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
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
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 |
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
Sources: https://worldwide.espacenet.com/publicationDetails/biblio?DB=EPODOC&II=0&ND=3&adjacent=true&locale=en_EP&FT=D&date=19720316&CC=DE&NR=2144048A1&KC=A1https://books.google.ru/books?id=_J2ti4EkYpkC&pg=PA1338&lpg=PA1338&dq=DINOPROSTONE retrieved from Pharmaceutical Manufacturing Encyclopedia William Andrew Publishing, p.1338
Curator's Comment: Introduced as Prostin E2 by Upjohn, UK, in 1972
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1881 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12788892 |
|||
Target ID: CHEMBL1811 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12788892 |
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Target ID: CHEMBL1836 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12643927 |
3.0 nM [EC50] | ||
Target ID: CHEMBL1881 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24279689 |
2.1 nM [EC50] | ||
Target ID: CHEMBL1811 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17531488 |
9.1 nM [Ki] | ||
Target ID: CHEMBL3710 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17531488 |
0.33 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | CERVIDIL Approved UseCervidil 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 Date1995 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.75 min |
unknown, unknown |
DINOPROSTONE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
PubMed
Title | Date | PubMed |
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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 |
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The involvement of K+ channels and Gi/o protein in the antinociceptive action of the gallic acid ethyl ester. | 1999 Aug 20 |
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Endogenous prostaglandin formation in the field-stimulated guinea-pig vas deferens: comparison of the inhibitory effects of indomethacin and NS-398. | 1999 Dec |
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Dexamethasone inhibits dendritic cell maturation by redirecting differentiation of a subset of cells. | 1999 Dec |
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Prostaglandin E2 inhibits T cell activation-induced apoptosis and Fas-mediated cellular cytotoxicity by blockade of Fas-ligand induction. | 1999 Jul |
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Role of prostaglandins generated by cyclooxygenase-1 and cyclooxygenase-2 in healing of ischemia-reperfusion-induced gastric lesions. | 1999 Nov 26 |
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Oral antinociception and oedema inhibition produced by NPC 18884, a non-peptidic bradykinin B2 receptor antagonist. | 1999 Sep |
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L-NAME causes antinociception by stimulation of the arginine-NO-cGMP pathway. | 2000 |
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Chronic intrathecal cannulation enhances nociceptive responses in rats. | 2000 Aug |
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Induction of cyclooxygenase-2 by overexpression of the human catalase gene in cerebral microvascular endothelial cells. | 2000 Aug |
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Nitric oxide metabolites, prostaglandins and trigeminal vasoactive peptides in internal jugular vein blood during spontaneous migraine attacks. | 2000 Dec |
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Transcriptional regulation of cyclooxygenase-2 gene expression: novel effects of nonsteroidal anti-inflammatory drugs. | 2000 Feb 15 |
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The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs. | 2000 Jan 17 |
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Prostaglandin E2 and the protein kinase A pathway mediate arachidonic acid induction of c-fos in human prostate cancer cells. | 2000 Jun |
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Identification of mu-class glutathione transferases M2-2 and M3-3 as cytosolic prostaglandin E synthases in the human brain. | 2000 May |
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Cyclooxygenase-2 expression in lipopolysaccharide-stimulated human monocytes is modulated by cyclic AMP, prostaglandin E(2), and nonsteroidal anti-inflammatory drugs. | 2000 Nov 30 |
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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 |
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Prostaglandin levels in stimulated macrophages are controlled by phospholipase A2-activating protein and by activation of phospholipase C and D. | 2001 Feb 23 |
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Effects of YM905, a novel muscarinic M3-receptor antagonist, on experimental models of bowel dysfunction in vivo. | 2001 Jul |
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Modulation of haem oxygenase-1 expression by nitric oxide and leukotrienes in zymosan-activated macrophages. | 2001 Jul |
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Characterization of EP receptor subtypes responsible for prostaglandin E2-induced pain responses by use of EP1 and EP3 receptor knockout mice. | 2001 Jun |
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Antinociceptive effects of delta-opioid agonists in Rhesus monkeys: effects on chemically induced thermal hypersensitivity. | 2001 Mar |
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Neurohormonal regulation of secretion from isolated rat stomach ECL cells: a critical reappraisal. | 2001 Mar 2 |
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Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. | 2001 May |
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Deficiency in inducible nitric oxide synthase protects mice from ozone-induced lung inflammation and tissue injury. | 2002 Apr |
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Human organic anion transporters and human organic cation transporters mediate renal transport of prostaglandins. | 2002 Apr |
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Trophic effects of the cyclooxygenase-2 product prostaglandin E(2) in cardiac myocytes. | 2002 Feb |
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A comparative study of the antipyretic effects of indomethacin and dipyrone in rats. | 2002 Jan |
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Characterization of the bone-resorptive effect of interleukin-11 in cultured mouse calvarial bones. | 2002 Jul |
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Nuclear factor-kappaB mediates over-expression of cyclooxygenase-2 during activation of RAW 264.7 macrophages in selenium deficiency. | 2002 May 1 |
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A novel human fibroblast growth factor treats experimental intestinal inflammation. | 2002 Oct |
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Role of NFAT and AP-1 in PGE2-mediated T cell suppression in burn injury. | 2002 Sep |
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Angiotensin II receptor blocker-associated angioedema: on the heels of ACE inhibitor angioedema. | 2002 Sep |
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Contribution of 5- and 12-lipoxygenase products to mechanical hyperalgesia induced by prostaglandin E(2) and epinephrine in the rat. | 2003 Feb |
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Dexamethasone or interleukin-10 blocks interleukin-1beta-induced uterine contractions in pregnant rhesus monkeys. | 2003 Jan |
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PGE(2) is generated by specific COX-2 activity and increases VEGF production in COX-2-expressing human pancreatic cancer cells. | 2003 Jul 11 |
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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 Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12788892
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
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Record UNII |
K7Q1JQR04M
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Validated (UNII)
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LOINC |
12836-3
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70091-4
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2853-0
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C78568
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G02AD02
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14006-1
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C782
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N0000007706
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QG02AD02
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N0000007706
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N0000175454
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N0000007706
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196514
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206-656-6
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PROSTAGLANDIN E2
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363-24-6
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1883
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Dinoprostone
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CHEMBL548
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1213103
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m9258
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C61727
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Related Record | Type | Details | ||
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TARGET -> AGONIST |
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LABELED -> NON-LABELED |
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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INHIBITOR -> TARGET |
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TARGET -> AGONIST |
Ki
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TARGET -> AGONIST |
Ki
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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TARGET -> AGONIST |
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INHIBITOR OF FORMATION->TARGET |
In-vitro in rat polymorphonuclear neutrophils (PMNs)
IC50
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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SALT/SOLVATE -> PARENT |
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
EP
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TARGET -> AGONIST |
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TARGET -> AGONIST |
Ki
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TARGET -> AGONIST |
Ki
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TARGET -> AGONIST |
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
For the calculation of contents, multiply the peak areas by 0.7
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
For the calculation of contents, multiply the peak areas by 0.2
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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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
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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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
|
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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
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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