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C7971

Cilostamide

Name: Cilostamide
Brand: SIGMA

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

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.

Storage Class Code

11 - Combustible Solids

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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Functional regulatory T cells produced by inhibiting cyclic nucleotide phosphodiesterase type 3 prevent allograft rejection.

Gang Feng et al.

Science translational medicine, 3(83), 83ra40-83ra40 (2011-05-20)

Regulatory T cells (T(regs)) manipulated ex vivo have potential as cellular therapeutics in autoimmunity and transplantation. Although it is possible to expand naturally occurring T(regs), an attractive alternative possibility, particularly suited to solid organ and bone marrow transplantation, is the

Assessment of a new in vitro maturation system for mouse and human cumulus-enclosed oocytes: three-dimensional prematuration culture in the presence of a phosphodiesterase 3-inhibitor.

L Vanhoutte et al.

Human reproduction (Oxford, England), 24(8), 1946-1959 (2009-04-28)

Controlling nuclear maturation during oocyte culture might improve nuclear-cytoplasmic maturation synchrony. In the present study, the quality of mouse and human cumulus-enclosed oocytes (CEOs) was examined after a two-step culture consisting of a three-dimensional prematuration culture (3D-PMC), followed by in

Photoaffinity labelling of cyclic GMP-inhibited phosphodiesterase (PDE III) in human and rat platelets and rat tissues: effects of phosphodiesterase inhibitors.

K M Tang et al.

European journal of pharmacology, 268(1), 105-114 (1994-06-15)

Ultraviolet irradiation of human platelet cytosol in the presence of 32P-labelled cyclic GMP (cGMP) can specifically label 110, 80, 55, 49 and 38 kDa proteins; the 110 kDa species is the subunit of cGMP-inhibited phosphodiesterase (PDE III) and the 80

Gap junction-mediated communications regulate chromatin remodeling during bovine oocyte growth and differentiation through cAMP-dependent mechanism(s).

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

Simulated physiological oocyte maturation (SPOM): a novel in vitro maturation system that substantially improves embryo yield and pregnancy outcomes.

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

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