Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H34O5.C4H11NO3 |
Molecular Weight | 475.616 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
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)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O
InChI
InChIKey=IYGXEHDCSOYNKY-RZHHZEQLSA-N
InChI=1S/C20H34O5.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/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25);6-8H,1-3,5H2/b7-4-,13-12+;/t15-,16+,17+,18-,19+;/m0./s1
Dinoprost is the synthetic or partially synthetic, naturally-occurring prostaglandin F2 alpha (trade mark Prostin F2 alpha). Dinoprost has been used for therapeutic termination of pregnancy. Although the exact mode of action in pregnancy termination in humans is not fully defined, when Prostin F2 alpha is administered by the intrauterine route it initiates rhythmical uterine contractions which, if continued for a sufficient time, are capable of expelling the contents of
the uterus. Sensitivity of the pregnant uterus to prostaglandins is lower during early and mid-pregnancy than at term.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22609937 | https://www.ncbi.nlm.nih.gov/pubmed/24076168
Curator's Comment: Dinoprost (prostaglandin F2 alpha) is naturally-occurring prostaglandin F2 alpha. It is present in CNS endogenously.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1987 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14733708 |
29.0 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | PROSTIN F2 ALPHA Approved UseTherapeutic termination of pregnancy.
Prostin F2 alpha is indicated for the therapeutic termination of pregnancy during the
first or second trimester.
Prostin F2 alpha may be used for evacuation of the uterus in cases of fetal death in
utero, missed abortion, as a non-surgical treatment for the evacuation of hydatidiform
moles and as an alternative measure to complete therapeutic termination of pregnancy
when intra-amniotic saline injections have failed. |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
249.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22553220/ |
5 mg single, intravenous dose: 5 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
DINOPROST plasma | Equus caballus population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.2 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22553220/ |
5 mg single, intravenous dose: 5 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
DINOPROST plasma | Equus caballus population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
25.9 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22553220/ |
5 mg single, intravenous dose: 5 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
DINOPROST plasma | Equus caballus population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
PubMed
Title | Date | PubMed |
---|---|---|
The induction of labor at term. Comparisons between prostaglandin F 2 and oxytocin infusions. | 1973 Jan |
|
A generalized epileptiform convulsion after intra-amniotic prostaglandin with intravenous oxytocin infusion: a case report. | 1978 Jan 7 |
|
Prostaglandins as abortifacients in Denmark. | 1983 |
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Prostaglandin-oxytocin induction of mid-trimester abortion complicated by grand mal-like seizures. | 1983 |
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Effect of prostaglandins on morphine-induced catalepsy in mice. | 1983 Sep-Dec |
|
Salicylate nephropathy in the Gunn rat: potential role of prostaglandins. | 1985 Sep |
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Participation of prostaglandins E2 and F2 alpha in the action of fibrinopeptides A and B on the central dopaminergic system. | 1986 Jan-Feb |
|
Evidence for increased activity of mouse brain fatty acid cyclooxygenase following drug-induced convulsions. | 1987 Apr 7 |
|
Prostaglandin F2-alpha bladder irrigation for control of intractable cyclophosphamide-induced hemorrhagic cystitis. | 1987 Jun |
|
Plasma level of histamine in aspirin-sensitive urticaria. | 1987 Sep |
