U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of DINOPROST

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

HIDE SMILES / InChI
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

Curator's Comment: Dinoprost (prostaglandin F2 alpha) is naturally-occurring prostaglandin F2 alpha. It is present in CNS endogenously.

Originator

Curator's Comment: Prostaglandin F2a or Dinoprost is a naturally occuring prostaglandin. Tromethamine salt was prepared at Upjohn.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
29.0 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
PROSTIN F2 ALPHA

Approved Use

Therapeutic 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

Cmax

ValueDoseCo-administeredAnalytePopulation
249.1 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
3.2 ng × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
25.9 min
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
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
The induction of labor at term. Comparisons between prostaglandin F 2 and oxytocin infusions.
1973 Jan
[Effect of prostaglandins F2alpha and E1 on systemic and regional hemodynamics].
1975 Sep-Oct
Prostaglandin-oxytocin induction of mid-trimester abortion complicated by grand mal-like seizures.
1983
Evidence for increased activity of mouse brain fatty acid cyclooxygenase following drug-induced convulsions.
1987 Apr 7
Self-differentiation of human fetal lung organ culture: the role of prostaglandins PGE2 and PGF2 alpha.
1991 May
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
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
Importance of the extracellular domain for prostaglandin EP(2) receptor function.
1999 Sep
Pharmacological characterization of [(3)H]-prostaglandin E(2) binding to the cloned human EP(4) prostanoid receptor.
2000 Aug
Opposite effect of prolactin and prostaglandin F(2 alpha) on the expression of luteal genes as revealed by rat cDNA expression array.
2001 Sep
Cloned human EP1 prostanoid receptor pharmacology characterized using radioligand binding techniques.
2002 Apr
A comparative study of the antipyretic effects of indomethacin and dipyrone in rats.
2002 Jan
Complete recovery after 2 h of cardiopulmonary resuscitation following high-dose prostaglandin treatment for atonic uterine haemorrhage.
2002 Oct
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
Expression and molecular pharmacology of the mouse CRTH2 receptor.
2003 Aug
Plasma membrane calcium ATPase overexpression in arterial smooth muscle increases vasomotor responsiveness and blood pressure.
2003 Oct 3
Renal transport of organic compounds mediated by mouse organic anion transporter 3 (mOat3): further substrate specificity of mOat3.
2004 May
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
Inhibition by licochalcone A, a novel flavonoid isolated from liquorice root, of IL-1beta-induced PGE2 production in human skin fibroblasts.
2005 Dec
Prostaglandins differently regulate FGF-2 and FGF receptor expression and induce nuclear translocation in osteoblasts via MAPK kinase.
2005 Feb
PGF2alpha increases FGF-2 and FGFR2 trafficking in Py1a rat osteoblasts via clathrin independent and importin beta dependent pathway.
2006 Apr 15
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
GW627368X ((N-{2-[4-(4,9-diethoxy-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetyl} benzene sulphonamide): a novel, potent and selective prostanoid EP4 receptor antagonist.
2006 Jun
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
Involvement of endogenous prostaglandin F2alpha on kainic acid-induced seizure activity through FP receptor: the mechanism of proconvulsant effects of COX-2 inhibitors.
2008 Feb 8
Expression of cyclooxygenase genes and production of prostaglandins during ovulation in the ovarian follicles of Xenopus laevis.
2008 Jun
NMDA-induced seizure intensity is enhanced in COX-2 deficient mice.
2008 Nov
Low peripheral progesterone and late embryonic/early fetal loss in suckled beef and lactating dairy cows.
2009 Feb
Conjugated linoleic acid-mediated inflammation and insulin resistance in human adipocytes are attenuated by resveratrol.
2009 Feb
Prostaglandin F2alpha differentially affects mRNA expression relating to angiogenesis, vasoactivation and prostaglandins in the early and mid corpus luteum in the cow.
