METESIND GLUCURONATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H24N4O3S.C6H10O7
Molecular Weight	630.666
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O.CN(CC1=CC=C(C=C1)S(=O)(=O)N2CCOCC2)C3=CC=C4N=C(N)C5=CC=CC3=C45

InChI

InChIKey=WGYHOPIXAFLRPR-LRDBBFHQSA-N

InChI=1S/C23H24N4O3S.C6H10O7/c1-26(21-10-9-20-22-18(21)3-2-4-19(22)23(24)25-20)15-16-5-7-17(8-6-16)31(28,29)27-11-13-30-14-12-27;7-1-2(8)3(9)4(10)5(11)6(12)13/h2-10H,11-15H2,1H3,(H2,24,25);1-5,8-11H,(H,12,13)/t;2-,3+,4-,5-/m.0/s1

HIDE SMILES / InChI

Molecular Formula	C23H24N4O3S
Molecular Weight	436.527
Charge	0
Count

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

Molecular Formula	C6H10O7
Molecular Weight	194.1394
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8004755 | https://www.ncbi.nlm.nih.gov/pubmed/7579730 | https://www.ncbi.nlm.nih.gov/pubmed/7882359 | https://adisinsight.springer.com/drugs/800003304

Metesind (AG-331) is a lipophilic thymidylate synthase inhibitor. It inhibits the cofactor binding site of the enzyme. It exerts cytotoxic properties. Metesind was being developed as an anticancer and antimetabolite agent.

Originator

Approval Year

PubMed

Title	Date	PubMed
Biological activity of a novel rationally designed lipophilic thymidylate synthase inhibitor.	1994	8004755
Product development of AG-331 lyophilized powder for injection.	1994 Jan-Feb	8004414
Contrasting patterns of DNA fragmentation induced by thymidylate synthase inhibitors, ZD1694 and AG-331.	1995	7579730

Sample Use Guides

In Vitro Use Guide

H35 cells treated with 10 microM AG-331 were shown to accumulate in the S phase of the cell cycle. However, when treatments were conducted at a 5-fold higher concentration of AG-331, no S-phase block was apparent, suggesting the loss of a TS-directed effect at high inhibitor concentrations.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:31:27 GMT 2023` Edited by `admin` on `Fri Dec 15 15:31:27 GMT 2023`
Record UNII	8EC044476N
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

METESIND GLUCURONATE

Official Name

English

AG-331

Code

English

4-((.ALPHA.-((2-AMINOBENZ(CD)INDOL-6-YL)METHYLAMINO)-P-TOLYL)SULFONYL)MORPHOLINE MONO-D-GLUCURONATE

Common Name

English

Metesind glucuronate [WHO-DD]

Common Name

English

AG331

Code

English

METESIND GLUCURONATE [USAN]

Common Name

English

D-GLUCURONIC ACID, COMPD. WITH 4-((4-(((2-AMINOBENZ(CD)INDOL-6-YL)METHYLAMINO)METHYL)PHENYL)SULFONYL)MORPHOLINE (1:1)

Common Name

English

MORPHOLINE, 4-((4-(((2-AMINOBENZ(CD)INDOL-6-YL)METHYLAMINO)METHYL)PHENYL)SULFONYL)-, MONO-D-GLUCURONATE

Common Name

English

Code System Code Type Description

CAS

157182-23-5