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Purity: ≥98%
AC-262536 (AC262536) is a novel selective androgen receptor modulator (SARM) that has positive effects on growth. It suppresses luteinizing hormone and exhibits partial agonist activity toward testosterone. Its anabolic effects are beneficial and its androgenic effects are mild. AC-262536 is a new class of anabolic steroids that are selective androgen receptor modulators (SARMs).
| Targets |
SARMs/selective androgen receptor modulators
|
|---|---|
| ln Vitro |
AC-262536 dose-dependently prevents the proliferation of LNCaP that is induced by dihydroxytestosterone (DHT). The effects peak at 1 μM treatment (%inhibition 50.7±7.6) and are statistically significant at 100 nM AC-262536 (%inhibition 47.2±12.2). In prostate cells, AC-262536 can therefore function as a functional antagonist[1].
AC-262536 exhibited potent agonist activity at the androgen receptor, with an affinity in the low nanomolar range (1–10 nM) as demonstrated in two functional assays and binding assay. This prototype lead has no detectable agonist activity at other nuclear receptors including the steroid receptors ERa, ERb, GR, MR and PR. In contrast to steroidal androgens and published SARMs, AC-262536 was found to be a partial agonist relative to testosterone, both in cell proliferation and transcriptional assays. Its activity was about 70–75% that of DHT. Additionally, a number of AR mutants were generated to further confirm the partial agonist nature of AC-262536. The mutations were chosen because they impair the response of AR to testosterone. Thus, such receptor mutants being less sensitive to the full agonist testosterone, should only respond marginally or not at all to a partial agonist. Indeed, AC-262536 was weakly responsive further supporting its partial agonist nature. [1] |
| ln Vivo |
In castrated rats, AC-262536 (3, 10, 30 mg/kg) reverses the luteinizing hormone (LH) spike[1].
A 2-week study in castrated male rats was conducted to evaluate and compare the effects of AC-262536 to testosterone. AC-262536 suppressed castration-induced elevations in plasma LH. These effects were similar in potency and efficacy to that of testosterone. Additionally, robust anabolic effects were evident on muscle weight. AC-262536 restored the weight of levator ani to about 70% of the maximum effect seen with testosterone. At doses where AC-262536 displayed significant anabolic effects on muscle, the androgenic effects on prostate and seminal vesicles were weak. Furthermore, it appeared that the maximum effects of AC-262536 produced in these tissues were much less relative to testosterone. These effects are consistent with the results observed in the prostate cancer cell line LNCaP, where AC-262536 functionally antagonized the proliferative properties of the full agonist DHT.[1] |
| Enzyme Assay |
Binding assays[1]
Hamster DDT cells were grown in DMEM 5% charcoal-stripped FBS in presence of 10 nM testosterone. Cells were plated at 25,000 cells/well in a 24-well plate (500 μl/well) and grown to 80% confluency (typically 3 days). At that stage, the media was replaced and 3H-DHT added to a final concentration of 2 nM, along with varying concentrations of the test ligands. Cells were incubated for an additional 24-h period. Cells were then washed multiple times with ice-cold HBSS (Hank's balanced salt solution) then resuspended in 100% ethanol (100 μl/well). Plates were then sealed and shaken for 6 h. Extracts were then quantified in a Beckman scintillation counter. |
| Cell Assay |
DHT/dihydroxytestosterone-induced proliferation of LNCaP[1]
Human prostate cancer LNCaP cells were plated at 30,000 cells per 96-well overnight. Media was then replaced by DMEM 2% charcoal-stripped FBS in presence of 10 nM DHT. AC-262536 was added at the indicated doses. Media was replenished every other day. After 5 days, the media was removed and cell proliferation measured by incubating with the tetrazolium salt WST-1 according to manufacturer's instructions (Roche Diagnostics). Absorbance at 405 nM was measured using a microplate reader after a 1-h incubation at 37 °C.[1] |
| Animal Protocol |
Male Sprague-Dawley rats (200-225 g)[1]
3, 10 and 30 mg/kg Administered subcutaneously; once daily for 14 consecutive days Male Sprague–Dawley rats (200–225 g) were either castrated or sham-operated and allowed to recover for 5 days. Thereafter, castrated animals (n = 8 per group) were treated once daily with vehicle, testosterone propionate (TP 1 mg/kg) or AC-262536 (3, 10 and 30 mg/kg) administered subcutaneously for 14 consecutive days. Twenty-four hours following the last injection, animals were sacrificed. The plasma samples were then obtained and the organs harvested. The levator ani muscle, the prostate glands and the seminal vesicles were dissected free of adipose tissue, blotted dry and their respective weights determined. Plasma levels of luteinizing hormone (LH) were quantified using a commercially available ELISA kit according to manufacturer's instructions [1]. |
| References | |
| Additional Infomation |
A selective androgen receptor modulator.
|
| Molecular Formula |
C18H18N2O
|
|---|---|
| Molecular Weight |
278.36
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| Exact Mass |
278.142
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| Elemental Analysis |
C, 77.67; H, 6.52; N, 10.06; O, 5.75
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| CAS # |
870888-46-3
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| Related CAS # |
870888-46-3
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| PubChem CID |
44512434
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| Appearance |
White to off-white solid powder
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| LogP |
3.268
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
1
|
| Heavy Atom Count |
21
|
| Complexity |
428
|
| Defined Atom Stereocenter Count |
2
|
| SMILES |
O[C@H]1C[C@H]2CC[C@H](N2C2C=CC(C#N)=C3C=CC=CC=23)C1
|
| InChi Key |
ATKWLNSCJYLXPF-YIONKMFJSA-N
|
| InChi Code |
InChI=1S/C18H18N2O/c19-11-12-5-8-18(17-4-2-1-3-16(12)17)20-13-6-7-14(20)10-15(21)9-13/h1-5,8,13-15,21H,6-7,9-10H2/t13-,14+,15?
|
| Chemical Name |
4-[(1R,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl]naphthalene-1-carbonitrile
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| Synonyms |
AC-262536; AC262536; 870888-46-3; U8VS41J5O6; 4-(3-endo-Hydroxy-8-azabicyclo(3.2.1)oct-8-yl)naphthalene-1-carbonitrile; AC 262536; 4-[(3-endo)-3-hydroxy-8-azabicyclo[3.2.1]oct-8-yl]-1-naphthalenecarbonitrile; 4-[(1R,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl]naphthalene-1-carbonitrile; 4-(3-hydroxy-8-azabicyclo[3.2.1]oct-8-yl)naphthalene-1-carbonitrile; AC 262536
|
| 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: ~50 mg/mL (~179.6 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.98 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 25.0 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. Solubility in Formulation 2: ≥ 2.5 mg/mL (8.98 mM) (saturation unknown) in 10% DMSO + 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 DMSO stock solution to 900 μL of corn oil and mix evenly. View More
Solubility in Formulation 3: ≥ 0.56 mg/mL (2.01 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.5925 mL | 17.9624 mL | 35.9247 mL | |
| 5 mM | 0.7185 mL | 3.5925 mL | 7.1849 mL | |
| 10 mM | 0.3592 mL | 1.7962 mL | 3.5925 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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