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

Stem definition	Drug id	CAS RN
prostaglandins	913	363-24-6

Description:

Molecule	Description
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

Molecule

Description

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:

Dose	Unit	Route
0.50	mg	O
0.50	mg	V

ADMET properties:

Property	Value	Reference
MRTD (Maximum Recommended Therapeutic Daily Dose)	4.05 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

Approvals:

Date	Agency	Company	Orphan
Aug. 23, 1977	FDA	PHARMACIA AND UPJOHN
Jan. 23, 2020	PMDA	Ferring Pharmaceuticals Co., Ltd.

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Uterine hyperstimulation	293.97	63.67	31	846	33	63488112
Exposure during pregnancy	175.15	63.67	69	808	155478	63332667
Uterine hypertonus	158.40	63.67	21	856	279	63487866
Uterine tachysystole	153.13	63.67	16	861	14	63488131
Uterine rupture	116.96	63.67	19	858	1067	63487078
Caesarean section	116.19	63.67	30	847	17002	63471143
Meconium in amniotic fluid	91.81	63.67	13	864	286	63487859
Premature separation of placenta	87.11	63.67	16	861	1845	63486300
Anaphylactoid syndrome of pregnancy	85.47	63.67	10	867	42	63488103
Disseminated intravascular coagulation	80.38	63.67	23	854	19028	63469117
Postpartum haemorrhage	79.75	63.67	15	862	1966	63486179
Maternal exposure during pregnancy	72.21	63.67	42	835	220020	63268125

FDA Adverse Event Reporting System (Male)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Foetal exposure during pregnancy	200.03	177.28	46	179	38055	34918651

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Exposure during pregnancy	211.94	67.44	61	524	101071	79642732
Uterine hypertonus	128.11	67.44	16	569	255	79743548
Uterine hyperstimulation	125.60	67.44	13	572	29	79743774
Caesarean section	115.76	67.44	25	560	12510	79731293
Meconium in amniotic fluid	111.21	67.44	13	572	114	79743689
Premature separation of placenta	103.71	67.44	16	569	1230	79742573
Maternal exposure during pregnancy	98.68	67.44	37	548	136501	79607302
Uterine tachysystole	90.75	67.44	9	576	10	79743793
Uterine rupture	73.15	67.44	11	574	710	79743093

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
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 agents
CHEBI has role	CHEBI:75771	Mus musculus metabolites
CHEBI has role	CHEBI:77746	Homo sapiens metabolite
MeSH PA	D010120	Oxytocics
MeSH PA	D012102	Reproductive Control Agents

Drug Use | Suggest Off label Use Form| |View source of the data|

Disease	Relation	SNOMED_ID	DOID
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

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	4.79	acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Prostaglandin E2 receptor EP4 subtype	GPCR	P35408	PE2R4_HUMAN	AGONIST	Ki	9.77	CHEMBL	CHEMBL
Prostaglandin E2 receptor EP3 subtype	GPCR	P43115	PE2R3_HUMAN	AGONIST	Ki	9.48	CHEMBL	CHEMBL
Prostaglandin E2 receptor EP2 subtype	GPCR	P43116	PE2R2_HUMAN	AGONIST	Ki	8.77	CHEMBL	CHEMBL
Prostaglandin E2 receptor EP1 subtype	GPCR	P34995	PE2R1_HUMAN	AGONIST	Ki	8.04	CHEMBL	CHEMBL
Prostaglandin D2 receptor	GPCR	Q13258	PD2R_HUMAN	AGONIST	Ki	7	IUPHAR
Prostaglandin F2-alpha receptor	GPCR	P43088	PF2R_HUMAN	AGONIST	Ki	6.90	IUPHAR
Cation channel sperm-associated protein 1	Ion channel	Q8NEC5	CTSR1_HUMAN	ACTIVATOR	EC50	6.30	IUPHAR
Cation channel sperm-associated protein 2	Ion channel	Q96P56	CTSR2_HUMAN	ACTIVATOR	EC50	6.30	IUPHAR
Cation channel sperm-associated protein 3	Ion channel	Q86XQ3	CTSR3_HUMAN	ACTIVATOR	EC50	6.30	IUPHAR
Cation channel sperm-associated protein 4	Ion channel	Q7RTX7	CTSR4_HUMAN	ACTIVATOR	EC50	6.30	IUPHAR
Prostaglandin D2 receptor 2	GPCR	Q9Y5Y4	PD2R2_HUMAN	AGONIST	Ki	5.30	IUPHAR
Prostacyclin receptor	GPCR	P43119	PI2R_HUMAN		IC50	6.59	CHEMBL
Thromboxane A2 receptor	GPCR	P21731	TA2R_HUMAN	AGONIST	Ki	4.50	IUPHAR
Prostaglandin E2 receptor EP1 subtype	GPCR		PE2R1_MOUSE		Ki	8.22	CHEMBL
Prostaglandin E2 receptor EP2 subtype	GPCR		PE2R2_MOUSE		Ki	7.66	CHEMBL
Prostaglandin E2 receptor EP3 subtype	GPCR		PE2R3_MOUSE		Ki	8.30	CHEMBL
Prostaglandin E2 receptor EP4 subtype	GPCR		PE2R4_MOUSE		Ki	8.51	CHEMBL
Solute carrier family 22 member 6	Transporter		S22A6_MOUSE		Ki	5.47	CHEMBL
Solute carrier family 22 member 20	Transporter		S22AK_MOUSE		Ki	4.74	CHEMBL
Prostaglandin F2-alpha receptor	GPCR		PF2R_MOUSE	AGONIST	Ki	7	IUPHAR
Prostaglandin E2 receptor EP2 subtype	GPCR		PE2R2_RAT		IC50	8.28	CHEMBL
Prostaglandin E2 receptor EP4 subtype	GPCR		PE2R4_RAT		IC50	8.68	CHEMBL
Prostaglandin D2 receptor 2	GPCR		PD2R2_MOUSE	AGONIST	Ki	5.50	IUPHAR
Prostaglandin E2 receptor EP3 subtype	GPCR		PE2R3_RAT	AGONIST	EC50	9.39	IUPHAR
Prostaglandin E2 receptor EP1 subtype	GPCR		PE2R1_RAT	AGONIST	Ki	7.70	IUPHAR

External reference:

ID	Source
4018093	VUID
N0000146431	NUI
D00079	KEGG_DRUG
3478	RXNORM
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
4609	MMSL
001309	NDDF
387245009	SNOMEDCT_US
44798001	SNOMEDCT_US

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Prepidil	HUMAN PRESCRIPTION DRUG LABEL	1	0009-3359	GEL	0.50 mg	VAGINAL	NDA	20 sections
CERVIDIL	HUMAN PRESCRIPTION DRUG LABEL	1	55566-2800	INSERT	10 mg	VAGINAL	NDA	26 sections
CERVIDIL	HUMAN PRESCRIPTION DRUG LABEL	1	55566-2800	INSERT	10 mg	VAGINAL	NDA	26 sections
CERVIDIL	HUMAN PRESCRIPTION DRUG LABEL	1	55566-2800	INSERT	10 mg	VAGINAL	NDA	26 sections