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4,?5-?Dimethoxycanthin-?6-?one

$1,530

  • Brand : BIOFRON

  • Catalogue Number : AV-S05730

  • Specification : 98%

  • CAS number : 18110-87-7

  • Formula : C16H12N2O3

  • Molecular Weight : 280.28

  • PUBCHEM ID : 638215

  • Volume : 20mg

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Catalogue Number

AV-S05730

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

280.28

Appearance

Yellow powder

Botanical Source

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

COC1=C(C(=O)N2C3=CC=CC=C3C4=C2C1=NC=C4)OC

Synonyms

Nigakinon-methylether/Methyl nigakinone/4,5-Dimethoxy-canthin-6-on/4,5-Dimethoxy-6H-indolo[3,2,1-de][1,5]naphthyridin-6-one/6H-Indolo(3,2,1-de)(1,5)naphthyridin-6-one, 4,5-dimethoxy-/6H-Indolo[3,2,1-de][1,5]naphthyridin-6-one, 4,5-dimethoxy-/4,5-dimethoxy-6H-indolo[3,2,1-de]-1,5-naphthyridin-6-one/4,5-Dimethoxy-6-oxo-6H-indolo<3.2.1-de><1.5>naphthyridin

IUPAC Name

3,4-dimethoxy-1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one

Applications

1377

Density

1.4±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

229.0±28.7 °C

Boiling Point

455.1±45.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C16H12N2O3/c1-20-14-12-13-10(7-8-17-12)9-5-3-4-6-11(9)18(13)16(19)15(14)21-2/h3-8H,1-2H3

InChl Key

ATONBUGCNDSBBC-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:18110-87-7) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

28962866

Abstract

AIMS:
P. quassioides is a traditional Chinese medicine used for the treatment of gastroenteritis, snakebite, infection and hypertension in China. 4, 5-dimethoxycanthin-6-one is one of the main active canthinone alkaloid isolated from P. quassioides. The aim of this work was to identify the cytochrome P (CYP) 450 enzymes responsible for the metabolism of 4, 5-dimethoxycanthin-6-one (DCO) and to evaluate the inhibitory effect of DCO on CYP activity in human liver microsomes (HLM) in vitro.

MATERIALS AND METHODS:
the CYP isoforms responsible for DCO metabolism and the inhibitory effects of DCO on CYP activity was studied in HLM.

KEY FINDINGS:
The in vitro metabolic enzyme of DCO was CYP3A4 (mediated the formation of metabolites M1-M5), CYP2C9 (mediated the formation of metabolites M1-M3, M6 and M8) and CYP2D6 (mediated the formation of metabolite M3) in HLM. Furthermore, the present work found that DCO uncompetitively inhibited CYP1A2-mediated phenacetin O-deethylation with an IC50 value of 1.7μM and a Ki value of 2.6μM.

SIGNIFICANCE:
The results suggested that the metabolic interaction should be existed when the substrate drugs of CYP1A2 were co-administered with DCO or traditional Chinese medicine containing it, such as the extract of P. quassioides and Kumu injection.

Copyright ? 2017. Published by Elsevier Inc.

KEYWORDS

4,5-dimethoxycanthin-6-one; Cytochrome P450; Human liver microsome; Metabolic interaction

Title

In vitro metabolism of 4, 5-dimethoxycanthin-6-one by human liver microsomes and its inhibition on human CYP1A2.

Author

Miao X1, You J1, Wang J2, Chen Y3.

Publish date

2017 Dec 1

PMID

28258983

Abstract

4,5-Dimethoxycanthin-6-one and 5-hydroxy-4-methoxycanthin-6-one are the active ingredients of P. quassiodes. In the present work, a LC-MS/MS method was developed for the determination of 4,5-dimethoxycanthin-6-one and its major metabolites 5-hydroxy-4-methoxycanthin-6-one (M1) and 4-hydroxy-5-methoxycanthin-6-one (M2) in rat plasma and tissues, and applied to study their pharmacokinetics and tissue distribution after intramuscular administration of 4,5-dimethoxycanthin-6-one to rats. By protein precipitation with methanol for plasma samples and liquid-liquid extraction with ethyl acetate for tissue samples, the analytes were separated on an ODS C18 column with a mobile phase consisted of methanol and water (0.1% formic acid), and quantified by a MS detector in positive multiple reaction monitoring (MRM) mode. MS transitions were m/z 281.0→167.1 for 4,5-dimethoxycanthin-6-one, m/z 267.0→168.1 for M1 and M2, m/z 251.0→195.1 for 3-methylcanthin-2,6-dione (IS). The pharmacokinetic results indicate that 4,5-dimethoxycanthin-6-one is absorbed rapidly (Tmax=5.4-6.4min), distributed rapidly and widely in the order of liver>kidney?lung?large intestine?small intestine, and eliminated quickly (t1/2z=64.9-77.7min) following the intramuscular administration. Furthermore, M1 and M2 were detected only in rat plasma and liver at the indicated times after the intramuscular administration.

Copyright ? 2017 Elsevier B.V. All rights reserved.

KEYWORDS

4,5-Dimethoxycanthin-6-one; LC-MS/MS; Metabolites; Pharmacokinetics; Tissue distribution

Title

Pharmacokinetics and tissue distribution of 4,5-dimethoxycanthin-6-one and its major metabolites in rats.

Author

Miao X1, Wang J1, Chen Y2.

Publish date

2017 May 30

PMID

27030894

Abstract

4,5-Dimthexycanthin-6-one and 5-hydroxy-4-methoxycanthin-6-one are the main active ingredients of Picrasma quassioides, which is a widely used herbal medicine for the treatment of gastroenteritis, snakebite, infection and hypertension in China. In the present study, the in vitro metabolites of 4,5-dimethoxycanthin-6-one in rat, mouse, dog and human liver microsomes, as well as the in vivo metabolites in rat plasma and urine following a single oral dose of 4,5-dimethoxycanthin-6-one, were identified by high-performance liquid chromatography combined with triple TOF mass spectrometry (HPLC-TOF/MS/MS). The metabolites were elucidated based on an accurate mass measurement, the MS/MS fragmentation patterns, the retention times of the parent drug and its metabolites, and the relevant drug biotransformation rules. After incubation in liver mcrosomes for 50 min, 4,5-dimethoxycanthin-6-one produced 8 phase I metabolites including 2 mono-demethylated metabolites (M1, M2), 3 mono-hydroxylated metabolites (M3-M5), and 3 mono-demethylated and mono-hydroxylated metabolites (M6-M8) in rat and mouse liver microsomes, 7 phase I metabolites (without M7) in dog and human liver microsomes. After a single oral administration of 4,5-dimethoxycanthin-6-one to rats, there were 3 phase I metabolites (M1, M2 and M5) detected in rat plasma and 5 phase I metabolites (M1-M5) in rat urine. Phase II metabolites were not detected in rat plasma and urine. Among these metabolites, mono-demethylated metabolites (M1 and M2) were the major metabolites of 4,5-dimethoxycanthin-6-one, mono-hydroxylated metabolites (M3-M5) were the minor metabolites of 4,5-dimethoxycanthin-6-one.

Copyright ? 2016 Elsevier B.V. All rights reserved.

KEYWORDS

4,5-Dimethoxycanthin-6-one; HPLC-TOF/MS/MS; In vitro and in vivo; Metabolite identification

Title

Identification of in vivo and in vitro metabolites of 4,5-dimethoxycanthin-6-one by HPLC-Q-TOF-MS/MS.

Author

Miao X1, Wang J1, Chen L1, Peng Z1, Chen Y2.

Publish date

2016 May 1