Dinoprostone | CAS# 363-24-6 | vasodilator

MedKoo Cat#: 412678 | Name: Dinoprostone

Description:

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

Dinoprostone, also known as PGE2, Prostaglandin E₂, is a product of arachidonic acid metabolism that binds to EP1, EP2, EP3, & EP4 receptors with high affinity (Kd = 1-10 nM). Involved in vasodilator actions of kinins

Chemical Structure

Dinoprostone

CAS#363-24-6 (free acid)

Theoretical Analysis

MedKoo Cat#: 412678

Name: Dinoprostone

CAS#: 363-24-6 (free acid)

Chemical Formula: C20H32O5

Exact Mass: 352.2250

Molecular Weight: 352.47

Elemental Analysis: C, 68.15; H, 9.15; O, 22.70

Price and Availability

Size	Price	Availability
10mg	USD 150.00	2 Weeks
25mg	USD 250.00	2 Weeks
50mg	USD 450.00	2 Weeks
100mg	USD 750.00	2 Weeks
200mg	USD 1,250.00	2 Weeks
500mg	USD 2,650.00	2 Weeks
1g	USD 3,850.00	2 Weeks
2g	USD 6,450.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

53697-17-9 (sodium) 363-24-6 (free acid)

Synonym

PGE2; Prostaglandin E2; Dinoprostone; Prostin E2; U 12062; U12062; U-12062; NSC-165560; NSC165560; NSC 165560; NSC-196514; NSC196514; NSC 196514

IUPAC/Chemical Name

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

InChi Key

XEYBRNLFEZDVAW-ARSRFYASSA-N

InChi Code

InChI=1S/C20H32O5/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/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1

SMILES Code

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

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Prostaglandin E2 (PGE2) is a hormone-like substance that participate in a wide range of body functions such as the contraction and relaxation of smooth muscle, the dilation and constriction of blood vessels, control of blood pressure, and modulation of inflammation.

In vitro activity:

Exogenous PGE2 has been reported to prevent phagocytosis of macrophages, and in this study’s experimental system, starting with a concentration of 50 ng/ml, PGE2 significantly inhibited the phagocytosis of E. coli by HL‐60 cells. At 1000 ng/ml, PGE2 reduced the phagocytic percentage of HL‐60 cells by about 50% (Figure 1A,B). PGE2 also inhibited the phagocytosis of E. coli by freshly isolated neutrophils (Figure 1C,D). Reference: Immun Inflamm Dis. 2022 Jul;10(7):e662. https://pubmed.ncbi.nlm.nih.gov/35759236/

In vivo activity:

Indeed, PGE2-induced phosphorylation of AKT was dampened in cells from the EP4LysM mice but was rescued in the presence of 3-isobutyl-1-methylxanthine (IBMX), which protects against cAMP degradation (Fig. 8e). Furthermore, PGE2-induced migration (P < 0.05; Fig. S7a) and differentiation (P < 0.05; Fig. S7a) of the WT mice were significantly suppressed following treatment with an AKT inhibitor (GSK2141795). Reference: Bone Res. 2022 Mar 9;10(1):27. https://pubmed.ncbi.nlm.nih.gov/35260562/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	283.71
	Ethanol	100.0	283.71
	Water	70.0	198.60

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 352.47 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. Wang Z, Wei X, Ji C, Yu W, Song C, Wang C. PGE2 inhibits neutrophil phagocytosis through the EP2R-cAMP-PTEN pathway. Immun Inflamm Dis. 2022 Jul;10(7):e662. doi: 10.1002/iid3.662. PMID: 35759236; PMCID: PMC9186335. 2. Zhang GL, Lin ZB. Dinoprostone potentiates cytokines and lipopolysaccharides inducing nitric oxide production in cultured rat hepatocytes. Zhongguo Yao Li Xue Bao. 1999 Mar;20(3):262-6. PMID: 10452104. 3. Jiang W, Jin Y, Zhang S, Ding Y, Huo K, Yang J, Zhao L, Nian B, Zhong TP, Lu W, Zhang H, Cao X, Shah KM, Wang N, Liu M, Luo J. PGE2 activates EP4 in subchondral bone osteoclasts to regulate osteoarthritis. Bone Res. 2022 Mar 9;10(1):27. doi: 10.1038/s41413-022-00201-4. PMID: 35260562; PMCID: PMC8904489. 4. Karaki SI, Tanaka R. Role of PGE2 in colonic motility: PGE2 attenuates spontaneous contractions of circular smooth muscle via EP4 receptors in the rat colon. J Physiol Sci. 2021 Feb 23;71(1):8. doi: 10.1186/s12576-021-00791-4. PMID: 33622238.

