Dinoprost | CAS#551-11-1 | prostaglandin

MedKoo Cat#: 597705 | Name: Dinoprost

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Dinoprost, also known as Prostaglandin F2alpha, is a naturally occurring prostaglandin that has oxytocic, luteolytic, and abortifacient activities. It is a naturally occurring prostaglandin used in medicine to induce labor.

Chemical Structure

Dinoprost

CAS#551-11-1 (free acid)

Theoretical Analysis

MedKoo Cat#: 597705

Name: Dinoprost

CAS#: 551-11-1 (free acid)

Chemical Formula: C20H34O5

Exact Mass: 354.2406

Molecular Weight: 354.49

Elemental Analysis: C, 67.77; H, 9.67; O, 22.57

Price and Availability

Size	Price	Availability
5mg	USD 265.00	2 Weeks
10mg	USD 485.00	2 Weeks
25mg	USD 850.00	2 Weeks

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Related CAS #

551-11-1 (free acid) 101913-98-8 (methoxyamine) 38562-01-5 (tromethamine)

Synonym

Prostaglandin F2α; PGF2α; Prostaglandin F2alpha; Prostaglandin F2a; Panacelan; Cerviprost;

IUPAC/Chemical Name

(Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((S,E)-3-hydroxyoct-1-en-1-yl)cyclopentyl)hept-5-enoic acid

InChi Key

PXGPLTODNUVGFL-YNNPMVKQSA-N

InChi Code

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

SMILES Code

CCCCC[C@H](O)/C=C/[C@@H]1[C@H]([C@@H](O)C[C@H]1O)C/C=C\CCCC(O)=O

Appearance

Solid powder

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

Shelf Life

>3 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

2934.99.03.00

More Info

The PGF2α isoform 8-iso-PGF2α was found in significantly increased amounts in patients with endometriosis, thus being a potential causative link in endometriosis-associated oxidative stress.

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Dinoprost (Prostaglandin F2α) 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	100.0	282.10
	Water	100.0	282.10

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 354.49 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:

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: Mekuriaw Z, Assefa H, Tegegne A, Muluneh D. Estrus response and fertility of Menz and crossbred ewes to single prostaglandin injection protocol. Trop Anim Health Prod. 2016 Jan;48(1):53-7. doi: 10.1007/s11250-015-0919-z. Epub 2015 Oct 6. PubMed PMID: 26439244. 3: Prévost S, Thai K, Schützenmeister N, Coulthard G, Erb W, Aggarwal VK. Synthesis of prostaglandin analogues, latanoprost and bimatoprost, using organocatalysis via a key bicyclic enal intermediate. Org Lett. 2015 Feb 6;17(3):504-7. doi: 10.1021/ol503520f. Epub 2015 Jan 12. PubMed PMID: 25582321. 4: Santos VG, Castro T, Bettencourt EM, Ginther OJ. Oxytocin induction of pulses of a prostaglandin metabolite and luteolysis in mares. Theriogenology. 2015 Mar 1;83(4):730-8. doi: 10.1016/j.theriogenology.2014.11.006. Epub 2014 Nov 13. PubMed PMID: 25523835. 5: Maślanka T. Pharmacology of topical prostaglandin F2 α analogs and their place in the treatment of glaucoma in small animals. J Vet Pharmacol Ther. 2015 Apr;38(2):105-12. doi: 10.1111/jvp.12161. Epub 2014 Sep 17. Review. PubMed PMID: 25230091. 6: Santos JM, Jurban M, Kim H. Could sewage epidemiology be a strategy to assess lifestyle and wellness of a large scale population? Med Hypotheses. 2015 Oct;85(4):408-11. doi: 10.1016/j.mehy.2015.06.020. Epub 2015 Jun 26. PubMed PMID: 26146131. 7: Deaver SE, Felix AM, Rhoads ML. Reproductive performance of lactating dairy cattle after intrauterine administration of a prostaglandin F2α receptor antagonist 4 days after insemination. Theriogenology. 2015 Mar 1;83(4):560-6. doi: 10.1016/j.theriogenology.2014.10.019. Epub 2014 Oct 30. PubMed PMID: 25488790. 8: Łuczaj W, Moniuszko A, Rusak M, Zajkowska J, Pancewicz S, Skrzydlewska E. Peroxidative metabolism of arachidonic acid in the course of Lyme arthritis. Ann Agric Environ Med. 2015;22(3):433-7. doi: 10.5604/12321966.1167708. PubMed PMID: 26403109. 9: Atanasov B, De Koster J, Bommelé L, Dovenski T, Opsomer G. Pathways of the dominant follicle after exposure to sub-luteal circulating progesterone concentrations are different in lactating dairy cows versus non-lactating heifers. Anim Reprod Sci. 2015 Mar;154:8-15. doi: 10.1016/j.anireprosci.2015.01.002. Epub 2015 Jan 19. PubMed PMID: 25637465. 10: Helmersson-Karlqvist J, Ärnlöv J, Larsson A, Basu S. Prostaglandin F2α formation is associated with mortality in a Swedish community-based cohort of older males. Eur Heart J. 2015 Jan 21;36(4):238-43. doi: 10.1093/eurheartj/eht212. Epub 2013 Jun 20. PubMed PMID: 23786857. 11: Greene JM, Ginther OJ. Circulating nitric oxide metabolites during luteolysis and the effect of luteinizing hormone on circulating nitric oxide metabolites in heifers. Theriogenology. 2015 Jan 15;83(2):213-21. doi: 10.1016/j.theriogenology.2014.09.010. Epub 2014 Sep 21. PubMed PMID: 25442387. 12: Mizuno K, Kataoka H. Analysis of urinary 8-isoprostane as an oxidative stress biomarker by stable isotope dilution using automated online in-tube solid-phase microextraction coupled with liquid chromatography-tandem mass spectrometry. J Pharm Biomed Anal. 2015 Aug 10;112:36-42. doi: 10.1016/j.jpba.2015.04.020. Epub 2015 Apr 23. PubMed PMID: 25956225. 13: Ahmad SF, Akoum A, Horne AW. Selective modulation of the prostaglandin F2α pathway markedly impacts on endometriosis progression in a xenograft mouse model. Mol Hum Reprod. 2015 Dec;21(12):905-16. doi: 10.1093/molehr/gav056. Epub 2015 Oct 15. PubMed PMID: 26472819. 14: Nagai N, Kaji H, Onami H, Katsukura Y, Ishikawa Y, Nezhad ZK, Sampei K, Iwata S, Ito S, Nishizawa M, Nakazawa T, Osumi N, Mashima Y, Abe T. A platform for controlled dual-drug delivery to the retina: protective effects against light-induced retinal damage in rats. Adv Healthc Mater. 2014 Oct;3(10):1555-60, 1524. doi: 10.1002/adhm.201400114. Epub 2014 Apr 19. PubMed PMID: 24753450. 15: Martins JP, Policelli RK, Pursley JR. Luteolytic effects of cloprostenol sodium in lactating dairy cows treated with G6G/Ovsynch. J Dairy Sci. 2011 Jun;94(6):2806-14. doi: 10.3168/jds.2010-3650. PubMed PMID: 21605750. 16: 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. 17: Siemieniuch MJ, Jursza E, Szóstek AZ, Zschockelt L, Boos A, Kowalewski MP. Placental origin of prostaglandin F2α in the domestic cat. Mediators Inflamm. 2014;2014:364787. doi: 10.1155/2014/364787. Epub 2014 Feb 11. PubMed PMID: 24659861; PubMed Central PMCID: PMC3934528. 18: Dehnhard M, Naidenko SV, Jewgenow K. Comparative metabolism of PGFM (13,14-dihydro-15-keto-PGF2α) in feces of felids. Theriogenology. 2014 Mar 15;81(5):733-43. doi: 10.1016/j.theriogenology.2013.12.007. Epub 2013 Dec 18. PubMed PMID: 24433781. 19: Hadzi-Petrushev N, Stojkovski V, Mitrov D, Mladenov M. D-galactose induced inflammation lipid peroxidation and platelet activation in rats. Cytokine. 2014 Sep;69(1):150-3. doi: 10.1016/j.cyto.2014.05.006. Epub 2014 Jun 6. PubMed PMID: 24907931. 20: Kumagai A, Yoshioka S, Sakumoto R, Okuda K. Auto-amplification system for prostaglandin F2α in bovine corpus luteum. Mol Reprod Dev. 2014 Jul;81(7):646-54. doi: 10.1002/mrd.22332. Epub 2014 May 9. PubMed PMID: 24733743.