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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H16ClN5O2
Molecular Weight 393.826
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RAD-140

SMILES

C[C@H](O)[C@@H](NC1=CC=C(C#N)C(Cl)=C1C)C2=NN=C(O2)C3=CC=C(C=C3)C#N

InChI

InChIKey=XMBUPPIEVAFYHO-KPZWWZAWSA-N
InChI=1S/C20H16ClN5O2/c1-11-16(8-7-15(10-23)17(11)21)24-18(12(2)27)20-26-25-19(28-20)14-5-3-13(9-22)4-6-14/h3-8,12,18,24,27H,1-2H3/t12-,18+/m0/s1

HIDE SMILES / InChI

Description

RAD140 is a potent, orally bioavailable, nonsteroidal selective androgen receptor modulator (SARM). It was developed to overcome increased risks of prostate cancer, dysfunction and disease in androgen-responsive tissues, including brain, caused by testosterone therapy in men experiencing decline in testosterone levels during normal aging. It was characterized in several rat and monkey models of anabolic androgen action and demonstrated neuroprotective actions relevant to cachexia, Alzheimer's disease and related neurodegenerative diseases. In experiments with gonadectomized, adult male rats, RAD140 was shown to exhibit peripheral tissue-specific androgen action that largely spared prostate, neural efficacy as demonstrated by activation of androgenic gene regulation effects, and neuroprotection of hippocampal neurons against cell death caused by systemic administration of the excitotoxin kainate. In cultured hippocampal neurons, RAD140 was as effective as testosterone in reducing cell death induced by apoptotic insults. RAD140 neuroprotection was dependent upon MAPK signaling, as evidenced by elevation of ERK phosphorylation and inhibition of protection by the MAPK kinase inhibitor U0126.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
25.0 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preventing
PubMed

PubMed

TitleDatePubMed
Design, Synthesis, and Preclinical Characterization of the Selective Androgen Receptor Modulator (SARM) RAD140.
2011 Feb 10
Expanding sports drug testing assays: mass spectrometric characterization of the selective androgen receptor modulator drug candidates RAD140 and ACP-105.
2013 Jun 15
Selective androgen receptor modulator RAD140 is neuroprotective in cultured neurons and kainate-lesioned male rats.
2014 Apr

Sample Use Guides

In Vivo Use Guide
Sexually immature rats castrated or SHAM-castrated were dosed with 10, 3, 1, 0.3, 0.1 mg/kg RAD140 for 11 days.
Route of Administration: oral gavage
In Vitro Use Guide
To test RAD140 protection of cultured neurons against apoptotic insults neuron cultures were pretreated for 1 hour with 10 nM testosterone, 100 nM RAD140, or 100 nM RAD192, and then exposed for 24 hours to Aβ, AAII, or H2O2.
Name Type Language
RAD-140
Common Name English
2-CHLORO-4-(((1R,2S)-1-(5-(4-CYANOPHENYL)-1,3,4-OXADIAZOL-2-YL)-2-HYDROXYPROPYL)AMINO)-3-METHYLBENZONITRILE
Systematic Name English
RAD140
Code English
BENZONITRILE, 2-CHLORO-4-(((1R,2S)-1-(5-(4-CYANOPHENYL)-1,3,4-OXADIAZOL-2-YL)-2-HYDROXYPROPYL)AMINO)-3-METHYL-
Systematic Name English
Code System Code Type Description
CAS
1182367-47-0
Created by admin on Tue Oct 22 12:45:16 UTC 2019 , Edited by admin on Tue Oct 22 12:45:16 UTC 2019
PRIMARY
PUBCHEM
44200882
Created by admin on Tue Oct 22 12:45:16 UTC 2019 , Edited by admin on Tue Oct 22 12:45:16 UTC 2019
PRIMARY
WIKIPEDIA
RAD140
Created by admin on Tue Oct 22 12:45:16 UTC 2019 , Edited by admin on Tue Oct 22 12:45:16 UTC 2019
PRIMARY RAD140 is an investigational selective androgen receptor modulator (SARM) for the treatment of conditions such as muscle wasting, currently under development by Radius Health, Inc. (RDUS).