2010 Aug
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
Effects of PCB126 and 17β-oestradiol on endothelium-derived vasoactive factors in human endothelial cells.
2011 Jul 11
Cyclooxygenase-2 contributes to VX-induced cell death in cultured cortical neurons.
2012 Apr 5
Stereocontrolled organocatalytic synthesis of prostaglandin PGF2α in seven steps.
2012 Sep 13
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
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.
Name Type Language
DINOPROST
HSDB   INN   MART.   USAN   WHO-DD  
USAN   INN  
Official Name English
DINOPROST [JAN]
Common Name English
Dinoprost [WHO-DD]
Common Name English
PROSTAGLANDIN F2.ALPHA. [MI]
Common Name English
U-14583
Code English
PROSTAGLANDIN F2ALPHA
Common Name English
PGF2A
Common Name English
U-14,583
Code English
DINOPROST [HSDB]
Common Name English
PROSTAGLANDIN F2-ALPHA
Common Name English
PROSMON
Brand Name English
PGF2ALPHA
Common Name English
DINOPROST [USAN]
Common Name English
DINOPROST [MART.]
Common Name English
(E,Z)-(1R,2R,3R,5S)-7-[3,5-Dihydroxy-2-[(3S)-(3-hydroxy-1-octenyl)]cyclopentyl]-5-heptenoic acid
Systematic Name English
dinoprost [INN]
Common Name English
PGF2α
Common Name English
PROSTAGLANDIN F2.ALPHA.
MI  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C78568
Created by admin on Fri Dec 15 16:30:33 UTC 2023 , Edited by admin on Fri Dec 15 16:30:33 UTC 2023
CFR 21 CFR 522.690
Created by admin on Fri Dec 15 16:30:33 UTC 2023 , Edited by admin on Fri Dec 15 16:30:33 UTC 2023
WHO-ATC G02AD01
Created by admin on Fri Dec 15 16:30:33 UTC 2023 , Edited by admin on Fri Dec 15 16:30:33 UTC 2023
WHO-VATC QG02AD01
Created by admin on Fri Dec 15 16:30:33 UTC 2023 , Edited by admin on Fri Dec 15 16:30:33 UTC 2023
NCI_THESAURUS C782
Created by admin on Fri Dec 15 16:30:33 UTC 2023 , Edited by admin on Fri Dec 15 16:30:33 UTC 2023
Code System Code Type Description
CAS
551-11-1
Created by admin on Fri Dec 15 16:30:33 UTC 2023 , Edited by admin on Fri Dec 15 16:30:33 UTC 2023
PRIMARY
DRUG CENTRAL
912
Created by admin on Fri Dec 15 16:30:33 UTC 2023 , Edited by admin on Fri Dec 15 16:30:33 UTC 2023
PRIMARY
DRUG BANK
DB12789
Created by admin on Fri Dec 15 16:30:33 UTC 2023 , Edited by admin on Fri Dec 15 16:30:33 UTC 2023
PRIMARY
PUBCHEM
5280363
Created by admin on Fri Dec 15 16:30:33 UTC 2023 , Edited by admin on Fri Dec 15 16:30:33 UTC 2023
PRIMARY
ChEMBL
CHEMBL815
Created by admin on Fri Dec 15 16:30:33 UTC 2023 , Edited by admin on Fri Dec 15 16:30:33 UTC 2023
PRIMARY
MERCK INDEX
m9259
Created by admin on Fri Dec 15 16:30:33 UTC 2023 , Edited by admin on Fri Dec 15 16:30:33 UTC 2023
PRIMARY Merck Index
DAILYMED
B7IN85G1HY
Created by admin on Fri Dec 15 16:30:33 UTC 2023 , Edited by admin on Fri Dec 15 16:30:33 UTC 2023
PRIMARY
RXCUI
3477
Created by admin on Fri Dec 15 16:30:33 UTC 2023 , Edited by admin on Fri Dec 15 16:30:33 UTC 2023
PRIMARY RxNorm
EVMPD
SUB07194MIG
Created by admin on Fri Dec 15 16:30:33 UTC 2023 , Edited by admin on Fri Dec 15 16:30:33 UTC 2023
PRIMARY
SMS_ID
100000088322
Created by admin on Fri Dec 15 16:30:33 UTC 2023 , Edited by admin on Fri Dec 15 16:30:33 UTC 2023
PRIMARY
EPA CompTox
DTXSID9022946
Created by admin on Fri Dec 15 16:30:33 UTC 2023 , Edited by admin on Fri Dec 15 16:30:33 UTC 2023
PRIMARY
WIKIPEDIA
PROSTAGLANDIN F2ALPHA
Created by admin on Fri Dec 15 16:30:33 UTC 2023 , Edited by admin on Fri Dec 15 16:30:33 UTC 2023
PRIMARY
INN
3074
Created by admin on Fri Dec 15 16:30:33 UTC 2023 , Edited by admin on Fri Dec 15 16:30:33 UTC 2023
PRIMARY
CHEBI
15553
Created by admin on Fri Dec 15 16:30:33 UTC 2023 , Edited by admin on Fri Dec 15 16:30:33 UTC 2023
PRIMARY
CHEBI
57404
Created by admin on Fri Dec 15 16:30:33 UTC 2023 , Edited by admin on Fri Dec 15 16:30:33 UTC 2023
PRIMARY
FDA UNII
B7IN85G1HY
Created by admin on Fri Dec 15 16:30:33 UTC 2023 , Edited by admin on Fri Dec 15 16:30:33 UTC 2023
PRIMARY
MESH
D015237
Created by admin on Fri Dec 15 16:30:33 UTC 2023 , Edited by admin on Fri Dec 15 16:30:33 UTC 2023
PRIMARY
NCI_THESAURUS
C65413
Created by admin on Fri Dec 15 16:30:33 UTC 2023 , Edited by admin on Fri Dec 15 16:30:33 UTC 2023
PRIMARY
HSDB
3315
Created by admin on Fri Dec 15 16:30:33 UTC 2023 , Edited by admin on Fri Dec 15 16:30:33 UTC 2023
PRIMARY