4-((5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO)BENZOIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H25NO3
Molecular Weight	351.4388
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of 4-((5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO)BENZOIC ACID

Structure Search

SMILES

CC1(C)CCC(C)(C)C2=C1C=CC(=C2)C(=O)NC3=CC=C(C=C3)C(O)=O

InChI

InChIKey=SZWKGOZKRMMLAJ-UHFFFAOYSA-N

InChI=1S/C22H25NO3/c1-21(2)11-12-22(3,4)18-13-15(7-10-17(18)21)19(24)23-16-8-5-14(6-9-16)20(25)26/h5-10,13H,11-12H2,1-4H3,(H,23,24)(H,25,26)

HIDE SMILES / InChI

Molecular Formula	C22H25NO3
Molecular Weight	351.4388
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/11034091 | https://www.ncbi.nlm.nih.gov/pubmed/8608243 | https://www.ncbi.nlm.nih.gov/pubmed/7506665

AM580 is a selective agonist of retinoic acid receptor α (RARα) with IC50 and EC50 values of 8 nM and 0.36 nM, respectively. AM580 has been shown to induce differentiation in leukemic cell lines and inhibit angiogenesis in chick embryos. AM580 exhibited anti-angiogenic activity in vivo. Treatment involving AM580 might have potential therapeutic efficacy in various angiogenesis-dependent disorders, including solid tumors, psoriasis, rheumatoid arthritis and diabetic retinopathy.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Retinoic acid receptor alpha 11 Target ID: CHEMBL2055 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19058965 \| https://www.ncbi.nlm.nih.gov/pubmed/11034091	Agonist 2752		0.3 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22920668 http://adisinsight.springer.com/drugs/800004524 https://www.ncbi.nlm.nih.gov/pubmed/8608243 https://www.ncbi.nlm.nih.gov/pubmed/21310893	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Reversal by RARα agonist Am580 of c-Myc-induced imbalance in RARα/RARγ expression during MMTV-Myc tumorigenesis.	2012-08-24	22920668
Retinoic acid inhibits endometrial cancer cell growth via multiple genomic mechanisms.	2011-04	21310893
Activation of retinoic acid receptor alpha is sufficient for full induction of retinoid responses in SK-BR-3 and T47D human breast cancer cells.	2000-10-01	11034091
AM580, a stable benzoic derivative of retinoic acid, has powerful and selective cyto-differentiating effects on acute promyelocytic leukemia cells.	1996-02-15	8608243
Three novel synthetic retinoids, Re 80, Am 580 and Am 80, all exhibit anti-angiogenic activity in vivo.	1993-11-02	7506665

Patents

Sample Use Guides

In Vivo Use Guide

Mice: Three-month-old uniparous MMTV-Myc female mice (30 mice/group) were fed with 0.3 mg/kg/day of AM580. Treatment of MMTV-Myc mice with AM580 led to significant inhibition of mammary tumor growth (~90%, P<0.001), lung metastasis (P<0.01) and extended tumor latency in 63% of mice.

Route of Administration: Oral

In Vitro Use Guide

In SK-BR-3 and T47D breast cancer cell lines, treatment with AM580 at concentrations of 1 nM and 10 nM for 7 days resulted in the decrease in the number of cells.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:24:44 GMT 2025` Edited by `admin` on `Mon Mar 31 19:24:44 GMT 2025`
Record UNII	VZ5S5G9ZFZ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AM 580

Preferred Name

English

4-((5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO)BENZOIC ACID

Common Name

English

AM580

Common Name

English

AM-580

Code

English

Code System Code Type Description

EPA CompTox

DTXSID5040758