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SML0308

Sigma-Aldrich

Carbazeran

≥95% (HPLC)

Synonym(s):

N-Ethyl-carbamic acid 1-(6,7-dimethoxy-1-phthalazinyl)-4-piperidinyl ester, UK 31557

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About This Item

Empirical Formula (Hill Notation):
C18H24N4O4
CAS Number:
70724-25-3
Molecular Weight:
360.41
MDL number:
MFCD00867107
UNSPSC Code:
41106305
PubChem Substance ID:
329825313
NACRES:
NA.77

Assay

≥95% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: ≥2 mg/mL at warmed

storage temp.

2-8°C

SMILES string

CCNC(=O)OC1CCN(CC1)c2nncc3cc(OC)c(OC)cc23

InChI

1S/C18H24N4O4/c1-4-19-18(23)26-13-5-7-22(8-6-13)17-14-10-16(25-3)15(24-2)9-12(14)11-20-21-17/h9-11,13H,4-8H2,1-3H3,(H,19,23)

InChI key

QJGVXJYGDBSPSJ-UHFFFAOYSA-N

General description

Carbazeran is usedin the treatment of heart failure.

Biochem/physiol Actions

Carbazeran is an Aldehyde oxidase (AO) substrate and a phosphodiesterase inhibitor that produces concentration-dependent positive inotropic responses. In humans, the compound is almost completely cleared via 4-hydroxylation to the phthalazinone metabolite by AO.

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.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Shotaro Uehara et al.
Drug metabolism and disposition: the biological fate of chemicals, 48(7), 580-586 (2020-05-03)
Carbazeran is a potent phosphodiesterase inhibitor with species-dependent metabolic profiles in rats, dogs, and humans. In this study, we investigated the aldehyde oxidase (AOX)-mediated oxidation of carbazeran to 4-oxo derivatives in chimeric NOD/Shi-scid IL2 receptor gamma-null mice expressing a herpes
D el Allaf et al.
Archives internationales de physiologie et de biochimie, 92(4), S69-S79 (1984-11-01)
Compounds with phosphodiesterase inhibitory activity stimulate myocardial contractility by increasing the intracellular cyclic AMP concentrations. They can also increase Ca2+ entry and inhibit Ca2+ sequestration by the sarcoplasmic reticulum. Xanthines produce bronchodilation with associated venous and arteriolar dilation. However, their
Drug Metabolism: Towards the Next Millennium, 45-45 (1998)
B Price et al.
Biochemical pharmacology, 36(23), 4047-4054 (1987-12-01)
Extraction of frozen canine cardiac muscle rendered soluble over 90% of the cyclic AMP phosphodiesterase activity. The residual activity was membrane-bound. Ion exchange chromatography of the soluble activity on DE-52 allowed for the resolution of three distinct cyclic AMP phosphodiesterase
Maki Miyamoto et al.
Xenobiotica; the fate of foreign compounds in biological systems, 47(12), 1052-1063 (2016-11-29)
1. The aim of the present study was to evaluate the usefulness of chimeric mice with humanised liver (PXB mice) for the prediction of clearance (CL
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