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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

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

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
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
Pinacidil-induced relaxation in pulmonary arteries isolated from pulmonary hypertensive and normotensive rats and pre-contracted with different spasmogens.
1994 Dec
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
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
by admin
on Fri Dec 15 16:30:33 GMT 2023
Edited
by admin
on Fri Dec 15 16:30:33 GMT 2023
Record UNII
B7IN85G1HY
Record Status Validated (UNII)
Record Version
  • Download
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 GMT 2023 , Edited by admin on Fri Dec 15 16:30:33 GMT 2023
CFR 21 CFR 522.690
Created by admin on Fri Dec 15 16:30:33 GMT 2023 , Edited by admin on Fri Dec 15 16:30:33 GMT 2023
WHO-ATC G02AD01
Created by admin on Fri Dec 15 16:30:33 GMT 2023 , Edited by admin on Fri Dec 15 16:30:33 GMT 2023
WHO-VATC QG02AD01
Created by admin on Fri Dec 15 16:30:33 GMT 2023 , Edited by admin on Fri Dec 15 16:30:33 GMT 2023
NCI_THESAURUS C782
Created by admin on Fri Dec 15 16:30:33 GMT 2023 , Edited by admin on Fri Dec 15 16:30:33 GMT 2023
Code System Code Type Description
CAS
551-11-1
Created by admin on Fri Dec 15 16:30:33 GMT 2023 , Edited by admin on Fri Dec 15 16:30:33 GMT 2023
PRIMARY
DRUG CENTRAL
912
Created by admin on Fri Dec 15 16:30:33 GMT 2023 , Edited by admin on Fri Dec 15 16:30:33 GMT 2023
PRIMARY
DRUG BANK
DB12789
Created by admin on Fri Dec 15 16:30:33 GMT 2023 , Edited by admin on Fri Dec 15 16:30:33 GMT 2023
PRIMARY
PUBCHEM
5280363
Created by admin on Fri Dec 15 16:30:33 GMT 2023 , Edited by admin on Fri Dec 15 16:30:33 GMT 2023
PRIMARY
ChEMBL
CHEMBL815
Created by admin on Fri Dec 15 16:30:33 GMT 2023 , Edited by admin on Fri Dec 15 16:30:33 GMT 2023
PRIMARY
MERCK INDEX
m9259
Created by admin on Fri Dec 15 16:30:33 GMT 2023 , Edited by admin on Fri Dec 15 16:30:33 GMT 2023
PRIMARY Merck Index
DAILYMED
B7IN85G1HY
Created by admin on Fri Dec 15 16:30:33 GMT 2023 , Edited by admin on Fri Dec 15 16:30:33 GMT 2023
PRIMARY
RXCUI
3477
Created by admin on Fri Dec 15 16:30:33 GMT 2023 , Edited by admin on Fri Dec 15 16:30:33 GMT 2023
PRIMARY RxNorm
EVMPD
SUB07194MIG
Created by admin on Fri Dec 15 16:30:33 GMT 2023 , Edited by admin on Fri Dec 15 16:30:33 GMT 2023
PRIMARY
SMS_ID
100000088322
Created by admin on Fri Dec 15 16:30:33 GMT 2023 , Edited by admin on Fri Dec 15 16:30:33 GMT 2023
PRIMARY
EPA CompTox
DTXSID9022946
Created by admin on Fri Dec 15 16:30:33 GMT 2023 , Edited by admin on Fri Dec 15 16:30:33 GMT 2023
PRIMARY
WIKIPEDIA
PROSTAGLANDIN F2ALPHA
Created by admin on Fri Dec 15 16:30:33 GMT 2023 , Edited by admin on Fri Dec 15 16:30:33 GMT 2023
PRIMARY
INN
3074
Created by admin on Fri Dec 15 16:30:33 GMT 2023 , Edited by admin on Fri Dec 15 16:30:33 GMT 2023
PRIMARY
CHEBI
15553
Created by admin on Fri Dec 15 16:30:33 GMT 2023 , Edited by admin on Fri Dec 15 16:30:33 GMT 2023
PRIMARY
CHEBI
57404
Created by admin on Fri Dec 15 16:30:33 GMT 2023 , Edited by admin on Fri Dec 15 16:30:33 GMT 2023
PRIMARY
FDA UNII
B7IN85G1HY
Created by admin on Fri Dec 15 16:30:33 GMT 2023 , Edited by admin on Fri Dec 15 16:30:33 GMT 2023
PRIMARY
MESH
D015237
Created by admin on Fri Dec 15 16:30:33 GMT 2023 , Edited by admin on Fri Dec 15 16:30:33 GMT 2023
PRIMARY
NCI_THESAURUS
C65413
Created by admin on Fri Dec 15 16:30:33 GMT 2023 , Edited by admin on Fri Dec 15 16:30:33 GMT 2023
PRIMARY
HSDB
3315
Created by admin on Fri Dec 15 16:30:33 GMT 2023 , Edited by admin on Fri Dec 15 16:30:33 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> AGONIST
BINDING
Ki
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
BINDING
Ki
Related Record Type Details
METABOLITE -> PARENT
URINE
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
ACTIVE MOIETY