U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ABSOLUTE
Molecular Formula C20H32O5
Molecular Weight 352.4651
Optical Activity ( - )
Defined Stereocenters 4 / 4
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of DINOPROSTONE

SMILES

CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O

InChI

InChIKey=XEYBRNLFEZDVAW-ARSRFYASSA-N
InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1

HIDE SMILES / InChI

Molecular Formula C20H32O5
Molecular Weight 352.4651
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 2
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including

Dinoprostone is a naturally occurring prostaglandin E2 (PGE2). Dinoprostone is equivalent to prostaglandin E2 (PGE2). It stimulates labor and delivery by stimulating the uterine, and thus terminates pregnancy. Dinoprostone is also capable of stimulating the smooth muscle of the gastrointestinal tract of man. This activity may be responsible for the vomiting and/or diarrhea that is not uncommon when dinoprostone is used to terminate pregnancy. Dinoprostone administered intravaginally stimulates the myometrium of the gravid uterus to contract in a manner that is similar to the contractions seen in the term uterus during labor, resulting in the evacuation of the products of conception from the uterus. It is believed that dinoprostone exerts its uterine effects via direct myometrial stimulation. It is used for the termination of pregnancy during the second trimester (from the 12th through the 20th gestational week as calculated from the first day of the last normal menstrual period), as well as for evacuation of the uterine contents in the management of missed abortion or intrauterine fetal death up to 28 weeks of gestational age as calculated from the first day of the last normal menstrual period. Also used in the management of nonmetastatic gestational trophoblastic disease (benign hydatidiform mole). Other indications include improving the cervical inducibility (cervical "ripening") in pregnant women at or near term with a medical or obstetrical need for labor induction, and the management of postpartum hemorrhage.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CERVIDIL

Approved Use

Cervidil Vaginal Insert (dinoprostone, 10 mg) is indicated for the initiation and/or continuation of cervical ripening in patients at or near term in whom there is a medical or obstetrical indication for the induction of labor.

