CYCLOVIROBUXINE D

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C26H46N2O
Molecular Weight	402.6562
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]1([C@H](C)NC)[C@H](O)C[C@@]2(C)[C@]3([H])CC[C@]4([H])[C@]5(C[C@@]35CC[C@]12C)CC[C@H](NC)C4(C)C

InChI

InChIKey=GMNAPBAUIVITMI-ABNIRSKTSA-N

InChI=1S/C26H46N2O/c1-16(27-6)21-17(29)14-24(5)19-9-8-18-22(2,3)20(28-7)10-11-25(18)15-26(19,25)13-12-23(21,24)4/h16-21,27-29H,8-15H2,1-7H3/t16-,17+,18-,19-,20-,21-,23+,24-,25+,26-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C26H46N2O
Molecular Weight	402.6562
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	9 / 10
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21497594
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/24758922 https://www.ncbi.nlm.nih.gov/pubmed/17555743

Cyclovirobuxine D (CVB-D) is an active compound extracted from Buxus microphylla, which has been used of cardiac insufficiency and arrhythmias in China. The antiarrhythmic and proarrhythmic potential of this drug might be concerned with prolongation of action potential duration and QT interval. Human-ether-a-go-go-related gene (HERG) has an important role in the repolarization of the cardiac action potential. CVB-D inhibits HERG encoded potassium channels and this action might be a molecular mechanism for the previously reported APD prolongation and QT interval prolongation with this drug. Currently pharmacological studies on CVB-D have been conducted extensively for treatment of cancers. However, whether and how CVB-D affects other cellular processes and the tumorigenesis pathway of cancer cells is still largely unknown.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
HERG 92 Target ID: CHEMBL240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21497594	Inhibitor 8297		19.7 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Coronary heart disease 41 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6628220	Preventing	Phase I 428	Unknown Approved Use Unknown
Acute myocardial ischemia 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17555743	Primary	Phase I 428	Unknown Approved Use Unknown
Breast cancer 434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24758922	Primary	Basic research	Unknown Approved Use Unknown
Gastric cancer 53 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26610442	Primary	Basic research	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
6.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16765010	2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered:		CYCLOVIROBUXINE D plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
47.22 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16765010	2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered:		CYCLOVIROBUXINE D plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
27.51 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16765010	2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered:		CYCLOVIROBUXINE D plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
2 mg single, intravenous Studied dose Dose: 2 mg Route: intravenous Route: single Dose: 2 mg Sources: https://pubmed.ncbi.nlm.nih.gov/16765010	healthy, ADULT n = 16 Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Population Size: 16 Sources: https://pubmed.ncbi.nlm.nih.gov/16765010	Sources: https://pubmed.ncbi.nlm.nih.gov/16765010

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00IKZR	https://www.1pchem.com/search?query=1P00IKZR
A2B Chem	AI66215	http://a2bchem.com/prod/AI66215
AK Scientific	V1510	https://aksci.com/item_detail.php?cat=V1510
AstaTech	41965	http://astatechinc.com/CPSResult.php?CRNO=41965
BOC Sciences	860-79-7	http://www.bocsci.com/description.asp?cas=860-79-7
BioSynth	Q-100865	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-100865
Biopurify Phytochemicals	BP0442	https://www.phytopurify.com/search.do?a=s&searchtype=3&psize=10&q=BP0442&searchhtmp=simplesearch&t=1
Chem Scene	CS-0007794	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0007794
ChemShuttle	151674	https://www.chemshuttle.com/catalogsearch/result/?q=151674
KeyOrganics	AS-17717	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-17717
MedChem Express	HY-N0107	https://www.medchemexpress.com/search.html?q=HY-N0107&ft=&fa=&fp=
MolPort	MolPort-016-633-348	https://www.molport.com/shop/molecule-link/MolPort-016-633-348
MolPort	MolPort-039-052-255	https://www.molport.com/shop/molecule-link/MolPort-039-052-255
Ryan Scientific	Scopoletin	https://ryansci.com/products?q=Scopoletin&list_q=&search_type=exact
TargetMol	T2974	https://www.targetmol.com/search?keyword=T2974
Tetrahedron	TS81166	http://www.thsci.com/search.do?q=TS81166
eMolecules	32452871	https://orderbb.emolecules.com/search/#?query=32452871
eNovation Chemicals	D630814	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D630814&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-3381418699	https://mcule.com/MCULE-3381418699/
mcule	MCULE-4198040345	https://mcule.com/MCULE-4198040345/

PubMed

Title	Date	PubMed
[Anti-atrial fibrillation effects of cyclovirobuxine-D and its electrophysiological mechanism studied on guinea pig atria].	1996	9772688
Cyclovirobuxine D inhibits the currents of HERG potassium channels stably expressed in HEK293 cells.	2011 Jun 25	21497594

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Intravenous

In Vitro Use Guide

To study the potential role(s) of Cyclovirobuxine D (CVB-D) in gastric cancer cells, ﬁrstly tested the cell viability of MGC-803 and MKN 28 cells after CVB-D treatment. After incubation with 0, 30, 60, 120 and 240 umol/L CVB-D for 24, 48 and 72 h, the viabilities of MGC-803 and MKN28 cells were measured using the MTT assay. CVB-D reduced cell viability and colony formation ability of MGC-803 and MKN28 cells in a time- and concentration-dependent manner. Flow cytometry showed that cell cycle of CVB-D treated cells was arrested at the S-phase. CVB-D also induced apoptosis in MGC-803 and MKN28 cells, especially early stage apoptosis. Furthermore, mitochondria membrane potential (Δψm) was reduced and apoptosis-related proteins, cleaved Caspase-3 and Bax/Bcl-2, were up-regulated in CVB-D-treated MGC-803 and MKN28 cells. Taken together, our studies found that CVB-D plays important roles in inhibition of gastric tumorigenesis via arresting cell cycle and inducing mitochondria-mediated apoptosis, suggesting the potential application of CVB-D in gastric cancer therapy.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 02:12:01 GMT 2023` Edited by `admin` on `Sat Dec 16 02:12:01 GMT 2023`
Record UNII	51GY352868
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CYCLOVIROBUXINE D

Common Name

English

CYCLOVIROBUXIN D

Common Name

English

HUANWEIHUANGYANGXING D

Common Name

English

CYCLOVIROBUXINE [INCI]

Common Name

English

BEBUXINE

Brand Name

English

CYCLOVIROBUXINUM D

Common Name

English

NSC-91722

Code

English

CYCLOVIROBUXINE

Official Name

English

CYCLOVIROBUXINUM D [CHP]

Common Name

English

Cyclovirobuxine D [WHO-DD]

Common Name

English

9,19-CYCLO-5.ALPHA.,9.BETA.-PREGNAN-16.ALPHA.-OL, 4,4,14-TRIMETHYL-3.BETA.,20.ALPHA.-BIS(METHYLAMINO)-

Common Name

English

9,19-CYCLOPREGNAN-16-OL, 4,4,14-TRIMETHYL-3,20-BIS(METHYLAMINO)-, (3.BETA.,5.ALPHA.,16.ALPHA.,20S)-

Common Name

English

Code System Code Type Description

PUBCHEM

260439