BENZOYLMESACONINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C31H43NO10
Molecular Weight	589.6738
Optical Activity	UNSPECIFIED
Defined Stereocenters	16 / 16
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12C[C@]3(O)[C@H](OC(=O)C4=CC=CC=C4)[C@]1([H])[C@@](O)([C@@H]5[C@H](OC)[C@@]6([H])[C@]27C5N(C)C[C@]6(COC)[C@H](O)C[C@@H]7OC)[C@@H](O)[C@@H]3OC

InChI

InChIKey=PULWZCUZNRVAHT-PUAFOYDXSA-N

InChI=1S/C31H43NO10/c1-32-13-28(14-38-2)17(33)11-18(39-3)30-16-12-29(36)25(42-27(35)15-9-7-6-8-10-15)19(16)31(37,24(34)26(29)41-5)20(23(30)32)21(40-4)22(28)30/h6-10,16-26,33-34,36-37H,11-14H2,1-5H3/t16-,17-,18+,19-,20?,21+,22-,23-,24+,25-,26+,28+,29-,30+,31-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25329869
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/7997462 | https://www.ncbi.nlm.nih.gov/pubmed/8282271 | https://www.ncbi.nlm.nih.gov/pubmed/9682963 | https://www.ncbi.nlm.nih.gov/pubmed/9682964 | |https://www.ncbi.nlm.nih.gov/pubmed/12543043

Benzoylmesaconine (BMA) is the main Aconitum alkaloid in Radix Aconiti Lateralis Preparata. Notably, the high levels of toxicity of Radix Aconiti are derived from diester aconitum alkaloids, including aconitine, mesaconitine and hypaconitine, which can be hydrolyzed to benzoylaconine, benzoylmesaconine and benzoylhypaconine, respectively. Benzoylmesaconine exhibits biological effects, including analgesic, antiviral and antifungal activities.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 3A5 2 Target ID: CHEMBL3019 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23864901	Substrate 661
Cytochrome P450 3A4 127 Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23864901	Substrate 661

Conditions

Condition	Modality	Highest Phase	Product
Candida infections 20 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9682963 https://www.ncbi.nlm.nih.gov/pubmed/9682964	Primary	Preclinical	Unknown Approved Use Unknown
Herpes simplex virus type 1 infection 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9682963 https://www.ncbi.nlm.nih.gov/pubmed/9682964 https://www.ncbi.nlm.nih.gov/pubmed/12543043	Primary	Preclinical	Unknown Approved Use Unknown
Pain 619 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7997462 https://www.ncbi.nlm.nih.gov/pubmed/8282271	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Pharmacokinetic comparisons of benzoylmesaconine in rats using ultra-performance liquid chromatography-tandem mass spectrometry after administration of pure benzoylmesaconine and Wutou decoction.	2014-10-17	25329869
Monoester-Diterpene Aconitum Alkaloid Metabolism in Human Liver Microsomes: Predominant Role of CYP3A4 and CYP3A5.	2013	23864901
An optimized high-performance liquid chromatography (HPLC) method for benzoylmesaconine determination in Radix Aconiti Lateralis Preparata (Fuzi, aconite roots) and its products.	2008-05-30	18513409
Therapeutic effects of IL-12 combined with benzoylmesaconine, a non-toxic aconitine-hydrolysate, against herpes simplex virus type 1 infection in mice following thermal injury.	2003-02	12543043
The regulation of burn-associated infections with herpes simplex virus type 1 or Candida albicans by a non-toxic aconitine-hydrolysate, benzoylmesaconine. Part 1: Antiviral and anti-fungal activities in thermally injured mice.	1998-06	9682963
The regulation of burn-associated infections with herpes simplex virus type 1 or Candida albicans by a non-toxic aconitine-hydrolysate, benzoylmesaconine. Part 2: Mechanism of the antiviral action.	1998-06	9682964
Antinociceptive mechanism of the aconitine alkaloids mesaconitine and benzoylmesaconine.	1994-10	7997462
[Analgesic effect of benzoylmesaconine].	1993-12	8282271

Patents

Sample Use Guides

In Vivo Use Guide

Benzoylmesaconine at the dosage of 30 mg/kg (per os) significantly increased the pain threshold in rats. Benzoylmesaconine (5 mg/kg i.v.) produced a weak temporary hypotension in rats which was blocked to some extent by atropine.

Route of Administration: Other

In Vitro Use Guide

Unknown

Name

Type

Language

14-O-BENZOYLMESACONINE

Preferred Name

English

BENZOYLMESACONINE

Common Name

English

ACONITANE-3,8,13,14,15-PENTOL, 4-(METHOXYMETHYL)-20-METHYL-1,6,16-TRIMETHOXY-, 14-BENZOATE, (1-.ALPHA.,3-.ALPHA.,6-.ALPHA.,14-.ALPHA.,15-.ALPHA.,16-.BETA.)-

Common Name

English

O8-DEACETYLMESACONITINE

Common Name

English

MESACONINE 14-BENZOATE

Common Name

English

Code System Code Type Description

PUBCHEM

102004490