Robalzotan

Robalzotan
Clinical data
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	In general: uncontrolled;
Identifiers
	IUPAC name (3R)-3-[di(cyclobutyl)amino]-8-fluoro-3,4-dihydro-2H-chromene-5-carboxamide;
CAS Number	169758-66-1 ;
PubChem CID	3055171;
IUPHAR/BPS	72;
ChemSpider	2316732 ;
UNII	I18M56OGME;
CompTox Dashboard (EPA)	DTXSID30168743 ;
Chemical and physical data
Formula	C18H23FN2O2
Molar mass	318.392 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CC(C1)N(C2CCC2)[C@@H]3CC4=C(C=CC(=C4OC3)F)C(=O)N;
	InChI InChI=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 ; Key:MQTUXRKNJYPMCG-CYBMUJFWSA-N ;
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Robalzotan (NAD-299, AZD-7371) is a selective antagonist at the 5-HT_1A receptor.^[1] 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.^[2] It was subsequently investigated by AstraZeneca as a potential antidepressant but like many other 5-HT_1A ligands was discontinued.^[3] Later on it was researched for other indications such as irritable bowel syndrome but was dropped once again.^[4]

References

^ Jerning E, Svantesson GT, Mohell N (1998). "Receptor binding characteristics of [3H]NAD-299, a new selective 5-HT1A receptor antagonist". Eur J Pharmacol. 360 (2–3): 219–225. doi:10.1016/S0014-2999(98)00667-0. PMID 9851589.
^ Arborelius L, Wallsten C, Ahlenius S, Svensson TH (1999). "The 5-HT(1A) receptor antagonist robalzotan completely reverses citalopram-induced inhibition of serotonergic cell firing". Eur J Pharmacol. 382 (2): 133–138. doi:10.1016/S0014-2999(99)00592-0. PMID 10528148.
^ Mucke HA. (2000). "Robalzotan AstraZeneca". Curr Opin Investig Drugs. 1 (2): 236–240. PMID 11249580.
^ Drossman DA, Danilewitz M, Naesdal J, Hwang C, Adler J, Silberg DG (October 2008). "Randomized, double-blind, placebo-controlled trial of the 5-HT1A receptor antagonist AZD7371 tartrate monohydrate (robalzotan tartrate monohydrate) in patients with irritable bowel syndrome". The American Journal of Gastroenterology. 103 (10): 2562–9. doi:10.1111/j.1572-0241.2008.02115.x. PMID 18775020.

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Clinical data

Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name (3R)-3-[di(cyclobutyl)amino]-8-fluoro-3,4-dihydro-2H-chromene-5-carboxamide
CAS Number	169758-66-1^Y
PubChem CID	3055171
IUPHAR/BPS	72
ChemSpider	2316732^N
UNII	I18M56OGME
CompTox Dashboard (EPA)	DTXSID30168743
Chemical and physical data
Formula	C₁₈H₂₃FN₂O₂
Molar mass	318.392 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1CC(C1)N(C2CCC2)[C@@H]3CC4=C(C=CC(=C4OC3)F)C(=O)N
InChI InChI=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^N Key:MQTUXRKNJYPMCG-CYBMUJFWSA-N^N
^NY (what is this?) (verify)