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(+)-Cloprostenol (D-Cloprostenol) Sale

(Synonyms: (+)-氯前列烯醇,D-Cloprostenol) 目录号 : GC30743

A FP receptor agonist and potent luteolytic agent

(+)-Cloprostenol (D-Cloprostenol) Chemical Structure

Cas No.:54276-21-0

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产品描述

(+)-Cloprostenol is a synthetic analog of prostaglandin F (PGF). It is an FP receptor agonist and a potent luteolytic agent in rats and hamsters. (+)-Cloprostenol is the optically active, 15(R) enantiomer of cloprostenol responsible for the majority of its biological activity. It is 200 times more potent than PGF in terminating pregnancy when given subcutaneously at a daily dose of 0.125 μg/kg in rats and hamsters, without the side effects associated with PGF.1 (+)-Cloprostenol was also shown to be a potent inhibitor of rat adipose precursor differentiation in primary cultures with an IC50 value of 3 pM.2

1.Dukes, M., Russell, W., and Walpole, A.L.Potent luteolytic agents related to prostaglandin F2αNature250(464)330-331(1974) 2.Serrero, G., and Lepak, N.M.Prostaglandin F2α receptor (FP receptor) agonists are potent adipose differentiation inhibitors for primary culture of adipocyte precursors in defined mediumBiochem. Biophys. Res. Commun.233(1)200-202(1997)

Chemical Properties

Cas No. 54276-21-0 SDF
别名 (+)-氯前列烯醇,D-Cloprostenol
Canonical 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
分子式 C22H29ClO6 分子量 424.92
溶解度 DMSO: 100 mg/mL (235.34 mM); Ethanol: 50 mg/mL (117.67 mM) 储存条件 Store at -20°C
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1 mM 2.3534 mL 11.7669 mL 23.5338 mL
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Research Update

D-Cloprostenol enhances estrus synchronization in tropical hair sheep

Trop Anim Health Prod2018 Jun;50(5):991-996.PMID:29429114DOI:10.1007/s11250-018-1522-x

To compare the effects of PGF2α (dinoprost tromethamine) and D-Cloprostenol in a two-dose protocol for estrus synchronization in hair sheep during breeding season in Yucatán, México, two experiments were conducted. In experiment 1, 61 cyclic hair sheep were divided into two groups: G1 (control n = 30), two doses of 50 μg of dinoprost tromethamine IM with 12 days between applications, and G2 (n = 31), two doses of 50 μg of D-Cloprostenol IM at the same time interval. For determination of progesterone levels, 16 ewes from each group were randomly selected. In experiment 2, 70 cyclic hair sheep were assigned at the same treatments (G1 and G2, n = 35) and 48 h after the second application, the ewes in estrus were detected by two vasectomized rams. Sheep with detected estrus were inseminated, and 45 days after, pregnant animals were identified by ultrasonography. An exact Fisher's test was performed for the analysis of ewes in estrus (experiments 1 and 2) and number of pregnant ewes (experiment 2); for the comparison of time between end of treatment-estrus presentation, a survival analysis was used. Duration of estrus in hours was analyzed using a generalized mixed model (GLM) ANOVA whereas plasma progesterone concentrations were analyzed by non-linear regression. There were significant differences (P < 0.05) in the proportion of ewes in estrus upon treatments (G1, 57% vs G2, 87% and G1, 37.1% vs G2, 65.7% in experiments 1 and 2, respectively), and between the end of treatment-onset estrus interval (P < 0.01), survival curves showed the highest number of sheep in estrus between 40 and 48 h (G1, 43.7 + 8.05 h vs G2, 42.9 + 6.7 h, experiment 1). There were no significant differences (P > 0.05) in duration of estrus (G1, 42 + 6.1 h, vs G2, 41.1 + 11.2 h, experiment 1) and pregnancy in the ewes that presented estrus, and were inseminated (G1, 38.4% vs 52.1%, experiment 2). With regard to concentrations of progesterone, significant differences (P < 0.01) were found between treatments, and progesterone levels before the second application of D-Cloprostenol were higher. In consideration of the results, it can be concluded that in a two-dose protocol of a luteolytic agent, more ewes presented estrus in response to D-Cloprostenol compared to dinoprost tromethamine with similar pregnancy rates.

Effects of D-Cloprostenol on different layers and regions of the bovine uterus during the follicular and luteal phases

Theriogenology2017 Jul 1;96:92-96.PMID:28532844DOI:10.1016/j.theriogenology.2017.04.012

Introduction: D-Cloprostenol is a synthetic PGF2α, commonly used in bovine reproduction, that increases myometral contractility. However, little is known regarding its contractile behaviour and how it depends on the reproductive state and uterine topography (regions and muscular layers). Hypothesis and objectives: These aspects would affect the action of D-Cloprostenol on the uterus. Therefore, we hypothesize a possible use of this drug at the time of artificial insemination, to improve conception rates and, in the post-partum, in order to accelerate uterine involution in dairy cattle. The purpose of the present study was to investigates the modulatory effect of D-Cloprostenol on contractility of the bovine uterine region (horn and corpus) and their muscle layers (circular and longitudinal), in follicular and luteal phases. To our knowledge, motility effects of D-Cloprostenol on different regions from healthy bovine uterus have not been described up to now. Materials and methods: Uterine specimens were collected from uterine body and horn of cattle in the follicular (n = 28) and luteal phase (n = 32) of the estrous cycle at slaughter. Two strips were prepared from each regions corresponding to the circular and the longitudinal muscular layers, respectively. Samples were cultured in an organ bath, exposed to synthetic prostaglandin (1 μM D-Cloprostenol) and their contractile activity was monitored for 10 min. The functionality of the strip throughout the experiment was tested by a dose of carbachol (10-5 M). Results: The mean basal amplitude of contractions was higher in the follicular compared to the luteal phase in uterine horn samples, but not in muscles collected from the uterine body. The amplitude of contractions increased after D-Cloprostenol administration in all tissues with a greater increase in samples from cattle in the follicular phase. The frequency of contractions increased after D-Cloprostenol administration in longitudinal but not in circular fibrees. Conclusion: The contractile responses to D-Cloprostenol in both horn and corpus were strongest in the circular muscles but weak in the longitudinal muscles.

