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BM0034

Sigma-Aldrich

BMS-764459

≥98% (HPLC)

Synonym(s):

(S)-4-(1-Cyclopropyl-2-methoxyethyl)-6-(6-(difluoromethoxy)-2,5-dimethylpyridin-3-ylamino)-5-oxo-4,5-dihydropyrazine-2-carbonitrile, 4-[(1S)-1-Cyclopropyl-2-methoxyethyl]-6-[[6-(difluoromethoxy)-2,5-dimethyl-3-pyridinyl]amino]-4,5-dihydro-5-oxo-2-pyrazinecarbonitrile

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About This Item

Empirical Formula (Hill Notation):
C19H21F2N5O3
CAS Number:
1188407-45-5
Molecular Weight:
405.40
MDL number:
MFCD18642630
UNSPSC Code:
12352200

Assay

≥98% (HPLC)

form

powder

color

white to light brown

solubility

DMSO: 20 mg/mL, clear

storage temp.

room temp

SMILES string

O=C1C(NC2=CC(C)=C(OC(F)F)N=C2C)=NC(C#N)=CN1[C@H](COC)C3CC3

InChI

1S/C19H21F2N5O3/c1-10-6-14(11(2)23-17(10)29-19(20)21)25-16-18(27)26(8-13(7-22)24-16)15(9-28-3)12-4-5-12/h6,8,12,15,19H,4-5,9H2,1-3H3,(H,24,25)/t15-/m1/s1

InChI key

PJMUNXORSUNUCV-OAHLLOKOSA-N

Biochem/physiol Actions

BMS-764459 is a pyrazinone-containing antagonist that targets corticotropin-releasing factor/hormone (CRF or CRH) receptor 1 (CRF1, CRF-R1, CRFR-1, CRH-R1, CRHR-1) with high affinity (IC50 = 0.86 nM against 150 pM ovine CRF for binding rat CRF-R1), potency (IC50 = 1.9 nM against 1 nM CRF-stimulated cAMP production in human Y-79 retinoblastoma cells), and selectivity, displaying little affinity toward CRF-R2/CRF2 and 43 other receptor/channel/transporter proteins (IC50 >10 μM). BMS-764459 exhibits anxiolytic efficacy in a rat defensive withdrawal model of anxiety in vivo (1-3 mg/kg p.o.) with good oral bioavailability (F in dogs = 53% with 2 mg/kg in suspension and 70% with 3 mg/kg in solution).
BMS-764459 is a pyrazinone-containing antagonist that targets corticotropin-releasing factor/hormone (CRF or CRH) receptor 1 (CRF1, CRF-R1, CRFR-1, CRH-R1, CRHR-1).

Features and Benefits

BMS-764459 is available through a partnership with Bristol-Myers Squibb (BMS). To learn more and view other BMS compounds, visit sigma.com/BMS.

Legal Information

Sold for research purposes only under agreement from BMS.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
126M4744V

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Damir Simic et al.
Toxicology, 311(3), 169-177 (2013-07-09)
The corticotrophin releasing factor (CRF) receptor I antagonist, BMS-764459 (evaluated as a potential treatment of affective disorders), was orally dosed to female Sprague-Dawley rats once daily for 2 weeks (vehicle control or 175mg/kg/day). To investigate the mechanism of BMS-764459-related liver
Richard A Hartz et al.
Journal of medicinal chemistry, 52(23), 7653-7668 (2009-12-04)
Detailed metabolic characterization of 8, an earlier lead pyrazinone-based corticotropin-releasing factor-1 (CRF(1)) receptor antagonist, revealed that this compound formed significant levels of reactive metabolites, as measured by in vivo and in vitro biotransformation studies. This was of particular concern due

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