxicam may increase the hyperkalemic activities of Drospirenone.
PosaconazoleThe serum concentration of Drospirenone can be increased when it is combined with Posaconazole.
PramlintideThe therapeutic efficacy of Pramlintide can be decreased when used in combination with Drospirenone.
PropacetamolPropacetamol may increase the hyperkalemic activities of Drospirenone.
Protein CThe therapeutic efficacy of Protein C can be decreased when used in combination with Drospirenone.
ProtocatechualdehydeThe therapeutic efficacy of Protocatechualdehyde can be decreased when used in combination with Drospirenone.
PTC299PTC299 may increase the hyperkalemic activities of Drospirenone.
QuinaprilQuinapril may increase the hyperkalemic activities of Drospirenone.
RamiprilRamipril may increase the hyperkalemic activities of Drospirenone.
RemifentanilThe risk or severity of adverse effects can be increased when Remifentanil is combined with Drospirenone.
RepaglinideThe therapeutic efficacy of Repaglinide can be decreased when used in combination with Drospirenone.
RescinnamineRescinnamine may increase the hyperkalemic activities of Drospirenone.
ResveratrolResveratrol may increase the hyperkalemic activities of Drospirenone.
ReviparinThe therapeutic efficacy of Reviparin can be decreased when used in combination with Drospirenone.
RitonavirThe serum concentration of Drospirenone can be increased when it is combined with Ritonavir.
RivaroxabanThe therapeutic efficacy of Rivaroxaban can be decreased when used in combination with Drospirenone.
RofecoxibRofecoxib may increase the hyperkalemic activities of Drospirenone.
RosiglitazoneThe therapeutic efficacy of Rosiglitazone can be decreased when used in combination with Drospirenone.
SalicylamideSalicylamide may increase the hyperkalemic activities of Drospirenone.
Salicylic acidSalicylic acid may increase the hyperkalemic activities of Drospirenone.
SalsalateSalsalate may increase the hyperkalemic activities of Drospirenone.
SaprisartanSaprisartan may increase the hyperkalemic activities of Drospirenone.
SaquinavirThe serum concentration of Drospirenone can be increased when it is combined with Saquinavir.
SaralasinSaralasin may increase the hyperkalemic activities of Drospirenone.
SaxagliptinThe therapeutic efficacy of Saxagliptin can be decreased when used in combination with Drospirenone.
SeratrodastSeratrodast may increase the hyperkalemic activities of Drospirenone.
SitagliptinThe therapeutic efficacy of Sitagliptin can be decreased when used in combination with Drospirenone.
SpiraprilSpirapril may increase the hyperkalemic activities of Drospirenone.
SpironolactoneDrospirenone may increase the hyperkalemic activities of Spironolactone.
SRT501SRT501 may increase the hyperkalemic activities of Drospirenone.
SufentanilThe risk or severity of adverse effects can be increased when Sufentanil is combined with Drospirenone.
SulfasalazineSulfasalazine may increase the hyperkalemic activities of Drospirenone.
SulindacSulindac may increase the hyperkalemic activities of Drospirenone.
SulodexideThe therapeutic efficacy of Sulodexide can be decreased when used in combination with Drospirenone.
SuprofenSuprofen may increase the hyperkalemic activities of Drospirenone.
TapentadolThe risk or severity of adverse effects can be increased when Tapentadol is combined with Drospirenone.
TasosartanTasosartan may increase the hyperkalemic activities of Drospirenone.
TelaprevirThe serum concentration of Drospirenone can be increased when it is combined with Telaprevir.
TelithromycinThe serum concentration of Drospirenone can be increased when it is combined with Telithromycin.
TelmisartanTelmisartan may increase the hyperkalemic activities of Drospirenone.
TemocaprilTemocapril may increase the hyperkalemic activities of Drospirenone.
TenoxicamTenoxicam may increase the hyperkalemic activities of Drospirenone.
TepoxalinTepoxalin may increase the hyperkalemic activities of Drospirenone.
TeriflunomideTeriflunomide may increase the hyperkalemic activities of Drospirenone.
Tiaprofenic acidTiaprofenic acid may increase the hyperkalemic activities of Drospirenone.
TolazamideThe therapeutic efficacy of Tolazamide can be decreased when used in combination with Drospirenone.
TolbutamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Drospirenone.
Tolfenamic AcidTolfenamic Acid may increase the hyperkalemic activities of Drospirenone.
TolmetinTolmetin may increase the hyperkalemic activities of Drospirenone.
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Drospirenone.
TrandolaprilTrandolapril may increase the hyperkalemic activities of Drospirenone.
TranilastTranilast may increase the hyperkalemic activities of Drospirenone.
TriamtereneDrospirenone may increase the hyperkalemic activities of Triamterene.
Trisalicylate-cholineTrisalicylate-choline may increase the hyperkalemic activities of Drospirenone.
TroglitazoneThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Drospirenone.
UlipristalThe therapeutic efficacy of Drospirenone can be decreased when used in combination with Ulipristal.
ValdecoxibValdecoxib may increase the hyperkalemic activities of Drospirenone.
ValsartanValsartan may increase the hyperkalemic activities of Drospirenone.
VildagliptinThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Drospirenone.
VogliboseThe therapeutic efficacy of Voglibose can be decreased when used in combination with Drospirenone.
VoriconazoleThe serum concentration of Drospirenone can be increased when it is combined with Voriconazole.
WarfarinThe therapeutic efficacy of Warfarin can be decreased when used in combination with Drospirenone.
XimelagatranThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Drospirenone.
ZaltoprofenZaltoprofen may increase the hyperkalemic activities of Drospirenone.
ZileutonZileuton may increase the hyperkalemic activities of Drospirenone.
ZomepiracZomepirac may increase the hyperkalemic activities of Drospirenone.
Food Interactions
  • Food reduces the rate of absorption, but not the extent of absorption.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor isoform B (PRB) is involved activation of c-SRC/MAPK signaling on hormone stimulation.Isoform A: inactive in stimulating c-Src/MAPK signaling on hormone stimulation.Isoform 4: Increases mitochondrial ...
Gene Name:
PGR
Uniprot ID:
P06401
Molecular Weight:
98979.96 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Zinc ion binding
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:
107066.575 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Zinc ion 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 and ZIPK/DAPK3.
Gene Name:
AR
Uniprot ID:
P10275
Molecular Weight:
98987.9 Da
References
  1. Krattenmacher R: Drospirenone: pharmacology and pharmacokinetics of a unique progestogen. Contraception. 2000 Jul;62(1):29-38. [PubMed:11024226 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Prostaglandin-endoperoxide synthase activity
Specific Function:
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and brain, and in pathological conditions, such as in cancer. PTGS2 is responsible for production of inflammatory prostaglandins. Up-regulation of PTGS2 is also associated with increased cell adhesion, p...
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular Weight:
68995.625 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Identical protein binding
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 Da
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 ]
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Drug created on July 08, 2007 11:03 / Updated on September 28, 2016 02:27