Y-39983 free base

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

MedKoo CAT#: 526780

CAS#: 199433-58-4 (free base)

Description: Y-39983 (free base), also known as Y-33075, is a potent and selective inhibitor of ROCK family with IC50 value of 3.6nM for ROCK. Y-39983 attenuates experimental autoimmune encephalomyelitis via inhibition of demyelination. Y-39983 downregulates RhoA/Rho-associated kinase expression during its promotion of axonal regeneration. Y-39983, promotes regeneration of crushed axons of retinal ganglion cells into the optic nerve of adult cats.


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Y-33075 is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 526780
Name: Y-39983 free base
CAS#: 199433-58-4 (free base)
Chemical Formula: C16H16N4O
Exact Mass: 280.1324
Molecular Weight: 280.331
Elemental Analysis: C, 68.55; H, 5.75; N, 19.99; O, 5.71


Related CAS #: 173897-44-4 (2HCl)   199433-58-4 (free base)    

Synonym: Y-39983; Y 39983; Y39983; Y-33075; Y 33075; Y33075.

IUPAC/Chemical Name: (R)-4-(1-aminoethyl)-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)benzamide

InChi Key: JTVBXQAYBIJXRP-SNVBAGLBSA-N

InChi Code: InChI=1S/C16H16N4O/c1-10(17)11-2-4-12(5-3-11)16(21)20-14-7-9-19-15-13(14)6-8-18-15/h2-10H,17H2,1H3,(H2,18,19,20,21)/t10-/m1/s1

SMILES Code: O=C(NC1=C2C(NC=C2)=NC=C1)C3=CC=C([C@H](N)C)C=C3


Technical Data

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).

Harmonized System Code:
293490


References

1: Inoue T, Tanihara H, Tokushige H, Araie M. Efficacy and safety of SNJ-1656 in primary open-angle glaucoma or ocular hypertension. Acta Ophthalmol. 2015 Aug;93(5):e393-5. doi: 10.1111/aos.12641. Epub 2015 Mar 17. PubMed PMID: 25783615.

2: Chen KG, Hamilton RS, Robey PG, Mallon BS. Alternative cultures for human pluripotent stem cell production, maintenance, and genetic analysis. J Vis Exp. 2014 Jul 24;(89). doi: 10.3791/51519. PubMed PMID: 25077932; PubMed Central PMCID: PMC4206262.

3: Chen HH, Namil A, Severns B, Ward J, Kelly C, Drace C, McLaughlin MA, Yacoub S, Li B, Patil R, Sharif N, Hellberg MR, Rusinko A, Pang IH, Combrink KD. In vivo optimization of 2,3-diaminopyrazine Rho Kinase inhibitors for the treatment of glaucoma. Bioorg Med Chem Lett. 2014 Apr 15;24(8):1875-9. doi: 10.1016/j.bmcl.2014.03.017. Epub 2014 Mar 19. PubMed PMID: 24684843.

4: Van de Velde S, Van Bergen T, Sijnave D, Hollanders K, Castermans K, Defert O, Leysen D, Vandewalle E, Moons L, Stalmans I. AMA0076, a novel, locally acting Rho kinase inhibitor, potently lowers intraocular pressure in New Zealand white rabbits with minimal hyperemia. Invest Ophthalmol Vis Sci. 2014 Feb 18;55(2):1006-16. doi: 10.1167/iovs.13-13157. PubMed PMID: 24474276.

5: Okumura N, Nakano S, Kay EP, Numata R, Ota A, Sowa Y, Sakai T, Ueno M, Kinoshita S, Koizumi N. Involvement of cyclin D and p27 in cell proliferation mediated by ROCK inhibitors Y-27632 and Y-39983 during corneal endothelium wound healing. Invest Ophthalmol Vis Sci. 2014 Jan 15;55(1):318-29. doi: 10.1167/iovs.13-12225. PubMed PMID: 24106120.

6: Gao C, Huang L, Long Y, Zheng J, Yang J, Pu S, Xie L. Y-39983, a selective Rho-kinase inhibitor, attenuates experimental autoimmune encephalomyelitis via inhibition of demyelination. Neuroimmunomodulation. 2013;20(6):334-40. doi: 10.1159/000353568. Epub 2013 Aug 30. PubMed PMID: 24008512.

