DINOPROSTONE

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12788892http://www.drugbank.ca/drugs/DB00917
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Prostanoid EP2 receptor 20 Target ID: CHEMBL1881 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12788892	Agonist 2752
Prostanoid EP1 receptor 14 Target ID: CHEMBL1811 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12788892	Agonist 2752
Prostanoid EP4 receptor 12 Target ID: CHEMBL1836 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12643927	Agonist 2752	3.0 nM [EC50]
Prostanoid EP2 receptor 20 Target ID: CHEMBL1881 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24279689	Agonist 2752	2.1 nM [EC50]
Prostanoid EP1 receptor 14 Target ID: CHEMBL1811 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17531488	Agonist 2752	9.1 nM [Ki]
Prostanoid EP3 receptor 11 Target ID: CHEMBL3710 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17531488	Agonist 2752	0.33 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596
Labor complications 8 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020411s027lbl.pdf	Primary		Approved 8583	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

C_max

Value	Dose	Co-administered	Analyte	Population
433 pg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019617s010lbl.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
3.75 min DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/020411s023lbl.pdf	unknown, unknown		DINOPROSTONE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
10 mg single, vaginal Recommended Dose: 10 mg Route: vaginal Route: single Dose: 10 mg Sources: https://pubmed.ncbi.nlm.nih.gov/19034471	healthy Health Status: healthy Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/19034471	Sources: https://pubmed.ncbi.nlm.nih.gov/19034471

Sourcing

Vendor/Aggregator	ID	URL
AA Blocks	AA0034P3	https://www.aablocks.com/goods/Goods/detail?id=AA0034P3
Aaron Chemicals	AR0035GV	http://www.aaronchem.com/363-24-6
abcr GmbH	AB505720	http://www.abcr.com/shop/en/AB505720
AbMole Bioscience	M5929	http://www.abmole.com/products/prostaglandin-e2.html
Achemtek	0104-029995	http://www.achemtek.com/363-24-6
Acros Organics	AC233560100	https://www.fishersci.com/shop/products/prostaglandin-e2-98-acros-organics/AC233560100
AHH Chemical co.,ltd	MT-58226	http://www.ahhchemical.com/product/MT-58226.html
AK Scientific, Inc. (AKSCI)	69847	http://www.aksci.com/item_detail.php?cat=69847
Alfa Chemistry	AP363246	https://reagents.alfa-chemistry.com/product/prostaglandin-e2-cas-363-24-6-10652.html
ApexBio Technology	B7005	http://www.apexbt.com/prostaglandin-e2-30253.html
Aurora Fine Chemicals LLC	A13.105.901	http://online.aurorafinechemicals.com/info?ID=A13.105.901
AvaChem Scientific	2640	http://www.avachem.com/productSearch.asp?2640
BioSynth	J-502620	https://www.biosynth.com/en/products/all-products/products/J-502620.html
Boerchem	BC219642	http://www.boerchem.com/?product_37058.html
Calbiochem	538904	http://www.emdbiosciences.com/product/538904
Chem Scene	CS-6932	http://www.chemscene.com/363-24-6.html
ChemMol	30112344	http://www.chemmol.com/chemmol/30112344.html
ChemMol	44006061	http://www.chemmol.com/chemmol/44006061.html
Chemspace	CSSB00020654893	https://chem-space.com/CSSB00020654893
EMD Millipore	538904	http://www.emdbiosciences.com/product/538904
eNovation Chemicals	D674480	https://www.enovationchem.com/ProductDetails.asp?ProductID=D674480
eNovation Chemicals	D765099	https://www.enovationchem.com/ProductDetails.asp?ProductID=D765099
eNovation Chemicals	D954167	https://www.enovationchem.com/ProductDetails.asp?ProductID=D954167
eNovation Chemicals	Y0974233	https://www.enovationchem.com/ProductDetails.asp?ProductID=Y0974233
Excenen	EX-A1773	http://www.excenen.com/searchresultlist.php?id=363-24-6
Glentham Life Sciences	GL2480	http://www.glentham.com/products/product/GL2480/
Hello Bio	HB3460	https://www.hellobio.com/prostaglandin-e2.html
iChemical	EBD2199766	http://www.ichemical.com/products/363-24-6.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network	LN00190301	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00190301
LGC Standards	DRE-A12800200AL-100	https://www.lgcstandards.com/US/en/p/DRE-A12800200AL-100
Matrix Scientific	90192	https://www.matrixscientific.com/090192.html
MedChem Express	HY-101952	https://www.medchemexpress.com/Prostaglandin_E2.html
MuseChem	R009261	https://www.musechem.com/product/R009261.html
OChem	12234	http://www.ocheminc.com/index.php?act=psearch&pid=363P246
Renno Tech	RP17686	http://www.rennotech.com/product_show.asp?id=23564
Selleck Chemicals	S3003	http://www.selleckchem.com/products/prostaglandin-e2-cervidil.html
Sigma-Aldrich	1213103_USP	https://www.sigmaaldrich.com/catalog/product/usp/1213103?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	D2250000_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/d2250000?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	P0409_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/p0409?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	P5640_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/p5640?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	P6532_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/p6532?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S526225	http://www.smolecule.com/products/s526225
Smolecule	S800500	https://www.smolecule.com/products/s800500
TCI (Tokyo Chemical Industry)	P1884	http://www.tcichemicals.com/eshop/en/us/commodity/P1884/index.html
THE BioTek	bt-265319	https://www.thebiotek.com/product/inhibitors/bt-265319
Tocris	2296	https://www.tocris.com/products/prostaglandin-e2_2296
VladaChem	VL277460-10MG	https://www.vladachem.com/product.php?products=363-24-6
Yuhao Chemical	LL0733	http://www.chemyuhao.com/363-24-6.html

