AL-6598

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H39ClO5
Molecular Weight	431.006
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)OC(=O)COC\C=C/C[C@H]1[C@H](Cl)C[C@@H](O)[C@@H]1CC[C@@H](O)C2CCCCC2

InChI

InChIKey=GXLUEHGRKZQLOO-QMAHXAMHSA-N

InChI=1S/C23H39ClO5/c1-16(2)29-23(27)15-28-13-7-6-10-18-19(22(26)14-20(18)24)11-12-21(25)17-8-4-3-5-9-17/h6-7,16-22,25-26H,3-5,8-15H2,1-2H3/b7-6-/t18-,19-,20-,21-,22-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C23H39ClO5
Molecular Weight	431.006
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	1
Optical Activity	UNSPECIFIED

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Prostanoid DP receptor 16 Target ID: CHEMBL4427 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11937363	Agonist 2752		3.2 µM [Ki]

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:03:21 GMT 2025` Edited by `admin` on `Mon Mar 31 18:03:21 GMT 2025`
Record UNII	XE6G6DQ45F
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ACETIC ACID, (((2Z)-4-((1R,2R,3R,5R)-5-CHLORO-2-((3R)-3-CYCLOHEXYL-3-HYDROXYPROPYL)-3-HYDROXYCYCLOPENTYL)-2-BUTENYL)OXY)-, 1-METHYLETHYL ESTER

Preferred Name

English

AL-6598

Code

English

ACETIC ACID, ((4-(5-CHLORO-2-(3-CYCLOHEXYL-3-HYDROXYPROPYL)-3-HYDROXYCYCLOPENTYL)-2-BUTENYL)OXY)-, 1-METHYLETHYL ESTER, (1R-(1.ALPHA.(Z),2.BETA.(R*),3.ALPHA.,5.BETA.))-

Systematic Name

English

9-CHLORO-15-CYCLOHEXYL-11,15-DIHYDRO-3-OXA-16,17,18,19,20-PENTANOR-PROSTENOIC ACID ISOPROPYL ESTER (5Z,9R,11R,15R)

Systematic Name

English

Code System Code Type Description

FDA UNII

XE6G6DQ45F

Created by admin on Mon Mar 31 18:03:21 GMT 2025 , Edited by admin on Mon Mar 31 18:03:21 GMT 2025

PRIMARY

MANUFACTURER PRODUCT INFORMATION

AL-6598

Created by admin on Mon Mar 31 18:03:21 GMT 2025 , Edited by admin on Mon Mar 31 18:03:21 GMT 2025

PRIMARY

Elevated intraocular pressure (IOP) is an important risk factor in developing glaucoma. Certain prostaglandins such as PGF2.ALPHA. and PGD2, have been shown to reduce IOP. AL 6598 is the isopropyl ester prodrug of AL 6556, a PGD2 receptor agonist that binds to DP receptors with a Ki value of 3.2 undefined M and demonstrates an EC50 value of 0.80 undefinedM in an in vitro functional assay. Designed to enhance corneal absorption, AL 6598 produces a maximum 53% drop in IOP of the ocular hypertensive monkey with a 1 undefinedg dose given twice daily.

PUBCHEM

9832594

Created by admin on Mon Mar 31 18:03:21 GMT 2025 , Edited by admin on Mon Mar 31 18:03:21 GMT 2025

PRIMARY

CAS

170291-06-2

Created by admin on Mon Mar 31 18:03:21 GMT 2025 , Edited by admin on Mon Mar 31 18:03:21 GMT 2025

PRIMARY

Related Record Type Details


					XE6G6DQ45F

AL-6598

ACTIVE MOIETY

Comments:

AL-6556 and AL-6598 had an affinity (Ki) of 2.66-4.43 microM for DP receptors but a much lower affinity (K(i)s = 38-103 microM) for EP3, FP, IP, and TP receptors (n = 3-5). In addition, AL-6556 and AL-6598 exhibited K(i)s > 100 microM for 19 nonprostanoid receptors. Both PGs stimulated cAMP production (EC50 = 1.07 +/- 0.1 microM and EC50 = 2.64 +/- 0.84 microM n = 3) by way of DP receptors in embryonic bovine tracheal fibroblasts. While AL-6556 and AL-6598 were partial agonists (EC(50)s = 0.47-0.69 microM E(max) = 35%-46%) at EP2 receptors in human nonpigmented epithelial cells, neither had any agonist activity at EP4, IP, or FP receptors.