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Chemistry

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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

Dapiprazole

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 Formula	C₁₉H₂₇N₅
Molecular Weight	325.5 g/mol
XLogP3	2.4
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	4
Exact Mass	325.22664588 g/mol
Monoisotopic Mass	325.22664588 g/mol
Topological Polar Surface Area	37.2 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	395
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.

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