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Merck

C7971

Cilostamide

≥97% (HPLC), PDE3 inhibitor, powder

Synonym(s):

6-[3-(N-Cyclohexyl-N-methylcarbamoyl)propoxy]quinolin-2[1H]-one, OPC 3689

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About This Item

Empirical Formula (Hill Notation):
C20H26N2O3
CAS Number:
68550-75-4
Molecular Weight:
342.43
UNSPSC Code:
12352202
PubChem Substance ID:
24278337
NACRES:
NA.77
MDL number:
MFCD00673958

Key Documents

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Product Name

Cilostamide, phosphodiesterase inhibitor

Quality Level

100

assay

≥97% (HPLC)

form

powder

solubility

DMSO: 20 mg/mL, clear, colorless to faintly yellow

SMILES string

CN(C1CCCCC1)C(=O)CCCOc2ccc3NC(=O)C=Cc3c2

InChI

1S/C20H26N2O3/c1-22(16-6-3-2-4-7-16)20(24)8-5-13-25-17-10-11-18-15(14-17)9-12-19(23)21-18/h9-12,14,16H,2-8,13H2,1H3,(H,21,23)

InChI key

UIAYVIIHMORPSJ-UHFFFAOYSA-N

Gene Information

human ... PDE3A(5139), PDE3B(5140), PDE5A(8654), PDE7A(5150)
rat ... Pde2a(81743), Pde4a(25638)

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Biochem/physiol Actions

Selective cGMP-inhibited phosphodiesterase inhibitor (PDE3); IC50 = 70 ± 9 nM.
Selective inhibitor of PDE3 (cGMP-inhibited phosphodiesterase); IC50 = 70 ± 9 nM. This inhibitory effect increases intracellular cAMP and inhibits platelet aggregation.
PDE3 catalyzes the phosphodiester bond hydrolysis, observed in secondory messengers such as cyclic adenosine monophosphate (cAMP) and cyclic guanosine monophosphate (cGMP). Inhibitors of PDE3 are generally inotropic and vasodilatory. They are being recognized for its use in treating heart failures. Cilostamide is known to delay meiotic progression.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ7413
MKCP1197
MKCM7956
MKCL9528
MKCL2541

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Byung Chul Jee et al.
Fertility and sterility, 91(5 Suppl), 2037-2042 (2008-06-17)
To investigate the effect of a phosphodiesterase type 3 inhibitor in oocyte maturation medium on subsequent embryo development. Animal study. University laboratory. CD-1 mice. Immature oocytes were arrested meiotically in medium containing a specific phosphodiesterase type 3 inhibitor, cilostamide (1
Alberto M Luciano et al.
Biology of reproduction, 85(6), 1252-1259 (2011-08-06)
Oocyte development is characterized by impressive changes in chromatin structure and function in the germinal vesicle (GV) that are crucial in conferring to the oocyte meiotic and developmental competence. During oogenesis, oocyte and follicular cells communicate by paracrine and junctional
Targeting tumor cells based on Phosphodiesterase 3A expression
Nazir M, et al.
Experimental Cell Research, 361(2), 308-315 (2017)
F K Albuz et al.
Human reproduction (Oxford, England), 25(12), 2999-3011 (2010-09-28)
Oocyte in vitro maturation (IVM) reduces the need for gonadotrophin-induced ovarian hyperstimulation and its associated health risks but the unacceptably low conception/pregnancy rates have limited its clinical uptake. We report the development of a novel in vitro simulated physiological oocyte
Effects of cilostamide and forskolin on the meiotic resumption and embryonic development of immature human oocytes
Shu Y, et al.
Human Reproduction, 23(3), 504-513 (2008)
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