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
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Iatrogenically induced mydriasis •••••••••••• •••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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
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Oral LD50 is 1189-2100 mg/kg in mice, rats and rabbits.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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. - 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; Powder, for solution 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
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Angelini pharmaceuticals inc
- Packagers
- American Cyanamid Co.
- Dosage Forms
Form Route Strength Kit; powder, for solution 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 splash10-002s-3910000000-c735602ffc4fd3bbf5c0 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-0009000000-d57974aeaae9ab77a3d1 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-0009000000-930dc9d4b8e5e5f59e08 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-0209000000-e972b32077fdf04281b0 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00xs-0195000000-4cdda80ed9b628a7993a Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0udi-4951000000-e9d502c397639f3af946 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0m5v-1950000000-4388a0a323d57542fb98 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 180.2772678 predictedDarkChem Lite v0.1.0 [M-H]- 181.4568678 predictedDarkChem Lite v0.1.0 [M-H]- 173.99927 predictedDeepCCS 1.0 (2019) [M+H]+ 180.2579678 predictedDarkChem Lite v0.1.0 [M+H]+ 181.2991678 predictedDarkChem Lite v0.1.0 [M+H]+ 176.35728 predictedDeepCCS 1.0 (2019) [M+Na]+ 180.0164678 predictedDarkChem Lite v0.1.0 [M+Na]+ 181.4763678 predictedDarkChem Lite v0.1.0 [M+Na]+ 182.45042 predictedDeepCCS 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
- 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 02, 2024 22:54