ALPRENOXIME HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H22N2O2.ClH
Molecular Weight	298.808
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CC(C)NCC(COC1=C(CC=C)C=CC=C1)=NO

InChI

InChIKey=ZFLRDGZJSCQDSR-UHFFFAOYSA-N

InChI=1S/C15H22N2O2.ClH/c1-4-7-13-8-5-6-9-15(13)19-11-14(17-18)10-16-12(2)3;/h4-6,8-9,12,16,18H,1,7,10-11H2,2-3H3;1H

HIDE SMILES / InChI

Molecular Formula	C15H22N2O2
Molecular Weight	262.3474
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7475898 | https://www.ncbi.nlm.nih.gov/pubmed/8590263 | https://adisinsight.springer.com/drugs/800003470 | https://www.ncbi.nlm.nih.gov/pubmed/7783133

Alprenoxime is a prodrug to alprenolol. Alprenoxime is a β-blocker that was in phase II clinical trials with Pharmos in the USA as an antiglaucoma agent. Alprenoxime is a potent ocular antihypertensive agent. Alprenoxime was designed to undergo metabolic activation to the beta-blocker, alprenolol, specifically within the eye using hydrolase and reductase enzymes that reside in the iris-ciliary body. Previous studies in rabbits confirmed that intraocular pressure (IOP) significantly decreased after topically instilling ophthalmic drops of alprenoxime, while heart rates remained essentially unchanged after intravenous dosing. Alprenoxime has no significant cardiac activity at doses much greater than potential therapeutic levels, supporting that alprenoxime could be safely used in treating glaucoma. Alprenoxime was taken to clinical trials and has successfully passed Phase I studies, demonstrating complete lack of cardiovascular side effects, even in humans, including isoprenaline induced tachycardia.

Approval Year

PubMed

Title	Date	PubMed
Sequential bioactivation of methoxime analogs of beta-adrenergic antagonists in the eye.	1995 Fall	8590263
Ocular delivery of the beta-adrenergic antagonist alprenolol by sequential bioactivation of its methoxime analogue.	1995 May 26	7783133

Patents

Sample Use Guides

In Vivo Use Guide

Rabbits: Alprenoxime produced significant reduction of the IOP starting at 30 min and lasting for more than 6 hr after its topical administration. Both in rats and in rabbits the i.v. bolus injection of Alprenoxime (6 mg/kg) led to insignificant transient bradycardia, while no activity was found after oral or topical administration.

Route of Administration: Other

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:46:54 GMT 2023` Edited by `admin` on `Fri Dec 15 15:46:54 GMT 2023`
Record UNII	C13VQZ839K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ALPRENOXIME HYDROCHLORIDE

Official Name

English

ALPRENOXIME HCL

Common Name

English

HGP-5

Code

English

1-(O-ALLYLPHENOXY)-3-(ISOPROPYLAMINO)-2-PROPANONE OXIME, MONOHYDROCHLORIDE

Systematic Name

English

CDDD-1815

Code

English

ALPRENOXIME HYDROCHLORIDE [USAN]

Common Name

English

2-PROPANONE, 1-((1-METHYLETHYL)AMINO)-3-(2-(2-PROPENYL)PHENOXY)-, OXIME, MONOHYDROCHLORIDE

Systematic Name

English

CDDD 1815

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C29705