ABT-724

ABT-724
Identifiers
	IUPAC name 2-(4-pyridin-2-ylpiperazin-1-ylmethyl)-1H-benzimidazole;
CAS Number	70006-24-5 ;
PubChem CID	5025739;
ChemSpider	4204515 ;
UNII	4WV2575JWT;
ChEMBL	ChEMBL440687 ;
Chemical and physical data
Formula	C17H19N5
Molar mass	293.366 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES n2c1ccccc1[nH]c2CN(CC4)CCN4c3ncccc3;
	InChI InChI=1S/C17H19N5/c1-2-6-15-14(5-1)19-16(20-15)13-21-9-11-22(12-10-21)17-7-3-4-8-18-17/h1-8H,9-13H2,(H,19,20) ; Key:FRPJGTNLZNXQEX-UHFFFAOYSA-N ;
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ABT-724 is a drug which acts as a dopamine agonist, and is selective for the D₄ subtype.[1] It was developed as a possible drug for the treatment of erectile dysfunction,[2] although poor oral bioavailability means alternative drugs such as ABT-670 may be more likely to be developed commercially.[3] Nonetheless, it continues to be used in scientific research into the function of the D₄ receptor.[4][5]

References

Brioni JD, Moreland RB, Cowart M, Hsieh GC, Stewart AO, Hedlund P, Donnelly-Roberts DL, Nakane M, Lynch JJ, Kolasa T, Polakowski JS, Osinski MA, Marsh K, Andersson KE, Sullivan JP (April 2004). "Activation of dopamine D4 receptors by ABT-724 induces penile erection in rats". Proceedings of the National Academy of Sciences of the United States of America. 101 (17): 6758–63. doi:10.1073/pnas.0308292101. PMC 404118. PMID 15087502.
Cowart M, Latshaw SP, Bhatia P, Daanen JF, Rohde J, Nelson SL, Patel M, Kolasa T, Nakane M, Uchic ME, Miller LN, Terranova MA, Chang R, Donnelly-Roberts DL, Namovic MT, Hollingsworth PR, Martino BR, Lynch JJ, Sullivan JP, Hsieh GC, Moreland RB, Brioni JD, Stewart AO (July 2004). "Discovery of 2-(4-pyridin-2-ylpiperazin-1-ylmethyl)-1H-benzimidazole (ABT-724), a dopaminergic agent with a novel mode of action for the potential treatment of erectile dysfunction". Journal of Medicinal Chemistry. 47 (15): 3853–64. doi:10.1021/jm030505a. PMID 15239663.
Patel MV, Kolasa T, Mortell K, Matulenko MA, Hakeem AA, Rohde JJ, Nelson SL, Cowart MD, Nakane M, Miller LN, Uchic ME, Terranova MA, El-Kouhen OF, Donnelly-Roberts DL, Namovic MT, Hollingsworth PR, Chang R, Martino BR, Wetter JM, Marsh KC, Martin R, Darbyshire JF, Gintant G, Hsieh GC, Moreland RB, Sullivan JP, Brioni JD, Stewart AO (December 2006). "Discovery of 3-methyl-N-(1-oxy-3',4',5',6'-tetrahydro-2'H-[2,4'-bipyridine]-1'-ylmethyl)benzamide (ABT-670), an orally bioavailable dopamine D4 agonist for the treatment of erectile dysfunction". Journal of Medicinal Chemistry. 49 (25): 7450–65. doi:10.1021/jm060662k. PMID 17149874.
Newman-Tancredi A, Heusler P, Martel JC, Ormière AM, Leduc N, Cussac D (May 2008). "Agonist and antagonist properties of antipsychotics at human dopamine D4.4 receptors: G-protein activation and K+ channel modulation in transfected cells". The International Journal of Neuropsychopharmacology. 11 (3): 293–307. doi:10.1017/S1461145707008061. PMID 17897483.
Marona-Lewicka D, Chemel BR, Nichols DE (April 2009). "Dopamine D4 receptor involvement in the discriminative stimulus effects in rats of LSD, but not the phenethylamine hallucinogen DOI". Psychopharmacology. 203 (2): 265–77. doi:10.1007/s00213-008-1238-0. PMID 18604600.

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[pmid15087502-1] Brioni JD, Moreland RB, Cowart M, Hsieh GC, Stewart AO, Hedlund P, Donnelly-Roberts DL, Nakane M, Lynch JJ, Kolasa T, Polakowski JS, Osinski MA, Marsh K, Andersson KE, Sullivan JP (April 2004). "Activation of dopamine D4 receptors by ABT-724 induces penile erection in rats". Proceedings of the National Academy of Sciences of the United States of America. 101 (17): 6758–63. doi:10.1073/pnas.0308292101. PMC 404118. PMID 15087502.

[pmid15239663-2] Cowart M, Latshaw SP, Bhatia P, Daanen JF, Rohde J, Nelson SL, Patel M, Kolasa T, Nakane M, Uchic ME, Miller LN, Terranova MA, Chang R, Donnelly-Roberts DL, Namovic MT, Hollingsworth PR, Martino BR, Lynch JJ, Sullivan JP, Hsieh GC, Moreland RB, Brioni JD, Stewart AO (July 2004). "Discovery of 2-(4-pyridin-2-ylpiperazin-1-ylmethyl)-1H-benzimidazole (ABT-724), a dopaminergic agent with a novel mode of action for the potential treatment of erectile dysfunction". Journal of Medicinal Chemistry. 47 (15): 3853–64. doi:10.1021/jm030505a. PMID 15239663.

[pmid17149874-3] Patel MV, Kolasa T, Mortell K, Matulenko MA, Hakeem AA, Rohde JJ, Nelson SL, Cowart MD, Nakane M, Miller LN, Uchic ME, Terranova MA, El-Kouhen OF, Donnelly-Roberts DL, Namovic MT, Hollingsworth PR, Chang R, Martino BR, Wetter JM, Marsh KC, Martin R, Darbyshire JF, Gintant G, Hsieh GC, Moreland RB, Sullivan JP, Brioni JD, Stewart AO (December 2006). "Discovery of 3-methyl-N-(1-oxy-3',4',5',6'-tetrahydro-2'H-[2,4'-bipyridine]-1'-ylmethyl)benzamide (ABT-670), an orally bioavailable dopamine D4 agonist for the treatment of erectile dysfunction". Journal of Medicinal Chemistry. 49 (25): 7450–65. doi:10.1021/jm060662k. PMID 17149874.

[pmid17897483-4] Newman-Tancredi A, Heusler P, Martel JC, Ormière AM, Leduc N, Cussac D (May 2008). "Agonist and antagonist properties of antipsychotics at human dopamine D4.4 receptors: G-protein activation and K+ channel modulation in transfected cells". The International Journal of Neuropsychopharmacology. 11 (3): 293–307. doi:10.1017/S1461145707008061. PMID 17897483.

[pmid18604600-5] Marona-Lewicka D, Chemel BR, Nichols DE (April 2009). "Dopamine D4 receptor involvement in the discriminative stimulus effects in rats of LSD, but not the phenethylamine hallucinogen DOI". Psychopharmacology. 203 (2): 265–77. doi:10.1007/s00213-008-1238-0. PMID 18604600.

ABT-724

See also

References