Andarine

Andarine

Systematic (IUPAC) name
(2S)-3-(4-acetamido-phenoxy)-2-hydroxy-2-methyl-N-(4-nitro-3-trifluoromethyl-phenyl)-propionamide
Clinical data
Legal status	Investigational new drug
Identifiers
CAS Number	401900-40-1
ATC code	none
PubChem	CID 9824562
IUPHAR/BPS	7849
DrugBank	DB07423
ChemSpider	8000309
ChEMBL	CHEMBL125236
Chemical data
Formula	C19H18F3N3O6
Molar mass	441.357 g/mol
SMILES FC(F)(F)c1cc(ccc1[N+]([O-])=O)NC(=O)[C@@](O)(COc2ccc(cc2)NC(=O)C)C
InChI InChI=1S/C19H18F3N3O6/c1-11(26)23-12-3-6-14(7-4-12)31-10-18(2,28)17(27)24-13-5-8-16(25(29)30)15(9-13)19(20,21)22/h3-9,28H,10H2,1-2H3,(H,23,26)(H,24,27)/t18-/m0/s1 Key:YVXVTLGIDOACBJ-SFHVURJKSA-N
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Andarine (GTx-007, S-4) is an investigational selective androgen receptor modulator (SARM) developed by GTX, Inc for treatment of conditions such as muscle wasting, osteoporosis and benign prostatic hypertrophy,^[1] using the non-steroidal androgen antagonist bicalutamide as a lead compound.^[2]

Andarine is an orally active partial agonist for androgen receptors. It is less potent in both anabolic and androgenic effects than other SARMs. In an animal model of benign prostatic hypertrophy, andarine was shown to reduce prostate weight with similar efficacy to finasteride, but without producing any reduction in muscle mass or anti-androgenic side effects.^[3] This suggests that it is able to competitively block binding of dihydrotestosterone to its receptor targets in the prostate gland, but its partial agonist effects at androgen receptors prevent the side effects associated with the anti-androgenic drugs traditionally used for treatment of BPH.^[4]

References

1. Hott, J. L.; Borkman, R. F. (1989). "The non-fluorescence of 4-fluorotryptophan". The Biochemical journal 264 (1): 297–9. doi:10.1124/jpet.102.040840. PMC 1133577. PMID 2604714.
2. Chen, J; Kim, J; Dalton, J. T. (2005). "Discovery and therapeutic promise of selective androgen receptor modulators". Molecular interventions 5 (3): 173–88. doi:10.1124/mi.5.3.7. PMC 2072877. PMID 15994457.
3. GGao, W; Kearbey, J. D.; Nair, V. A.; Chung, K; Parlow, A. F.; Miller, D. D.; Dalton, J. T. (2004). "Comparison of the pharmacological effects of a novel selective androgen receptor modulator, the 5alpha-reductase inhibitor finasteride, and the antiandrogen hydroxyflutamide in intact rats: New approach for benign prostate hyperplasia". Endocrinology 145 (12): 5420–8. doi:10.1210/en.2004-0627. PMC 2098692. PMID 15308613.
4. Gao, W; Kim, J; Dalton, J. T. (2006). "Pharmacokinetics and pharmacodynamics of nonsteroidal androgen receptor ligands". Pharmaceutical Research 23 (8): 1641–58. doi:10.1007/s11095-006-9024-3. PMC 2072875. PMID 16841196.