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
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 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 |
|
| Differential regulation of renal prostaglandin receptor mRNAs by dietary salt intake in the rat. | 1999 Aug |
|
| The involvement of K+ channels and Gi/o protein in the antinociceptive action of the gallic acid ethyl ester. | 1999 Aug 20 |
|
| Indomethacin inhibits expansion of experimental aortic aneurysms via inhibition of the cox2 isoform of cyclooxygenase. | 1999 May |
|
| The role of nitric oxide and prostaglandin E2 on the hyperalgesia induced by excitatory amino acids in rats. | 2000 Apr |
|
| Chronic intrathecal cannulation enhances nociceptive responses in rats. | 2000 Aug |
|
| Regulation of prostaglandin endoperoxide H synthase-2 induction by dioxin in rat hepatocytes: possible c-Src-mediated pathway. | 2000 Dec |
|
| Effect of endogenous and exogenous prostaglandin E(2) on interleukin-1 beta-induced cyclooxygenase-2 expression in human airway smooth-muscle cells. | 2000 Dec |
|
| Sulindac sulfone inhibits K-ras-dependent cyclooxygenase-2 expression in human colon cancer cells. | 2000 Dec 1 |
|
| Prostaglandin E2 and the protein kinase A pathway mediate arachidonic acid induction of c-fos in human prostate cancer cells. | 2000 Jun |
|
| A protective role for cyclooxygenase-2 in drug-induced liver injury in mice. | 2001 Dec |
|
| Flurbiprofen enantiomers inhibit inducible nitric oxide synthase expression in RAW 264.7 macrophages. | 2001 Feb |
|
| Stimulative effect of cadmium on prostaglandin E2 production in primary mouse osteoblastic cells. | 2001 Mar |
|
| Antinociceptive effects of delta-opioid agonists in Rhesus monkeys: effects on chemically induced thermal hypersensitivity. | 2001 Mar |
|
| Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. | 2001 May |
|
| Cloned human EP1 prostanoid receptor pharmacology characterized using radioligand binding techniques. | 2002 Apr |
|
| Peripheral group II metabotropic glutamate receptors (mGluR2/3) regulate prostaglandin E2-mediated sensitization of capsaicin responses and thermal nociception. | 2002 Aug 1 |
|
| 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 |
|
| 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 |
|
| Downregulation of COX-2 and iNOS by amentoflavone and quercetin in A549 human lung adenocarcinoma cell line. | 2002 May-Jun |
|
| 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 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 |
|
| 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 |
|
| Mechanisms of cytosolic Ca2+ suppression by prostaglandin E2 receptors in rat melanotrophs. | 2003 Jan |
|
| PGE(2) is generated by specific COX-2 activity and increases VEGF production in COX-2-expressing human pancreatic cancer cells. | 2003 Jul 11 |
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.
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SUBSTANCE RECORD
