TAN-821

TAN-821
Identifiers
	IUPAC name (1R,2S,6R,14R,15R,16S)-5-(cyclopropylmethyl)-11,15-dihydroxy-N-methyl-N-(2-phenylethyl)-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11,18-tetraene-16-carboxamide;
PubChem CID	46907011;
ChemSpider	25032059;
ChEMBL	ChEMBL1163923;
Chemical and physical data
Formula	C32H36N2O4
Molar mass	512.650 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN(CCC1=CC=CC=C1)C(=O)[C@H]2C[C@@]34C=C[C@@]2([C@H]5[C@@]36CCN([C@@H]4CC7=C6C(=C(C=C7)O)O5)CC8CC8)O;
	InChI InChI=1S/C32H36N2O4/c1-33(15-11-20-5-3-2-4-6-20)28(36)23-18-30-12-13-32(23,37)29-31(30)14-16-34(19-21-7-8-21)25(30)17-22-9-10-24(35)27(38-29)26(22)31/h2-6,9-10,12-13,21,23,25,29,35,37H,7-8,11,14-19H2,1H3/t23-,25-,29-,30-,31+,32-/m1/s1; Key:XTSYSSUSRFOCHS-ZZVPPEEFSA-N;

TAN-821 is an opioid drug which was originally reported as an agonist for the putative ε-opioid receptor, however this is now thought not to be a separate opioid receptor in its own right but is more likely a heteromer made from hybridisation of known opioid receptor subunits. It has subsequently been shown to have potent affinity for the kappa opioid receptor.^[1]^[2]^[3]^[4]^[5]

References

^ Fujii H, Narita M, Mizoguchi H, Murachi M, Tanaka T, Kawai K, et al. (August 2004). "Drug design and synthesis of epsilon opioid receptor agonist: 17-(cyclopropylmethyl)-4,5alpha-epoxy-3,6beta-dihydroxy-6,14-endoethenomorphinan-7alpha-(N-methyl-N-phenethyl)carboxamide (TAN-821) inducing antinociception mediated by putative epsilon opioid receptor". Bioorganic & Medicinal Chemistry. 12 (15): 4133–4145. doi:10.1016/j.bmc.2004.05.024. PMID 15246090.
^ Fujii H, Narita M, Mizoguchi H, Hirokawa J, Kawai K, Tanaka T, et al. (August 2004). "Rational drug design and synthesis of a selective opioid receptor antagonist on the basis of the accessory site concept". Bioorganic & Medicinal Chemistry Letters. 14 (16): 4241–4243. doi:10.1016/j.bmcl.2004.06.004. PMID 15261278.
^ Fujii H, Nagase H (2006). "Rational drug design of selective epsilon opioid receptor agonist TAN-821 and antagonist TAN-1014". Current Medicinal Chemistry. 13 (10): 1109–1118. doi:10.2174/092986706776360851. PMID 16719773.
^ Fujii H, Watanabe Y, Osa Y, Nemoto T, Sato N, Nagase H (2009). "Novel rearrangement reaction of a 6,14-endoethanomorphinan derivative to a benzomorphan derivative". Tetrahedron. 65 (25): 4808–4813. doi:10.1016/j.tet.2009.04.055.
^ Yamaotsu N, Fujii H, Nagase H, Hirono S (June 2010). "Identification of the three-dimensional pharmacophore of kappa-opioid receptor agonists". Bioorganic & Medicinal Chemistry. 18 (12): 4446–4452. doi:10.1016/j.bmc.2010.04.069. PMID 20478711.

[1] Fujii H, Narita M, Mizoguchi H, Murachi M, Tanaka T, Kawai K, et al. (August 2004). "Drug design and synthesis of epsilon opioid receptor agonist: 17-(cyclopropylmethyl)-4,5alpha-epoxy-3,6beta-dihydroxy-6,14-endoethenomorphinan-7alpha-(N-methyl-N-phenethyl)carboxamide (TAN-821) inducing antinociception mediated by putative epsilon opioid receptor". Bioorganic & Medicinal Chemistry. 12 (15): 4133–4145. doi:10.1016/j.bmc.2004.05.024. PMID 15246090.

[2] Fujii H, Narita M, Mizoguchi H, Hirokawa J, Kawai K, Tanaka T, et al. (August 2004). "Rational drug design and synthesis of a selective opioid receptor antagonist on the basis of the accessory site concept". Bioorganic & Medicinal Chemistry Letters. 14 (16): 4241–4243. doi:10.1016/j.bmcl.2004.06.004. PMID 15261278.

[3] Fujii H, Nagase H (2006). "Rational drug design of selective epsilon opioid receptor agonist TAN-821 and antagonist TAN-1014". Current Medicinal Chemistry. 13 (10): 1109–1118. doi:10.2174/092986706776360851. PMID 16719773.

[4] Fujii H, Watanabe Y, Osa Y, Nemoto T, Sato N, Nagase H (2009). "Novel rearrangement reaction of a 6,14-endoethanomorphinan derivative to a benzomorphan derivative". Tetrahedron. 65 (25): 4808–4813. doi:10.1016/j.tet.2009.04.055.

[5] Yamaotsu N, Fujii H, Nagase H, Hirono S (June 2010). "Identification of the three-dimensional pharmacophore of kappa-opioid receptor agonists". Bioorganic & Medicinal Chemistry. 18 (12): 4446–4452. doi:10.1016/j.bmc.2010.04.069. PMID 20478711.

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See also

References