drospirenone Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
aldosterone antagonists, spironolactone derivates 968 67392-87-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • drospirenone
  • dihydrospirorenone
  • drospirenona
a progestational compound with antimineralocorticoid and antiandrogenic activity; structure given in first source. It is used in combination with estetrol (nextstellis) as oral contraceptive.
  • Molecular weight: 366.50
  • Formula: C24H30O3
  • CLOGP: 2.84
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 0
  • TPSA: 43.37
  • ALOGS: -5.21
  • ROTB: 0

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.10 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.12 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 76 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
May 11, 2001 FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Pulmonary embolism 740.83 19.96 393 9806 108192 46567671
Injury 697.61 19.96 286 9913 43741 46632122
Deep vein thrombosis 630.32 19.96 319 9880 79454 46596409
Embolism arterial 415.52 19.96 86 10113 1077 46674786
Emotional distress 364.95 19.96 163 10036 30544 46645319
Cerebrovascular accident 192.02 19.96 166 10033 100873 46574990
Pregnancy on oral contraceptive 167.14 19.96 42 10157 1292 46674571
Anxiety 144.96 19.96 188 10011 181769 46494094
Pelvic venous thrombosis 131.33 19.96 36 10163 1561 46674302
Pain 129.89 19.96 306 9893 476642 46199221
Thrombosis 118.41 19.96 98 10101 55971 46619892
Anhedonia 110.36 19.96 51 10148 10284 46665579
Cerebral venous sinus thrombosis 104.41 19.96 31 10168 1794 46674069
Thrombophlebitis superficial 98.01 19.96 38 10161 4965 46670898
General physical health deterioration 89.46 19.96 118 10081 115651 46560212
Transverse sinus thrombosis 83.15 19.96 21 10178 659 46675204
Superior sagittal sinus thrombosis 55.35 19.96 16 10183 842 46675021
Death 55.11 19.96 5 10194 335543 46340320
Cerebral infarction 51.69 19.96 42 10157 23324 46652539
Fear of disease 51.54 19.96 16 10183 1076 46674787
Withdrawal bleed 49.06 19.96 10 10189 115 46675748
Vena cava thrombosis 47.88 19.96 18 10181 2161 46673702
Acne 44.47 19.96 36 10163 19883 46655980
Abnormal withdrawal bleeding 43.30 19.96 10 10189 213 46675650
Pulmonary infarction 40.92 19.96 17 10182 2654 46673209
Hemiparesis 38.04 19.96 33 10166 20036 46655827
Cerebral thrombosis 37.17 19.96 14 10185 1689 46674174
Hypoaesthesia 33.89 19.96 78 10121 118791 46557072
Ischaemic stroke 32.71 19.96 28 10171 16694 46659169
Cerebral venous thrombosis 30.78 19.96 13 10186 2114 46673749
Fall 30.53 19.96 17 10182 329080 46346783
Mesenteric vein thrombosis 30.31 19.96 10 10189 818 46675045
Rheumatoid arthritis 29.53 19.96 8 10191 240207 46435656
Polyarteritis nodosa 29.28 19.96 8 10191 342 46675521
Menstruation irregular 29.05 19.96 18 10181 6521 46669342
Genital haemorrhage 28.98 19.96 18 10181 6548 46669315
Ectopic pregnancy under hormonal contraception 28.54 19.96 5 10194 23 46675840
Migraine 28.23 19.96 53 10146 69973 46605890
Psychological trauma 27.46 19.96 10 10189 1098 46674765
Mood swings 27.37 19.96 25 10174 16227 46659636
Hemianaesthesia 27.26 19.96 8 10191 444 46675419
Embolic stroke 26.96 19.96 14 10185 3625 46672238
Headache 26.66 19.96 187 10012 478165 46197698
Cerebral artery occlusion 25.10 19.96 9 10190 945 46674918
Speech disorder 23.55 19.96 34 10165 36133 46639730
Product substitution issue 23.15 19.96 22 10177 15009 46660854
Peripheral artery thrombosis 22.71 19.96 10 10189 1799 46674064
Libido decreased 22.15 19.96 11 10188 2594 46673269
Drug hypersensitivity 22.01 19.96 13 10186 243812 46432051
Aphasia 21.82 19.96 29 10170 28538 46647325
Depression 21.78 19.96 84 10115 170020 46505843
Product use in unapproved indication 21.19 19.96 55 10144 90218 46585645
Venous thrombosis limb 21.17 19.96 11 10188 2852 46673011
Vaginal haemorrhage 21.12 19.96 27 10172 25577 46650286
Hemiplegia 20.91 19.96 15 10184 6923 46668940
Acute kidney injury 20.70 19.96 13 10186 235842 46440021
Porphyria non-acute 20.48 19.96 6 10193 331 46675532
Transient ischaemic attack 20.13 19.96 31 10168 34872 46640991

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event

Pharmacologic Action:

SourceCodeDescription
ATC G03AA12 GENITO URINARY SYSTEM AND SEX HORMONES
SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE
Progestogens and estrogens, fixed combinations
ATC G03AA18 GENITO URINARY SYSTEM AND SEX HORMONES
SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE
Progestogens and estrogens, fixed combinations
ATC G03AC10 GENITO URINARY SYSTEM AND SEX HORMONES
SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE
Progestogens
ATC G03FA17 GENITO URINARY SYSTEM AND SEX HORMONES
SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
PROGESTOGENS AND ESTROGENS IN COMBINATION
Progestogens and estrogens, fixed combinations
FDA CS M0447349 Progesterone Congeners
FDA EPC N0000175602 Progestin
MeSH PA D004232 Diuretics
MeSH PA D006727 Hormone Antagonists
MeSH PA D000451 Mineralocorticoid Receptor Antagonists
MeSH PA D045283 Natriuretic Agents
CHEBI has role CHEBI:49323 contraceptive agent
CHEBI has role CHEBI:59826 progestins

