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52365-63-6 molecular structure
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2-[(2,2-dimethylpropanoyl)oxy]-5-[1-hydroxy-2-(methylamino)ethyl]phenyl 2,2-dimethylpropanoate

ChemBase ID: 332
Molecular Formular: C19H29NO5
Molecular Mass: 351.43726
Monoisotopic Mass: 351.20457303
SMILES and InChIs

SMILES:
O(C(=O)C(C)(C)C)c1c(OC(=O)C(C)(C)C)ccc(C(O)CNC)c1
Canonical SMILES:
CNCC(c1ccc(c(c1)OC(=O)C(C)(C)C)OC(=O)C(C)(C)C)O
InChI:
InChI=1S/C19H29NO5/c1-18(2,3)16(22)24-14-9-8-12(13(21)11-20-7)10-15(14)25-17(23)19(4,5)6/h8-10,13,20-21H,11H2,1-7H3
InChIKey:
OCUJLLGVOUDECM-UHFFFAOYSA-N

Cite this record

CBID:332 http://www.chembase.cn/molecule-332.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-[(2,2-dimethylpropanoyl)oxy]-5-[1-hydroxy-2-(methylamino)ethyl]phenyl 2,2-dimethylpropanoate
IUPAC Traditional name
dipivefrin
Brand Name
AKPro
DPE
Dipivefrin HCL
Dipivefrin [USAN]
Dipivefrina [INN-Spanish]
Dipivefrine
Dipivefrinum [INN-Latin]
Ophtho-Dipivefrin
Propine
Propine C Cap B.I.D.
Synonyms
Dipivefrin
CAS Number
52365-63-6
PubChem SID
46504716
160963795
PubChem CID
3105

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
DrugBank DB00449 external link
PubChem 3105 external link
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 14.00017  H Acceptors
H Donor LogD (pH = 5.5) 0.5729072 
LogD (pH = 7.4) 1.8021725  Log P 3.7148545 
Molar Refractivity 94.9381 cm3 Polarizability 37.906097 Å3
Polar Surface Area 84.86 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 3.17  LOG S -3.78 
Solubility (Water) 5.82e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
Freely soluble as HCl salt expand Show data source
Hydrophobicity(logP)
1.7 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00449 external link
Item Information
Drug Groups approved
Description Dipivefrin is a prodrug of adrenaline, which is used to treat glaucoma. It is available as ophthalmic solution (eye drops).
Indication Dipivefrin is a prodrug which is used as initial therapy for the control of intraocular pressure in chronic open-angle glaucoma.
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.
Toxicity Oral LD50 in rat is 183 mg/kg.
Affected Organisms
Humans and other mammals
Biotransformation Dipivefrin is converted to epinephrine inside the human eye by enzyme hydrolysis.
Absorption Well absorbed following occular administration.
External Links
Wikipedia
RxList
PDRhealth
Drugs.com

REFERENCES

REFERENCES

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PATENTS

PATENTS

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