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C7971

Sigma-Aldrich

Cilostamide

phosphodiesterase inhibitor

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
MDL number:
MFCD00673958
UNSPSC Code:
12352202
PubChem Substance ID:
24278337
NACRES:
NA.77

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)

Biochem/physiol Actions

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.
Selective inhibitor of PDE3 (cGMP-inhibited phosphodiesterase); IC50 = 70 ± 9 nM. This inhibitory effect increases intracellular cAMP and inhibits platelet aggregation.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Xiaofei Zhu et al.
BMC urology, 17(1), 54-54 (2017-07-09)
It has been shown that hosphodiesterases (PDEs) play an important role in mediating the smooth muscle tone of rat urinary bladder. However, the gene expression profiles of them were still unknown. Urinary bladder Strips were obtained from both neonatal and
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)
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
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