Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H32O5 |
| Molecular Weight | 352.4651 |
| Optical Activity | UNSPECIFIED |
| 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-BRNHSORCSA-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 |
|||
Target ID: CHEMBL1811 |
|||
Target ID: CHEMBL1836 |
3.0 nM [EC50] | ||
Target ID: CHEMBL1881 |
2.1 nM [EC50] | ||
Target ID: CHEMBL1811 |
9.1 nM [Ki] | ||
Target ID: CHEMBL3710 |
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 |
|---|---|---|
| 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 |
|
| Regulation of RANTES and ICAM-1 expression in murine mesangial cells. | 1997 Apr |
|
| Differential regulation of renal prostaglandin receptor mRNAs by dietary salt intake in the rat. | 1999 Aug |
|
| The influence of indomethacin on the metabolism and cytokine secretion of human aneurysmal aorta. | 1999 Jul |
|
| Prostaglandins and leukotriene B4 are potent inhibitors of 11beta-hydroxysteroid dehydrogenase type 2 activity in human choriocarcinoma JEG-3 cells. | 1999 Jul |
|
| Pharmacological modulation of secondary mediator systems--cyclic AMP and cyclic GMP--on inflammatory hyperalgesia. | 1999 Jun |
|
| Arachidonic acid and PGE2 regulation of hepatic lipogenic gene expression. | 1999 Jun |
|
| Effect of the 5-hydroxytryptamine3 (5-HT3)-receptor antagonist KB-R6933 on experimental diarrhea models. | 1999 May |
|
| A KATP-channel opener as a potential treatment modality for erectile dysfunction. | 1999 May |
|
| Indomethacin inhibits expansion of experimental aortic aneurysms via inhibition of the cox2 isoform of cyclooxygenase. | 1999 May |
|
| 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 |
|
| Regulation of leptin release and lipolysis by PGE2 in rat adipose tissue. | 2000 Oct |
|
| 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 |
|
| Stimulation of cyclooxygenase-2-activity by nitric oxide-derived species in rat chondrocyte: lack of contribution to loss of cartilage anabolism. | 2001 Apr 15 |
|
| 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 |
|
| Sex hormones regulate the contribution of PKCepsilon and PKA signalling in inflammatory pain in the rat. | 2001 Jun |
|
| Characterization of EP receptor subtypes responsible for prostaglandin E2-induced pain responses by use of EP1 and EP3 receptor knockout mice. | 2001 Jun |
|
| Prostaglandin E(2) is a selective inducer of interleukin-12 p40 (IL-12p40) production and an inhibitor of bioactive IL-12p70 heterodimer. | 2001 Jun 1 |
|
| Stimulative effect of cadmium on prostaglandin E2 production in primary mouse osteoblastic cells. | 2001 Mar |
|
| Involvement of cyclooxygenase-derived prostaglandin E2 and nitric oxide in the protection of rat pancreas afforded by low dose of lipopolysaccharide. | 2001 Mar |
|
| Interactions of inflammatory mediators stimulating release of calcitonin gene-related peptide, substance P and prostaglandin E(2) from isolated rat skin. | 2001 Mar |
|
| Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. | 2001 May |
|
| Possible role of prostaglandin E2 in human amniotic epithelial cell death: an in vitro study. | 2001 Oct |
|
| 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 |
|
| 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 |
|
| ATP can enhance the proton-induced CGRP release through P2Y receptors and secondary PGE(2) release in isolated rat dura mater. | 2002 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 |
|
| 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 |
|
| 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
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 |
6V30L285LP
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| Record Status |
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
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