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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]23D + 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]24D + 10° (c 1.94, CHC13) and the O,N,N-triacetyl derivative, m.p. 246-8°C with [α]24D - 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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Cyclovirobuxin D Suppliers

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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
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
Shaanxi Dideu Medichem Co. Ltd
Product
Cyclovirobuxin D 860-79-7
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99.0%
Supply Ability
500 MT
Release date
2020-05-11

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