PubMed

Title	Date	PubMed
Expression and molecular pharmacology of the mouse CRTH2 receptor.	2003-08	12721327
PGE(2) is generated by specific COX-2 activity and increases VEGF production in COX-2-expressing human pancreatic cancer cells.	2003-07-11	12821125
Eugenol suppresses cyclooxygenase-2 expression in lipopolysaccharide-stimulated mouse macrophage RAW264.7 cells.	2003-06-06	12757841
S+ -flurbiprofen but not 5-HT1 agonists suppress basal and stimulated CGRP and PGE2 release from isolated rat dura mater.	2003-06	12791437
[Isolated peripheral arterial ischaemia and medullary neurostimulation: case report].	2003-05-15	12746806
Deficient prostaglandin E2 production by bronchial fibroblasts of asthmatic patients, with special reference to aspirin-induced asthma.	2003-05	12743569
Identification by site-directed mutagenesis of amino acids contributing to ligand-binding specificity or signal transduction properties of the human FP prostanoid receptor.	2003-04-15	12519077
Role of the dorsomedial hypothalamus in thermogenesis and tachycardia caused by microinjection of prostaglandin E2 into the preoptic area in anesthetized rats.	2003-04-03	12648744
Glucosamine inhibits IL-1beta-induced NFkappaB activation in human osteoarthritic chondrocytes.	2003-04	12681956
Contribution of 5- and 12-lipoxygenase products to mechanical hyperalgesia induced by prostaglandin E(2) and epinephrine in the rat.	2003-02	12582831
Cyclooxygenase-2 expression by nonsteroidal anti-inflammatory drugs in human airway smooth muscle cells: role of peroxisome proliferator-activated receptors.	2003-01-15	12517972
Dexamethasone or interleukin-10 blocks interleukin-1beta-induced uterine contractions in pregnant rhesus monkeys.	2003-01	12548226
Mechanisms of cytosolic Ca2+ suppression by prostaglandin E2 receptors in rat melanotrophs.	2003-01	12535167
Interleukin 1beta induces functional prostaglandin E synthase in cultured human umbilical vein endothelial cells.	2002-12	12512699
Molecular pharmacology of the human prostaglandin D2 receptor, CRTH2.	2002-12	12466225
Selective cyclooxygenase-2 inhibitors show a differential ability to inhibit proliferation and induce apoptosis of colon adenocarcinoma cells.	2002-11-06	12417326
Role of STAT6 and mast cells in IL-4- and IL-13-induced alterations in murine intestinal epithelial cell function.	2002-10-15	12370375
Arsenic induces peroxynitrite generation and cyclooxygenase-2 protein expression in aortic endothelial cells: possible role in atherosclerosis.	2002-10-01	12392964
A novel human fibroblast growth factor treats experimental intestinal inflammation.	2002-10	12360478
Role of NFAT and AP-1 in PGE2-mediated T cell suppression in burn injury.	2002-09	12353920
Angiotensin II receptor blocker-associated angioedema: on the heels of ACE inhibitor angioedema.	2002-09	12222553
Suppression of N-nitrosomethylbenzylamine (NMBA)-induced esophageal tumorigenesis in F344 rats by resveratrol.	2002-09	12189197
Peripheral group II metabotropic glutamate receptors (mGluR2/3) regulate prostaglandin E2-mediated sensitization of capsaicin responses and thermal nociception.	2002-08-01	12151517
Downregulation of COX-2 and iNOS by amentoflavone and quercetin in A549 human lung adenocarcinoma cell line.	2002-07-30	12144868
N-acetylcysteine and celecoxib lessen cadmium cytotoxicity which is associated with cyclooxygenase-2 up-regulation in mouse neuronal cells.	2002-07-12	11997384
