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 ;
CompTox Dashboard (EPA)	DTXSID001025592 ;
Chemical and physical data
Formula	C17H19N5
Molar mass	293.374 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, et al. (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): 6758–6763. Bibcode:2004PNAS..101.6758B. doi:10.1073/pnas.0308292101. PMC 404118. PMID 15087502.
^ Cowart M, Latshaw SP, Bhatia P, Daanen JF, Rohde J, Nelson SL, et al. (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): 3853–3864. doi:10.1021/jm030505a. PMID 15239663.
^ Patel MV, Kolasa T, Mortell K, Matulenko MA, Hakeem AA, Rohde JJ, et al. (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): 7450–7465. 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): 265–277. 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, et al. (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): 6758–6763. Bibcode:2004PNAS..101.6758B. doi:10.1073/pnas.0308292101. PMC 404118. PMID 15087502.

[pmid15239663-2] Cowart M, Latshaw SP, Bhatia P, Daanen JF, Rohde J, Nelson SL, et al. (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): 3853–3864. doi:10.1021/jm030505a. PMID 15239663.

[pmid17149874-3] Patel MV, Kolasa T, Mortell K, Matulenko MA, Hakeem AA, Rohde JJ, et al. (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): 7450–7465. 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): 265–277. doi:10.1007/s00213-008-1238-0. PMID 18604600.

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Identifiers

IUPAC name 2-(4-pyridin-2-ylpiperazin-1-ylmethyl)-1H-benzimidazole
CAS Number	70006-24-5^N
PubChem CID	5025739
ChemSpider	4204515^Y
UNII	4WV2575JWT
ChEMBL	ChEMBL440687^Y
CompTox Dashboard (EPA)	DTXSID001025592
Chemical and physical data
Formula	C₁₇H₁₉N₅
Molar mass	293.374 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)^Y Key:FRPJGTNLZNXQEX-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

ABT-724

See also

References