Ipsapirone

Ipsapirone is a selective 5-HT_1A receptor partial agonist of the piperazine and azapirone chemical classes.^[1] It produces antidepressant, anxiolytic, and antiaggressive effects.^[1]^[2] Ipsapirone was studied in several placebo-controlled trials for depression and continues to be used in research.^[3] It has been found to increase oxytocin levels in rodents,^[4]^[5]^[6]^[7] whereas findings in humans have been mixed.^[8]^[9]

Routes of
administrationOral

Drug classSerotonin 5-HT_1A receptor partial agonist

ATC code

none

Legal status

In general: uncontrolled

Quick facts Clinical data, Routes ofadministration ...

Ipsapirone
Clinical data

Routes of administration	Oral
Drug class	Serotonin 5-HT_1A receptor partial agonist
ATC code	none
Legal status
Legal status	In general: uncontrolled
Pharmacokinetic data
Elimination half-life	1.3–2.7 hours^{[medical citation needed]}
Identifiers
IUPAC name 9,9-dioxo-8-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]- 9λ⁶-thia-8-azabicyclo[4.3.0]nona-1,3,5-trien-7-one
CAS Number	95847-70-4^Y
PubChem CID	56971
IUPHAR/BPS	42
ChemSpider	51365^Y
UNII	6J9B11MN0K
ChEMBL	ChEMBL8412^Y
CompTox Dashboard (EPA)	DTXSID4045688
Chemical and physical data
Formula	C₁₉H₂₃N₅O₃S
Molar mass	401.49 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C2c1ccccc1S(=O)(=O)N2CCCCN4CCN(c3ncccn3)CC4
InChI InChI=1S/C19H23N5O3S/c25-18-16-6-1-2-7-17(16)28(26,27)24(18)11-4-3-10-22-12-14-23(15-13-22)19-20-8-5-9-21-19/h1-2,5-9H,3-4,10-15H2^Y Key:TZJUVVIWVWFLCD-UHFFFAOYSA-N^Y
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References

[1]
Fanelli RJ, Schuurman T, Glaser T, Traber J (1990). "Ipsapirone: a novel anxiolytic and selective 5-HT1A receptor ligand". Progress in Clinical and Biological Research. 361: 461–467. PMID 1981264.
[2]
de Boer SF, Koolhaas JM (December 2005). "5-HT1A and 5-HT1B receptor agonists and aggression: a pharmacological challenge of the serotonin deficiency hypothesis". Eur J Pharmacol. 526 (1–3): 125–139. doi:10.1016/j.ejphar.2005.09.065. PMID 16310183.
[3]
Chessick CA, Allen MH, Thase M, Batista Miralha da Cunha AB, Kapczinski FF, de Lima MS, dos Santos Souza JJ (July 2006). "Azapirones for generalized anxiety disorder". The Cochrane Database of Systematic Reviews. 2006 (3) CD006115. doi:10.1002/14651858.CD006115. PMC 8915394. PMID 16856115.
[4]
Bagdy G, Kalogeras KT (May 1993). "Stimulation of 5-HT1A and 5-HT2/5-HT1C receptors induce oxytocin release in the male rat". Brain Res. 611 (2): 330–332. doi:10.1016/0006-8993(93)90521-n. PMID 8334526.
[5]
Li Q, Brownfield MS, Levy AD, Battaglia G, Cabrera TM, Van de Kar LD (September 1994). "Attenuation of hormone responses to the 5-HT1A agonist ipsapirone by long-term treatment with fluoxetine, but not desipramine, in male rats". Biol Psychiatry. 36 (5): 300–308. doi:10.1016/0006-3223(94)90627-0. PMID 7993956.
[6]
Bagdy G (1996). "Role of the hypothalamic paraventricular nucleus in 5-HT1A, 5-HT2A and 5-HT2C receptor-mediated oxytocin, prolactin and ACTH/corticosterone responses". Behav Brain Res. 73 (1–2): 277–280. doi:10.1016/0166-4328(96)00112-x. PMID 8788518.
[7]
Bagdy G (1996). "Studies on the sites and mechanisms of 5-HT1A receptor-mediated in vivo actions". Acta Physiol Hung. 84 (4): 399–401. PMID 9328612.
[8]
Cleare AJ, Forsling M, Bond AJ (January 1998). "Neuroendocrine and hypothermic effects of 5-HT1A receptor stimulation with ipsapirone in healthy men: a placebo-controlled study". Int Clin Psychopharmacol. 13 (1): 23–32. doi:10.1097/00004850-199801000-00004. PMID 9988364.
[9]
Newman ME, Li Q, Gelfin Y, Van de Kar LD, Lerer B (July 1999). "Low doses of ipsapirone increase growth hormone but not oxytocin secretion in normal male and female subjects". Psychopharmacology (Berl). 145 (1): 99–104. doi:10.1007/s002130051037. PMID 10445378.

See also

References

External links

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