THIQ

THIQ is a drug used in scientific research, which is the first non-peptide agonist developed that is selective for the melanocortin receptor subtype MC4.[1][2] In animal studies, THIQ stimulated sexual activity in rats,[3] but with little effect on appetite or inflammation.[4] This supports possible application of MC4 selective agonists for the treatment of sexual dysfunction in humans,[5] although THIQ itself has poor oral bioavailability and a short duration of action so improved analogues will need to be developed.[6]

THIQ
Identifiers
IUPAC name
  • N-[(3R)-1,2,3,4-tetrahydroisoquinolinium-3-ylcarbonyl]-(1R)-1-(4-chlorobenzyl) -2-[4-cyclohexyl-4-(1H-1,2,4-triazol-1ylmethyl)piperidin-1-yl]-2-oxoethylamine
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC33H41ClN6O2
Molar mass589.169 g·mol−1
3D model (JSmol)
SMILES
  • C1CCC(CC1)C2(CCN(CC2)C(=O)[C@@H](CC3=CC=C(C=C3)Cl)NC(=O)[C@H]4CC5=CC=CC=C5CN4)CN6C=NC=N6
InChI
  • InChI=1S/C33H41ClN6O2/c34-28-12-10-24(11-13-28)18-30(38-31(41)29-19-25-6-4-5-7-26(25)20-36-29)32(42)39-16-14-33(15-17-39,21-40-23-35-22-37-40)27-8-2-1-3-9-27/h4-7,10-13,22-23,27,29-30,36H,1-3,8-9,14-21H2,(H,38,41)/t29-,30-/m1/s1
  • Key:HLCHESOMJVGDSJ-LOYHVIPDSA-N
  (verify)

See also

References
  1. Mutulis F, Yahorava S, Mutule I, Yahorau A, Liepinsh E, Kopantshuk S, Veiksina S, Tars K, Belyakov S, Mishnev A, Rinken A, Wikberg JE (August 2004). "New substituted piperazines as ligands for melanocortin receptors. Correlation to the X-ray structure of "THIQ"". Journal of Medicinal Chemistry. 47 (18): 4613–26. doi:10.1021/jm0311285. PMID 15317471.
  2. Pogozheva ID, Chai BX, Lomize AL, Fong TM, Weinberg DH, Nargund RP, Mulholland MW, Gantz I, Mosberg HI (August 2005). "Interactions of human melanocortin 4 receptor with nonpeptide and peptide agonists". Biochemistry. 44 (34): 11329–41. doi:10.1021/bi0501840. PMC 2532597. PMID 16114870.
  3. Martin WJ, McGowan E, Cashen DE, Gantert LT, Drisko JE, Hom GJ, Nargund R, Sebhat I, Howard AD, Van der Ploeg LH, MacIntyre DE (November 2002). "Activation of melanocortin MC(4) receptors increases erectile activity in rats ex copula". European Journal of Pharmacology. 454 (1): 71–9. doi:10.1016/S0014-2999(02)02479-2. PMID 12409007.
  4. Muceniece R, Zvejniece L, Vilskersts R, Liepinsh E, Baumane L, Kalvinsh I, Wikberg JE, Dambrova M (December 2007). "Functional evaluation of THIQ, a melanocortin 4 receptor agonist, in models of food intake and inflammation". Basic & Clinical Pharmacology & Toxicology. 101 (6): 416–20. doi:10.1111/j.1742-7843.2007.00133.x. PMID 18028105.
  5. Shadiack AM, Sharma SD, Earle DC, Spana C, Hallam TJ (2007). "Melanocortins in the treatment of male and female sexual dysfunction". Current Topics in Medicinal Chemistry. 7 (11): 1137–44. CiteSeerX 10.1.1.326.8017. doi:10.2174/156802607780906681. PMID 17584134.
  6. King SH, Mayorov AV, Balse-Srinivasan P, Hruby VJ, Vanderah TW, Wessells H (2007). "Melanocortin receptors, melanotropic peptides and penile erection". Current Topics in Medicinal Chemistry. 7 (11): 1098–1106. doi:10.2174/1568026610707011111. PMC 2694735. PMID 17584130.


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