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 Date7.9643522E11 |
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 unknown | 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 |
|
| 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
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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Edited
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| Record UNII |
6V30L285LP
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| Record Status |
Validated (UNII)
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| Record Version |
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5283116
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DTXSID40189722
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36150-00-2
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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