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(±)-Cloprostenol sodium salt

CAS# 55028-72-3

(±)-Cloprostenol sodium salt

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Chemical structure

(±)-Cloprostenol sodium salt

3D structure

Chemical Properties of (±)-Cloprostenol sodium salt

Cas No. 55028-72-3 SDF Download SDF
PubChem ID 23665638 Appearance Powder
Formula C22H28ClNaO6 M.Wt 446.9
Type of Compound N/A Storage Desiccate at -20°C
Solubility H2O : ≥ 150 mg/mL (335.65 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name sodium;(Z)-7-[(1R,3R,5S)-2-[(E,3R)-4-(3-chlorophenoxy)-3-hydroxybut-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoate
SMILES C1C(C(C(C1O)C=CC(COC2=CC(=CC=C2)Cl)O)CC=CCCCC(=O)[O-])O.[Na+]
Standard InChIKey IFEJLMHZNQJGQU-UDEWSXLWSA-M
Standard InChI InChI=1S/C22H29ClO6.Na/c23-15-6-5-7-17(12-15)29-14-16(24)10-11-19-18(20(25)13-21(19)26)8-3-1-2-4-9-22(27)28;/h1,3,5-7,10-12,16,18-21,24-26H,2,4,8-9,13-14H2,(H,27,28);/q;+1/p-1/b3-1-,11-10+;/t16-,18-,19?,20+,21-;/m1./s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of (±)-Cloprostenol sodium salt

DescriptionWater-soluble prostaglandin F2α (PGF2α) analog; acts as a potent FP receptor agonist (EC50 = 0.84 nM). Potently inhibits differentiation of adipocyte precursor cells. Luteolytic agent in vivo.

(±)-Cloprostenol sodium salt Dilution Calculator

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Preparing Stock Solutions of (±)-Cloprostenol sodium salt

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.2376 mL 11.1882 mL 22.3764 mL 44.7527 mL 55.9409 mL
5 mM 0.4475 mL 2.2376 mL 4.4753 mL 8.9505 mL 11.1882 mL
10 mM 0.2238 mL 1.1188 mL 2.2376 mL 4.4753 mL 5.5941 mL
50 mM 0.0448 mL 0.2238 mL 0.4475 mL 0.8951 mL 1.1188 mL
100 mM 0.0224 mL 0.1119 mL 0.2238 mL 0.4475 mL 0.5594 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on (±)-Cloprostenol sodium salt

NMR studies of the inclusion complex of cloprostenol sodium salt with beta-cyclodextrin in aqueous solution.[Pubmed:18064541]

Pharm Res. 2008 May;25(5):1142-9.

PURPOSE: Cloprostenol sodium salt (referred as cloprostenol) may be used for the synchronization of estrous cycles in farm animal species. Cyclodextrins (CDs) have potential as drug delivery systems through the formation of inclusion complexes between CDs and drugs. This is the first study of the inclusion complex of cloprostenol with beta-cyclodextrin (beta-CD) in aqueous solution using NMR and 3D molecular dynamics simulations. METHODS: 1D proton NMR spectra of beta-CD, a complex of cloprostenol with beta-CD, and cloprostenol in D(2)O were assigned and confirmed. The cross relaxation interactions from ROESY were used as constraints for 3D molecular modeling studies. RESULTS: In the 2D ROESY of the complex, cross-peaks were observed between the aromatic protons of cloprostenol and protons of the beta-CD as well as between aliphatic protons and protons of the beta-CD. The stoichiometry of the complex was found that beta-CD forms a 1:1 inclusion complex with cloprostenol. The association constant K was 968 +/- 120 M(-1) at 298 K. CONCLUSIONS: Aromatic side and/or aliphatic side chains of the cloprostenol is included in the beta-CD while aliphatic side and/or aromatic side chains wraps around beta-CD, respectively. The molecular modeling also confirms that beta-CD forms a 1:1 inclusion complex with cloprostenol.

Pharmacological characterization of an FP prostaglandin receptor on rat vascular smooth muscle cells (A7r5) coupled to phosphoinositide turnover and intracellular calcium mobilization.[Pubmed:9655886]

J Pharmacol Exp Ther. 1998 Jul;286(1):411-8.

An FP prostaglandin (PG) receptor on the A7r5 rat aorta smooth muscle cell line has been characterized by assays of phosphoinositide (PI) turnover and intracellular calcium mobilization stimulated by structurally diverse PGs. In the PI turnover assay, cloprostenol was the most potent PG tested, with a potency (EC50) of 0.84 +/- 0.06 nM (mean +/- S.E.M., n = 34), and was a full agonist. Other known FP receptor agonists tested in this assay had efficacies > or = 85% of the cloprostenol value and high potencies: 16-phenoxy PGF2 alpha (2.05 +/- 0.19 nM), 17-phenyl PGF2 alpha (2.80 +/- 0.59 nM), fluprostenol (4.45 +/- 0.19 nM), PGF2 alpha (30.9 +/- 2.82 nM) and PhXA85 (43.5 +/- 11.4 nM). Other classes of PGs evaluated (PGD2, enprostil, 17-phenyl PGE2, PGE2, sulprostone and U-46619) were less potent and less efficacious than the FP receptor agonists, or were inactive. For a large group of standard PGs evaluated in the PI turnover assay, both potencies and efficacies correlated well with those reported for the FP receptor of Swiss mouse 3T3 fibroblasts. The potencies of fluprostenol and PGF2 alpha as stimuli of intracellular calcium mobilization matched well their potencies in the PI turnover assay, but fluprostenol had twice the efficacy of PGF2 alpha. Both signaling responses stimulated by fluprostenol were significantly inhibited by U73122, a selective inhibitor of phosphoinositide turnover (IC50 = 1.25 +/- 0.16 microM for PI turnover), and by chelation of calcium in the medium. Together with the PI turnover data, these studies of intracellular calcium mobilization linked to activation of the FP receptor, provide additional characterization of the pharmacological properties of this receptor.

Description

Cloprostenol sodium salt (ICI 80996 sodium salt) is a potent synthetic prostaglandin analogue, acts as a luteolytic agent, and is a PGF2α receptor agonist.

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