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Identification
NameDapiprazole
Accession NumberDB00298  (APRD00902)
TypeSmall Molecule
GroupsApproved
Description

Dapiprazole (U.S. trade name Rev-Eyes) is an alpha blocker. It is used to reverse mydriasis after eye examination. [Wikipedia]

Structure
Thumb
Synonyms
5,6,7,8-Tetrahydro-3-(2-(4-(O-tolyl)-1-piperazinyl)ethyl)-S-triazolo(4,3-a)pyridine
Dapiprazol
Dapiprazolum
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
Rev-EyesNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Dapiprazole hydrochloride
ThumbNot applicableDBSALT001438
Categories
UNII5RNZ8GJO7K
CAS number72822-12-9
WeightAverage: 325.4512
Monoisotopic: 325.226645889
Chemical FormulaC19H27N5
InChI KeyInChIKey=RFWZESUMWJKKRN-UHFFFAOYSA-N
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
IUPAC Name
1-(2-methylphenyl)-4-(2-{5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyridin-3-yl}ethyl)piperazine
SMILES
CC1=CC=CC=C1N1CCN(CCC2=NN=C3CCCCN23)CC1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpiperazines. These are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazinanes
Sub ClassPiperazines
Direct ParentPhenylpiperazines
Alternative Parents
Substituents
  • N-arylpiperazine
  • Phenylpiperazine
  • Triazolopyridine
  • Aminotoluene
  • Substituted aniline
  • Dialkylarylamine
  • Aralkylamine
  • N-alkylpiperazine
  • Toluene
  • Aniline
  • Benzenoid
  • Pyridine
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • 1,2,4-triazole
  • Triazole
  • Azole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationUsed in the treatment of iatrogenically induced mydriasis produced by adrenergic (phenylephrine) or parasympatholytic (tropicamide) agents used in certain eye examinations.
PharmacodynamicsDapiprazole 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.
Mechanism of actionDapiprazole acts through blocking the alpha1-adrenergic receptors in smooth muscle. It produces miosis through an effect on the dilator muscle of the iris and does not have any significant activity on ciliary muscle contraction and, therefore does not induce a significant change in the anterior chamber depth or the thickness of the lens.
Related Articles
AbsorptionSystemic absorption is negligible.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityOral LD50 is 1189-2100 mg/kg in mice, rats and rabbits.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9832
Caco-2 permeable+0.5899
P-glycoprotein substrateSubstrate0.657
P-glycoprotein inhibitor IInhibitor0.8074
P-glycoprotein inhibitor IIInhibitor0.9107
Renal organic cation transporterInhibitor0.7481
CYP450 2C9 substrateNon-substrate0.8296
CYP450 2D6 substrateNon-substrate0.5563
CYP450 3A4 substrateSubstrate0.5833
CYP450 1A2 substrateInhibitor0.6905
CYP450 2C9 inhibitorNon-inhibitor0.5324
CYP450 2D6 inhibitorNon-inhibitor0.632
CYP450 2C19 inhibitorInhibitor0.7506
CYP450 3A4 inhibitorInhibitor0.7338
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9357
Ames testNon AMES toxic0.6215
CarcinogenicityNon-carcinogens0.8546
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7573 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.6592
hERG inhibition (predictor II)Inhibitor0.7292
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Angelini pharmaceuticals inc
Packagers
  • American Cyanamid Co.
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubilitySolubleNot Available
logP2.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.751 mg/mLALOGPS
logP2.78ALOGPS
logP2.42ChemAxon
logS-2.6ALOGPS
pKa (Strongest Basic)7.67ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area37.19 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity100.22 m3·mol-1ChemAxon
Polarizability38.23 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesS01EX02
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (114 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Protein heterodimerization activity
Specific Function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine(PE)-stimulated ERK signaling in cardiac myocytes.
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular Weight:
51486.005 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Eltze M: Affinity of the miotic drug, dapiprazole, at alpha 1-adrenoceptor subtypes A, B and D. J Pharm Pharmacol. 1997 Nov;49(11):1091-5. [PubMed:9401944 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Alpha1-adrenergic receptor activity
Specific Function:
This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium.
Gene Name:
ADRA1D
Uniprot ID:
P25100
Molecular Weight:
60462.205 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Protein heterodimerization activity
Specific Function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine (PE)-stimulated ERK signaling in cardiac myocytes.
Gene Name:
ADRA1B
Uniprot ID:
P35368
Molecular Weight:
56835.375 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
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Drug created on June 13, 2005 07:24 / Updated on November 30, 2015 12:10