MK-0773Selective androgen receptor modulators CAS# 606101-58-0 |
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Quality Control & MSDS
3D structure
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| Cas No. | 606101-58-0 | SDF | Download SDF |
| PubChem ID | 11950726 | Appearance | Powder |
| Formula | C27H34FN5O2 | M.Wt | 479.59 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Synonyms | PF-05314882 | ||
| Solubility | DMSO : 33.33 mg/mL (69.50 mM; Need ultrasonic) | ||
| Chemical Name | (1S,3aS,3bS,5aR,9aS,9bS,11aS)-8-fluoro-N-(1H-imidazo[4,5-b]pyridin-2-ylmethyl)-6,9a,11a-trimethyl-7-oxo-2,3,3a,3b,4,5,5a,9b,10,11-decahydro-1H-indeno[5,4-f]quinoline-1-carboxamide | ||
| SMILES | CC12CCC3C(C1CCC2C(=O)NCC4=NC5=C(N4)C=CC=N5)CCC6C3(C=C(C(=O)N6C)F)C | ||
| Standard InChIKey | GBEUKTWTUSPHEE-JWJWXJQQSA-N | ||
| Standard InChI | InChI=1S/C27H34FN5O2/c1-26-11-10-17-15(6-9-21-27(17,2)13-19(28)25(35)33(21)3)16(26)7-8-18(26)24(34)30-14-22-31-20-5-4-12-29-23(20)32-22/h4-5,12-13,15-18,21H,6-11,14H2,1-3H3,(H,30,34)(H,29,31,32)/t15-,16-,17-,18+,21+,26-,27+/m0/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. |
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| 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. |
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| 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. | ||
| Description | MK-0773 is a selective modulator of androgen receptor with IC50 value of 6.6 nM. | |||||
| Targets | androgen receptor | |||||
| IC50 | 6.6 nM | |||||
MK-0773 Dilution Calculator
MK-0773 Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.0851 mL | 10.4256 mL | 20.8511 mL | 41.7023 mL | 52.1279 mL |
| 5 mM | 0.417 mL | 2.0851 mL | 4.1702 mL | 8.3405 mL | 10.4256 mL |
| 10 mM | 0.2085 mL | 1.0426 mL | 2.0851 mL | 4.1702 mL | 5.2128 mL |
| 50 mM | 0.0417 mL | 0.2085 mL | 0.417 mL | 0.834 mL | 1.0426 mL |
| 100 mM | 0.0209 mL | 0.1043 mL | 0.2085 mL | 0.417 mL | 0.5213 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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MK-0773
Description:
IC50: 6.6 nM
Selective androgen receptor modulators (SARMs) are androgen receptor (AR) ligands that induce anabolism while having reduced effects in reproductive tissues. MK-0773(PF05314882), one of SARMs, is a 4-aza-steroid exhibiting tissue selectivity in human [1].
In vitro: Previous study showed that the IC50 of MK-0773 binding to AR was increased 3.5-fold in the presence of 25% rat serum and 13-fold in the presence of 25% human serum, indicating that MK-0773 binds to serum proteins. In addition, the AR affinity of MK-0773 across species was evaluated using AR transfected COS cells, and it was found that IC50 values were very similar in four studied species (rat, 0.50 nM; dog, 0.55 nM; rhesus, 0.45 nM; human, 0.65 nM) [1].
In vivo: MK-0773 was subcutaneously given to the OVX rat (6 and 80 mg/kg) for 24 days resulting in plasma exposures over 24 h of 6.6 and 62 μM•h. The MK-0773 treatment produced exposure-related stimulatory effects on cortical BFR and LBM. The maximal anabolic effects of MK-0773 were found to be equivalent to the SARM TFM-4AS-1 and ~80% of 3 mg/kg DHT. In summary, MK-0773 exhibits the profile of an anabolic SARM with limited effects on the sebaceous glands and reproductive tracts of OVX rats. [1].
Clinical trial: In a phase IIA clinical trial, participants receiving MK-0773 showed a statistically significant increase in LBM from baseline at Month 6 vs. placebo (p<0.001). Participants receiving both MK-0773 and placebo showed a statistically significant increase in strength from baseline to Month 6, but the mean difference between the two groups was not significant (p=0.269) [2].
Reference:
[1] Schmidt A, Kimmel DB, Bai C, Discovery of the selective androgen receptor modulator MK-0773 using a rational development strategy based on differential transcriptional requirements for androgenic anabolism versus reproductive physiology. J Biol Chem. 2010;285(22):17054-64.
[2] Papanicolaou DA, Ather SN, Zhu H, A phase IIA randomized, placebo-controlled clinical trial to study the efficacy and safety of the selective androgen receptor modulator (SARM), MK-0773 in female participants with sarcopenia. J Nutr Health Aging. 2013;17(6):533-43.
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A phase IIA randomized, placebo-controlled clinical trial to study the efficacy and safety of the selective androgen receptor modulator (SARM), MK-0773 in female participants with sarcopenia.[Pubmed:23732550]
J Nutr Health Aging. 2013;17(6):533-43.
BACKGROUND: Sarcopenia, the age-related loss of muscle mass [defined as appendicular LBM/Height2 (aLBM/ht2) below peak value by>1SD], strength and function, is a major contributing factor to frailty in the elderly. MK-0773 is a selective androgen receptor modulator designed to improve muscle function while minimizing effects on other tissues. OBJECTIVES: The primary objective of this study was to demonstrate an improvement in muscle strength and lean body mass (LBM) in sarcopenic frail elderly women treated with MK-0773 relative to placebo. DESIGN: This was a randomized, double-blind, parallel-arm, placebo-controlled, multicenter, 6-month study. Participants were randomized in a 1:1 ratio to receive either MK-0773 50mg b.i.d. or placebo; all participants received Vitamin D and protein supplementation. SETTING: General community. PARTICIPANTS: 170 Women aged >/=65 with sarcopenia and moderate physical dysfunction. MEASUREMENTS: Dual energy X-ray absorptiometry, muscle strength and power, physical performance measures. RESULTS: Participants receiving MK-0773 showed a statistically significant increase in LBM from baseline at Month 6 vs. placebo (p<0.001). Participants receiving both MK-0773 and placebo showed a statistically significant increase in strength from baseline to Month 6, but the mean difference between the two groups was not significant (p=0.269). Both groups showed significant improvement from baseline at Month 6 in physical performance measures, but there were no statistically significant differences between participants receiving MK-0773 and placebo. A greater number of participants experienced elevated transaminases in the MK-0773 group vs. placebo, which resolved after discontinuation of study therapy. MK-0773 was generally well-tolerated with no evidence of androgenization. CONCLUSIONS: The MK-0773-induced increase in LBM did not translate to improvement in strength or function vs. placebo. The improvement of strength and physical function in the placebo group could be at least partly attributed to protein and vitamin D supplementation.
Identification of selected in vitro generated phase-I metabolites of the steroidal selective androgen receptor modulator MK-0773 for doping control purposes.[Pubmed:27419898]
Eur J Mass Spectrom (Chichester). 2016;22(2):49-59.
Research into developing anabolic agents for various therapeutic purposes has been pursued for decades. As the clinical utility of anabolic-androgenic steroids has been found to be limited because of their lack of tissue selectivity and associated off-target effects, alternative drug entities have been designed and are commonly referred to as selective androgen receptor modulators (SARMs). While most of these SARMs are of nonsteroidal structure, the drug candidate MK-0773 comprises a 4-aza-steroidal nucleus. Besides the intended therapeutic use, SARMs have been found to be illicitly distributed and misused as doping agents in sport, necessitating frequently updated doping control analytical assays. As steroidal compounds reportedly undergo considerable metabolic transformations, the phase-I metabolism of MK-0773 was simulated using human liver microsomal (HLM) preparations and electrochemical conversion. Subsequently, major metabolic products were identified and characterized employing liquid chromatography-high-resolution/high- accuracy tandem mass spectrometry with electrospray (ESI) and atmospheric pressure chemical ionization (APCI) as well as nuclear magnetic resonance (NMR) spectroscopy. MK-0773 produced numerous phase-I metabolites under the chosen in vitro incubation reactions, mostly resulting from mono- and bisoxygenation of the steroid. HLM yielded at least 10 monooxygenated species, while electrochemistry-based experiments resulted predominantly in three monohydroxylated metabolites. Elemental composition data and product ion mass spectra were generated for these analytes, ESI/APCI measurements corroborated the formation of at least two N-oxygenated metabolites, and NMR data obtained from electrochemistry-derived products supported structures suggested for three monohydroxylated compounds. Hereby, the hydroxylation of the A-ring located N- bound methyl group was found to be of particular intensity. In the absence of controlled elimination studies, the produced information enables the implementation of new target analytes into routine doping controls and expands the focus of anti-doping efforts concerning this new anabolic agent.
Discovery of the selective androgen receptor modulator MK-0773 using a rational development strategy based on differential transcriptional requirements for androgenic anabolism versus reproductive physiology.[Pubmed:20356837]
J Biol Chem. 2010 May 28;285(22):17054-64.
Selective androgen receptor modulators (SARMs) are androgen receptor (AR) ligands that induce anabolism while having reduced effects in reproductive tissues. In various experimental contexts SARMs fully activate, partially activate, or even antagonize the AR, but how these complex activities translate into tissue selectivity is not known. Here, we probed receptor function using >1000 synthetic AR ligands. These compounds produced a spectrum of activities in each assay ranging from 0 to 100% of maximal response. By testing different classes of compounds in ovariectomized rats, we established that ligands that transactivated a model promoter 40-80% of an agonist, recruited the coactivator GRIP-1 <15%, and stabilized the N-/C-terminal interdomain interaction <7% induced bone formation with reduced effects in the uterus and in sebaceous glands. Using these criteria, multiple SARMs were synthesized including MK-0773, a 4-aza-steroid that exhibited tissue selectivity in humans. Thus, AR activated to moderate levels due to reduced cofactor recruitment, and N-/C-terminal interactions produce a fully anabolic response, whereas more complete receptor activation is required for reproductive effects. This bimodal activation provides a molecular basis for the development of SARMs.