Effects of D-Cloprostenol administrations with 7.5 and 11.5-day intervals between administrations on pregnancy rates after artificial insemination in estrous cyclic dairy goats

Anim Reprod Sci2019 Oct;209:106172.PMID:31514929DOI:10.1016/j.anireprosci.2019.106172

This study was conducted to evaluate effects of two administrations of D-Cloprostenol at different intervals to synchronize the time of estrus and ovulation among estrous cyclic goats. In Experiment 1, 32 does were treated with 30 μg D-Cloprostenol at 7.5 (T7.5, n = 16) or 11.5-day (T11.5, n = 16) intervals. In Experiment 2, the same treatments were administered and there was AI of the does (T7.5, n = 40 and T11.5, n = 38). In Experiment 1, ultrasonic assessments of ovaries were conducted at the time of the second administration of D-Cloprostenol, every 12 h until detection of ovulation, and 7 days after estrous onset to detect the corpora lutea, as well as for pregnancy diagnosis 40 days after AI. In Experiment 1, the estrous response (90.6%, 29/32) was similar (P > 0.05) in both groups. Diameter of the largest follicle at the time of administration of the second dose was larger (P = 0.01) in the T7.5 than T11.5 group (7.0 compared with 5.7 mm), while the values for ovarian variables were similar (P > 0.05). In Experiment 2, the greatest (P < 0.001) synchrony in timing of initiation of estrus in does (T7.5 = 83.3% and T11.5 = 50.0%) occurred after the second day (36-48 h). The pregnancy rate tended (P = 0.0836) to be greater for does in the T7.5 (71.4%, 40/56) than T11.5 (55.6%, 30/54) group. With use of both protocols, there were acceptable estrous synchronization and pregnancy rates in estrous cyclic dairy goats.

Combined treatment with oestradiol benzoate, D-Cloprostenol and oxytocin permits cervical dilation and nonsurgical embryo recovery in ewes

Reprod Domest Anim2019 Jan;54(1):118-125.PMID:30171642DOI:10.1111/rda.13318

This study examined the feasibility of transcervical embryo recovery after the hormonal treatment to induce cervical dilation, following the 7-day oestrous synchronization protocol in multiparous Santa Inês ewes. A total of 23 cyclic ewes received two doses of 37.5 μg of D-Cloprostenol by latero-vulvar route 7 days apart. After the second injection of D-Cloprostenol, the ewes were checked for oestrus (every 12 hr) and then mated by fertile rams throughout the oestrous period. All ewes received 37.5 μg of D-Cloprostenol (latero-vulvar) and 1 mg of oestradiol benzoate by either intramuscular (EBim group; n = 12) or intravaginal (EBivg group; n = 11) route 16 hr before embryo flushing. Twenty minutes before the flushing, 50 IU of oxytocin were administered intravenously. The oestrous response (i.e., the percentage of ewes that showed signs of oestrous behaviour after the second D-Cloprostenol injection) was 91.3% (21/23). The proportion of successfully penetrated ewes (81.8% compared with 80.0%), the mean duration of embryo flushing (24.7 ± 2.0 min compared 26.2 ± 1.9 min), the flushing fluid recovery rate (94.8 ± 1.3% compared with 91.0 ± 2.9%) and the average number of structures recovered per ewe (0.5 ± 0.4 compared with 0.8 ± 0.4) did not vary (p > 0.05) between the EBim and EBivg groups. Viable embryos were recovered from 41.2% (7/17) of successfully penetrated ewes. It can be concluded that nonsurgical (i.e., transcervical) embryo collection can be performed in oestrous-synchronized Santa Inês ewes pretreated with D-Cloprostenol, oxytocin and oestradiol benzoate, with the latter hormone administered by either the intramuscular or intravaginal route.

Specific binding of dl-cloprostenol and D-Cloprostenol to PGF2 alpha receptors in bovine corpus luteum and myometrial cell membranes

J Vet Pharmacol Ther1994 Dec;17(6):455-8.PMID:7707491DOI:10.1111/j.1365-2885.1994.tb00277.x

Prostaglandin F2 alpha receptors (PGF2 alpha Rs) were measured in bovine corpus luteum and myometrial cell membranes using a radiometric method. The inhibition of labelled PGF2 alpha binding exerted by D-Cloprostenol, dl-cloprostenol, PGF2 alpha and PGE1 (10(-11) M to 10(-4) M) was evaluated in vitro. Results strongly suggest that cloprostenol binding to PGF2 alpha Rs is stereospecific. D-Cloprostenol and PGF2 alpha were equipotent, about 150 times more potent than dl-cloprostenol (P < 0.05) and approximately 280 times more potent than PGE1 (P < 0.05) in inhibiting [3H]PGF2 alpha binding to corpus luteum cell membranes. Such differences were less evident in myometrial cell membranes, where D-Cloprostenol and PGF2 alpha were about 10 times more potent than dl-cloprostenol (P < 0.05) and approximately 95 times more potent than PGE1 (P < 0.05).