Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C19H14F3N3O3 |
| Molecular Weight | 389.328 |
| Optical Activity | ( - ) |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1C(=O)N(C(=O)[C@@]1(CO)C2=CC=CC=C2)C3=CC=C(C#N)C(=C3)C(F)(F)F
InChI
InChIKey=VAJGULUVTFDTAS-GOSISDBHSA-N
InChI=1S/C19H14F3N3O3/c1-24-17(28)25(14-8-7-12(10-23)15(9-14)19(20,21)22)16(27)18(24,11-26)13-5-3-2-4-6-13/h2-9,26H,11H2,1H3/t18-/m1/s1
| Molecular Formula | C19H14F3N3O3 |
| Molecular Weight | 389.328 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: http://files.glpg.com/docs/Galapagos_Annual_Report_2012.pdf | http://akashirx.com/pipeline/Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23523664
Sources: http://files.glpg.com/docs/Galapagos_Annual_Report_2012.pdf | http://akashirx.com/pipeline/
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23523664
GLPG-0492, an orally available selective androgen receptor modulator (SARM) was tested in a Phase I Proof of Mechanism study to assess the effect on muscle function in healthy volunteers. A biomarker effect similar to that of Oxandrolone was observed, but the data were insufficient for Galapagos to pursue GLPG-0492 further in cachexia, and further development of the compound was discontinued. GLPG-0492 is currently under development for musculo-skeletal diseases such as sarcopenia and Duchenne muscular dystrophy.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1871 Sources: http://akashirx.com/pipeline/ |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2362 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22957947 |
3 mg/kg single, intravenous dose: 3 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
GLPG-0492 plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
4675 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22957947 |
10 mg/kg single, oral dose: 10 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
GLPG-0492 plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22957947 |
3 mg/kg single, intravenous dose: 3 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
GLPG-0492 plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
2.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22957947 |
10 mg/kg single, oral dose: 10 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
GLPG-0492 plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| GLPG0492, a novel selective androgen receptor modulator, improves muscle performance in the exercised-mdx mouse model of muscular dystrophy. | 2013 Jun |
|
| Characterization of GLPG0492, a selective androgen receptor modulator, in a mouse model of hindlimb immobilization. | 2014 Sep 3 |
Patents
| Substance Class |
Chemical
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8O59X1ACZT
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GLPG-0492
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PRIMARY | GLPG0492 has very good pharmacokinetic properties, including bioavailability in rat (F > 50%), and is currently under evaluation in phase I clinical trials. GLPG0492 is a new non-steroidal selective androgen receptor modulator that is currently under development for musculo-skeletal diseases such as sarcopenia and cachexia. In acute exhaustion tests, a surrogate of the 6-min walking test used in DMD patients, GLPG0492 preserved running performance, whereas vehicle- or comparator-treated animals showed a significant increase in fatigue (30-50%). GLPG0492 treatment partially prevents immobilization-induced muscle atrophy with a trend to promote muscle fiber hypertrophy in a dose-dependent manner. Interestingly, GLPG0492 was found as efficacious as TP at reducing muscle loss while sparing reproductive tissues. Furthermore, gene expression studies performed on tibialis samples revealed that both GLPG0492 and TP were slowing down muscle loss by negatively interfering with major signaling pathways controlling muscle mass homeostasis. | ||
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CHEMBL3545417
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ACTIVE MOIETY |
Official Title: Assessment of the Muscle Protein Fractional Synthesis Rate Induced by Repeated Administrations of GLPG0492 to Healthy Male Subjects and Assessment of the Safety, Tolerability and Pharmacokinetics of Repeated Administrations of GLPG0492 to Healthy Postmenopausal Women.
Purpose: GLPG0492 is a selective androgen receptor modulator: the compound should help protect against (or help restore) muscle loss in case of immobilization (e.g. after orthopedic surgery) or due to aging (androgenic effect), but without anabolic effects (e.g. effect on testosterone). In the first part of the current study it will be tested whether GLPG0492 given orally to healthy male volunteers increases the protein synthesis in muscle, as measured by the uptake into the muscle of intravenously infused phenylalanine.
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ACTIVE MOIETY |
Purpose: GLPG0492 is a selective androgen receptor modulator: the compound should help protect against (or help restore) muscle loss in case of immobilization (e.g. after orthopedic surgery) or due to aging (androgenic effect), but without anabolic effects (e.g. effect on testosterone). In the first part of the current study it will be tested whether GLPG0492 given orally to healthy male volunteers increases the protein synthesis in muscle, as measured by the uptake into the muscle of intravenously infused phenylalanine.
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ACTIVE MOIETY |
Originator: ProSkelia; Developer: Akashi Therapeutics, Galapagos NV; Class: Small molecule; Mechanism of Action: Selective androgen receptor modulator; Orphan Drug Status: No; On Fast track: No; New Molecular Entity: Yes; Highest Development Phases: Preclinical for Duchenne muscular dystrophy, Discontinued for Cachexia; Most Recent Events: 15 Sep 2014 Preclinical trials in Duchenne muscular dystrophy in USA (PO), 24 Jun 2014 DART Therapeutics is now called Akashi Therapeutics, 20 Mar 2013 DART Therapeutics plans a phase IIa trial in Healthy volunteers
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