Altrenogest

CAS# 850-52-2

Altrenogest

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Chemical structure

Altrenogest

3D structure

Chemical Properties of Altrenogest

Cas No. 850-52-2 SDF Download SDF
PubChem ID 13324 Appearance Powder
Formula C21H26O2 M.Wt 310.43
Type of Compound N/A Storage Desiccate at -20°C
Synonyms A35957; Allyltrenbolone; R2267; RU2267
Solubility DMSO : ≥ 100 mg/mL (322.13 mM)
H2O : < 0.1 mg/mL (insoluble)
*"≥" means soluble, but saturation unknown.
Chemical Name 17-hydroxy-13-methyl-17-prop-2-enyl-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
SMILES CC12C=CC3=C4CCC(=O)C=C4CCC3C1CCC2(CC=C)O
Standard InChIKey VWAUPFMBXBWEQY-UHFFFAOYSA-N
Standard InChI InChI=1S/C21H26O2/c1-3-10-21(23)12-9-19-18-6-4-14-13-15(22)5-7-16(14)17(18)8-11-20(19,21)2/h3,8,11,13,18-19,23H,1,4-7,9-10,12H2,2H3
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 Altrenogest

DescriptionAltrenogest(A35957; RU2267) is a progestogen structurally related to veterinary steroid trenbolone. Target: Progesterone Receptor Altrenogest is a progestogen structurally related to veterinary steroid trenbolone. Treatment of embryo-recipient mares with altrenogest appears to be beneficial in extending the degree of donor-recipient synchrony required for successful embryo transfer. Altrenogest treatment also seems to be conductive to pregnancy maintenance in recipients experiencing luteal dysfunction [1]. The oil and gel altrenogest preparations are equally effective in modulating estrous behavior and time to estrus and ovulation. Altrenogest treatment started late in diestrus appears to result in a high incidence of ovulation during treatment and when luteolysis and ovulation occur during treatment; the subsequent luteal phase is frequently prolonged due to failure of regression of the CL [2].

References:
[1]. Parry-Weeks, L.C. and D.W. Holtan, Effect of altrenogest on pregnancy maintenance in unsynchronized equine embryo recipients. J Reprod Fertil Suppl, 1987. 35: p. 433-8. [2]. Daels, P.F., et al., Persistence of the luteal phase following ovulation during altrenogest treatment in mares. Theriogenology, 1996. 46(5): p. 799-811.

Altrenogest Dilution Calculator

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Preparing Stock Solutions of Altrenogest

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.2213 mL 16.1067 mL 32.2134 mL 64.4268 mL 80.5335 mL
5 mM 0.6443 mL 3.2213 mL 6.4427 mL 12.8854 mL 16.1067 mL
10 mM 0.3221 mL 1.6107 mL 3.2213 mL 6.4427 mL 8.0533 mL
50 mM 0.0644 mL 0.3221 mL 0.6443 mL 1.2885 mL 1.6107 mL
100 mM 0.0322 mL 0.1611 mL 0.3221 mL 0.6443 mL 0.8053 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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Background on Altrenogest

Altrenogest is a progestogen structurally related to veterinary steroid trenbolone.

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References on Altrenogest

Circumventing the natural, frequent oestrogen waves of the female cheetah (Acinonyx jubatus) using oral progestin (Altrenogest).[Pubmed:27483379]

Reprod Fertil Dev. 2017 Aug;29(8):1486-1498.

Cheetah are induced ovulators, experiencing short, variable oestrogen waves year-round. Exogenous gonadotrophin administration induces ovulation, but success is variable and often improves if ovaries are quiescent. After affirming the presence of short-term oestrogenic waves, we examined the effect of the timing of administration of exogenous equine and human chorionic gonadotrophins (eCG-hCG) within the oestrogen concentration pattern on subsequent follicle development and oocyte and corpus luteum quality. We also investigated ovarian suppression using an oral progestin (Altrenogest, 7 days) and assessed whether Altrenogest moderated adrenal activity by reducing glucocorticoid metabolites. All cheetahs exhibited short (every ~7-10 days), sporadic, year-round increases in faecal oestradiol punctuated by unpredictable periods (4-10 weeks) of baseline oestradiol (anoestrous). Gonadotrophin (eCG-hCG) efficacy was not affected by oestradiol 'wave' pattern if administered >/=3 days after an oestrogen peak. Such cheetahs produced normative faecal progestagen patterns and higher numbers (P<0.06) of mature oocytes than females given gonadotrophins Altrenogest supplementation expanded the interval between oestradiol peaks to 12.9 days compared with 7.3 days without progestin pretreatment. Altrenogest-fed females excreted less (P<0.05) glucocorticoid metabolites than non-supplemented counterparts. Results show that Altrenogest is effective for suppressing follicular activity, may contribute to reduced glucocorticoid production and may result in more effective ovulation induction via gonadotrophin therapy.

