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
Molecular Formula | C20H34O5 |
Molecular Weight | 354.481 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 2 |
Optical Activity | UNSPECIFIED |
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 |
|
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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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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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 |
|
Arachidonic acid and PGE2 regulation of hepatic lipogenic gene expression. | 1999 Jun |
|
The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs. | 2000 Jan 17 |
|
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 |
|
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 |
|
Prostaglandins differently regulate FGF-2 and FGF receptor expression and induce nuclear translocation in osteoblasts via MAPK kinase. | 2005 Feb |
|
Transport mechanism and substrate specificity of human organic anion transporter 2 (hOat2 [SLC22A7]). | 2005 May |
|
Enhancement of transformed foci and induction of prostaglandins in Balb/c 3T3 cells by palytoxin: in vitro model reproduces carcinogenic responses in animal models regarding the inhibitory effect of indomethacin and reversal of indomethacin's effect by exogenous prostaglandins. | 2006 Jan |
|
Evidence that the preovulatory rise in intrafollicular progesterone may not be required for ovulation in cattle. | 2007 Mar |
|
Anti-apoptotic roles of prostaglandin E2 and F2alpha in bovine luteal steroidogenic cells. | 2008 Aug |
|
Induction of heparanase in bovine granulosa cells by luteinizing hormone: possible role during the ovulatory process. | 2009 Jan |
|
Chinese hamster monomeric carbonyl reductases of the short-chain dehydrogenase/reductase superfamily. | 2009 Mar 16 |
|
Expression of type I GNRH receptor and in vivo and in vitro GNRH-I effects in corpora lutea of pseudopregnant rabbits. | 2010 Dec |
|
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 |
|
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.
Substance Class |
Chemical
Created
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admin
on
Edited
Fri Dec 15 16:30:33 GMT 2023
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Record UNII |
B7IN85G1HY
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Record Status |
Validated (UNII)
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Record Version |
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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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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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100000088322
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DTXSID9022946
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PROSTAGLANDIN F2ALPHA
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3074
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D015237
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C65413
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3315
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Related Record | Type | Details | ||
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TARGET -> AGONIST |
BINDING
Ki
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SALT/SOLVATE -> PARENT |
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TARGET -> AGONIST |
BINDING
Ki
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Related Record | Type | Details | ||
---|---|---|---|---|
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METABOLITE -> PARENT |
URINE
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PRODRUG -> METABOLITE ACTIVE |
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Related Record | Type | Details | ||
---|---|---|---|---|
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ACTIVE MOIETY |
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