Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H34O5 |
Molecular Weight | 354.481 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 2 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
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=PXGPLTODNUVGFL-YNNPMVKQSA-N
InChI=1S/C20H34O5/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/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/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 |
---|---|---|
Plasma level of histamine in aspirin-sensitive urticaria. | 1987 Sep |
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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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Effect of frusemide on the induction and potentiation of cough induced by prostaglandin F2 alpha. | 1992 May |
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Influences of cyclooxygenase inhibitors on the cataleptic behavior induced by haloperidol in mice. | 1992 May |
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Pinacidil-induced relaxation in pulmonary arteries isolated from pulmonary hypertensive and normotensive rats and pre-contracted with different spasmogens. | 1994 Dec |
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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 |
|
Prostaglandins and leukotriene B4 are potent inhibitors of 11beta-hydroxysteroid dehydrogenase type 2 activity in human choriocarcinoma JEG-3 cells. | 1999 Jul |
|
Effects of mexiletine on algogenic mediator-induced nociceptive responses in mice. | 1999 Jul-Aug |
|
Arachidonic acid and PGE2 regulation of hepatic lipogenic gene expression. | 1999 Jun |
|
Matrix metalloproteinase (MMP)-2 and MMP-9 and their inhibitor, TIMP-1, in human term decidua and fetal membranes: the effect of prostaglandin F(2alpha) and indomethacin. | 2001 Dec |
|
Opposite effect of prolactin and prostaglandin F(2 alpha) on the expression of luteal genes as revealed by rat cDNA expression array. | 2001 Sep |
|
Molecular pharmacology of the human prostaglandin D2 receptor, CRTH2. | 2002 Dec |
|
Renal transport of organic compounds mediated by mouse organic anion transporter 3 (mOat3): further substrate specificity of mOat3. | 2004 May |
|
In vivo and in vitro inhibition of cyp19 gene expression by prostaglandin F2alpha in murine luteal cells: implication of GATA-4. | 2004 Nov |
|
Effects of selective protein kinase c isozymes in prostaglandin2alpha-induced Ca2+ signaling and luteinizing hormone-induced progesterone accumulation in the mid-phase bovine corpus luteum. | 2005 Apr |
|
Transport mechanism and substrate specificity of human organic anion transporter 2 (hOat2 [SLC22A7]). | 2005 May |
|
Inhibition of prostaglandin F2alpha synthesis and oxytocin receptor by progesterone antagonists in bovine endometrial cells in vitro. | 2006 Sep |
|
Infusion of exogenous tumor necrosis factor dose dependently alters the length of the luteal phase in cattle: differential responses to treatment with indomethacin and L-NAME, a nitric oxide synthase inhibitor. | 2007 Apr |
|
Anti-apoptotic roles of prostaglandin E2 and F2alpha in bovine luteal steroidogenic cells. | 2008 Aug |
|
NMDA-induced seizure intensity is enhanced in COX-2 deficient mice. | 2008 Nov |
|
Combined bezafibrate and medroxyprogesterone acetate: potential novel therapy for acute myeloid leukaemia. | 2009 Dec 7 |
|
Low peripheral progesterone and late embryonic/early fetal loss in suckled beef and lactating dairy cows. | 2009 Feb |
|
p66Shc links alpha1-adrenergic receptors to a reactive oxygen species-dependent AKT-FOXO3A phosphorylation pathway in cardiomyocytes. | 2009 Mar 13 |
|
Involvement of the transcription factor STAT1 in the regulation of porcine ovarian granulosa cell functions treated and not treated with ghrelin. | 2009 Sep |
|
Ovarian steroids regulate prostaglandin secretion in the feline endometrium. | 2010 Jul |
|
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 |
|
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 |
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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CFR |
21 CFR 522.690
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G02AD01
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QG02AD01
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NCI_THESAURUS |
C782
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551-11-1
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912
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DB12789
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5280363
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CHEMBL815
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M9259
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B7IN85G1HY
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3477
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SUB07194MIG
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DTXSID9022946
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PROSTAGLANDIN F2ALPHA
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3074
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15553
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B7IN85G1HY
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D015237
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C65413
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3315
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ACTIVE MOIETY
METABOLITE (PARENT)
PRODRUG (METABOLITE ACTIVE)
SALT/SOLVATE (PARENT)