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

Stem definitionDrug idCAS RN
prostaglandins 913 363-24-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • dinoprostone
  • cerviprost
  • Minprositin E2
  • primiprost
  • prostaglandin E2
  • PGE2
The most common and most biologically active of the mammalian prostaglandins. It exhibits most biological activities characteristic of prostaglandins and has been used extensively as an oxytocic agent. The compound also displays a protective effect on the intestinal mucosa.
  • Molecular weight: 352.47
  • Formula: C20H32O5
  • CLOGP: 2.01
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 3
  • TPSA: 94.83
  • ALOGS: -3.90
  • ROTB: 12

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
0.50 mg O
0.50 mg V

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 4.05 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

Approvals:

DateAgencyCompanyOrphan
Aug. 23, 1977 FDA PHARMACIA AND UPJOHN
Jan. 23, 2020 PMDA Ferring Pharmaceuticals Co., Ltd.

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
Uterine hyperstimulation 278.80 54.84 30 832 26 46685174
Exposure during pregnancy 217.06 54.84 79 783 108133 46577067
Caesarean section 196.22 54.84 48 814 16555 46668645
Uterine hypertonus 182.55 54.84 23 839 143 46685057
Uterine rupture 118.77 54.84 20 842 1044 46684156
Uterine tachysystole 118.37 54.84 13 849 16 46685184
Postpartum haemorrhage 95.55 54.84 18 844 1779 46683421
Meconium in amniotic fluid 94.28 54.84 13 849 172 46685028
Premature separation of placenta 89.93 54.84 17 845 1711 46683489
Disseminated intravascular coagulation 86.68 54.84 26 836 18979 46666221
Anaphylactoid syndrome of pregnancy 75.95 54.84 9 853 30 46685170
Maternal exposure during pregnancy 66.69 54.84 34 828 102515 46582685

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 G02AD02 GENITO URINARY SYSTEM AND SEX HORMONES
OTHER GYNECOLOGICALS
UTEROTONICS
Prostaglandins
FDA CS M0017805 Prostaglandins
FDA EPC N0000175454 Prostaglandin Analog
CHEBI has role CHEBI:36063 oxytocic
CHEBI has role CHEBI:75771 mus musculus metabolite
CHEBI has role CHEBI:77746 h. sapiens metabolites
MeSH PA D010120 Oxytocics
MeSH PA D012102 Reproductive Control Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Incomplete miscarriage indication 156072005
Induction of labor indication 236958009
Cervical ripening procedure indication 236959001
Pregnancy with abortive outcome indication 363681007
Hydatidiform mole, benign indication 417044008
Ocular hypertension contraindication 4210003 DOID:9282
Multiple pregnancy contraindication 16356006
Grand multipara contraindication 18656007
Disorder of lung contraindication 19829001 DOID:850
Glaucoma contraindication 23986001 DOID:1686
Disproportion between fetus and pelvis contraindication 25749005
Genital herpes simplex contraindication 33839006 DOID:8704
Placenta previa contraindication 36813001 DOID:11060
Inflammation of cervix contraindication 37610005 DOID:2568
Hypertensive disorder contraindication 38341003 DOID:10763
Low blood pressure contraindication 45007003
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Disseminated intravascular coagulation contraindication 67406007 DOID:11247
Diabetes mellitus contraindication 73211009 DOID:9351
Stenosis of cervix contraindication 83536006
Kidney disease contraindication 90708001 DOID:557
Uterine leiomyoma contraindication 95315005 DOID:13223
Female genital tract infection contraindication 125585007
Seizure disorder contraindication 128613002
Fetal distress contraindication 130955003
Spontaneous rupture of membranes contraindication 169734005
Asthma contraindication 195967001 DOID:2841
Deliveries by cesarean contraindication 200144004
Disease of liver contraindication 235856003 DOID:409
Anemia contraindication 271737000 DOID:2355
Abnormal uterine bleeding unrelated to menstrual cycle contraindication 312984006
Endocervical Lesions contraindication
Uterine Hypertonic Patterns contraindication
Gynecological Surgery contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 4.79 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Prostaglandin E2 receptor EP3 subtype GPCR AGONIST Ki 9.48 CHEMBL CHEMBL
Prostaglandin E2 receptor EP4 subtype GPCR AGONIST Ki 9.77 CHEMBL CHEMBL
Prostaglandin E2 receptor EP1 subtype GPCR AGONIST Ki 8.04 CHEMBL CHEMBL
Prostaglandin E2 receptor EP2 subtype GPCR AGONIST Ki 8.77 CHEMBL CHEMBL
Prostacyclin receptor GPCR IC50 6.59 CHEMBL
Cation channel sperm-associated protein 4 Ion channel ACTIVATOR EC50 6.30 IUPHAR
Cation channel sperm-associated protein 3 Ion channel ACTIVATOR EC50 6.30 IUPHAR
Cation channel sperm-associated protein 1 Ion channel ACTIVATOR EC50 6.30 IUPHAR
Cation channel sperm-associated protein 2 Ion channel ACTIVATOR EC50 6.30 IUPHAR
Prostaglandin D2 receptor GPCR AGONIST Ki 7 IUPHAR
Prostaglandin F2-alpha receptor GPCR AGONIST Ki 6.90 IUPHAR
Prostaglandin D2 receptor 2 GPCR AGONIST Ki 5.30 IUPHAR
Thromboxane A2 receptor GPCR AGONIST Ki 4.50 IUPHAR
Solute carrier family 22 member 6 Transporter Ki 5.47 CHEMBL
Solute carrier family 22 member 20 Transporter Ki 4.74 CHEMBL
Prostaglandin E2 receptor EP2 subtype GPCR Ki 7.66 CHEMBL
Prostaglandin E2 receptor EP1 subtype GPCR Ki 8.22 CHEMBL
Prostaglandin E2 receptor EP3 subtype GPCR Ki 8.30 CHEMBL
Prostaglandin E2 receptor EP4 subtype GPCR Ki 8.51 CHEMBL
Prostaglandin E2 receptor EP2 subtype GPCR IC50 8.28 CHEMBL
Prostaglandin E2 receptor EP4 subtype GPCR IC50 8.68 CHEMBL
Prostaglandin E2 receptor EP3 subtype Unclassified AGONIST EC50 9.39 IUPHAR
Prostaglandin F2-alpha receptor GPCR AGONIST Ki 7 IUPHAR
Prostaglandin E2 receptor EP1 subtype Unclassified AGONIST Ki 7.70 IUPHAR
Prostaglandin D2 receptor 2 Unclassified AGONIST Ki 5.50 IUPHAR

External reference:

IDSource
4018093 VUID
N0000146431 NUI
D00079 KEGG_DRUG
4018093 VANDF
C0012472 UMLSCUI
CHEBI:15551 CHEBI
P2E PDB_CHEM_ID
CHEMBL548 ChEMBL_ID
DB00917 DRUGBANK_ID
D015232 MESH_DESCRIPTOR_UI
5280360 PUBCHEM_CID
3075 INN_ID
K7Q1JQR04M UNII
3478 RXNORM
4609 MMSL
001309 NDDF
387245009 SNOMEDCT_US
44798001 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Prostin E2 HUMAN PRESCRIPTION DRUG LABEL 1 0009-0827 SUPPOSITORY 20 mg VAGINULLL NDA 20 sections
Prepidil HUMAN PRESCRIPTION DRUG LABEL 1 0009-3359 GEL 0.50 mg VAGINULLL NDA 20 sections
CERVIDIL HUMAN PRESCRIPTION DRUG LABEL 1 55566-2800 INSERT 10 mg VAGINULLL NDA 26 sections