|
The use of prostaglandin F2 alpha for the prophylaxis of cyclophosphamide induced cystitis in rats. | 1990 Dec |
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[A case of myocardial infarction associated with pulmonary edema during curettage for hydatidiform mole]. | 1991 Jan |
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Prostaglandins antagonize fibroblast proliferation stimulated by tumor necrosis factor. | 1991 Jan 31 |
|
Self-differentiation of human fetal lung organ culture: the role of prostaglandins PGE2 and PGF2 alpha. | 1991 May |
|
Relative contributions of direct and indirect mechanisms mediating endothelin-induced contraction of guinea-pig trachea. | 1993 Nov |
|
Pinacidil-induced relaxation in pulmonary arteries isolated from pulmonary hypertensive and normotensive rats and pre-contracted with different spasmogens. | 1994 Dec |
|
Successful treatment of hemorrhagic cystitis secondary to cyclophosphamide chemotherapy with intravesical instillation of prostaglandin F2 alpha. | 1994 Sep |
|
Relationship of human liver dihydrodiol dehydrogenases to hepatic bile-acid-binding protein and an oxidoreductase of human colon cells. | 1996 Jan 15 |
|
Molecular cloning and characterization of the four rat prostaglandin E2 prostanoid receptor subtypes. | 1997 Dec 11 |
|
Inhibition of nuclear factor kappa B by prostaglandin A1: an effect associated with heat shock transcription factor activation. | 1997 Jan 21 |
|
Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells. | 1997 Sep |
|
Characterization of the recombinant human prostanoid DP receptor and identification of L-644,698, a novel selective DP agonist. | 1998 Apr |
|
Combined bezafibrate and medroxyprogesterone acetate: potential novel therapy for acute myeloid leukaemia. | 2009 Dec 7 |
|
Functional selectivity of natural and synthetic prostaglandin EP4 receptor ligands. | 2009 Oct |
|
The effect of progesterone on oxytocin-stimulated intracellular Ca2+ mobilisation and prostaglandin secretion in porcine endometrium. | 2010 |
|
Prostaglandin F2alpha differentially affects mRNA expression relating to angiogenesis, vasoactivation and prostaglandins in the early and mid corpus luteum in the cow. | 2010 Aug |
|
Expression of type I GNRH receptor and in vivo and in vitro GNRH-I effects in corpora lutea of pseudopregnant rabbits. | 2010 Dec |
|
Prostaglandin F2α (PGF2α) stimulates PTGS2 expression and PGF2α synthesis through NFKB activation via reactive oxygen species in the corpus luteum of pseudopregnant rats. | 2010 Dec |
|
Inactivation of lipid glyceryl ester metabolism in human THP1 monocytes/macrophages by activated organophosphorus insecticides: role of carboxylesterases 1 and 2. | 2010 Dec 20 |
|
Aldo-keto reductase 1C3 expression in MCF-7 cells reveals roles in steroid hormone and prostaglandin metabolism that may explain its over-expression in breast cancer. | 2010 Feb 15 |
|
Ovarian steroids regulate prostaglandin secretion in the feline endometrium. | 2010 Jul |
|
A novel transporter of SLC22 family specifically transports prostaglandins and co-localizes with 15-hydroxyprostaglandin dehydrogenase in renal proximal tubules. | 2010 Jul 16 |
|
Effect of progesterone withdrawal on hypothalamic mechanisms related to prolactin release in late pregnant rats. | 2011 |
|
Niacin promotes adipogenesis by reducing production of anti-adipogenic PGF2α through suppression of C/EBPβ-activated COX-2 expression. | 2011 Apr |
|
Expression of matrix metalloproteinase (MMP)-2, MMP-14 and tissue inhibitor of matrix metalloproteinase (TIMP)-2 during bovine placentation and at term with or without placental retention. | 2011 Apr 1 |
|
SIRT1 is a novel regulator of key pathways of human labor. | 2011 Jan |
|
Effect of decreasing intraluteal progesterone on sensitivity of the early porcine corpus luteum to the luteolytic actions of prostaglandin F2alpha. | 2011 Jan |
|
Induction of mRNA for chemokines and chemokine receptors by prostaglandin F2α is dependent upon stage of the porcine corpus luteum and intraluteal progesterone. | 2011 Jul |