Aberrant effects of altrenogest and exposure to exogenous gonadotropins on follicular cysts appearance in gilts.[Pubmed:28043359]

Theriogenology. 2017 Feb;89:250-254.

Research was conducted to determine the effect of Altrenogest and exposure to exogenous gonadotropins on ovarian function in prepubertal and mature gilts. Crossbred, presumably sexually mature gilts (n = 51), were fed with Altrenogest for 18 consecutive days and the day after the last feeding with Altrenogest, gilts were treated with eCG and 72 hours later challenged with hCG. Animals were slaughtered on Days 10 to 13 of their gonadotropins synchronized estrous cycle. Ovaries were examined for the number of CL, number of follicular cysts, and presence of corpora albicantia. Gilts were divided into two groups: those possessing corpora albicantia (group A-mature; n = 36) and those without corpora albicantia (Group W-prepubertal; n = 15) on their ovaries. In addition, each group was divided into two subgroups depending on the presence of follicular cysts (AC and WC) or their absence (AO and WO). There was no difference between the number of CL in group A and group W. Presence of corpora albicantia determined percentage of gilts possessing follicular cysts (13.9% group A vs. 66.7% group W). Gilts without follicular cysts (AO plus WO; n = 36) had higher number of CL (P < 0.01) than gilts bearing cysts (AC plus WC; n = 15). Comparison AO-AC did not show significant difference (P = 0.075) between CL number in mature cyst-free and cysts bearing gilts. A prepubertal gilts not bearing follicular cysts (WO) had higher (P < 0.02) number of CL than gilts bearing cysts. A significant negative correlation between the number of CL and number of follicular cysts was found (r = -0.664; P = 0.007). There were no differences in blood plasma progesterone and estradiol concentration between cyst-free and cyst-bearing gilts. These results indicate: (1) a higher follicular cysts appearance in prepubertal than mature gilts challenged with Altrenogest and exposed to exogenous gonadotropins and (2) a negative effect of follicular cysts on the number of CL (ovulations) in prepubertal gilts.

Environmental Photochemistry of Altrenogest: Photoisomerization to a Bioactive Product with Increased Environmental Persistence via Reversible Photohydration.[Pubmed:27356268]

Environ Sci Technol. 2016 Jul 19;50(14):7480-8.

Despite its wide use as a veterinary pharmaceutical, environmental fate data is lacking for Altrenogest, a potent synthetic progestin. Here, it is reported that direct photolysis of Altrenogest under environmentally relevant conditions was extremely efficient and rapid (half-life approximately 25 s). Photolysis rates (observed rate constant kobs = 2.7 +/- 0.2 x 10(-2) s(-1)) were unaffected by changes in pH or temperature but were sensitive to oxygen concentrations (N2-saturated kobs = 9.10 +/- 0.32 x 10(-2) s(-1); O2-saturated kobs = 1.38 +/- 0.11 x 10(-2) s(-1)). The primary photoproduct was identified as an isomer formed via an internal 2 + 2 cycloaddition reaction; the triplet lifetime (8.4 +/- 0.2 mus) and rate constant (8 x 10(4) s(-1)) of this reaction were measured using transient absorption spectroscopy. Subsequent characterization determined that this primary cycloaddition photoproduct undergoes photohydration. The resultant photostable secondary photoproducts are subject to thermal dehydration in dark conditions, leading to reversion to the primary cycloaddition photoproduct on a time scale of hours to days, with the photohydration and dehydration repeatable over several light/dark cycles. This dehydration reaction occurs more rapidly at higher temperatures and is also accelerated at both high and low pH values. In vitro androgen receptor (AR)-dependent gene transcriptional activation cell assays and in silico nuclear hormone receptor screening revealed that certain photoproducts retain significant androgenic activity, which has implications for exposure risks associated with the presence and cycling of Altrenogest and its photoproducts in the environment.

Description

Altrenogest (Allyltrenbolone) is a progestogen structurally related to veterinary steroid trenbolone.

Keywords:

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