Dapiprazole

Identification

Generic Name
Dapiprazole
DrugBank Accession Number
DB00298
Background

Dapiprazole (U.S. trade name Rev-Eyes) is an alpha blocker. It is found in ophthalmic solutions used to reverse mydriasis after an eye examination.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 325.4512
Monoisotopic: 325.226645889
Chemical Formula
C19H27N5
Synonyms
  • 5,6,7,8-Tetrahydro-3-(2-(4-(o-tolyl)-1-piperazinyl)ethyl)-s-triazolo(4,3-a)pyridine
  • Dapiprazol
  • Dapiprazole
  • Dapiprazolum

Pharmacology

Indication

Used in the treatment of iatrogenically induced mydriasis produced by adrenergic (phenylephrine) or parasympatholytic (tropicamide) agents used in certain eye examinations.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofIatrogenically induced mydriasis••••••••••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

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.

Mechanism of action

Dapiprazole 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.

TargetActionsOrganism
AAlpha-1A adrenergic receptor
antagonist
Humans
AAlpha-1D adrenergic receptor
antagonist
Humans
AAlpha-1B adrenergic receptor
antagonist
Humans
Absorption

Systemic absorption is negligible.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Oral LD50 is 1189-2100 mg/kg in mice, rats and rabbits.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AlfuzosinDapiprazole may increase the hypotensive activities of Alfuzosin.
AvanafilDapiprazole may increase the hypotensive activities of Avanafil.
BaclofenBaclofen may increase the central nervous system depressant (CNS depressant) activities of Dapiprazole.
ClobazamThe risk or severity of sedation, somnolence, and CNS depression can be increased when Clobazam is combined with Dapiprazole.
CyclobenzaprineThe risk or severity of CNS depression can be increased when Cyclobenzaprine is combined with Dapiprazole.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Dapiprazole hydrochlorideDS9UJN1I0X72822-13-0ZIODNPFQZIHCOE-UHFFFAOYSA-N
International/Other Brands
Rev-Eyes
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
DapiprazoleKit; Powder, for solution25 mg/5mLOphthalmicBaradaina, LLC2019-07-31Not applicableUS flag

Categories

ATC Codes
S01EX02 — Dapiprazole
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazinanes
Sub Class
Piperazines
Direct Parent
Phenylpiperazines
Alternative Parents
N-arylpiperazines / Triazolopyridines / Dialkylarylamines / Aniline and substituted anilines / Aminotoluenes / N-alkylpiperazines / Aralkylamines / Pyridines and derivatives / Triazoles / Heteroaromatic compounds
show 4 more
Substituents
1,2,4-triazole / Amine / Aminotoluene / Aniline or substituted anilines / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Dialkylarylamine
show 16 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
N-arylpiperazine, pyridines, N-alkylpiperazine (CHEBI:51066)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
5RNZ8GJO7K
CAS number
72822-12-9
InChI Key
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

References

General References
  1. FDA Approved Products: Dapiprazole kit [Link]
Human Metabolome Database
HMDB0014443
KEGG Drug
D07775
PubChem Compound
3033538
PubChem Substance
46508859
ChemSpider
2298190
RxNav
22298
ChEBI
51066
ChEMBL
CHEMBL1201216
ZINC
ZINC000000001246
Therapeutic Targets Database
DAP000298
PharmGKB
PA164749109
Drugs.com
Drugs.com Drug Page
Wikipedia
Dapiprazole
FDA label
Download (131 KB)
MSDS
Download (114 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
  • Angelini pharmaceuticals inc
Packagers
  • American Cyanamid Co.
Dosage Forms
FormRouteStrength
Kit; powder, for solutionOphthalmic25 mg/5mL
Solution / dropsOphthalmic
Prices
Not Available
Patents
Not Available

Properties

State
Solid
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)7.64Chemaxon
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 RuleNoChemaxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-002s-3910000000-c735602ffc4fd3bbf5c0
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0009000000-d57974aeaae9ab77a3d1
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0009000000-930dc9d4b8e5e5f59e08
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0209000000-e972b32077fdf04281b0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00xs-0195000000-4cdda80ed9b628a7993a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-4951000000-e9d502c397639f3af946
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0m5v-1950000000-4388a0a323d57542fb98
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-180.2772678
predicted
DarkChem Lite v0.1.0
[M-H]-181.4568678
predicted
DarkChem Lite v0.1.0
[M-H]-173.99927
predicted
DeepCCS 1.0 (2019)
[M+H]+180.2579678
predicted
DarkChem Lite v0.1.0
[M+H]+181.2991678
predicted
DarkChem Lite v0.1.0
[M+H]+176.35728
predicted
DeepCCS 1.0 (2019)
[M+Na]+180.0164678
predicted
DarkChem Lite v0.1.0
[M+Na]+181.4763678
predicted
DarkChem Lite v0.1.0
[M+Na]+182.45042
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
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) prot...
Gene Name
ADRA1A
Uniprot ID
P35348
Uniprot Name
Alpha-1A adrenergic receptor
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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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
Uniprot Name
Alpha-1D adrenergic receptor
Molecular Weight
60462.205 Da
References
  1. Allinson RW, Gerber DS, Bieber S, Hodes BL: Reversal of mydriasis by dapiprazole. Ann Ophthalmol. 1990 Apr;22(4):131-3, 138. [Article]
  2. 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. [Article]
Kind
Protein
Organism
Humans
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) prot...
Gene Name
ADRA1B
Uniprot ID
P35368
Uniprot Name
Alpha-1B adrenergic receptor
Molecular Weight
56835.375 Da
References
  1. Allinson RW, Gerber DS, Bieber S, Hodes BL: Reversal of mydriasis by dapiprazole. Ann Ophthalmol. 1990 Apr;22(4):131-3, 138. [Article]
  2. 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. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 03, 2024 02:23