Umespirone

Umespirone
Systematic (IUPAC) name
	3-butyl-7-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl]-9,9-dimethyl-3,7-diazabicyclo[3.3.1]nonane-2,4,6,8-tetrone
Clinical data
Pregnancy cat.	?
Legal status	uncontrolled
Routes	oral
Pharmacokinetic data
Half-life	Unknown but effects last much longer than other azapirones, up to 23 hours after a single dose in human clinical studies.
Identifiers
CAS number	107736-98-1
ATC code	None
PubChem	CID 65902
ChemSpider	59311
UNII	FG0A3VRL5K
Chemical data
Formula	C28H40N4O5
Mol. mass	512.64 g/mol
	SMILES O=C1N(C(=O)C2C(=O)N(C(=O)C1C2(C)C)CCCCN4CCN(c3ccccc3OC)CC4)CCCC;

Umespirone (KC-9172) is a drug of the azapirone class which possesses anxiolytic and antipsychotic properties.^[2]^[3]^[4]^[5] It behaves as a 5-HT_1A receptor partial agonist (K_i = 15 nM), D₂ receptor partial agonist (K_i = 23 nM), and α₁-adrenoceptor receptor antagonist (K_i = 14 nM), and also has weak affinity for the sigma receptor (K_i = 558 nM).^[2]^[6]^[7] Unlike many other anxiolytics and antipsychotics, umespirone produces minimal sedation, cognitive/memory impairment, catalepsy, and extrapyramidal symptoms.^[1]^[5]^[6]

[edit] See also

Azapirone

[edit] References

^ ^a ^b Holland RL, Wesnes K, Dietrich B (1994). "Single dose human pharmacology of umespirone". European Journal of Clinical Pharmacology 46 (5): 461–8. PMID 7957544.
^ ^a ^b Barnes NM, Costall B, Domeney AM, et al. (September 1991). "The effects of umespirone as a potential anxiolytic and antipsychotic agent". Pharmacology, Biochemistry, and Behavior 40 (1): 89–96. doi:10.1016/0091-3057(91)90326-W. PMID 1685786.
^ Ruhland M, Krähling H, Fuchs A, Schön U (November 1988). "KC 9172 (free base of KC 7218)--an antipsychotic/anxiolytic compound. I. Antipsychotic and anxiolytic activity in comparison with chlorpromazine, clozapine, diazepam and buspirone". Pharmacopsychiatry 21 (6): 396–8. doi:10.1055/s-2007-1017024. PMID 2907649.
^ Krähling H, Fuchs A, Ruhland M, Schön U, Mol F, Tulp M (November 1988). "KC 9172 (free base of KC 7218)--an antipsychotic/anxiolytic compound. II. Discrimination from typical neuroleptics and benzodiazepine-like minor tranquilizers". Pharmacopsychiatry 21 (6): 399–401. doi:10.1055/s-2007-1017025. PMID 2907650.
^ ^a ^b Schmidt WJ, Krähling H, Ruhland M (1991). "Antagonism of AP-5-induced sniffing stereotypy links umespirone to atypical antipsychotics". Life Sciences 48 (6): 499–505. doi:10.1016/0024-3205(91)90464-M. PMID 1671523.
^ ^a ^b Ahlenius S, Wijkström A (November 1992). "Mixed agonist-antagonist properties of umespirone at neostriatal dopamine receptors in relation to its behavioral effects in the rat". European Journal of Pharmacology 222 (1): 69–74. doi:10.1016/0014-2999(92)90464-F. PMID 1361441.
^ Itzhak Y, Ruhland M, Krähling H (February 1990). "Binding of umespirone to the sigma receptor: evidence for multiple affinity states". Neuropharmacology 29 (2): 181–4. doi:10.1016/0028-3908(90)90058-Y. PMID 1970425.

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[pmid7957544-1] Holland RL, Wesnes K, Dietrich B (1994). "Single dose human pharmacology of umespirone". European Journal of Clinical Pharmacology 46 (5): 461–8. PMID 7957544.

[pmid1685786-2] Barnes NM, Costall B, Domeney AM, et al. (September 1991). "The effects of umespirone as a potential anxiolytic and antipsychotic agent". Pharmacology, Biochemistry, and Behavior 40 (1): 89–96. doi:10.1016/0091-3057(91)90326-W. PMID 1685786.

[pmid2907649-3] Ruhland M, Krähling H, Fuchs A, Schön U (November 1988). "KC 9172 (free base of KC 7218)--an antipsychotic/anxiolytic compound. I. Antipsychotic and anxiolytic activity in comparison with chlorpromazine, clozapine, diazepam and buspirone". Pharmacopsychiatry 21 (6): 396–8. doi:10.1055/s-2007-1017024. PMID 2907649.

[pmid2907650-4] Krähling H, Fuchs A, Ruhland M, Schön U, Mol F, Tulp M (November 1988). "KC 9172 (free base of KC 7218)--an antipsychotic/anxiolytic compound. II. Discrimination from typical neuroleptics and benzodiazepine-like minor tranquilizers". Pharmacopsychiatry 21 (6): 399–401. doi:10.1055/s-2007-1017025. PMID 2907650.

[pmid1671523-5] Schmidt WJ, Krähling H, Ruhland M (1991). "Antagonism of AP-5-induced sniffing stereotypy links umespirone to atypical antipsychotics". Life Sciences 48 (6): 499–505. doi:10.1016/0024-3205(91)90464-M. PMID 1671523.

[pmid1361441-6] Ahlenius S, Wijkström A (November 1992). "Mixed agonist-antagonist properties of umespirone at neostriatal dopamine receptors in relation to its behavioral effects in the rat". European Journal of Pharmacology 222 (1): 69–74. doi:10.1016/0014-2999(92)90464-F. PMID 1361441.

[pmid1970425-7] Itzhak Y, Ruhland M, Krähling H (February 1990). "Binding of umespirone to the sigma receptor: evidence for multiple affinity states". Neuropharmacology 29 (2): 181–4. doi:10.1016/0028-3908(90)90058-Y. PMID 1970425.

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Umespirone

[edit] See also

[edit] References

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