Synonym
Dinoprost Tromethamine; Dinoprost Trometamol; Zinoprost; Prostamate; Dinolytic; Prostaglandin F Tromethamine Salt; U 14585; U14585; U-14585; NSC 196515; NSC196515; NSC-196515;
IUPAC/Chemical Name
Prosta-5,13-dien-1-oic acid, 9,11,15-trihydroxy-, (5Z,9α,11α,13E,15S)-, compd. with 2-amino-2-(hydroxymethyl)-1,3-propanediol (1:1)
InChi Key
IYGXEHDCSOYNKY-RZHHZEQLSA-N
InChi Code
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
SMILES Code
CCCCC[C@@H](/C=C/[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)O)O)O.C(C(CO)(CO)N)O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Dinoprost tromethamine salt (Prostaglandin F2α tromethamine salt) is an orally active, potent prostaglandin F (PGF) receptor (FP receptor) agonist.
In vitro activity:
The ET-1-induced (10(-8) M) contraction in isolated BTM was inhibited by PGF2alpha (10(-6) M) and fluprostenol (10(-6) M). This effect was blocked by FP receptor antagonists. In cultured TM cells, ET-1 caused a transient increase in [Ca2+]i that was reduced by PGF2alpha.
Reference: Invest Ophthalmol Vis Sci. 2006 Mar;47(3):938-45. https://pubmed.ncbi.nlm.nih.gov/16505027/
In vivo activity:
PGF2α decreased PTGFR expression in bovine cells derived from the 4th month of gestation (p < 0.05).
Reference: Molecules. 2022 Nov 1;27(21):7420. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9653824/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
80.9 |
170.00 |
| Ethanol |
71.3 |
149.87 |
| Water |
97.5 |
205.00 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
475.62
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Wen X, Liu L, Li S, Lin P, Chen H, Zhou D, Tang K, Wang A, Jin Y. Prostaglandin F2α Induces Goat Corpus Luteum Regression via Endoplasmic Reticulum Stress and Autophagy. Front Physiol. 2020 Sep 11;11:868. doi: 10.3389/fphys.2020.00868. PMID: 33013430; PMCID: PMC7516216.
2. Thieme H, Schimmat C, Münzer G, Boxberger M, Fromm M, Pfeiffer N, Rosenthal R. Endothelin antagonism: effects of FP receptor agonists prostaglandin F2alpha and fluprostenol on trabecular meshwork contractility. Invest Ophthalmol Vis Sci. 2006 Mar;47(3):938-45. doi: 10.1167/iovs.05-0527. PMID: 16505027.
3. Jamioł M, Sozoniuk M, Wawrzykowski J, Kankofer M. Effect of Sex Steroids and PGF2α on the Expression of Their Receptors and Decorin in Bovine Caruncular Epithelial Cells in Early-Mid Pregnancy. Molecules. 2022 Nov 1;27(21):7420. doi: 10.3390/molecules27217420. PMID: 36364246; PMCID: PMC9653824.
4. Sun Y, Yan Y, Kang X. Packed-Fiber Solid Phase-Extraction Coupled with HPLC-MS/MS for Rapid Determination of Lipid Oxidative Damage Biomarker 8-Iso-Prostaglandin F2α in Urine. Molecules. 2022 Jul 10;27(14):4417. doi: 10.3390/molecules27144417. PMID: 35889290; PMCID: PMC9318247.
In vitro protocol:
1. Wen X, Liu L, Li S, Lin P, Chen H, Zhou D, Tang K, Wang A, Jin Y. Prostaglandin F2α Induces Goat Corpus Luteum Regression via Endoplasmic Reticulum Stress and Autophagy. Front Physiol. 2020 Sep 11;11:868. doi: 10.3389/fphys.2020.00868. PMID: 33013430; PMCID: PMC7516216.
2. Thieme H, Schimmat C, Münzer G, Boxberger M, Fromm M, Pfeiffer N, Rosenthal R. Endothelin antagonism: effects of FP receptor agonists prostaglandin F2alpha and fluprostenol on trabecular meshwork contractility. Invest Ophthalmol Vis Sci. 2006 Mar;47(3):938-45. doi: 10.1167/iovs.05-0527. PMID: 16505027.
In vivo protocol:
1. Jamioł M, Sozoniuk M, Wawrzykowski J, Kankofer M. Effect of Sex Steroids and PGF2α on the Expression of Their Receptors and Decorin in Bovine Caruncular Epithelial Cells in Early-Mid Pregnancy. Molecules. 2022 Nov 1;27(21):7420. doi: 10.3390/molecules27217420. PMID: 36364246; PMCID: PMC9653824.
2. Sun Y, Yan Y, Kang X. Packed-Fiber Solid Phase-Extraction Coupled with HPLC-MS/MS for Rapid Determination of Lipid Oxidative Damage Biomarker 8-Iso-Prostaglandin F2α in Urine. Molecules. 2022 Jul 10;27(14):4417. doi: 10.3390/molecules27144417. PMID: 35889290; PMCID: PMC9318247.
1: Pursley JR, Martins JP, Wright C, Stewart ND. Compared to dinoprost tromethamine, cloprostenol sodium increased rates of estrus detection, conception and pregnancy in lactating dairy cows on a large commercial dairy. Theriogenology. 2012 Sep 1;78(4):823-9. doi: 10.1016/j.theriogenology.2012.03.032. Epub 2012 May 22. PubMed PMID: 22626771.
2: Salverson RR, DeJarnette JM, Marshall CE, Wallace RA. Synchronization of estrus in virgin beef heifers using melengestrol acetate and PGF2alpha: an efficacy comparison of cloprostenol and dinoprost tromethamine. Theriogenology. 2002 Jan 15;57(2):853-8. PubMed PMID: 11991389.
3: Nie GJ, Goodin AN, Braden TD, Wenzel JG. Luteal and clinical response following administration of dinoprost tromethamine or cloprostenol at standard intramuscular sites or at the lumbosacral acupuncture point in mares. Am J Vet Res. 2001 Aug;62(8):1285-9. PubMed PMID: 11497452.
4: Bell WR, Wentz AC. Abortion and coagulation by prostaglandin. Intra-amniotic dinoprost tromethamine effect on the coagulation and fibrinolytic systems. JAMA. 1973 Aug 27;225(9):1082-4. PubMed PMID: 4740610.
5: Chebel RC, Santos JE, Rutigliano HM, Cerri RL. Efficacy of an injection of dinoprost tromethamine when given subcutaneously on luteal regression in lactating Holstein cows. Theriogenology. 2007 Feb;67(3):590-7. Epub 2006 Nov 28. PubMed PMID: 17126390.
6: Voh AA Jr, Oyedipe EO, Pathiraja N, Buvanendran V, Kumi-Diaka J. Peripheral plasma levels of progesterone in Nigerian Zebu cows following synchronization of oestrus with prostaglandin F2 alpha analogue (Dinoprost tromethamine). Br Vet J. 1987 May-Jun;143(3):254-63. PubMed PMID: 3594195.
7: Young IM, Anderson DB. Improved reproductive performance from dairy cows treated with dinoprost tromethamine soon after calving. Theriogenology. 1986 Aug;26(2):199-208. PubMed PMID: 16726184.
8: Young IM, Anderson DB. First service conception rate in dairy cows treated with dinoprost tromethamine early post partum. Vet Rec. 1986 Feb 22;118(8):212-3. PubMed PMID: 3716167.
9: Dinoprost tromethamine: first of the new wonder drugs? Nursing. 1974 Oct;4(10):81-2. PubMed PMID: 4497054.
