U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 unknown
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: Page: p.22
healthy
n = 56
Health Status: healthy
Condition: Labor induction
Sex: F
Population Size: 56
Sources: Page: p.22
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
Interleukin 1-induced cyclooxygenase and nitric oxide synthase gene expression in the rat dorsal root ganglia is modulated by antioxidants.
2001
Inhibition of nitric oxide synthase inhibitors and lipopolysaccharide induced inducible NOS and cyclooxygenase-2 gene expressions by rutin, quercetin, and quercetin pentaacetate in RAW 264.7 macrophages.
2001
Chemopreventive effects of ONO-8711, a selective prostaglandin E receptor EP(1) antagonist, on breast cancer development.
2001 Dec
A protective role for cyclooxygenase-2 in drug-induced liver injury in mice.
2001 Dec
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
Sex hormones regulate the contribution of PKCepsilon and PKA signalling in inflammatory pain in the rat.
2001 Jun
Possible role of prostaglandin E2 in human amniotic epithelial cell death: an in vitro study.
2001 Oct
R(+)-methanandamide induces cyclooxygenase-2 expression in human neuroglioma cells via a non-cannabinoid receptor-mediated mechanism.
2001 Sep 7
Cloned human EP1 prostanoid receptor pharmacology characterized using radioligand binding techniques.
2002 Apr
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
Peripheral group II metabotropic glutamate receptors (mGluR2/3) regulate prostaglandin E2-mediated sensitization of capsaicin responses and thermal nociception.
2002 Aug 1
Interleukin 1beta induces functional prostaglandin E synthase in cultured human umbilical vein endothelial cells.
2002 Dec
Molecular pharmacology of the human prostaglandin D2 receptor, CRTH2.
2002 Dec
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
Stabilization of hypoxia-inducible factor-1alpha is involved in the hypoxic stimuli-induced expression of vascular endothelial growth factor in osteoblastic cells.
2002 Jan 7
Characterization of the bone-resorptive effect of interleukin-11 in cultured mouse calvarial bones.
2002 Jul
Prostaglandin E2 induces vasodilation and pruritus, but no protein extravasation in atopic dermatitis and controls.
2002 Jul
Isolation, characterization and differential gene expression of multispecific organic anion transporter 2 in mice.
2002 Jul
N-acetylcysteine and celecoxib lessen cadmium cytotoxicity which is associated with cyclooxygenase-2 up-regulation in mouse neuronal cells.
2002 Jul 12
ATP can enhance the proton-induced CGRP release through P2Y receptors and secondary PGE(2) release in isolated rat dura mater.
2002 Jun
Regulation of cyclooxygenase-2 expression by phospholipase D in human amnion-derived WISH cells.
2002 Mar
Inhibition of cyclooxygenase 2 blocks human cytomegalovirus replication.
2002 Mar 19
Role of Ca(2+)-independent phospholipase A(2) and cyclooxygenase/lipoxygenase pathways in the nitric oxide production by murine macrophages stimulated by lipopolysaccharides.
2002 May
Role of melittin-like region within phospholipase A(2)-activating protein in biological function.
2002 May
Nuclear factor-kappaB mediates over-expression of cyclooxygenase-2 during activation of RAW 264.7 macrophages in selenium deficiency.
2002 May 1
Downregulation of COX-2 and iNOS by amentoflavone and quercetin in A549 human lung adenocarcinoma cell line.
2002 May-Jun
Selective cyclooxygenase-2 inhibitors show a differential ability to inhibit proliferation and induce apoptosis of colon adenocarcinoma cells.
2002 Nov 6
A novel human fibroblast growth factor treats experimental intestinal inflammation.
2002 Oct
Arsenic induces peroxynitrite generation and cyclooxygenase-2 protein expression in aortic endothelial cells: possible role in atherosclerosis.
2002 Oct 1
Role of STAT6 and mast cells in IL-4- and IL-13-induced alterations in murine intestinal epithelial cell function.
2002 Oct 15
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
Suppression of N-nitrosomethylbenzylamine (NMBA)-induced esophageal tumorigenesis in F344 rats by resveratrol.
2002 Sep
Glucosamine inhibits IL-1beta-induced NFkappaB activation in human osteoarthritic chondrocytes.
2003 Apr
Identification by site-directed mutagenesis of amino acids contributing to ligand-binding specificity or signal transduction properties of the human FP prostanoid receptor.
2003 Apr 15
Role of the dorsomedial hypothalamus in thermogenesis and tachycardia caused by microinjection of prostaglandin E2 into the preoptic area in anesthetized rats.
2003 Apr 3
Expression and molecular pharmacology of the mouse CRTH2 receptor.
2003 Aug
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
Mechanisms of cytosolic Ca2+ suppression by prostaglandin E2 receptors in rat melanotrophs.
2003 Jan
Cyclooxygenase-2 expression by nonsteroidal anti-inflammatory drugs in human airway smooth muscle cells: role of peroxisome proliferator-activated receptors.
2003 Jan 15
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
Eugenol suppresses cyclooxygenase-2 expression in lipopolysaccharide-stimulated mouse macrophage RAW264.7 cells.
2003 Jun 6
[Isolated peripheral arterial ischaemia and medullary neurostimulation: case report].
2003 Mar-Apr
Deficient prostaglandin E2 production by bronchial fibroblasts of asthmatic patients, with special reference to aspirin-induced asthma.
2003 May
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 Fri Dec 15 15:12:48 GMT 2023
Edited
by admin
on Fri Dec 15 15:12:48 GMT 2023
Record UNII
K7Q1JQR04M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
PROSTAGLANDIN E2
MI  
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 Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
LOINC 70091-4
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
LOINC 2853-0
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
NCI_THESAURUS C78568
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
WHO-ATC G02AD02
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
LOINC 14006-1
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
NCI_THESAURUS C782
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
NDF-RT N0000007706
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
WHO-VATC QG02AD02
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
NDF-RT N0000007706
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
NDF-RT N0000175454
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
NDF-RT N0000007706
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
Code System Code Type Description
EVMPD
SUB07195MIG
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
PRIMARY
DAILYMED
K7Q1JQR04M
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
PRIMARY
NSC
196514
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
PRIMARY
SMS_ID
100000092220
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
PRIMARY
EPA CompTox
DTXSID4022947
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
PRIMARY
ECHA (EC/EINECS)
206-656-6
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
PRIMARY
WIKIPEDIA
PROSTAGLANDIN E2
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
PRIMARY
CAS
363-24-6
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
PRIMARY
NSC
165560
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
PRIMARY
RXCUI
3478
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
PRIMARY RxNorm
FDA UNII
K7Q1JQR04M
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
PRIMARY
DRUG CENTRAL
913
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
PRIMARY
IUPHAR
1883
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
PRIMARY
LACTMED
Dinoprostone
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
PRIMARY
CHEBI
606564
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
PRIMARY
MESH
D015232
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
PRIMARY
ChEMBL
CHEMBL548
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
PRIMARY
RS_ITEM_NUM
1213103
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
PRIMARY
MERCK INDEX
m9258
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
PRIMARY Merck Index
DRUG BANK
DB00917
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
PRIMARY
INN
3075
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
PRIMARY
PUBCHEM
5280360
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
PRIMARY
CHEBI
15551
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
PRIMARY
NCI_THESAURUS
C61727
Created by admin on Fri Dec 15 15:12:48 GMT 2023 , Edited by admin on Fri Dec 15 15:12:48 GMT 2023
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
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