BMS-189453

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

MedKoo CAT#: 526659

CAS#: 166977-43-1

Description: BMS-189453, also known as BMS453, is a potent and selective RARβ agonist and a potent testicular toxin. In Sprague Dawley rats at daily oral doses of 15, 60, or 240 mg/kg for 1 month, BMS-189453 produced increases in leukocyte counts, alkaline phosphatase and alanine aminotransferase levels, and marked testicular degeneration and atrophy at all doses.


Chemical Structure

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BMS-189453
CAS# 166977-43-1

Theoretical Analysis

MedKoo Cat#: 526659
Name: BMS-189453
CAS#: 166977-43-1
Chemical Formula: C27H24O2
Exact Mass: 380.18
Molecular Weight: 380.487
Elemental Analysis: C, 85.23; H, 6.36; O, 8.41

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: BMS-189453; BMS189453; BMS189453; BMS453; BMS-453; BMS 453.

IUPAC/Chemical Name: E)-4-[2-(5,6-Dihydro-5,5-dimethyl-8-phenyl-2-naphthalenyl)ethenyl]-benzoic acid

InChi Key: VUODRPPTYLBGFM-CMDGGOBGSA-N

InChi Code: InChI=1S/C27H24O2/c1-27(2)17-16-23(21-6-4-3-5-7-21)24-18-20(12-15-25(24)27)9-8-19-10-13-22(14-11-19)26(28)29/h3-16,18H,17H2,1-2H3,(H,28,29)/b9-8+

SMILES Code: O=C(O)C1=CC=C(/C=C/C2=CC=C3C(C)(C)CC=C(C4=CC=CC=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, not in water

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 380.49 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: Zdrojewicz Z, Konieczny R, Papier P, Szten F. Brdt Bromodomains Inhibitors and Other Modern Means of Male Contraception. Adv Clin Exp Med. 2015 Jul-Aug;24(4):705-14. doi: 10.17219/acem/33827. Review. PubMed PMID: 26469117.

2: Nya-Ngatchou JJ, Amory JK. New approaches to male non-hormonal contraception. Contraception. 2013 Mar;87(3):296-9. doi: 10.1016/j.contraception.2012.08.016. Epub 2012 Sep 17. Review. PubMed PMID: 22995542; PubMed Central PMCID: PMC3529759.

3: Chung SS, Wang X, Roberts SS, Griffey SM, Reczek PR, Wolgemuth DJ. Oral administration of a retinoic Acid receptor antagonist reversibly inhibits spermatogenesis in mice. Endocrinology. 2011 Jun;152(6):2492-502. doi: 10.1210/en.2010-0941. Epub 2011 Apr 19. PubMed PMID: 21505053; PubMed Central PMCID: PMC3100616.

4: Cipollone D, Cozzi DA, Businaro R, Marino B. Congenital diaphragmatic hernia after exposure to a triple retinoic acid antagonist during pregnancy. J Cardiovasc Med (Hagerstown). 2010 Nov 23. [Epub ahead of print] PubMed PMID: 21107276.

5: Zhang Q, Jiang J, Han P, Yuan Q, Zhang J, Zhang X, Xu Y, Cao H, Meng Q, Chen L, Tian T, Wang X, Li P, Hescheler J, Ji G, Ma Y. Direct differentiation of atrial and ventricular myocytes from human embryonic stem cells by alternating retinoid signals. Cell Res. 2011 Apr;21(4):579-87. doi: 10.1038/cr.2010.163. Epub 2010 Nov 23. PubMed PMID: 21102549; PubMed Central PMCID: PMC3203651.

6: Amati F, Diano L, Campagnolo L, Vecchione L, Cipollone D, Bueno S, Prosperini G, Desideri A, Siracusa G, Chillemi G, Marino B, Novelli G. Hif1α down-regulation is associated with transposition of great arteries in mice treated with a retinoic acid antagonist. BMC Genomics. 2010 Sep 16;11:497. doi: 10.1186/1471-2164-11-497. PubMed PMID: 20846364; PubMed Central PMCID: PMC2996993.

7: Cipollone D, Carsetti R, Tagliani A, Rosado MM, Borgiani P, Novelli G, D'Amati G, Fumagalli L, Marino B, Businaro R. Folic acid and methionine in the prevention of teratogen-induced congenital defects in mice. Cardiovasc Pathol. 2009 Mar-Apr;18(2):100-9. doi: 10.1016/j.carpath.2008.02.007. Epub 2008 Apr 15. PubMed PMID: 18417366.

8: Johnson CS, Zucker RM, Hunter ES 3rd, Sulik KK. Perturbation of retinoic acid (RA)-mediated limb development suggests a role for diminished RA signaling in the teratogenesis of ethanol. Birth Defects Res A Clin Mol Teratol. 2007 Sep;79(9):631-41. PubMed PMID: 17676605.

9: Cipollone D, Amati F, Carsetti R, Placidi S, Biancolella M, D'Amati G, Novelli G, Siracusa G, Marino B. A multiple retinoic acid antagonist induces conotruncal anomalies, including transposition of the great arteries, in mice. Cardiovasc Pathol. 2006 Jul-Aug;15(4):194-202. PubMed PMID: 16844550.

10: Keegan BR, Feldman JL, Begemann G, Ingham PW, Yelon D. Retinoic acid signaling restricts the cardiac progenitor pool. Science. 2005 Jan 14;307(5707):247-9. PubMed PMID: 15653502.

11: Suzuki A, Ito T, Imai E, Yamato M, Iwatani H, Kawachi H, Hori M. Retinoids regulate the repairing process of the podocytes in puromycin aminonucleoside-induced nephrotic rats. J Am Soc Nephrol. 2003 Apr;14(4):981-91. PubMed PMID: 12660332.

12: Beehler BC, Hei YJ, Chen S, Lupisella JA, Ostrowski J, Starrett JE, Tortolani D, Tramposch KM, Reczek PR. Inhibition of disease progression by a novel retinoid antagonist in animal models of arthritis. J Rheumatol. 2003 Feb;30(2):355-63. PubMed PMID: 12563696.

13: Schulze GE, Clay RJ, Mezza LE, Bregman CL, Buroker RA, Frantz JD. BMS-189453, a novel retinoid receptor antagonist, is a potent testicular toxin. Toxicol Sci. 2001 Feb;59(2):297-308. PubMed PMID: 11158723.