Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H32O5.C4H11NO3 |
| Molecular Weight | 473.6001 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 2 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC(CO)(CO)CO.CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O
InChI
InChIKey=HNMGGLHQYYEEPD-FNCSRODBSA-N
InChI=1S/C20H32O5.C4H11NO3/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;5-4(1-6,2-7)3-8/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25);6-8H,1-3,5H2/b7-4-,13-12+;/t15-,16+,17+,19+;/m0./s1
| Molecular Formula | C4H11NO3 |
| Molecular Weight | 121.135 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| 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 unknown | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| The involvement of K+ channels and Gi/o protein in the antinociceptive action of the gallic acid ethyl ester. | 1999 Aug 20 |
|
| Prostaglandin E2 inhibits T cell activation-induced apoptosis and Fas-mediated cellular cytotoxicity by blockade of Fas-ligand induction. | 1999 Jul |
|
| Indomethacin inhibits expansion of experimental aortic aneurysms via inhibition of the cox2 isoform of cyclooxygenase. | 1999 May |
|
| Selective targeting of cyclooxygenase-2 reveals its role in renal medullary interstitial cell survival. | 1999 Sep |
|
| L-NAME causes antinociception by stimulation of the arginine-NO-cGMP pathway. | 2000 |
|
| Effect of endogenous and exogenous prostaglandin E(2) on interleukin-1 beta-induced cyclooxygenase-2 expression in human airway smooth-muscle cells. | 2000 Dec |
|
| Transcriptional regulation of cyclooxygenase-2 gene expression: novel effects of nonsteroidal anti-inflammatory drugs. | 2000 Feb 15 |
|
| Prostaglandin E2 and the protein kinase A pathway mediate arachidonic acid induction of c-fos in human prostate cancer cells. | 2000 Jun |
|
| Expression of cyclooxygenase (COX)-1 and COX-2 in adaptive cytoprotection induced by mild stress. | 2000 Mar-Apr |
|
| Regulation of leptin release and lipolysis by PGE2 in rat adipose tissue. | 2000 Oct |
|
| 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 |
|
| Flurbiprofen enantiomers inhibit inducible nitric oxide synthase expression in RAW 264.7 macrophages. | 2001 Feb |
|
| Involvement of cyclooxygenase-derived prostaglandin E2 and nitric oxide in the protection of rat pancreas afforded by low dose of lipopolysaccharide. | 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 |
|
| Molecular pharmacology of the human prostaglandin D2 receptor, CRTH2. | 2002 Dec |
|
| A comparative study of the antipyretic effects of indomethacin and dipyrone in rats. | 2002 Jan |
|
| Prostaglandin E2 induces vasodilation and pruritus, but no protein extravasation in atopic dermatitis and controls. | 2002 Jul |
|
| 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 |
|
| Arsenic induces peroxynitrite generation and cyclooxygenase-2 protein expression in aortic endothelial cells: possible role in atherosclerosis. | 2002 Oct 1 |
|
| Suppression of N-nitrosomethylbenzylamine (NMBA)-induced esophageal tumorigenesis in F344 rats by resveratrol. | 2002 Sep |
|
| 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
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 |
E318553LJ7
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| Record Status |
Validated (UNII)
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