Launch Date

1995
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
433 pg/mL
0.5 mg single, topical
dose: 0.5 mg
route of administration: Topical
experiment type: SINGLE
co-administered:
DINOPROSTONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.75 min
unknown, unknown
DINOPROSTONE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
10 mg single, vaginal
Recommended
Dose: 10 mg
Route: vaginal
Route: single
Dose: 10 mg
Sources:
healthy
Health Status: healthy
Sex: F
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Determination of 5-trans-prostaglandin E2 in prostaglandin E2 via high performance liquid chromatography of their p-nitrophenacyl esters on a silver ion-loaded cation exchange resin.
1976 Nov
The involvement of K+ channels and Gi/o protein in the antinociceptive action of the gallic acid ethyl ester.
1999 Aug 20
Endogenous prostaglandin formation in the field-stimulated guinea-pig vas deferens: comparison of the inhibitory effects of indomethacin and NS-398.
1999 Dec
Dexamethasone inhibits dendritic cell maturation by redirecting differentiation of a subset of cells.
1999 Dec
Prostaglandin E2 inhibits T cell activation-induced apoptosis and Fas-mediated cellular cytotoxicity by blockade of Fas-ligand induction.
1999 Jul
Role of prostaglandins generated by cyclooxygenase-1 and cyclooxygenase-2 in healing of ischemia-reperfusion-induced gastric lesions.
1999 Nov 26
Oral antinociception and oedema inhibition produced by NPC 18884, a non-peptidic bradykinin B2 receptor antagonist.
1999 Sep
L-NAME causes antinociception by stimulation of the arginine-NO-cGMP pathway.
2000
Chronic intrathecal cannulation enhances nociceptive responses in rats.
2000 Aug
Induction of cyclooxygenase-2 by overexpression of the human catalase gene in cerebral microvascular endothelial cells.
2000 Aug
Nitric oxide metabolites, prostaglandins and trigeminal vasoactive peptides in internal jugular vein blood during spontaneous migraine attacks.
2000 Dec
Transcriptional regulation of cyclooxygenase-2 gene expression: novel effects of nonsteroidal anti-inflammatory drugs.
2000 Feb 15
The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs.
2000 Jan 17
Prostaglandin E2 and the protein kinase A pathway mediate arachidonic acid induction of c-fos in human prostate cancer cells.
2000 Jun
Identification of mu-class glutathione transferases M2-2 and M3-3 as cytosolic prostaglandin E synthases in the human brain.
2000 May
Cyclooxygenase-2 expression in lipopolysaccharide-stimulated human monocytes is modulated by cyclic AMP, prostaglandin E(2), and nonsteroidal anti-inflammatory drugs.
2000 Nov 30
Interleukin-1beta down-regulates the expression of glucuronosyltransferase I, a key enzyme priming glycosaminoglycan biosynthesis: influence of glucosamine on interleukin-1beta-mediated effects in rat chondrocytes.
2001 Feb
Prostaglandin levels in stimulated macrophages are controlled by phospholipase A2-activating protein and by activation of phospholipase C and D.
2001 Feb 23
Effects of YM905, a novel muscarinic M3-receptor antagonist, on experimental models of bowel dysfunction in vivo.
2001 Jul
Modulation of haem oxygenase-1 expression by nitric oxide and leukotrienes in zymosan-activated macrophages.
2001 Jul
Characterization of EP receptor subtypes responsible for prostaglandin E2-induced pain responses by use of EP1 and EP3 receptor knockout mice.
2001 Jun
Antinociceptive effects of delta-opioid agonists in Rhesus monkeys: effects on chemically induced thermal hypersensitivity.
2001 Mar
Neurohormonal regulation of secretion from isolated rat stomach ECL cells: a critical reappraisal.
2001 Mar 2
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.
2001 May
Deficiency in inducible nitric oxide synthase protects mice from ozone-induced lung inflammation and tissue injury.
2002 Apr
Human organic anion transporters and human organic cation transporters mediate renal transport of prostaglandins.
2002 Apr
Trophic effects of the cyclooxygenase-2 product prostaglandin E(2) in cardiac myocytes.
2002 Feb
A comparative study of the antipyretic effects of indomethacin and dipyrone in rats.
2002 Jan
Characterization of the bone-resorptive effect of interleukin-11 in cultured mouse calvarial bones.
2002 Jul
Nuclear factor-kappaB mediates over-expression of cyclooxygenase-2 during activation of RAW 264.7 macrophages in selenium deficiency.
2002 May 1
A novel human fibroblast growth factor treats experimental intestinal inflammation.
2002 Oct
Role of NFAT and AP-1 in PGE2-mediated T cell suppression in burn injury.
2002 Sep
Angiotensin II receptor blocker-associated angioedema: on the heels of ACE inhibitor angioedema.
2002 Sep
Contribution of 5- and 12-lipoxygenase products to mechanical hyperalgesia induced by prostaglandin E(2) and epinephrine in the rat.
2003 Feb
Dexamethasone or interleukin-10 blocks interleukin-1beta-induced uterine contractions in pregnant rhesus monkeys.
2003 Jan
PGE(2) is generated by specific COX-2 activity and increases VEGF production in COX-2-expressing human pancreatic cancer cells.
2003 Jul 11
S+ -flurbiprofen but not 5-HT1 agonists suppress basal and stimulated CGRP and PGE2 release from isolated rat dura mater.
2003 Jun
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
Aromatase activity in adipose stromal cells was determined using the tritiated water-release assay and normalized to the number of cells in each flask. Cells in T-25 flasks were treated with 0.1% ethanol (control) dexamethasone (100 nm), and the following compounds at 1-mkM concentrations: indomethacin, PGE2, 5-trans PGE2, 17-phenyl trinor PGE2, 11-deoxy PGE1, and sulprostone. After 24 h, the cells were incubated for 6 h with fresh media and drugs along with 50 nm androstenedione including 2 mkCi [1beta-3H] androst-4-ene-3, 17-dione. Subsequently, the media was removed for extraction purposes and a 250-_l aliquot was counted in 5 ml of liquid scintillation mixture.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:50:23 GMT 2025
