Cyclovirobuxin D

ChemicalBook > CAS DataBase List > Cyclovirobuxin D

Product Name: Cyclovirobuxin D
CAS No.: 860-79-7
Chemical Name: Cyclovirobuxin D
Synonyms: cvb-d;bebuxine;NSC91722;cyclobuxine D;CYCLOVIROBUXINE;cyclovirobuxind;CYCLOVIROBUXINE D;-bis(methylamino)-;cyclovirobuxinum D;Cyclovirobuxine D, >=98%
CBNumber: CB3663206
Molecular Formula: C26H46N2O
Formula Weight: 402.66
MOL File: 860-79-7.mol

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Cyclovirobuxin D Property

Melting point:: 220-221 °C (decomp)(Solv: acetone (67-64-1))
Boiling point:: 524.75°C (rough estimate)
Density: 0.9815 (rough estimate)
refractive index: 1.5300 (estimate)
storage temp.: Store at -20°C
solubility: Soluble to 20 mg/mL (49.66 mM) in Ethanol
form: cryst.
pka: 15.12±0.70(Predicted)
color: White
LogP: 4.635 (est)
CAS DataBase Reference: 860-79-7(CAS DataBase Reference)

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Safety

Safety Statements: 24/25
HS Code: 29420000
Toxicity: LD50 oral in mouse: 293mg/kg

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML3384
Product name: Cyclovirobuxine D
Purity: ≥90% (HPLC)
Packaging: 10MG
Price: $79
Updated: 2023/01/07

Sigma-Aldrich

Product number: SML3384
Product name: Cyclovirobuxine D
Purity: ≥90% (HPLC)
Packaging: 50MG
Price: $319
Updated: 2023/01/07

Cayman Chemical

Product number: 22260
Product name: Cyclovirobuxine D
Purity: ≥95%
Packaging: 5mg
Price: $40
Updated: 2024/03/01

Cayman Chemical

Product number: 22260
Product name: Cyclovirobuxine D
Purity: ≥95%
Packaging: 10mg
Price: $72
Updated: 2024/03/01

Cayman Chemical

Product number: 22260
Product name: Cyclovirobuxine D
Purity: ≥95%
Packaging: 25mg
Price: $157
Updated: 2024/03/01

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Cyclovirobuxin D Chemical Properties,Usage,Production

Description

A Buxus alkaloid of the steroidal class, this base has been found in the strong base fraction of the alkaloidal extract from Buxus microphylla Sieb. et Zucco var. suffruticosa and B. microphylla Sieb. et Zucco var. suffruticosa Makino forma major. It is dextrorotatory having a specific rotation of [α]²³_D + 98° (c 4.40,CHC13)and yields a series of salts and derivatives including the dihydrobromide, m.p. 288-292°C (dec.); dihydriodide, m.p. 276-8°C (dec.); diperchlorate, m.p. 244- 5°C (dec.); dioxalate as an amorphous powder, m.p. 264-7°C (dec.): the N:Ndiacetyl derivative, m.p. 278-281°C (dec.) with [α]²⁴_D + 10° (c 1.94, CHC13) and the O,N,N-triacetyl derivative, m.p. 246-8°C with [α]²⁴_D - 12° (c 2.40, CHCI3)·
The structure and stereochemistry of the base have been elucidated from chemical analysis, spectroscopic evidence and comparison with other alkaloids of this class.

Physical properties

Appearance: colorless needle crystals. Solubility: sparingly soluble in acetone; slightly soluble in water; freely soluble in chloroform; soluble in methanol and ethanol. Melting point: 219–222?°C.

History

Cyclovirobuxine in the treatment of coronary heart disease began in 1969 . The medical teams of Chinese People’s Liberation Army No.86489 explored a treatment of coronary heart disease named Guo, prescription composed of Buxus microphylla (huangyangmu), Salvia miltiorrhiza Bge. (danshen), Ligustici Chuanxiong Rhizoma (chuanxiong), Belamcandae Rhizoma (shegan), Radix Aristolochiae (qingmuxiang) and Asari Radix et Rhizoma (xixin).
In 1978, the Anhui Huangyang Research Cooperation Group carried out systematic experiments to determine the chemical structure and the separation and identification method of cyclovirobuxine by melting point determination, thin-layer chromatography, infrared spectroscopy, mass spectrometry and NMR . Three studies containing more than 300 cases of coronary heart disease patients treated with cyclovirobuxine showed that this drug can significantly improve angina, chest tightness, arrhythmia and other symptoms caused by coronary heart disease.

Uses

Cyclovirobuxine D is a potential preventative agent of cardiac dysfunction.

Indications

It is mainly used for the treatment of cardiovascular and cerebrovascular diseases in China, such as the coronary heart disease, arrhythmia, cerebral arteriosclerosis, cerebral embolism and brain vascular accident which are caused by insufficiency of cerebral blood supply.

