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Chemical Compound Review

AC1L3LQM     9-[2-[4-(2- methylphenyl)pyrazin-1...

Synonyms: LS-177000, C19H27N5.HCl
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Disease relevance of 9-[2-[4-(o-tolyl)pyrazin-1-yl]ethyl]-1,7,8-triazabicyclo[4.3.0]nona-6,8-diene

  • RESULTS: Dapiprazole drops produced a Horner's miosis, but pupils were equally small after induction of anesthesia [1].
  • The authors hypothesized that the reflex was primarily a spinal sympathetic reflex that would be blocked by topical application of the alpha1-adrenergic blocking agent dapiprazole and that it would be present in organ donors with intact spinal reflexes and no history of hypoxia [2].
  • The results showed a significant reversal of mydriasis by intraocular dapiprazole, especially with the 0.25% and 0.5% concentrations which did not differ significantly in effectiveness and safety [3].
  • No difference in the toxicity parameters (inflammatory score, corneal thickness, endothelial cell counting, aqueous humor protein concentration, and intraocular pressure) was found between dapiprazole-treated eyes and saline-solution-treated eyes [4].
  • All of our subjects exhibited conjunctival hyperemia after the administration of dapiprazole [5].

High impact information on 9-[2-[4-(o-tolyl)pyrazin-1-yl]ethyl]-1,7,8-triazabicyclo[4.3.0]nona-6,8-diene


Chemical compound and disease context of 9-[2-[4-(o-tolyl)pyrazin-1-yl]ethyl]-1,7,8-triazabicyclo[4.3.0]nona-6,8-diene


Biological context of 9-[2-[4-(o-tolyl)pyrazin-1-yl]ethyl]-1,7,8-triazabicyclo[4.3.0]nona-6,8-diene


Anatomical context of 9-[2-[4-(o-tolyl)pyrazin-1-yl]ethyl]-1,7,8-triazabicyclo[4.3.0]nona-6,8-diene

  • Dapiprazole had relatively high affinity both at rat vas deferens alpha 1A-adrenoceptors (pA2 = 7.93) and at rat aortic alpha 1D-adrenoceptors (pA2 = 8.26), whereas its affinity at guinea-pig splenic alpha 1B-adrenoceptors (pA2 = 7.13) was lower [16].
  • The Ca2+-induced contractions of K+-depolarized ileum were also inhibited by dapiprazole [17].
  • The results suggest that dapiprazole might inhibit Ca2+ entry through both voltage-and receptor-operated channels of the smooth muscle membrane [17].

Associations of 9-[2-[4-(o-tolyl)pyrazin-1-yl]ethyl]-1,7,8-triazabicyclo[4.3.0]nona-6,8-diene with other chemical compounds


Gene context of 9-[2-[4-(o-tolyl)pyrazin-1-yl]ethyl]-1,7,8-triazabicyclo[4.3.0]nona-6,8-diene

  • The absence of induced myopia and the lack of dangerous vitreoretinal tractions on retinal periphery make dapiprazole a safe method to reduce exercise-induced pigment dispersion [19].
  • PURPOSE: The authors investigated the use of dapiprazole, an alpha-adrenergic blocking agent, in preventing pigment release and IOP increase after exercise in patients affected with PDS [19].

Analytical, diagnostic and therapeutic context of 9-[2-[4-(o-tolyl)pyrazin-1-yl]ethyl]-1,7,8-triazabicyclo[4.3.0]nona-6,8-diene


