AGN193109
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 531423

CAS#: 171746-21-7

Description: AGN193109 is a retinoic acid receptor (RAR) antagonist.

Chemical Structure

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AGN193109
CAS# 171746-21-7
Instruction

Theoretical Analysis

MedKoo Cat#: 531423
Name: AGN193109
CAS#: 171746-21-7
Chemical Formula: C28H24O2
Exact Mass: 392.18
Molecular Weight: 392.498
Elemental Analysis: Chemical Formula: C28H24O2 Exact Mass: 392.1776 Molecular Weight: 392.4980 Elemental Analysis: C, 85.68; H, 6.16; O, 8.15

Price and Availability

Size Price Availability Quantity
5mg USD 285 2 Weeks
25mg USD 950 2 Weeks
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Synonym: AGN193109

IUPAC/Chemical Name: 4-[2-[5,5-dimethyl-8-(4-methylphenyl)-6H-naphthalen-2-yl]ethynyl]benzoic acid

InChi Key: NCEQLLNVRRTCKJ-UHFFFAOYSA-N

InChi Code: InChI=1S/C28H24O2/c1-19-4-11-22(12-5-19)24-16-17-28(2,3)26-15-10-21(18-25(24)26)7-6-20-8-13-23(14-9-20)27(29)30/h4-5,8-16,18H,17H2,1-3H3,(H,29,30)

SMILES Code: O=C(O)C1=CC=C(C#CC2=CC=C3C(C)(C)CC=C(C4=CC=C(C)C=C4)C3=C2)C=C1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 392.50 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Agarwal C, Chandraratna RA, Johnson AT, Rorke EA, Eckert RL. AGN193109 is a highly effective antagonist of retinoid action in human ectocervical epithelial cells. J Biol Chem. 1996 May 24;271(21):12209-12. doi: 10.1074/jbc.271.21.12209. PMID: 8647816.


2: Russell RP, Fu Y, Liu Y, Maye P. Inverse agonism of retinoic acid receptors directs epiblast cells into the paraxial mesoderm lineage. Stem Cell Res. 2018 Jul;30:85-95. doi: 10.1016/j.scr.2018.05.016. Epub 2018 May 22. PMID: 29807258; PMCID: PMC6083448.


3: Andela VB, Rosier RN. The proteosome inhibitor MG132 attenuates retinoic acid receptor trans-activation and enhances trans-repression of nuclear factor kappaB. Potential relevance to chemo-preventive interventions with retinoids. Mol Cancer. 2004 Mar 22;3:8. doi: 10.1186/1476-4598-3-8. PMID: 15035668; PMCID: PMC398417.


4: You L, Zhu L, Li PZ, Wang G, Cai H, Song J, Long D, Berman Z, Lin L, Cheng X, Yang X. Dysbacteriosis-Derived Lipopolysaccharide Causes Embryonic Osteopenia through Retinoic-Acid-Regulated DLX5 Expression. Int J Mol Sci. 2020 Apr 4;21(7):2518. doi: 10.3390/ijms21072518. PMID: 32260461; PMCID: PMC7177785.


5: Efe OE, Aydos TR, Emre Aydingoz S. Mechanism of acitretin-induced relaxations in isolated rat thoracic aorta preparations. Can J Physiol Pharmacol. 2022 Jan;100(1):35-42. doi: 10.1139/cjpp-2021-0206. Epub 2021 Aug 19. PMID: 34411501.


6: Rausch S, Barholz M, Föller M, Feger M. Vitamin A regulates fibroblast growth factor 23 (FGF23). Nutrition. 2020 Nov-Dec;79-80:110988. doi: 10.1016/j.nut.2020.110988. Epub 2020 Aug 28. PMID: 32961447.


7: Lee YJ, McPherron A, Choe S, Sakai Y, Chandraratna RA, Lee SJ, Oh SP. Growth differentiation factor 11 signaling controls retinoic acid activity for axial vertebral development. Dev Biol. 2010 Nov 1;347(1):195-203. doi: 10.1016/j.ydbio.2010.08.022. Epub 2010 Aug 27. PMID: 20801112; PMCID: PMC2967481.


8: Kang JX, Bell J, Beard RL, Chandraratna RA. Mannose 6-phosphate/insulin-like growth factor II receptor mediates the growth-inhibitory effects of retinoids. Cell Growth Differ. 1999 Aug;10(8):591-600. PMID: 10470859.


