ADAPROLOL MALEATE

Details

Stereochemistry	RACEMIC
Molecular Formula	C26H39NO4.C4H4O4
Molecular Weight	545.6643
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)\C=C/C(O)=O.CC(C)NCC(O)COC1=CC=C(CC(=O)OCCC23CC4CC(CC(C4)C2)C3)C=C1

InChI

InChIKey=WEBILLRFBZTUIX-BTJKTKAUSA-N

InChI=1S/C26H39NO4.C4H4O4/c1-18(2)27-16-23(28)17-31-24-5-3-19(4-6-24)12-25(29)30-8-7-26-13-20-9-21(14-26)11-22(10-20)15-26;5-3(6)1-2-4(7)8/h3-6,18,20-23,27-28H,7-17H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1-

HIDE SMILES / InChI

Molecular Formula	C26H39NO4
Molecular Weight	429.5922
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Molecular Formula	C4H4O4
Molecular Weight	116.0722
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16594634
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/8773927 | https://www.ncbi.nlm.nih.gov/pubmed/10608921

Adaprolol is a beta-adrenergic antagonist that is being developed as a topical agent to treat glaucoma. Adaprolol demonstrated a safer cardiovascular profile, especially in the population over 70 years old. It was in Phase II clinical trials for the treatment of glaucoma. This research has been discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adrenergic receptor beta 87 Target ID: CHEMBL2094118 Sources: http://adisinsight.springer.com/drugs/800003472 \| https://www.ncbi.nlm.nih.gov/pubmed/8773927	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Glaucoma 57 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8773927	Primary		Phase II 1132	Unknown Approved Use Unknown
Tachyarrhythmia 17 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1673212	Primary		Preclinical	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY34049	https://www.001chemical.com/chem/101479-70-3
ABI Chem	AC1L1TTB
ABI Chem	AC1Q66Q3
Molcore	MC34049	https://www.molcore.com/product/101479-70-3
Smolecule	S517206	http://www.smolecule.com/products/s517206
THE BioTek	bt-257812	https://www.thebiotek.com/product/inhibitors/bt-257812

PubMed

Title	Date	PubMed
Cardiac electrophysiologic effects of adaprolol maleate, a new beta-blocker, in closed chest dogs.	1991	1673212
Synthesis and pharmacological activity of adaprolol enantiomers: a new soft drug for treating glaucoma.	1996 Summer	8773927
Soft drug design: general principles and recent applications.	2000 Jan	10608921
Ophthalmic drug design based on the metabolic activity of the eye: soft drugs and chemical delivery systems.	2005 Dec 7	16594634

Sample Use Guides

In Vivo Use Guide

Rabbit: 0.1 mL of 0.25% solution into each eye

Route of Administration: Topical

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:38:14 GMT 2023` Edited by `admin` on `Fri Dec 15 16:38:14 GMT 2023`
Record UNII	2I8RV6WL9A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ADAPROLOL MALEATE

Official Name

English

BENZENEACETIC ACID, 4-(2-HYDROXY-3-((1-METHYLETHYL)AMINO)PROPOXY)-, 2-TRICYCLO(3.3.1.1(SUP 3,7))DEC-1-YLETHYL ESTER, (±)-, (Z)-2-BUTENEDIOATE (1:1) (SALT)

Systematic Name

English

CDDD-2803

Code

English

ADAPROLOL MALEATE [USAN]

Common Name

English

(±)-2-(1-ADAMANTYL)ETHYL (P-(2-HYDROXY-3-(ISOPROPYLAMINO)PROPOXY)PHENYL)ACETATE, MALEATE (1:1) (SALT)

Systematic Name

English

HGP-2

Code

English

CDDD 2803

Code

English

HGP 2

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C29576