Andarine: Difference between revisions

Andarine
Clinical data
ATC code	none;
Legal status
Legal status	Investigational new drug;
Identifiers
	IUPAC name (2S)-3-(4-acetamido-phenoxy)-2-hydroxy-2-methyl-N-(4-nitro-3-trifluoromethyl-phenyl)-propionamide;
PubChem CID	10201099;
CompTox Dashboard (EPA)	DTXSID40193187 ;
ECHA InfoCard	100.230.653
Chemical and physical data
Formula	C19H18F3N3O6
Molar mass	441.357 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=N(=O)c1ccc(cc1C(F)(F)F)NC(=O)C(C)(O)COc2ccc(F)cc2;

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Revision as of 01:43, 24 February 2010

Andarine (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]

Clinical development of Andarine has been abandoned, given in humans it results in a series specific toxic metabolite ^[5].

References

^ Yin D, Gao W, Kearbey JD, Xu H, Chung K, He Y, Marhefka CA, Veverka KA, Miller DD, Dalton JT. Pharmacodynamics of selective androgen receptor modulators. Journal of Pharmacology and Experimental Therapeutics. 2003 Mar;304(3):1334-40. PMID 12604714
^ Chen J, Kim J, Dalton JT. Discovery and therapeutic promise of selective androgen receptor modulators. Molecular Interventions. 2005 Jun;5(3):173-88. PMID 15994457
^ Gao W, Kearbey JD, Nair VA, Chung K, Parlow AF, Miller DD, Dalton JT. 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. 2004 Dec;145(12):5420-8. PMID 15308613
^ Gao W, Kim J, Dalton JT. Pharmacokinetics and pharmacodynamics of nonsteroidal androgen receptor ligands. Pharmaceutical Research. 2006 Aug;23(8):1641-58. PMID 16841196
^ Gao W, et al. INTERSPECIES DIFFERENCES IN PHARMACOKINETICS AND METABOLISM OF S-3-(4-ACETYLAMINO-PHENOXY)-2-HYDROXY-2-METHYL-N-(4-NITRO-3-TRIFLUOROMETHYLPHENYL)-PROPIONAMIDE: THE ROLE OF N-ACETYLTRANSFERASE Drug Metabolism and Disposition. 10/2005;34(2):254-260. http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2039883/

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[ReferenceA-1] Yin D, Gao W, Kearbey JD, Xu H, Chung K, He Y, Marhefka CA, Veverka KA, Miller DD, Dalton JT. Pharmacodynamics of selective androgen receptor modulators. Journal of Pharmacology and Experimental Therapeutics. 2003 Mar;304(3):1334-40. PMID 12604714

[2] Chen J, Kim J, Dalton JT. Discovery and therapeutic promise of selective androgen receptor modulators. Molecular Interventions. 2005 Jun;5(3):173-88. PMID 15994457

[3] Gao W, Kearbey JD, Nair VA, Chung K, Parlow AF, Miller DD, Dalton JT. 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. 2004 Dec;145(12):5420-8. PMID 15308613

[4] Gao W, Kim J, Dalton JT. Pharmacokinetics and pharmacodynamics of nonsteroidal androgen receptor ligands. Pharmaceutical Research. 2006 Aug;23(8):1641-58. PMID 16841196

[5] Gao W, et al. INTERSPECIES DIFFERENCES IN PHARMACOKINETICS AND METABOLISM OF S-3-(4-ACETYLAMINO-PHENOXY)-2-HYDROXY-2-METHYL-N-(4-NITRO-3-TRIFLUOROMETHYLPHENYL)-PROPIONAMIDE: THE ROLE OF N-ACETYLTRANSFERASE Drug Metabolism and Disposition. 10/2005;34(2):254-260. http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2039883/

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 '''Andarine''' ('''S-4''') is an investigational [[selective androgen receptor modulator]] (SARM) developed by [http://www.gtxinc.com GTx Inc] for treatment of conditions such as [[muscle]] wasting, [[osteoporosis]] and [[benign prostatic hypertrophy]],<ref name="ReferenceA">Yin D, Gao W, Kearbey JD, Xu H, Chung K, He Y, Marhefka CA, Veverka KA, Miller DD, Dalton JT. Pharmacodynamics of selective androgen receptor modulators. ''Journal of Pharmacology and Experimental Therapeutics''. 2003 Mar;304(3):1334-40. PMID 12604714</ref> using the non-steroidal androgen antagonist [[bicalutamide]] as a lead compound.<ref>Chen J, Kim J, Dalton JT. Discovery and therapeutic promise of selective androgen receptor modulators. ''Molecular Interventions''. 2005 Jun;5(3):173-88. PMID 15994457</ref>
-Andarine is an orally active [[partial agonist]] for [[androgen receptor]]s. It is less potent in both anabolic and androgenic effects than other similar drugs such as [[ostarine]], but this is useful for some indications.<ref name="ReferenceA" /> 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.<ref>Gao W, Kearbey JD, Nair VA, Chung K, Parlow AF, Miller DD, Dalton JT. 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''. 2004 Dec;145(12):5420-8. PMID 15308613</ref> This suggests that it is able to 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 [[Antiandrogen|anti-androgenic]] drugs traditionally used for treatment of BPH.<ref>Gao W, Kim J, Dalton JT. Pharmacokinetics and pharmacodynamics of nonsteroidal androgen receptor ligands. ''Pharmaceutical Research''. 2006 Aug;23(8):1641-58. PMID 16841196</ref>
+Andarine is an orally active [[partial agonist]] for [[androgen receptor]]s. 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.<ref>Gao W, Kearbey JD, Nair VA, Chung K, Parlow AF, Miller DD, Dalton JT. 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''. 2004 Dec;145(12):5420-8. PMID 15308613</ref> 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 [[Antiandrogen|anti-androgenic]] drugs traditionally used for treatment of BPH.<ref>Gao W, Kim J, Dalton JT. Pharmacokinetics and pharmacodynamics of nonsteroidal androgen receptor ligands. ''Pharmaceutical Research''. 2006 Aug;23(8):1641-58. PMID 16841196</ref>
 Clinical development of Andarine has been abandoned, given in humans it results in a series specific toxic metabolite <ref>Gao W, et al. INTERSPECIES DIFFERENCES IN PHARMACOKINETICS AND METABOLISM OF S-3-(4-ACETYLAMINO-PHENOXY)-2-HYDROXY-2-METHYL-N-(4-NITRO-3-TRIFLUOROMETHYLPHENYL)-PROPIONAMIDE: THE ROLE OF N-ACETYLTRANSFERASE ''Drug Metabolism and Disposition''. 10/2005;34(2):254-260. http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2039883/</ref>.