9: Balasubramanian S, Chandraratna RA, Eckert RL. Suppression of human pancreatic cancer cell proliferation by AGN194204, an RXR-selective retinoid. Carcinogenesis. 2004 Aug;25(8):1377-85. doi: 10.1093/carcin/bgh122. Epub 2004 Feb 19. PMID: 14976133.


10: Lloret-Vilaspasa F, Jansen HJ, de Roos K, Chandraratna RA, Zile MH, Stern CD, Durston AJ. Retinoid signalling is required for information transfer from mesoderm to neuroectoderm during gastrulation. Int J Dev Biol. 2010;54(4):599-608. doi: 10.1387/ijdb.082705fl. PMID: 20209433.


11: Manikam SD, Stanslas J. Andrographolide inhibits growth of acute promyelocytic leukaemia cells by inducing retinoic acid receptor-independent cell differentiation and apoptosis. J Pharm Pharmacol. 2009 Jan;61(1):69-78. doi: 10.1211/jpp/61.01.0010. Erratum in: J Pharm Pharmacol. 2009 May;61(5):687. Manikam, Shiamala T [corrected to Manikam, Shiamala T]. PMID: 19126299.


12: Zhuang X, Ma J, Xu S, Zhang M, Xu G, Sun Z. All-Trans Retinoic Acid Attenuates Blue Light-Induced Apoptosis of Retinal Photoreceptors by Upregulating MKP-1 Expression. Mol Neurobiol. 2021 Aug;58(8):4157-4168. doi: 10.1007/s12035-021-02380-3. Epub 2021 May 5. PMID: 33950345.


13: Ewendt F, Lehmann A, Wodak MF, Stangl GI. All-trans Retinoic Acid and Beta-Carotene Increase Sclerostin Production in C2C12 Myotubes. Biomedicines. 2023 May 12;11(5):1432. doi: 10.3390/biomedicines11051432. PMID: 37239103; PMCID: PMC10216713.


14: Griffin JN, Pinali D, Olds K, Lu N, Appleby L, Doan L, Lane MA. 13-Cis- retinoic acid decreases hypothalamic cell number in vitro. Neurosci Res. 2010 Nov;68(3):185-90. doi: 10.1016/j.neures.2010.08.003. Epub 2010 Aug 11. PMID: 20708044.


15: Konta T, Xu Q, Furusu A, Nakayama K, Kitamura M. Selective roles of retinoic acid receptor and retinoid x receptor in the suppression of apoptosis by all- trans-retinoic acid. J Biol Chem. 2001 Apr 20;276(16):12697-701. doi: 10.1074/jbc.M011000200. Epub 2001 Jan 16. PMID: 11278809.


16: Bowles J, Knight D, Smith C, Wilhelm D, Richman J, Mamiya S, Yashiro K, Chawengsaksophak K, Wilson MJ, Rossant J, Hamada H, Koopman P. Retinoid signaling determines germ cell fate in mice. Science. 2006 Apr 28;312(5773):596-600. doi: 10.1126/science.1125691. Epub 2006 Mar 30. PMID: 16574820.


17: Sun SY, Yue P, Chandraratna RA, Tesfaigzi Y, Hong WK, Lotan R. Dual mechanisms of action of the retinoid CD437: nuclear retinoic acid receptor- mediated suppression of squamous differentiation and receptor-independent induction of apoptosis in UMSCC22B human head and neck squamous cell carcinoma cells. Mol Pharmacol. 2000 Sep;58(3):508-14. doi: 10.1124/mol.58.3.508. PMID: 10953043.


18: Samuel W, Kutty RK, Nagineni S, Vijayasarathy C, Chandraratna RA, Wiggert B. N-(4-hydroxyphenyl)retinamide induces apoptosis in human retinal pigment epithelial cells: retinoic acid receptors regulate apoptosis, reactive oxygen species generation, and the expression of heme oxygenase-1 and Gadd153. J Cell Physiol. 2006 Dec;209(3):854-65. doi: 10.1002/jcp.20774. PMID: 16972258.


19: Standeven AM, Johnson AT, Escobar M, Chandraratna RA. Specific antagonist of retinoid toxicity in mice. Toxicol Appl Pharmacol. 1996 May;138(1):169-75. doi: 10.1006/taap.1996.0110. PMID: 8658506.


20: Standeven AM, Davies PJ, Chandraratna RA, Mader DR, Johnson AT, Thomazy VA. Retinoid-induced epiphyseal plate closure in guinea pigs. Fundam Appl Toxicol. 1996 Nov;34(1):91-8. doi: 10.1006/faat.1996.0179. PMID: 8937896.