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Premenstrual dysphoric disorder indication 596004
Contraception indication 13197004
Atrophic vaginitis indication 52441000
Acne vulgaris indication 88616000
Menopausal flushing indication 198436008
Atrophic vulva indication 248861000 DOID:14275
Polycystic ovaries off-label use 69878008
Hyperlipoproteinemia contraindication 3744001 DOID:1168
Hypocalcemia contraindication 5291005
Hypercholesterolemia contraindication 13644009
Hyperkalemia contraindication 14140009
Myocardial infarction contraindication 22298006 DOID:5844
Diplopia contraindication 24982008
Retinal hemorrhage contraindication 28998008
Depressive disorder contraindication 35489007
Chloasma contraindication 36209000
Migraine contraindication 37796009 DOID:6364
Hypertensive disorder contraindication 38341003 DOID:10763
Disorder of gallbladder contraindication 39621005 DOID:0060262
Hypothyroidism contraindication 40930008 DOID:1459
Body fluid retention contraindication 43498006
Thrombosis of retinal vein contraindication 46085004
Humoral hypercalcemia of malignancy contraindication 47709007
Chronic heart failure contraindication 48447003
Dementia contraindication 52448006
Hepatic porphyria contraindication 55056006 DOID:3133
Systemic lupus erythematosus contraindication 55464009 DOID:9074
Hyperlipidemia contraindication 55822004 DOID:1168
Acute nephropathy contraindication 58574008
Thrombophlebitis contraindication 64156001 DOID:3875
Intermenstrual bleeding - irregular contraindication 64996003
Diabetes mellitus contraindication 73211009 DOID:9351
Epilepsy contraindication 84757009 DOID:1826
Breast lump contraindication 89164003
Kidney disease contraindication 90708001 DOID:557
Uterine leiomyoma contraindication 95315005 DOID:13223
Deep venous thrombosis contraindication 128053003
Seizure disorder contraindication 128613002
Endometriosis contraindication 129103003
Bed-ridden contraindication 160685001
Mammography abnormal contraindication 168750009
Asthma contraindication 195967001 DOID:2841
Cerebrovascular accident contraindication 230690007
Pulmonary thromboembolism contraindication 233935004
Thrombophilia contraindication 234467004 DOID:2452
Disease of liver contraindication 235856003 DOID:409
Endometrial carcinoma contraindication 254878006 DOID:2871
Chorea contraindication 271700006
Pregnancy, function contraindication 289908002
Hypertriglyceridemia contraindication 302870006
Functional visual loss contraindication 313165001
Malignant tumor of ovary contraindication 363443007 DOID:2394
Thromboembolic disorder contraindication 371039008
Adrenal cortical hypofunction contraindication 386584007 DOID:10493
Cardiovascular event risk contraindication 395112001
Disorder of coronary artery contraindication 414024009
Obesity contraindication 414916001 DOID:9970
Estrogen receptor positive tumor contraindication 416053008
Porphyria contraindication 418470004
Optic disc edema contraindication 423341008 DOID:146
Family history of malignant neoplasm of breast contraindication 429740004
Hypertensive urgency contraindication 443482000
Carcinoma of female breast contraindication 447782002
Smokes tobacco daily contraindication 449868002

Acid dissociation constants calculated using MoKa v3.0.0

None

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
4MG SLYND EXELTIS USA INC N211367 May 23, 2019 RX TABLET ORAL May 23, 2022 NEW PRODUCT
3MG;14.2MG NEXTSTELLIS MAYNE PHARMA N214154 April 15, 2021 RX TABLET ORAL April 15, 2026 NEW CHEMICAL ENTITY

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Progesterone receptor Nuclear hormone receptor AGONIST EC50 10.50 WOMBAT-PK CHEMBL
Mineralocorticoid receptor Nuclear hormone receptor ANTAGONIST IC50 10.50 WOMBAT-PK CHEMBL
Androgen receptor Nuclear hormone receptor IC50 8.50 WOMBAT-PK

External reference:

IDSource
4021271 VUID
N0000179010 NUI
D03917 KEGG_DRUG
4021271 VANDF
C0043822 UMLSCUI
CHEBI:50838 CHEBI
CHEMBL1509 ChEMBL_ID
DB01395 DRUGBANK_ID
C035144 MESH_SUPPLEMENTAL_RECORD_UI
68873 PUBCHEM_CID
2874 IUPHAR_LIGAND_ID
6519 INN_ID
N295J34A25 UNII
11636 RXNORM
16073 MMSL
d04759 MMSL
009133 NDDF
395275003 SNOMEDCT_US
410919000 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
SLYND HUMAN PRESCRIPTION DRUG LABEL 1 0642-7470 TABLET, FILM COATED 4 mg ORAL NDA 30 sections
Angeliq HUMAN PRESCRIPTION DRUG LABEL 2 50419-482 TABLET, FILM COATED 0.25 mg ORAL NDA 29 sections
Angeliq HUMAN PRESCRIPTION DRUG LABEL 2 50419-483 TABLET, FILM COATED 0.50 mg ORAL NDA 29 sections
Angeliq HUMAN PRESCRIPTION DRUG LABEL 2 54868-6184 TABLET, FILM COATED 0.50 mg ORAL NDA 24 sections