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    Dapiprazole

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    GLOBAL SALES INFORMATION

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    PharmaCompass
    $ API Ref.Price (USD/KG) : 28,244Xls

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    2D Structure
    Also known as: 72822-12-9, Dapiprazol, Dapiprazole [inn], Glamidolo, Reversil, Remydrial
    Molecular Formula
    C19H27N5
    Molecular Weight
    325.5  g/mol
    InChI Key
    RFWZESUMWJKKRN-UHFFFAOYSA-N
    FDA UNII
    5RNZ8GJO7K
    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.
    Dapiprazole is an alpha-Adrenergic Blocker. The mechanism of action of dapiprazole is as an Adrenergic alpha-Antagonist.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    3-[2-[4-(2-methylphenyl)piperazin-1-yl]ethyl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine
    2.1.2 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
    2.1.3 InChI Key
    RFWZESUMWJKKRN-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=CC=CC=C1N2CCN(CC2)CCC3=NN=C4N3CCCC4
    2.2 Other Identifiers
    2.2.1 UNII
    5RNZ8GJO7K
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 3-(2-(4-(2-methylphenyl)-1-piperazinyl)ethyl)-5,6,7,8,-tetrahydro-1,2,4-triazolo(4,3-a)pyridine Hydrochloride

    2. Dapiprazole Hydrochloride

    3. Remydrial

    4. Rev-eyes

    2.3.2 Depositor-Supplied Synonyms

    1. 72822-12-9

    2. Dapiprazol

    3. Dapiprazole [inn]

    4. Glamidolo

    5. Reversil

    6. Remydrial

    7. Dapiprazole (inn)

    8. 5,6,7,8-tetrahydro-3-(2-(4-(o-tolyl)-1-piperazinyl)ethyl)-s-triazolo(4,3-a)pyridine

    9. 5rnz8gjo7k

    10. 3-[2-[4-(2-methylphenyl)piperazin-1-yl]ethyl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine

    11. Chebi:51066

    12. 72822-12-9 (free Base)

    13. Dapiprazol [german]

    14. Dapirazolum

    15. Dapirazol

    16. Dapirazol [inn-spanish]

    17. Dapirazolum [inn-latin]

    18. 1,2,4-triazolo(4,3-a)pyridine, 5,6,7,8-tetrahydro-3-(2-(4-(2-methylphenyl)-1-piperazinyl)ethyl)-

    19. Dapiprazolum

    20. 1-(2-methylphenyl)-4-(2-{5h,6h,7h,8h-[1,2,4]triazolo[4,3-a]pyridin-3-yl}ethyl)piperazine

    21. Unii-5rnz8gjo7k

    22. Dapiprazole [mi]

    23. Dapiprazole [vandf]

    24. Dapiprazole [who-dd]

    25. Schembl152543

    26. Gtpl7155

    27. Zinc1246

    28. Chembl1201216

    29. Dtxsid90223140

    30. Hy-a0142

    31. Akos024463973

    32. Db00298

    33. 3-(2-(4-(o-tolyl)piperazin-1-yl)ethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine

    34. Ncgc00262927-03

    35. 3-{2-[4-(2-methylphenyl)piperazin-1-yl]ethyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine

    36. Db-055682

    37. Cs-0017462

    38. Ft-0603131

    39. D07775

    40. 822d129

    41. L000681

    42. Q901963

    43. 3-(2-(4-o-tolylpiperazin-1-yl)ethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine

    44. 5,6,7,8-tetrahydro-3-(2-(4-o-tolyl-1-piperazinyl)ethyl))-s-triazolo(4,3-a)pyridine

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 325.5 g/mol
    Molecular Formula C19H27N5
    XLogP32.4
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count4
    Exact Mass325.22664588 g/mol
    Monoisotopic Mass325.22664588 g/mol
    Topological Polar Surface Area37.2 Ų
    Heavy Atom Count24
    Formal Charge0
    Complexity395
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

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

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 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.

    5.2 MeSH Pharmacological Classification

    Adrenergic alpha-Antagonists

    Drugs that bind to but do not activate alpha-adrenergic receptors thereby blocking the actions of endogenous or exogenous adrenergic agonists. Adrenergic alpha-antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma. (See all compounds classified as Adrenergic alpha-Antagonists.)

    Antipsychotic Agents

    Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus. (See all compounds classified as Antipsychotic Agents.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    DAPIPRAZOLE
    5.3.2 FDA UNII
    5RNZ8GJO7K
    5.3.3 Pharmacological Classes
    Established Pharmacologic Class [EPC] - alpha-Adrenergic Blocker
    5.4 ATC Code

    S - Sensory organs

    S01 - Ophthalmologicals

    S01E - Antiglaucoma preparations and miotics

    S01EX - Other antiglaucoma preparations

    S01EX02 - Dapiprazole

    5.5 Absorption, Distribution and Excretion

    Absorption

    Systemic absorption is negligible.

    5.6 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.