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

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
Structure of DINOPROST TROMETHAMINE

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

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
A generalized epileptiform convulsion after intra-amniotic prostaglandin with intravenous oxytocin infusion: a case report.
1978 Jan 7
Prostaglandins as abortifacients in Denmark.
1983
Prostaglandin-oxytocin induction of mid-trimester abortion complicated by grand mal-like seizures.
1983
Effect of prostaglandins on morphine-induced catalepsy in mice.
1983 Sep-Dec
Salicylate nephropathy in the Gunn rat: potential role of prostaglandins.
1985 Sep
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
[A case of myocardial infarction associated with pulmonary edema during curettage for hydatidiform mole].
1991 Jan
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
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 TROMETHAMINE
GREEN BOOK   JAN   ORANGE BOOK   USAN   USP   USP-RS   VANDF  
USAN  
Official Name English
DINOPROST TROMETHAMINE [USP-RS]
Common Name English
PROSTAGLANDIN F2.ALPHA. TROMETHAMINE SALT [MI]
Common Name English
(E,Z)-(1R,2R,3R,5S)-7-[3,5-Dihydroxy-2-[(3S)-(3-hydroxy-1-octenyl)]cyclopentyl]-5-heptenoic acid compound with 2-amino-2-(hydroxymethyl)-1,3-propanediol (1:1)
Systematic Name English
PGF2ALPHA-THAM
Code English
DINOPROST TROMETHAMINE [USP MONOGRAPH]
Common Name English
DINOPROST TROMETHAMINE [GREEN BOOK]
Common Name English
PROSTAGLANDIN F2.ALPHA. TROMETHAMINE SALT
MI  
Common Name English
U-14,583E
Code English
NSC-196515
Code English
PROSTA-5,13-DIEN-1-OIC ACID, 9,11,15-TRIHYDROXY-, (5Z,9.ALPHA.,11.ALPHA.,13E,15S)-, COMPD. WITH 2-AMINO-2-(HYDROXYMETHYL)-1,3-PROPANEDIOL (1:1)
Common Name English
DINOPROST TROMETAMOL [MART.]
Common Name English
DINOPROST TROMETAMOL
EP   MART.   WHO-DD  
Common Name English
DINOPROST TROMETHAMINE [VANDF]
Common Name English
U-14-583E
Code English
Dinoprost trometamol [WHO-DD]
Common Name English
DINOPROST TROMETHAMINE [USAN]
Common Name English
PROSTIN F2 ALPHA
Brand Name English
DINOPROST TROMETAMOL [EP MONOGRAPH]
Common Name English
PROSTAGLANDIN F(SUB 2A) TROMETHAMINE
Common Name English
U-14583E
Code English
DINOPROST TROMETHAMINE [JAN]
Common Name English
PGF2A THAM
Code English
DINOPROST TROMETHAMINE [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C78568
Created by admin on Fri Dec 15 15:10:33 GMT 2023 , Edited by admin on Fri Dec 15 15:10:33 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C1074
Created by admin on Fri Dec 15 15:10:33 GMT 2023 , Edited by admin on Fri Dec 15 15:10:33 GMT 2023
PRIMARY
EVMPD
SUB75954
Created by admin on Fri Dec 15 15:10:33 GMT 2023 , Edited by admin on Fri Dec 15 15:10:33 GMT 2023
PRIMARY
ChEMBL
CHEMBL815
Created by admin on Fri Dec 15 15:10:33 GMT 2023 , Edited by admin on Fri Dec 15 15:10:33 GMT 2023
PRIMARY
EVMPD
SUB01758MIG
Created by admin on Fri Dec 15 15:10:33 GMT 2023 , Edited by admin on Fri Dec 15 15:10:33 GMT 2023
PRIMARY
RXCUI
23321
Created by admin on Fri Dec 15 15:10:33 GMT 2023 , Edited by admin on Fri Dec 15 15:10:33 GMT 2023
PRIMARY RxNorm
PUBCHEM
5282415
Created by admin on Fri Dec 15 15:10:33 GMT 2023 , Edited by admin on Fri Dec 15 15:10:33 GMT 2023
PRIMARY
EPA CompTox
DTXSID1045582
Created by admin on Fri Dec 15 15:10:33 GMT 2023 , Edited by admin on Fri Dec 15 15:10:33 GMT 2023
PRIMARY
RS_ITEM_NUM
1213001
Created by admin on Fri Dec 15 15:10:33 GMT 2023 , Edited by admin on Fri Dec 15 15:10:33 GMT 2023
PRIMARY
NSC
196515
Created by admin on Fri Dec 15 15:10:33 GMT 2023 , Edited by admin on Fri Dec 15 15:10:33 GMT 2023
PRIMARY
FDA UNII
CT6BBQ5A68
Created by admin on Fri Dec 15 15:10:33 GMT 2023 , Edited by admin on Fri Dec 15 15:10:33 GMT 2023
PRIMARY
MERCK INDEX
m9259
Created by admin on Fri Dec 15 15:10:33 GMT 2023 , Edited by admin on Fri Dec 15 15:10:33 GMT 2023
PRIMARY Merck Index
DRUG BANK
DB01160
Created by admin on Fri Dec 15 15:10:33 GMT 2023 , Edited by admin on Fri Dec 15 15:10:33 GMT 2023
PRIMARY
DAILYMED
CT6BBQ5A68
Created by admin on Fri Dec 15 15:10:33 GMT 2023 , Edited by admin on Fri Dec 15 15:10:33 GMT 2023
PRIMARY
MESH
C010714
Created by admin on Fri Dec 15 15:10:33 GMT 2023 , Edited by admin on Fri Dec 15 15:10:33 GMT 2023
PRIMARY
ECHA (EC/EINECS)
254-002-3
Created by admin on Fri Dec 15 15:10:33 GMT 2023 , Edited by admin on Fri Dec 15 15:10:33 GMT 2023
PRIMARY
SMS_ID
100000085192
Created by admin on Fri Dec 15 15:10:33 GMT 2023 , Edited by admin on Fri Dec 15 15:10:33 GMT 2023
PRIMARY
CAS
38562-01-5
Created by admin on Fri Dec 15 15:10:33 GMT 2023 , Edited by admin on Fri Dec 15 15:10:33 GMT 2023
PRIMARY