Pharmacology

Pharmacological studies have shown that cyclovirobuxine has a positive inotropic effect on the heart that may predominantly be due to the inhibition of cardiomyocyte membrane Na+-K+-ATPase activity and promotion of myocardial extracellular Ca2+ influx and cardiomyocyte Ca2+ release. Moreover, cyclovirobuxine could markedly reduce myocardial oxygen consumption and increase coronary blood flow, suggesting that it has definite anti-myocardial ischemia effect. Experiments also showed that cyclovirobuxine could induce marked inhibition of myocardial ischemia infarction and enhancement of anoxia tolerance in mice .
Besides, cyclovirobuxine could have protective effect on the acute experimental cerebral ischemia in mice by bilateral ligation of common carotid arteries, prolong the life span of mice, increase blood flow and decrease the formation of thrombus during cerebral ischemia . In vitro experiments have also shown that cyclovirobuxine has neuroprotective effects on neurons and restrains PC12 cells from excitatory amino acid-induced injury .

Clinical Use

After decades of clinical observation, cyclovirobuxine has the therapeutic role of anti-myocardial ischemia and antiarrhythmia and protects against acute cerebral ischemia. In addition, cyclovirobuxine can cross the blood-brain barrier and improve brain microcirculation and oxygen supply to treat cerebral arteriosclerosis insufficiency.

References

Nakano, Terao, Tetrahedron Lett., 1035, 1045, (1964)
Brown, Kupchan, J. Amer. Chem. Soc., 86, 4414, 4424 (1964)
Nakano, Terao,J. Chem. Soc., 4512, 4537 (1965)
Nakano, Hasegawa, ibid, 6688 (1965)

Cyclovirobuxin D Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Cyclovirobuxin D manufacturers

Shanghai Standard Technology Co., Ltd.

Product: Cyclovirobuxine D 860-79-7
Price: US $0.00/mg
Min. Order: 5mg
Purity: ≥98%(HPLC)
Supply Ability: 10 g
Release date: 2019-12-24

Dideu Industries Group Limited

Product: Cyclovirobuxin D 860-79-7
Price: US $1.10/g
Min. Order: 1g
Purity: 99.9%
Supply Ability: 100 Tons min
Release date: 2021-08-06

Zhuozhou Wenxi import and Export Co., Ltd

Product: Cyclovirobuxin D 860-79-7
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-06-26

860-79-7, Cyclovirobuxin DRelated Search:

Pachymic acid ALLEOSIDE A Poricoic acid A(F) Carboxyatractyloside Terrestrosin D roburic acid Terrestrosin K Madecassoside Madecassic acid dipotassium dihydrogen 15alpha-hydroxy-2beta-[[2-O-isovaleryl-3,4-di-O-sulphonato-beta-D-glucopyranosyl]oxy]kaur-16-ene-18,19-dioate Evodiamine Tiapride N-cyclodecylmethylamine N,N''-DIMETHYL-1,12-DIAMINODODECANE CYCLOVIROBUXINE:9,19-CYCLOPREGNANE-3,20-DIAMINE,N,N'',4,4,14-PENTAMETHYL-, (3,5,20S)- 4-TERT-BUTYLCYCLOHEXYLAMINE, CIS Cyclovirobuxin D SPIRO[2.5]OCTANE

CYCLOVIROBUXINE

CYCLOVIROBUXINE D

9,19-CYCLOPREGNANE-3,20-DIAMINE,N,N',4,4,14-PENTAMETHYL-, (3,5,20S)-

Cyclovirobuxin D(Bebuxine,Cyclovirobuxine D, NSC 91722 )

Cyclovirobuxin D(Bebuxine)

9,19-Cyclopregnan-16-ol, 4,4,14-trimethyl-3,20-bis(methylamino)-, (3β,5α,16α,20S)-

Cyclovirobuxine D, >=98%

NSC91722

Cyclovirobuxine D, 98%, from Buxus sinica (Rehd. et Wils.) Cheng

9,19-cyclo-5-alpha,9-beta-pregnan-16-alpha-ol,4,4,14-trimethyl-3-beta,20-alpha

bebuxine

-bis(methylamino)-

cvb-d

cyclovirobuxind

cyclovirobuxinum D

cyclobuxine D

9,19-Cyclopregnan-16-ol,4,4,14-trimethyl-3, 20-

bis(methylamino)-,(3β,5α,16α,20S)-

(3b,5a,16a,20S)-4,4,14-Trimethyl-3,20-bis(methylamino)-9,19-cyclopregnan-16-ol

Cyclovirobuxine D (CVB-D)

Cyclovirobuxin D USP/EP/BP

Cyclovirobuxin D (CVB-D)

860-79-7

860-79-1

C26H46N2

C26H46N2O

chemical reagent

pharmaceutical intermediate

phytochemical

reference standards from Chinese medicinal herbs (TCM).

standardized herbal extract

Inhibitors

Alkaloids