7: Yang Z, Wang J, Liu X, Cheng Y, Deng L, Zhong Y. Y-39983 downregulates RhoA/Rho-associated kinase expression during its promotion of axonal regeneration. Oncol Rep. 2013 Mar;29(3):1140-6. doi: 10.3892/or.2012.2205. Epub 2012 Dec 20. PubMed PMID: 23258382.

8: Tokushige H, Waki M, Takayama Y, Tanihara H. Effects of Y-39983, a selective Rho-associated protein kinase inhibitor, on blood flow in optic nerve head in rabbits and axonal regeneration of retinal ganglion cells in rats. Curr Eye Res. 2011 Oct;36(10):964-70. doi: 10.3109/02713683.2011.599106. PubMed PMID: 21950703.

9: Ramachandran C, Patil RV, Combrink K, Sharif NA, Srinivas SP. Rho-Rho kinase pathway in the actomyosin contraction and cell-matrix adhesion in immortalized human trabecular meshwork cells. Mol Vis. 2011;17:1877-90. Epub 2011 Jul 14. PubMed PMID: 21850162; PubMed Central PMCID: PMC3144732.

10: Watabe H, Abe S, Yoshitomi T. Effects of Rho-associated protein kinase inhibitors Y-27632 and Y-39983 on isolated rabbit ciliary arteries. Jpn J Ophthalmol. 2011 Jul;55(4):411-7. doi: 10.1007/s10384-011-0048-9. Epub 2011 Jun 11. PubMed PMID: 21667088.

11: Watanabe M. Regeneration of optic nerve fibers of adult mammals. Dev Growth Differ. 2010 Sep;52(7):567-76. doi: 10.1111/j.1440-169X.2010.01203.x. Review. PubMed PMID: 20887558.

12: Whitlock NA, McKnight B, Corcoran KN, Rodriguez LA, Rice DS. Increased intraocular pressure in mice treated with dexamethasone. Invest Ophthalmol Vis Sci. 2010 Dec;51(12):6496-503. doi: 10.1167/iovs.10-5430. Epub 2010 Jul 29. PubMed PMID: 20671272.

13: Whitlock NA, Harrison B, Mixon T, Yu XQ, Wilson A, Gerhardt B, Eberhart DE, Abuin A, Rice DS. Decreased intraocular pressure in mice following either pharmacological or genetic inhibition of ROCK. J Ocul Pharmacol Ther. 2009 Jun;25(3):187-94. doi: 10.1089/jop.2008.0142. PubMed PMID: 19456252.

14: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2008 Sep;30(7):543-88. PubMed PMID: 18985183.

15: Watanabe M. [Optic nerve regeneration in adult mammals]. Nihon Shinkei Seishin Yakurigaku Zasshi. 2008 Jun;28(3):143-8. Review. Japanese. PubMed PMID: 18646601.

16: Tokushige H, Inatani M, Nemoto S, Sakaki H, Katayama K, Uehata M, Tanihara H. Effects of topical administration of y-39983, a selective rho-associated protein kinase inhibitor, on ocular tissues in rabbits and monkeys. Invest Ophthalmol Vis Sci. 2007 Jul;48(7):3216-22. PubMed PMID: 17591891.

17: Sagawa H, Terasaki H, Nakamura M, Ichikawa M, Yata T, Tokita Y, Watanabe M. A novel ROCK inhibitor, Y-39983, promotes regeneration of crushed axons of retinal ganglion cells into the optic nerve of adult cats. Exp Neurol. 2007 May;205(1):230-40. Epub 2007 Feb 14. PubMed PMID: 17359977.

18: Nakajima E, Nakajima T, Minagawa Y, Shearer TR, Azuma M. Contribution of ROCK in contraction of trabecular meshwork: proposed mechanism for regulating aqueous outflow in monkey and human eyes. J Pharm Sci. 2005 Apr;94(4):701-8. PubMed PMID: 15682386.