Edited
by admin
on Mon Mar 31 17:50:23 GMT 2025
Record UNII
K7Q1JQR04M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PROSTAGLANDIN E2
MI  
Preferred Name English
DINOPROSTONE
EP   INN   JAN   MART.   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
DINOPROSTONE [EP MONOGRAPH]
Common Name English
DINOPROSTONE [USP-RS]
Common Name English
dinoprostone [INN]
Common Name English
NSC-165560
Code English
DINOPROSTONE [ORANGE BOOK]
Common Name English
CERVIDIL
Brand Name English
DINOPROSTONE [USP IMPURITY]
Common Name English
MINPROSTIN E2
Brand Name English
PROSTA-5,13-DIEN-1-OIC ACID, 11,15-DIHYDROXY-9-OXO-, (5Z,11.ALPHA.,13E,15S)-
Systematic Name English
PROSTIN E2
Brand Name English
DINOPROSTONE [USP MONOGRAPH]
Common Name English
PREPIDIL
Brand Name English
U-12,062
Code English
U-12062
Code English
ENZAPROST E
Brand Name English
DINOPROSTONE [VANDF]
Common Name English
Dinoprostone [WHO-DD]
Common Name English
DINOPROSTONE [MART.]
Common Name English
PGE2
Common Name English
PROPESS
Brand Name English
ALPROSTADIL IMPURITY G [EP IMPURITY]
Common Name English
(E,Z)-(1R,2R,3R)-7-[3-Hydroxy-2-[(3S)-(3-hydroxy-1-octenyl)]-5-oxocyclopentyl]-5-heptenoic acid
Systematic Name English
DINOPROSTONE [JAN]
Common Name English
DINOPROSTONE [USAN]
Common Name English
PROSTAGLANDIN E2 [MI]
Common Name English
NSC-196514
Code English
Classification Tree Code System Code
LOINC 12836-3
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
LOINC 70091-4
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
LOINC 2853-0
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
NCI_THESAURUS C78568
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
WHO-ATC G02AD02
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
LOINC 14006-1
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
NCI_THESAURUS C782
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
NDF-RT N0000007706
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
WHO-VATC QG02AD02
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
NDF-RT N0000007706
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
NDF-RT N0000175454
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
NDF-RT N0000007706
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
Code System Code Type Description
EVMPD
SUB07195MIG
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
DAILYMED
K7Q1JQR04M
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
NSC
196514
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
SMS_ID
100000092220
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
EPA CompTox
DTXSID4022947
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
ECHA (EC/EINECS)
206-656-6
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
WIKIPEDIA
PROSTAGLANDIN E2
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
CAS
363-24-6
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
NSC
165560
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
RXCUI
3478
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY RxNorm
FDA UNII
K7Q1JQR04M
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
DRUG CENTRAL
913
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
IUPHAR
1883
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
LACTMED
Dinoprostone
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
CHEBI
606564
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
MESH
D015232
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
ChEMBL
CHEMBL548
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
RS_ITEM_NUM
1213103
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
MERCK INDEX
m9258
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY Merck Index
DRUG BANK
DB00917
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
INN
3075
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
PUBCHEM
5280360
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
CHEBI
15551
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
NCI_THESAURUS
C61727
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
Related Record Type Details
TARGET -> AGONIST
LABELED -> NON-LABELED
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
INHIBITOR -> TARGET
TARGET -> AGONIST
Ki
TARGET -> AGONIST
Ki
PARENT -> CONSTITUENT ALWAYS PRESENT
TARGET -> AGONIST
INHIBITOR OF FORMATION->TARGET
In-vitro in rat polymorphonuclear neutrophils (PMNs)
IC50
PARENT -> CONSTITUENT ALWAYS PRESENT
SALT/SOLVATE -> PARENT
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
EP
TARGET -> AGONIST
TARGET -> AGONIST
Ki
TARGET -> AGONIST
Ki
TARGET -> AGONIST
PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
METABOLITE -> PARENT
Related Record Type Details
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 0.7
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 0.2
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
The sum of these three impurities is NMT 1.0%. (15-Oxo-dinoprostone, 15-Epi-dinoprostone,and 8-Isodinoprostone)
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
The sum of these three impurities is NMT 1.0%. (15-Oxo-dinoprostone, 15-Epi-dinoprostone,and 8-Isodinoprostone)
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
The sum of these three impurities is NMT 1.0%. (15-Oxo-dinoprostone, 15-Epi-dinoprostone,and 8-Isodinoprostone)
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY