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| Targets |
(+)-Cloprostenol targets the prostaglandin F receptor (FP receptor), a G protein-coupled receptor that mediates the actions of prostaglandin F2alpha. It also shows activity at the prostaglandin D2 receptor (PTGDR). As an FP receptor agonist, (+)-cloprostenol mimics the effects of natural PGF2alpha, including luteolytic activity, smooth muscle contraction, and inhibition of adipocyte differentiation. The compound is 200 times more potent than PGF2alpha in terminating pregnancy when given subcutaneously at a daily dose of 0.125 microg/kg in rats and hamsters.
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| ln Vitro |
The inhibition of [3H]PGF2α binding to the luteal cell membrane is about 150 times stronger than that of dl-cloprostenol (P<0.05) and about 280 times stronger than that of PGE1. The inhibitory effects of D-cloprostenol and PGF2α are comparable. On the other hand, d-cloprostenol and PGF2 alpha are roughly 95 times more effective than PGE1 and about 10 times more potent than dl-cloprostenol in the uterine myocyte membrane [2].
In vitro studies have demonstrated that (+)-cloprostenol is a potent inhibitor of rat adipose precursor differentiation in primary cultures, with an IC50 value of 3 × 10-¹2 M. It shows selective agonistic activity at the prostaglandin receptor. The compound's activity as an FP receptor agonist has been well characterized in various cell-based assays measuring receptor activation, calcium mobilization, and downstream signaling pathways. In primary cultures of rat adipose precursors, (+)-cloprostenol inhibits differentiation at picomolar concentrations without the side effects associated with PGF2alpha. |
| ln Vivo |
The lowest dosage required to produce a persistent abortion is 15 grams per head of D-croprostenol, which can have mild side effects in bitches weighing less than 10 kg, such as salivation, feces, and hyperventilation. An effective and safe method for causing abortion in female dogs is to administer a single modest dose of d-cloprostenol intravenously [1].
In vivo studies have shown that (+)-cloprostenol is a potent luteolytic agent in rats and hamsters. When administered subcutaneously at a daily dose of 0.125 microg/kg, it is 200 times more potent than PGF2alpha in terminating pregnancy in these species, without the side effects associated with PGF2alpha. The compound is used to induce ovulation in female mammals. Its potent luteolytic activity makes it valuable for research in reproductive biology and veterinary medicine. The compound's efficacy has been demonstrated in multiple animal models of reproductive function. |
| Enzyme Assay |
The in vitro receptor binding assay for (+)-cloprostenol typically involves competition binding studies using membranes prepared from cells expressing the FP receptor. Radiolabeled PGF2alpha (e.g., 3H-PGF2alpha) is incubated with membrane preparations and varying concentrations of (+)-cloprostenol (typically 0.001 nM to 10 uM) in binding buffer at room temperature or 4degC for 1-4 hours. Bound and free ligand are separated by filtration through glass fiber filters, and radioactivity is measured by scintillation counting. The inhibition constant (Ki) is calculated from IC50 values using the Cheng-Prusoff equation. Non-specific binding is determined in the presence of excess unlabeled PGF2alpha.
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| Cell Assay |
In vitro cellular assays for (+)-cloprostenol are conducted using cell lines expressing the FP receptor, such as 3T3-L1 preadipocytes or primary rat adipose precursor cultures. Cells are treated with varying concentrations of (+)-cloprostenol (typically 0.001 pM to 1 uM) for 24-96 hours. Adipocyte differentiation is assessed by Oil Red O staining and quantification of lipid accumulation. FP receptor activation is measured by assessing intracellular calcium mobilization using fluorescent calcium indicators (e.g., Fluo-4) or by measuring downstream signaling pathways including MAPK and PI3K/Akt activation by Western blotting. Cell viability is monitored to ensure that observed effects are not due to cytotoxicity.
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| Animal Protocol |
In vivo animal studies for (+)-cloprostenol typically involve administration to rodents (rats or hamsters) to assess luteolytic activity and reproductive effects. The compound is administered subcutaneously at doses ranging from 0.01-10 microg/kg/day. In pregnancy termination studies, female rodents are treated during early pregnancy, and the number of implantation sites or viable fetuses is assessed at necropsy. The compound's effects on corpus luteum regression are evaluated by measuring serum progesterone levels. In other models, the compound may be administered to assess its effects on smooth muscle contraction, intraocular pressure, or other FP receptor-mediated responses. Clinical observations and body weights are monitored throughout the study.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of (+)-cloprostenol have been characterized in research settings. The compound has a molecular weight of 424.9 and a molecular formula of C22H29ClO6. It is supplied as a solution in ethanol at a concentration suitable for research applications. The compound is soluble in DMSO and dimethyl formamide at approximately 100 mg/mL, and in PBS (pH 7.2) at approximately 16 mg/mL. For in vivo administration, the ethanol is evaporated under a gentle stream of nitrogen and the compound is dissolved in the desired vehicle. Aqueous solutions should not be stored for more than one day. The compound is stable for at least two years when stored at -20degC as supplied.
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| Toxicity/Toxicokinetics |
The toxicological profile of (+)-cloprostenol is characteristic of prostaglandin analogs. At therapeutic doses, the compound can cause side effects related to smooth muscle contraction, including gastrointestinal disturbances and uterine cramping. At higher doses, prostaglandin analogs may cause bronchoconstriction, vasoconstriction, and other systemic effects. However, (+)-cloprostenol has been shown to be 200 times more potent than PGF2alpha in terminating pregnancy without the side effects associated with PGF2alpha when given at a daily dose of 0.125 microg/kg in rats and hamsters. The compound is for laboratory research only and is not approved for human therapeutic use. Standard toxicology parameters are monitored in animal studies.
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| References |
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| Additional Infomation |
Cloprostenol is a prostaglandin analogue, a synthetic prostaglandin F2α analog. This compound has luteolytic activity and is used for estrus synchronization in cattle. See also: Cloprostenol sodium (in salt form).
(+)-Cloprostenol (CAS 54276-21-0) is also known as (+)-16-m-chlorophenoxy tetranor Prostaglandin F2alpha. It is the optically active 15(R) enantiomer of cloprostenol and is responsible for the majority of the biological activity of the racemic mixture. The compound is a synthetic analog of prostaglandin F2alpha and acts as a potent and selective FP receptor agonist. It is a potent luteolytic agent used in reproductive biology research and has been shown to inhibit adipocyte differentiation in vitro with picomolar potency. The compound is supplied for research purposes only with purity ≥97%. |
| Molecular Formula |
C22H29CLO6
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| Molecular Weight |
424.92
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| Exact Mass |
424.165
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| Elemental Analysis |
C, 62.19; H, 6.88; Cl, 8.34; O, 22.59
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| CAS # |
54276-21-0
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| Related CAS # |
55028-72-3 (mono-hydrochloride salt)
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| PubChem CID |
5311053
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| Appearance |
Colorless to light yellow ointment
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
628.0±55.0 °C at 760 mmHg
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| Flash Point |
333.6±31.5 °C
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| Vapour Pressure |
0.0±1.9 mmHg at 25°C
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| Index of Refraction |
1.623
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| LogP |
2.31
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
11
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| Heavy Atom Count |
29
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| Complexity |
551
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| Defined Atom Stereocenter Count |
5
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| SMILES |
OC(CCC/C=C\C[C@@H]1[C@H]([C@H](O)C[C@@H]1O)/C=C/[C@@H](O)COC2=CC(Cl)=CC=C2)=O
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| InChi Key |
VJGGHXVGBSZVMZ-QIZQQNKQSA-N
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| InChi Code |
InChI=1S/C22H29ClO6/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)/b3-1-,11-10+/t16-,18-,19-,20+,21-/m1/s1
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| Chemical Name |
(Z)-7-[(1R,2R,3R,5S)-2-[(E,3R)-4-(3-chlorophenoxy)-3-hydroxybut-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoic acid
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| Synonyms |
cloprostenol; 40665-92-7; Cloprostenolum; Oestrophane; Estrofan; Oestrophan;
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~235.34 mM)
Ethanol : ~50 mg/mL (~117.67 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: 5 mg/mL (11.77 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 50.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 5 mg/mL (11.77 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 50.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 5 mg/mL (11.77 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: ≥ 2.5 mg/mL (5.88 mM) (saturation unknown) in 10% EtOH + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear EtOH stock solution to 400 μL of PEG300 and mix evenly; then add 50 μL of Tween-80 to the above solution and mix evenly; then add 450 μL of normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 5: ≥ 2.5 mg/mL (5.88 mM) (saturation unknown) in 10% EtOH + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear EtOH stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 6: ≥ 2.5 mg/mL (5.88 mM) (saturation unknown) in 10% EtOH + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear EtOH stock solution to 900 μL of corn oil and mix evenly. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.3534 mL | 11.7669 mL | 23.5338 mL | |
| 5 mM | 0.4707 mL | 2.3534 mL | 4.7068 mL | |
| 10 mM | 0.2353 mL | 1.1767 mL | 2.3534 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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