1-(2-methylphenyl)-4-(2-{5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyridin-3-yl}ethyl)piperazine

• ChemBase ID: 183
• Molecular Formular: C19H27N5
• Molecular Mass: 325.45118
• Monoisotopic Mass: 325.22664589
• SMILES: N1(CCN(CC1)c1c(cccc1)C)CCc1n2CCCCc2nn1
• Canonical SMILES: Cc1ccccc1N1CCN(CC1)CCc1nnc2n1CCCC2
• InChI: InChI=1S/C19H27N5/c1-16-6-2-3-7-17(16)23-14-12-22(13-15-23)11-9-19-21-20-18-8-4-5-10-24(18)19/h2-3,6-7H,4-5,8-15H2,1H3
• InChIKey: RFWZESUMWJKKRN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(2-methylphenyl)-4-(2-{5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyridin-3-yl}ethyl)piperazine
• IUPAC Traditional name: dapiprazole
• Brand Name: Rev-Eyes
• Synonyms: Dapiprazole

Database IDs

• CAS Number: 72822-12-9
• PubChem SID: 160963646; 46508859
• PubChem CID: 3033538

CALCULATED PROPERTIES

JChem

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 0.26387095
• LogD (pH = 7.4): 1.9607973
• Log P: 2.4158738
• Molar Refractivity: 100.2216 cm^3
• Polarizability: 37.01138 Å^3
• Polar Surface Area: 37.19 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.78
• LOG S: -2.64
• Solubility (Water): 7.51e-01 g/l

PROPERTIES

Physical Property

• Solubility: Soluble
• Hydrophobicity(logP): 2.3

DETAILS

DrugBank - DB00298

• Drug Groups: approved
• Description: Dapiprazole (U.S. trade name Rev-Eyes) is an alpha blocker. It is used to reverse mydriasis after eye examination. [Wikipedia]
• Indication: Used in the treatment of iatrogenically induced mydriasis produced by adrenergic (phenylephrine) or parasympatholytic (tropicamide) agents used in certain eye examinations.
• Pharmacology: Dapiprazole is an alpha-adrenergic blocking agent. It produces miosis by blocking the alpha-adrenergic receptors on the dilator muscle of the iris. Dapiprazole produces no significant action on ciliary muscle contraction and thus, there are no changes in the depth of the anterior chamber of the thickness of the lens. It does not alter the IOP either in normal eyes or in eyes with elevated IOP. The rate of pupillary constriction may be slightly slower in clients with brown irises than in clients with blue or green irises.
• Toxicity: Oral LD₅₀ is 1189-2100 mg/kg in mice, rats and rabbits.
• Affected Organisms: Humans and other mammals
• Absorption: Systemic absorption is negligible.
• External Links: Wikipedia; Drugs.com