In vitro protocol:

In vivo protocol:

1. Jiang W, Jin Y, Zhang S, Ding Y, Huo K, Yang J, Zhao L, Nian B, Zhong TP, Lu W, Zhang H, Cao X, Shah KM, Wang N, Liu M, Luo J. PGE2 activates EP4 in subchondral bone osteoclasts to regulate osteoarthritis. Bone Res. 2022 Mar 9;10(1):27. doi: 10.1038/s41413-022-00201-4. PMID: 35260562; PMCID: PMC8904489. 2. Karaki SI, Tanaka R. Role of PGE2 in colonic motility: PGE2 attenuates spontaneous contractions of circular smooth muscle via EP4 receptors in the rat colon. J Physiol Sci. 2021 Feb 23;71(1):8. doi: 10.1186/s12576-021-00791-4. PMID: 33622238.

1: Shirley M. Dinoprostone Vaginal Insert: A Review in Cervical Ripening. Drugs. 2018 Oct;78(15):1615-1624. doi: 10.1007/s40265-018-0995-2. PMID: 30317521. 2: Cheng H, Huang H, Guo Z, Chang Y, Li Z. Role of prostaglandin E2 in tissue repair and regeneration. Theranostics. 2021 Aug 13;11(18):8836-8854. doi: 10.7150/thno.63396. PMID: 34522214; PMCID: PMC8419039. 3: Liu YR, Pu CX, Wang XY, Wang XY. Double-balloon catheter versus dinoprostone insert for labour induction: a meta-analysis. Arch Gynecol Obstet. 2019 Jan;299(1):7-12. doi: 10.1007/s00404-018-4929-8. Epub 2018 Oct 12. PMID: 30315411. 4: Park JY, Pillinger MH, Abramson SB. Prostaglandin E2 synthesis and secretion: the role of PGE2 synthases. Clin Immunol. 2006 Jun;119(3):229-40. doi: 10.1016/j.clim.2006.01.016. Epub 2006 Mar 15. PMID: 16540375. 5: Ye Y, Wang X, Jeschke U, von Schönfeldt V. COX-2-PGE2-EPs in gynecological cancers. Arch Gynecol Obstet. 2020 Jun;301(6):1365-1375. doi: 10.1007/s00404-020-05559-6. Epub 2020 May 3. PMID: 32363546; PMCID: PMC7246249. 6: Elhusein AM, Fadlalmola HA, Ebrahim RA, Mohammed AA, Mohmed SA, Mohamed SE, Hassani R, Eltaher NS, Ahmed SM, Mansour RK, Farg SJ, Hamid HI, Shaaeldein FR, Abbo NH, Salih SAA, Balola HHA, Idress EA, Osman AM, Omer SAS, Taha WH, Abedelwahed HH. Double-balloon catheter vs dinoprostone (PGE-2) insert for labour induction: A meta-analysis of 2493 pregnancies. Afr J Reprod Health. 2023 Apr;27(4):84-95. doi: 10.29063/ajrh2023/v27i4.10. PMID: 37584912. 7: Anh ND, Duc TA, Ha NT, Giang DT, Dat DT, Thuong PH, Toan NK, Duc NT, Duc NM. Dinoprostone Vaginal Insert for Induction of Labor in Women with Low-Risk Pregnancies: A Prospective Study. Med Arch. 2022 Feb;76(1):39-44. doi: 10.5455/medarh.2022.76.39-44. PMID: 35422562; PMCID: PMC8976886. 8: Cao Y, Mai W, Li R, Deng S, Li L, Zhou Y, Qin Q, Zhang Y, Zhou X, Han M, Liang P, Yan Y, Hao Y, Xie W, Yan J, Zhu L. Macrophages evoke autophagy of hepatic stellate cells to promote liver fibrosis in NAFLD mice via the PGE2/EP4 pathway. Cell Mol Life Sci. 2022 May 19;79(6):303. doi: 10.1007/s00018-022-04319-w. PMID: 35588334. 9: Nguyen TNTN, Vuong ADB, Nguyen PN, Nguyen NTT, Ho QN, Le QT. Using dinoprostone slow release vaginal insert for cervical ripening in term-pregnancy with oligohydramnios. J Obstet Gynaecol Res. 2023 Jul;49(7):1750-1761. doi: 10.1111/jog.15665. Epub 2023 May 27. PMID: 37245054. 10: Hughes EG, Kelly AJ, Kavanagh J. Dinoprostone vaginal insert for cervical ripening and labor induction: a meta-analysis. Obstet Gynecol. 2001 May;97(5 Pt 2):847-55. doi: 10.1016/s0029-7844(00)01216-3. PMID: 11336776. 11: Daykan Y, Biron-Shental T, Navve D, Miller N, Bustan M, Sukenik-Halevy R. Prediction of the efficacy of dinoprostone slow release vaginal insert (Propess) for cervical ripening: A prospective cohort study. J Obstet Gynaecol Res. 2018 Sep;44(9):1739-1746. doi: 10.1111/jog.13715. Epub 2018 Jul 6. PMID: 29978599. 12: Jindal N, Rao R, Dhiman B, Kandoria M, Jamwal A. Safety and efficacy of mifepristone versus dinoprostone gel in induction of labor: A randomized controlled trial. J Obstet Gynaecol Res. 2019 Aug;45(8):1530-1535. doi: 10.1111/jog.14010. Epub 2019 Jun 7. PMID: 31172644. 13: Brennan MC, Pevzner L, Wing DA, Powers BL, Rayburn WF. Retention of dinoprostone vaginal insert beyond 12 hours for induction of labor. Am J Perinatol. 2011 Jun;28(6):479-84. doi: 10.1055/s-0030-1271208. Epub 2011 Jan 11. PMID: 21225563. 14: Heckel S, Ohl J, Dellenbach P. Rupture d'un utérus non cicatriciel à terme, après application intracervicale d'un gel de dinoprostone (Prépidil) [Rupture of an unscarred uterus at full term after an intracervical application of dinoprostone (Prepidil) gel]. Rev Fr Gynecol Obstet. 1993 Mar;88(3):162-4. French. PMID: 8493447. 15: Ramsey PS, Harris DY, Ogburn PL Jr, Heise RH, Magtibay PM, Ramin KD. Comparative efficacy and cost of the prostaglandin analogs dinoprostone and misoprostol as labor preinduction agents. Am J Obstet Gynecol. 2003 Feb;188(2):560-5. doi: 10.1067/mob.2003.150. PMID: 12592272. 16: Lyndrup J. Prostaglandins and induction of labor. Eur J Obstet Gynecol Reprod Biol. 1996 Jan;64(1):1-2. doi: 10.1016/0301-2115(95)02266-x. PMID: 8801131. 17: Marconi AM, Bozzetti P, Morabito A, Pardi G. Comparing two dinoprostone agents for cervical ripening and induction of labor: a randomized trial. Eur J Obstet Gynecol Reprod Biol. 2008 Jun;138(2):135-40. doi: 10.1016/j.ejogrb.2007.08.009. Epub 2007 Sep 24. PMID: 17889983. 18: Zhao L, Lin Y, Jiang TT, Wang L, Li M, Wang Y, Sun GQ, Xiao M. Vaginal delivery among women who underwent labor induction with vaginal dinoprostone (PGE2) insert: a retrospective study of 1656 women in China. J Matern Fetal Neonatal Med. 2019 May;32(10):1721-1727. doi: 10.1080/14767058.2017.1416351. Epub 2017 Dec 21. PMID: 29268652. 19: Rietberg CC, Lotgering FK, Huikeshoven FJ. Dinoprostone priming of the cervix prior to termination of midgestation pregnancy with sulprostone. Eur J Obstet Gynecol Reprod Biol. 1995 Jun;60(2):157-60. doi: 10.1016/0028-2243(95)02103-y. PMID: 7641968. 20: Butler EG 2nd. Peripartum emergencies. Am Fam Physician. 1999 Jun;59(11):2989-90. PMID: 10392586.