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Dipivefrin

Dipivefrin structure

CAS No:
52365-63-6
Formula:
C19H29NO5
Chemical Name:
Dipivefrin
Synonyms:
Propanoic acid,2,2-dimethyl-,1,1′-[4-[1-hydroxy-2-(methylamino)ethyl]-1,2-phenylene] ester;Propanoic acid,2,2-dimethyl-,4-[1-hydroxy-2-(methylamino)ethyl]-1,2-phenylene ester,(±)-;Propanoic acid,2,2-dimethyl-,4-[1-hydroxy-2-(methylamino)ethyl]-1,2-phenylene ester;Dipivefrin;Dipivefrine;(±)-Dipivefrin;DPE;60902-39-8
Categories:
Active Pharmaceutical Ingredients > Specialty Drugs

Description

Solid

Dipivefrin is the dipivalate ester of (+-)-epinephrine (racepinephrine). A pro-drug of epinephrine, the hydrochloride is used topically as eye drops to reduce intra-ocular pressure in the treatment of open-angle glaucoma or ocular hypertension. It has a role as a prodrug, an adrenergic agonist, a sympathomimetic agent, an antiglaucoma drug and an ophthalmology drug. It is a member of ethanolamines and a pivalate ester. It derives from an adrenaline. It is a conjugate base of a dipivefrin(1+).|Dipivefrin is a prodrug of adrenaline, which is used to treat glaucoma. It is available as ophthalmic solution (eye drops).

Dipivefrin Basic Attributes

Molecular Weight：

351.44

Exact Mass：

351.44

DSSTox ID：

DTXSID1048544

ATC Code：

S - Sensory organs

HScode：

2922509090

Characteristics

PSA：

84.9

XLogP3：

1.7

Appearance：

Solid

Density：

1.097 g/cm3

Melting Point：

146-147 °C

Boiling Point：

473.7ºC at 760 mmHg

Flash Point：

240.3ºC

Refractive Index：

1.511

Water Solubility：

Freely soluble as HCl salt

Toxicity

Toxicity Summary：

Oral LD50 in rat is 183 mg/kg.

Drug Information

Drug Indication：

Dipivefrin is a prodrug which is used as initial therapy for the control of intraocular pressure in chronic open-angle glaucoma.|FDA Label

Pharmacology：

Dipivefrin is a member of a class of drugs known as prodrugs. Prodrugs are usually not active in themselves and require biotransformation to the parent compound before therapeutic activity is seen. These modifications are undertaken to enhance absorption, decrease side effects and enhance stability and comfort, thus making the parent compound a more useful drug. Enhanced absorption makes the prodrug a more efficient delivery system for the parent drug because less drug will be needed to produce the desired therapeutic response. Dipivefrin is a prodrug of epinephrine formed by the diesterification of epinephrine and pivalic acid. The addition of pivaloyl groups to the epinephrine molecule enhances its lipophilic character and, as a consequence, its penetration into the anterior chamber.

MeSH：

Drugs that bind to and activate adrenergic receptors. (See all compounds classified as Adrenergic Agonists.)

Absorption：

Well absorbed following occular administration.

Metabolism/Metabolites：

Dipivefrin is converted to epinephrine inside the human eye by enzyme hydrolysis.

Mechanism of Action：

Dipivefrin is a prodrug with little or no pharmacologically activity until it is hydrolyzed into epinephrine inside the human eye. The liberated epinephrine, an adrenergic agonist, appears to exert its action by stimulating α -and/or β₂-adrenergic receptors, leading to a decrease in aqueous production and an enhancement of outflow facility. The dipivefrin prodrug delivery system is a more efficient way of delivering the therapeutic effects of epinephrine, with fewer side effects than are associated with conventional epinephrine therapy.

MeSH Entry Terms：

adrenaline dipivalate

Dipivefrin Use and Manufacturing

Adrenergic (ophthalmic).

Computed Properties

Molecular Weight:351.4
XLogP3:2.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:9
Exact Mass:351.20457303
Monoisotopic Mass:351.20457303
Topological Polar Surface Area:84.9
Heavy Atom Count:25
Complexity:463
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes