dinoprostone indications/contra

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

Drug dosage:

DoseUnitRoute
0.50 mg O
0.50 mg V

Approvals:

DateAgencyCompanyOrphan
Aug. 23, 1977 FDA PHARMACIA AND UPJOHN

FDA Adverse Event Reporting System

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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
Caesarean section 313.72 152.72 52 205 4474 3381128
Exposure during pregnancy 291.36 152.72 65 192 27498 3358104
Premature separation of placenta 170.83 152.72 23 234 443 3385159
Uterine hypertonus 154.67 152.72 17 240 47 3385555

Pharmacologic Action:

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SourceCodeDescription
ATC G02AD02 GENITO URINARY SYSTEM AND SEX HORMONES
OTHER GYNECOLOGICALS
UTEROTONICS
Prostaglandins
FDA EPC N0000175454 Prostaglandin Analog
FDA Chemical/Ingredient N0000007706 Prostaglandins
CHEBI has role CHEBI:36063 oxytocic
MeSH PA D010120 Oxytocics
MeSH PA D012102 Reproductive Control Agents

Drug Use (View source of the data)

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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 DOID:3590
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:2527
Uterine leiomyoma contraindication 95315005 DOID:13223
Female genital tract infection contraindication 125585007
Seizure disorder contraindication 128613002 DOID:1826
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

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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:

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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:

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IDSource
4018093 VUID
N0000146431 NUI
C0012472 UMLSCUI
1883 IUPHAR_LIGAND_ID
D00079 KEGG_DRUG
CHEMBL548 ChEMBL_ID
DB00917 DRUGBANK_ID
3478 RXNORM
387245009 SNOMEDCT_US
44798001 SNOMEDCT_US
4609 MMSL
4018093 VANDF
N0000146431 NDFRT
N0000006989 NDFRT
001309 NDDF
5280360 PUBCHEM_CID
K7Q1JQR04M UNII
3075 INN_ID
D015232 MESH_DESCRIPTOR_UI
CHEBI:15551 CHEBI
P2E PDB_CHEM_ID

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Prostin HUMAN PRESCRIPTION DRUG LABEL 1 0009-0827 SUPPOSITORY 20 mg VAGINAL NDA 11 sections
Prepidil HUMAN PRESCRIPTION DRUG LABEL 1 0009-3359 GEL 0.50 mg VAGINAL NDA 13 sections
CERVIDIL HUMAN PRESCRIPTION DRUG LABEL 1 55566-2800 INSERT 10 mg VAGINAL NDA 15 sections
DINOPROSTONE HUMAN PRESCRIPTION DRUG LABEL 1 55566-9500 INSERT 10 mg VAGINAL NDA 15 sections