|
Effects of PCB126 and 17β-oestradiol on endothelium-derived vasoactive factors in human endothelial cells. | 2011 Jul 11 |
|
Role of the DLL4-NOTCH system in PGF2alpha-induced luteolysis in the pregnant rat. | 2011 May |
|
Endometrial HSD11B1 and cortisol regeneration in the ovine uterus: effects of pregnancy, interferon tau, and prostaglandins. | 2012 Apr |
|
Cyclooxygenase-2 contributes to VX-induced cell death in cultured cortical neurons. | 2012 Apr 5 |
|
The dietary fatty acid 10E12Z-CLA induces epiregulin expression through COX-2 dependent PGF(2α) synthesis in adipocytes. | 2012 Oct |
|
Roles of prostaglandin F2alpha and hydrogen peroxide in the regulation of Copper/Zinc superoxide dismutase in bovine corpus luteum and luteal endothelial cells. | 2012 Oct 26 |
|
Stereocontrolled organocatalytic synthesis of prostaglandin PGF2α in seven steps. | 2012 Sep 13 |
|
Preovulatory changes in the angiotensin II system in bovine follicles. | 2013 |
|
Identification of the major prostaglandin glycerol ester hydrolase in human cancer cells. | 2014 Dec 5 |
|
Glutathione peroxidase-1 deficiency potentiates dysregulatory modifications of endothelial nitric oxide synthase and vascular dysfunction in aging. | 2014 Feb |
|
Expression of AKR1B1, AKR1C3 and other genes of prostaglandin F2α biosynthesis and action in ovarian endometriosis tissue and in model cell lines. | 2015 Jun 5 |
|
Inflammatory-mediated pathway in association with organochlorine pesticides levels in the etiology of idiopathic preterm birth. | 2015 Nov |
Patents
Sample Use Guides
For Extra-amniotic Route
A solution containing 250 μg/mL Prostin F2 alpha should be prepared. Insert a 12 to 14
French gauge Foley catheter with self-retaining 30 mL balloon through the cervix into the
space between the fetal membranes and the uterine wall (extra-ovular or extra-amniotic), so
that the balloon passes just beyond the internal os. Fill the balloon with 30 mL sterile water
(a fine polyethylene catheter has also been used). The Prostin F2 alpha solution should then
be instilled through the catheter.
After filling the catheter system deadspace with a predetermined quantity of dilute solution,
the initial dose should be 1 mL. Subsequent instillations should be 3 mL, unless side effects
ensue, when the dose may be reduced to 1 or 2 mL or the interval between doses prolonged.
Two hours should usually elapse between each installation and never less than 1 hour.
For Intra-amniotic Route
A transabdominal tap of the amniotic sac should be accomplished with an appropriate sized
needle and at least 1 mL of amniotic fluid should be withdrawn, then 40 mg (8 mL) of Prostin
F2 alpha is slowly injected into the amniotic sac. It is suggested that the first millilitre be
injected very slowly to determine possible sensitivity prior to completing the total 40 mg
dose. Do not inject medication in the case of a bloody tap.
If within 24 hours of the initial dose the abortion process has not been established or completed
(and in the presence of intact membranes), an additional 10-40 mg (2-8 mL) of Prostin F2 alpha
may be administered.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25924700
Bobine luteal cells obtained at the mid-luteal stage (days 8-12 after ovulation) were cultured with prostaglandin F2α (PGF) (0.01, 0.1, 1 μM), interferon γ (IFNG) (0.05, 0.5, 5 nM) and tumor necrosis factor α (TNF) (0.05, 0.5, 0.5 nM) alone or in combination for 24 h. PGF and IFNG significantly increased the expression of MMP-1 mRNA. In addition, 1 μM PGF in combination with 5 nM IFNG stimulated MMP-1 and MMP-9 mRNA expression significantly more than either treatment alone. In contrast, IFNG significantly decreased the level of MMP-14 mRNA. The mRNA expression of TIMP-1, which preferentially inhibits MMP-1, was suppressed by 5 nM INFG. One μM PGF and 5 nM IFNG suppressed TIMP-2 mRNA expression.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C78568
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ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD