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SML0366

Sigma-Aldrich

Cipamfylline

≥98% (HPLC)

Synonym(s):

8-Amino-1,3-bis(cyclopropylmethyl)-3,9-dihydro-1H-Purine-2,6-dione, BRL 61063

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About This Item

Empirical Formula (Hill Notation):
C13H17N5O2
CAS Number:
132210-43-6
Molecular Weight:
275.31
UNSPSC Code:
41106305
PubChem Substance ID:
329825367
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: >10 mg/mL

storage temp.

2-8°C

SMILES string

Nc1nc2N(CC3CC3)C(=O)N(CC4CC4)C(=O)c2[nH]1

InChI

1S/C13H17N5O2/c14-12-15-9-10(16-12)17(5-7-1-2-7)13(20)18(11(9)19)6-8-3-4-8/h7-8H,1-6H2,(H3,14,15,16)

InChI key

KSPYMJJKQMWWNB-UHFFFAOYSA-N

Biochem/physiol Actions

Cipamfylline is a PDE4 inhibitor that has been shown to cause a cellular redistribution of PDE4A4 into accretion foci, through an association with the ubiquitin scaffolding protein p62.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Phosphodiesterases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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R N Willette et al.
Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism, 17(2), 210-219 (1997-02-01)
The role of the phosphodiesterase type IV isozyme (PDE IV) in the regulation of cerebrovascular tone was investigated in the canine basilar artery in vitro and in vivo. The PDE isozymes extracted from the canine basilar artery were isolated by
M Kumari et al.
British journal of pharmacology, 121(3), 459-468 (1997-06-01)
1. Previous studies in our laboratory have shown that the synthetic xanthine analogue denbufylline, a selective type 4 phosphodiesterase (PDE-4) inhibitor, is a potent activator of the hypothalamo-pituitary-adrenal (HPA) axis when given orally or intraperitoneally (i.p.) to adult male rats.
J M Kaplan et al.
Toxicology, 95(1-3), 187-196 (1995-01-06)
BRL 61063 is a novel xanthine phosphodiesterase (PDE) type IV inhibitor with selective inhibitory activity for tumor necrosis factor (TNF) alpha production. This compound inhibits TNF alpha production by activated human blood monocytes in vitro and in animal models of
D R Buckle et al.
Journal of medicinal chemistry, 37(4), 476-485 (1994-02-18)
Alkylation of the selective type IV phosphodiesterase inhibitor, 8-amino-1,3-bis(cyclopropylmethyl)-xanthine (1, BRL 61063), led exclusively to the N-7 substituted derivatives 2-9, which showed varying selectivities for the PDE type IV isoenzyme relative to PDE Va. The 4-methoxybenzyl derivative 6 in particular
A M Badger et al.
Circulatory shock, 44(4), 188-195 (1994-12-01)
Three inhibitors of calcium-dependent cyclic adenosine 3'5'-monophosphate (cAMP) dependent phosphodiesterase IV (PDE IV) were evaluated for their effects on lipopolysaccharide (LPS)-induced tumor necrosis factor (TNF) production in vitro and in vivo and for their ability to protect mice from LPS-induced
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Phosphodiesterases

Cyclic nucleotide phosphodiesterases (PDEs) catalyze the hydrolysis of cAMP and/or cGMP. There are 11 different mammalian PDE families.

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Cyclic nucleotides, including cyclic AMP (cAMP), cyclic GMP (cGMP) and cyclic ADP-ribose, have been extensively studied as second messengers of intracellular events initiated by activation of GPCRs. cAMP modifies cell function in all eukaryotic cells, principally through the activation of cAMP-dependent protein kinase (PKA), but also through cAMP-gated ion channels and guanine nucleotide exchange factors directly activated by cAMP.

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