Robalzotan

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 448230811

| IUPAC_name = (3R)-3-[di(cyclobutyl)amino]-8-fluoro-3,4-dihydro-2H-chromene-5-carboxamide

| image = Robalzotan 1.svg

| tradename =

| pregnancy_category =

| legal_status = Uncontrolled

| routes_of_administration = Oral

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| IUPHAR_ligand = 72

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 169758-66-1

| ATC_prefix = none

| ATC_suffix =

| PubChem = 3055171

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = I18M56OGME

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 2316732

| C=18 | H=23 | F=1 | N=2 | O=2

| smiles = C1CC(C1)N(C2CCC2)[C@@H]3CC4=C(C=CC(=C4OC3)F)C(=O)N

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C18H23FN2O2/c19-16-8-7-14(18(20)22)15-9-13(10-23-17(15)16)21(11-3-1-4-11)12-5-2-6-12/h7-8,11-13H,1-6,9-10H2,(H2,20,22)/t13-/m1/s1

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = MQTUXRKNJYPMCG-CYBMUJFWSA-N

}}

Robalzotan (NAD-299, AZD-7371) is a selective antagonist at the 5-HT_1A receptor.{{cite journal | doi = 10.1016/S0014-2999(98)00667-0 |vauthors=Jerning E, Svantesson GT, Mohell N | title = Receptor binding characteristics of [3H]NAD-299, a new selective 5-HT1A receptor antagonist. | journal = Eur J Pharmacol | volume = 360 | issue = 2–3 | pages = 219–225 | year = 1998 | pmid = 9851589 }} It was shown to completely reverse the autoreceptor-mediated inhibition of serotonin release induced by the administration of selective serotonin reuptake inhibitors like citalopram in rodent studies.{{cite journal | doi = 10.1016/S0014-2999(99)00592-0 |vauthors=Arborelius L, Wallsten C, Ahlenius S, Svensson TH | title = The 5-HT(1A) receptor antagonist robalzotan completely reverses citalopram-induced inhibition of serotonergic cell firing. | journal = Eur J Pharmacol | volume = 382 | issue = 2 | pages = 133–138 | year = 1999 | pmid = 10528148 }} It was subsequently investigated by AstraZeneca as a potential antidepressant but like many other 5-HT_1A ligands was discontinued.{{cite journal | author = Mucke HA. | title = Robalzotan AstraZeneca. | journal = Curr Opin Investig Drugs | volume = 1 | issue = 2 | pages = 236–240 | year = 2000 | pmid = 11249580 }} Later on it was researched for other indications such as irritable bowel syndrome but was dropped once again.{{cite journal |vauthors=Drossman DA, Danilewitz M, Naesdal J, Hwang C, Adler J, Silberg DG | title = Randomized, double-blind, placebo-controlled trial of the 5-HT1A receptor antagonist AZD7371 tartrate monohydrate (robalzotan tartrate monohydrate) in patients with irritable bowel syndrome | journal = The American Journal of Gastroenterology | volume = 103 | issue = 10 | pages = 2562–9 |date=October 2008 | pmid = 18775020 | doi = 10.1111/j.1572-0241.2008.02115.x }}