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Dapiprazole

Dapiprazole structure

CAS No:
72822-12-9
Formula:
C19H27N5
Chemical Name:
Dapiprazole
Synonyms:
1,2,4-Triazolo[4,3-a]pyridine,5,6,7,8-tetrahydro-3-[2-[4-(2-methylphenyl)-1-piperazinyl]ethyl]-;5,6,7,8-Tetrahydro-3-[2-[4-(2-methylphenyl)-1-piperazinyl]ethyl]-1,2,4-triazolo[4,3-a]pyridine;Dapiprazole
Categories:
Pharmaceutical Intermediates > Ophthalmic Agents

Description

Solid

Dapiprazole is a N-arylpiperazine, a N-alkylpiperazine and a member of pyridines. It has a role as an alpha-adrenergic antagonist, a miotic, an ophthalmology drug and an antipsychotic agent.|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.

Dapiprazole Basic Attributes

Molecular Weight：

325.45

Exact Mass：

325.45

UNII：

5RNZ8GJO7K

DSSTox ID：

DTXSID90223140

ATC Code：

S - Sensory organs

Characteristics

PSA：

37.2

XLogP3：

2.3

Appearance：

Solid

Density：

1.2±0.1 g/cm3

Melting Point：

158-160 °C

Boiling Point：

538.9±60.0 °C at 760 mmHg

Flash Point：

279.7±32.9 °C

Refractive Index：

1.658

Water Solubility：

H2O: soluble

Toxicity

Toxicity Summary：

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

Drug Information

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

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.

MeSH：

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.)|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.)

Absorption：

Systemic absorption is negligible.

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.

MeSH Entry Terms：

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

Dapiprazole Use and Manufacturing

Adrenergic (α-blocking); antiglaucoma agent; neuroleptic; psychotropic.

Computed Properties

Molecular Weight:325.5
XLogP3:2.4
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:325.22664588
Monoisotopic Mass:325.22664588
Topological Polar Surface Area:37.2
Heavy Atom Count:24
Complexity:395
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes