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
Structure for Dapiprazole (DB00298)
- 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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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.
Target Actions Organism AAlpha-1A adrenergic receptor antagonistHumans AAlpha-1D adrenergic receptor antagonistHumans AAlpha-1B adrenergic receptor antagonistHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAlfuzosin Dapiprazole may increase the hypotensive activities of Alfuzosin. Avanafil Dapiprazole may increase the hypotensive activities of Avanafil. Baclofen Baclofen may increase the central nervous system depressant (CNS depressant) activities of Dapiprazole. Clobazam The risk or severity of sedation, somnolence, and CNS depression can be increased when Clobazam is combined with Dapiprazole. Cyclobenzaprine The risk or severity of CNS depression can be increased when Cyclobenzaprine is combined with Dapiprazole. Daridorexant The risk or severity of CNS depression can be increased when Dapiprazole is combined with Daridorexant. Fluoxetine Dapiprazole may increase the central nervous system depressant (CNS depressant) activities of Fluoxetine. Haloperidol The risk or severity of CNS depression can be increased when Haloperidol is combined with Dapiprazole. Lasmiditan The risk or severity of adverse effects can be increased when Lasmiditan is combined with Dapiprazole. Metoclopramide The risk or severity of sedation can be increased when Metoclopramide is combined with Dapiprazole. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Dapiprazole hydrochloride DS9UJN1I0X 72822-13-0 ZIODNPFQZIHCOE-UHFFFAOYSA-N - International/Other Brands
- Rev-Eyes
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Dapiprazole Kit 25 mg/5mL Ophthalmic Baradaina, LLC 2019-07-31 Not applicable US 
Categories
- ATC Codes
- S01EX02 — Dapiprazole
- Drug Categories
- Adrenergic Agents
- Adrenergic alpha-1 Receptor Antagonists
- Adrenergic alpha-Antagonists
- Adrenergic Antagonists
- Agents that produce hypertension
- Antiglaucoma Preparations and Miotics
- Antipsychotic Agents
- Central Nervous System Agents
- Central Nervous System Depressants
- Neurotoxic agents
- Neurotransmitter Agents
- Ophthalmics
- Ophthalmologicals
- Sensory Organs
- Tranquilizing Agents
- 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
- FDA Approved Products: Dapiprazole kit [Link]
- External Links
- Human Metabolome Database
- HMDB0014443
- KEGG Drug
- D07775
- PubChem Compound
- 3033538
- PubChem Substance
- 46508859
- ChemSpider
- 2298190
- 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
Pharmacoeconomics
- Manufacturers
- Angelini pharmaceuticals inc
- Packagers
- American Cyanamid Co.
- Dosage Forms
Form Route Strength Kit Ophthalmic 25 mg/5mL Solution / drops Ophthalmic - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility Soluble Not Available logP 2.3 Not Available - Predicted Properties
Property Value Source Water Solubility 0.751 mg/mL ALOGPS logP 2.78 ALOGPS logP 2.42 Chemaxon logS -2.6 ALOGPS pKa (Strongest Basic) 7.64 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 37.19 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 100.22 m3·mol-1 Chemaxon Polarizability 38.23 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9832 Caco-2 permeable + 0.5899 P-glycoprotein substrate Substrate 0.657 P-glycoprotein inhibitor I Inhibitor 0.8074 P-glycoprotein inhibitor II Inhibitor 0.9107 Renal organic cation transporter Inhibitor 0.7481 CYP450 2C9 substrate Non-substrate 0.8296 CYP450 2D6 substrate Non-substrate 0.5563 CYP450 3A4 substrate Substrate 0.5833 CYP450 1A2 substrate Inhibitor 0.6905 CYP450 2C9 inhibitor Non-inhibitor 0.5324 CYP450 2D6 inhibitor Non-inhibitor 0.632 CYP450 2C19 inhibitor Inhibitor 0.7506 CYP450 3A4 inhibitor Inhibitor 0.7338 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.9357 Ames test Non AMES toxic 0.6215 Carcinogenicity Non-carcinogens 0.8546 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.7573 LD50, mol/kg Not applicable hERG inhibition (predictor I) Strong inhibitor 0.6592 hERG inhibition (predictor II) Inhibitor 0.7292
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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
- 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
Drug created at June 13, 2005 13:24 / Updated at February 03, 2023 08:06