  1. Sympathetic nervous system does not mediate reflex pupillary dilation during desflurane anesthesia. Larson, M.D., Tayefeh, F., Sessler, D.I., Daniel, M., Noorani, M. Anesthesiology (1996) [Pubmed]
  2. Mechanism of pupillary reflex dilation in awake volunteers and in organ donors. Yang, L.L., Niemann, C.U., Larson, M.D. Anesthesiology (2003) [Pubmed]
  3. Intraocular dapiprazole for the reversal of mydriasis after extracapsular cataract extraction with intraocular lens implantation. Part I: Dose-response correlation. Ponte, F., Cillino, S., Faranda, F., Casanova, F., Cucci, F. Journal of cataract and refractive surgery. (1991) [Pubmed]
  4. Effects of intraocular dapiprazole in the rabbit eye. Bonomi, L., Marchini, G., Pagello, P., Simonazzi, A., Durando, L., Ciarniello, M.G. Journal of cataract and refractive surgery. (1989) [Pubmed]
  5. Dapiprazole clinical efficiency for counteracting tropicamide 1%. Molinari, J.F., Johnson, M.E., Carter, J. Optometry and vision science : official publication of the American Academy of Optometry. (1994) [Pubmed]
  6. Effect of ibopamine on aqueous humor production in normotensive humans. McLaren, J.W., Herman, D.C., Brubaker, R.F., Nau, C.B., Wayman, L.L., Ciarniello, M.G., Rosignoli, M.T., Dionisio, P. Invest. Ophthalmol. Vis. Sci. (2003) [Pubmed]
  7. Brimonidine versus dapiprazole: Influence on pupil size at various illumination levels. Marx-Gross, S., Krummenauer, F., Dick, H.B., Pfeiffer, N. Journal of cataract and refractive surgery. (2005) [Pubmed]
  8. Intraocular dapiprazole for the reversal of mydriasis after extracapsular cataract extraction with intraocular lens implantation. Part II: Comparison with acetylcholine. Ponte, F., Cillino, S., Faranda, F., Casanova, F., Cucco, F. Journal of cataract and refractive surgery. (1991) [Pubmed]
  9. The clinical efficacy of paremyd with and without dapiprazole in subjects with light and dark brown irides. Anicho, U.M., Cooper, J., Feldman, J., Jaanus, S.D., Dignam, K. Optometry and vision science : official publication of the American Academy of Optometry. (1999) [Pubmed]
  10. Dose-response study of dapiprazole HCl in the reversal of mydriasis induced by 2.5% phenylephrine. Hogan, T.S., McDaniel, D.D., Bartlett, J.D., Hart, K.K., Paggiarino, D.A. Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics. (1997) [Pubmed]
  11. The additive miotic effects of dapiprazole and pilocarpine. Geyer, O., Loewenstein, A., Shalmon, B., Neudorfer, M., Lazar, M. Graefes Arch. Clin. Exp. Ophthalmol. (1995) [Pubmed]
  12. Effect of dapiprazole, an alpha-adrenergic blocking agent, on aqueous humor dynamics in pigmentary glaucoma. Mastropasqua, L., Carpineto, P., Ciancaglini, M., Lobefalo, L., Costagliola, C., Gallenga, P.E. Ophthalmic Res. (1996) [Pubmed]
  13. Corneal endothelial toxicity of dapiprazole hydrochloride. Cheeks, L., Chapman, J.M., Green, K. Lens and eye toxicity research. (1992) [Pubmed]
  14. The alpha 1-blocker dapiprazole inhibits diuresis but not drinking and feeding induced by U-50,488H. Nencini, P., Valeri, P., Pimpinella, G. Brain Res. Bull. (1992) [Pubmed]
  15. Ocular pharmacokinetics of dapiprazole. Valeri, P., Palmery, M., Severini, G., Piccinelli, D., Catanese, B. Pharmacological research communications. (1986) [Pubmed]
  16. Affinity of the miotic drug, dapiprazole, at alpha 1-adrenoceptor subtypes A, B and D. Eltze, M. J. Pharm. Pharmacol. (1997) [Pubmed]
  17. Effects of dapiprazole on contractile responses of guinea pig isolated ileum. Lograno, M.D., Reibaldi, A., Camerino, D.C. Pharmacological research communications. (1987) [Pubmed]
  18. Binding profile of trazodone and dapiprazole to some brain receptors. Valeri, P., Palmery, M., Silvestrini, B. Drugs under experimental and clinical research. (1988) [Pubmed]
  19. The effectiveness of dapiprazole in preventing exercise-induced IOP increase in patients with pigmentary dispersion syndrome. Mastropasqua, L., Carpineto, P., Ciancaglini, M., Gallenga, P.E. International ophthalmology. (1995) [Pubmed]
  20. Effects of dapiprazole on pupillary size and intraocular pressure in rabbits. Silvestrini, B., Bonomi, L., Lisciani, R., Perfetti, S., Belluci, R., Massa, F., Baldini, A. Arzneimittel-Forschung. (1982) [Pubmed]
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