Characterization of the bone-resorptive effect of interleukin-11 in cultured mouse calvarial bones.	2002-07	12110441
Prostaglandin E2 induces vasodilation and pruritus, but no protein extravasation in atopic dermatitis and controls.	2002-07	12077577
Isolation, characterization and differential gene expression of multispecific organic anion transporter 2 in mice.	2002-07	12065749
ATP can enhance the proton-induced CGRP release through P2Y receptors and secondary PGE(2) release in isolated rat dura mater.	2002-06	12044622
Nuclear factor-kappaB mediates over-expression of cyclooxygenase-2 during activation of RAW 264.7 macrophages in selenium deficiency.	2002-05-01	11978490
Role of Ca(2+)-independent phospholipase A(2) and cyclooxygenase/lipoxygenase pathways in the nitric oxide production by murine macrophages stimulated by lipopolysaccharides.	2002-05	12009843
Role of melittin-like region within phospholipase A(2)-activating protein in biological function.	2002-05	11821123
Cloned human EP1 prostanoid receptor pharmacology characterized using radioligand binding techniques.	2002-04	11999132
Deficiency in inducible nitric oxide synthase protects mice from ozone-induced lung inflammation and tissue injury.	2002-04	11919077
Human organic anion transporters and human organic cation transporters mediate renal transport of prostaglandins.	2002-04	11907186
Inhibition of cyclooxygenase 2 blocks human cytomegalovirus replication.	2002-03-19	11867761
Regulation of cyclooxygenase-2 expression by phospholipase D in human amnion-derived WISH cells.	2002-03	11854442
Trophic effects of the cyclooxygenase-2 product prostaglandin E(2) in cardiac myocytes.	2002-02	11882577
Stabilization of hypoxia-inducible factor-1alpha is involved in the hypoxic stimuli-induced expression of vascular endothelial growth factor in osteoblastic cells.	2002-01-07	11886167
A comparative study of the antipyretic effects of indomethacin and dipyrone in rats.	2002-01	11852909
Chemopreventive effects of ONO-8711, a selective prostaglandin E receptor EP(1) antagonist, on breast cancer development.	2001-12	11751431
A protective role for cyclooxygenase-2 in drug-induced liver injury in mice.	2001-12	11743745
Possible role of prostaglandin E2 in human amniotic epithelial cell death: an in vitro study.	2001-10	11713899
R(+)-methanandamide induces cyclooxygenase-2 expression in human neuroglioma cells via a non-cannabinoid receptor-mediated mechanism.	2001-09-07	11527419
Effects of YM905, a novel muscarinic M3-receptor antagonist, on experimental models of bowel dysfunction in vivo.	2001-07	11488427
Modulation of haem oxygenase-1 expression by nitric oxide and leukotrienes in zymosan-activated macrophages.	2001-07	11454666
Sex hormones regulate the contribution of PKCepsilon and PKA signalling in inflammatory pain in the rat.	2001-06	11454025
Interleukin 1-induced cyclooxygenase and nitric oxide synthase gene expression in the rat dorsal root ganglia is modulated by antioxidants.	2001	11530235
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	11500931
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.	1976-11	970637

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

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

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Name

Type

Language

PROSTAGLANDIN E2

Preferred Name

English

DINOPROSTONE

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