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Vincristin

Vincristine Struktur
57-22-7
CAS-Nr.
57-22-7
Bezeichnung:
Vincristin
Englisch Name:
Vincristine
Synonyma:
methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(1R,13S,15R,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0,12.0,1]nonadeca-4(12),5(10),6,8-tetraen-13-yl]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0;LCR;Leucid;Vincosid;Cristovin;VINCRISTINE;Leucristine;Pericristine;10MG/50MG/50G;(+)-Vincristine
CBNumber:
CB4375960
Summenformel:
C46H56N4O10
Molgewicht:
824.96
MOL-Datei:
57-22-7.mol

Vincristin Eigenschaften

Schmelzpunkt:
211-216 ºC
alpha 
D25 +17°; D25 +26.2° (ethylene chloride)
Siedepunkt:
761.92°C (rough estimate)
Dichte
1.1539 (rough estimate)
Brechungsindex
1.6000 (estimate)
storage temp. 
Store at -20°C, protect from light
L?slichkeit
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Aggregatzustand
Powder
pka
5.4(at 25℃)
Stabilit?t:
Stable, but may be heat sensitive. Incompatible with strong oxidizing agents.
CAS Datenbank
57-22-7
EPA chemische Informationen
Vincristine (57-22-7)

Sicherheit

RIDADR  1544
HazardClass  6.1(a)
PackingGroup  II
Giftige Stoffe Daten 57-22-7(Hazardous Substances Data)
Toxizit?t LD50 i.p. in mice: 5.2 mg/kg (Adamson)

Vincristin Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung

A complex dimeric alkaloid isolated from Vinca minor, this base has the structure given above based upon chemical and spectroscopic data. It resembles Vinblastine in its pharmacological action. Depending on the dosage, it causes either thrombocytosis with no effect upon the leucocytes, or thrombocytopenia accompanied by peucopenia in rats. Thrombocytosis persists even after prolonged treatment with drugs given in the correct dosage.

Chemische Eigenschaften

solid

Physikalische Eigenschaften

Appearance: needlelike crystals were produced when recrystallized by methanol. The other properties of vincristine are similar to vinblastine.

History

Vinblastine and vincristine were extracted from vinca, and researchers found that they are the main ingredient of vinca which have antitumor activity. This is an accidental harvest by hard work and inspiration during scientific research process. It was firstly reported as an important discovery by Annals of the New York Academy of Sciences, and one report was published by Robert Noble and Charles Thomas Beer . They demonstrated that vinblastine can cause severe leukopenia. In 1963, vincristine (trade name, Oncovin) developed by Eli Lilly was approved by the US FDA, it provided a good choice for tumor chemotherapy program and gradually became the essential tumor chemotherapy drugs.
At the early stages of the study, vinblastine and vincristine are directly extracted from the vinca, but the cost is high, and the extraction efficiency is low . Especially the specific chiral monomer compounds with biological activity are difficult to obtain. In the following years, the researchers used genetic engineering, biosynthesis, chemical synthesis, and other technical methods to explore and optimize the production process of vinblastine drugs. In particular, the rise of asymmetric synthesis provides a more economical choice for the synthesis of vinblastine compounds and increases productivity to more than 22% . At the same time, the pharmaceutical dosage forms were developed from the beginning as simple sulfate injection to liposomal preparations and nanoparticle preparations, which improve the efficacy, reduce adverse reactions, and play better antitumor effect.

Verwenden

Antineoplastic[Note—Graphic formula same as for Vinblastine Sulfate, except that R is CHO].

Indications

It was recorded in the Pharmacopoeia of the People’s Republic of China (2015), the British Pharmacopoeia (2017), the United States Pharmacopeia (40), the Japanese Pharmacopoeia (17th ed.), the European Pharmacopoeia (9th ed.), and The International Pharmacopoeia (5th ed.).
Vincristine sulfate injection is used to treat leukemia, lymphadenoma, non-small cell lung cancer, nephroblastoma, and neuroblastoma in clinical practice generally, but the effect of vinblastine is better than vincristine in Hodgkin lymphoma treatment.

Allgemeine Beschreibung

A white crystalline solid. Melting point 218°C. Used as an antineoplastic.

Health Hazard

Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Brandgefahr

Flash point data for Vincristine are not available, but Vincristine is probably combustible.

Pharmakologie

Vinblastine drugs have a strong inhibitory effect on monozygotic leukemia, breast cancer, liver cancer, ovarian cancer, head and neck cancer, testicular cancer, solid sarcoma, and malignant melanin in a variety of spontaneous or transplanted lymphocytic leukemias. Although the structure of vinblastine and vincristine is very similar, there are some differences in pharmacological effects, and there is no crossresistance .
The mechanism of vinblastine and vincristine is similar as cell cycle-specific antineoplastic agents. They all inhibit tubulin polymerization, interfere spindle microtubule formation, block the cell cycle in M phase, and then inhibit the proliferation of cancer cells . X-ray diffraction results showed that Vinblastine targets at the hydrophobic structure on tubulin, Vinblastine inserted into the trough as the wedge, blocking the polymerization of tubulin, making a spirochete structure of tubulin itself form, and loss of biological role . However, this antitumor effect can affect other rapid proliferation cells, and then small intestinal epithelial cells and bone marrow cells will be inhibited, which is one of the reasons of gastrointestinal side effects and bone marrow transplantation side effects. The effect of vincristine is better than vinblastine, and the dosage is lower, the probability and intensity of side effects are lower. Recently, it has been found that vinblastine and vincristine can also suppress growth of tumor cell by inhibiting the synthesis of RNA and protein.

Clinical Use

Vincristine is an important component of the curative combination chemotherapy for acute lymphoblastic leukemia, Hodgkin’s disease (the MOPP regimen), and non-Hodgkin’s lymphomas. It is also used in several regimens for pediatric solid tumors, including Wilms’ tumor, Ewing’s sarcoma, rhabdomyosarcoma, and neuroblastoma; in adult tumors of the breast, lung, and cervix; and in sarcomas. Its relative lack of myelosuppression makes it more attractive than vinblastine for use in combination with myelotoxic drugs.Vinblastine is especially useful in testicular carcinomas and is also active in Hodgkin’s disease, other types of lymphomas, breast cancer, and renal cell carcinoma.

Nebenwirkungen

All vinca alkaloids are severe vesicants that can induce necrosis, cellulitis, and/or thrombophlebitis. Proper needle placement before administration should be assured to eliminate the risk of extravasation. Unlike the tissue damage caused by the vesicant action of nitrogen mustards and antibiotic antineoplastics, cold exacerbates tissue destruction. If extravasation occurs, apply heat for 1 hour fours time a day for 3 to 5 days, coupled with local hyaluronidase injections. Vinca alkaloids are all Category D teratogens and are fatal if administered by the intrathecal route.

Einzelnachweise

Mokry et al., Experientia, 18, 564 (1962) Pharmacology: Chandorkar.,lnd. J. Physiol. Pharmacol., 17, 105 (1973)

Vincristin Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Vincristin Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

Global( 200)Lieferanten
Firmenname Telefon E-Mail Land Produktkatalog Edge Rate
Hebei Chuanghai Biotechnology Co,.LTD
+86-13131129325
sales1@chuanghaibio.com China 5889 58
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512
info@tianfuchem.com China 21634 55
Nanjing Finetech Chemical Co., Ltd.
025-85710122 17714198479
sales@fine-chemtech.com CHINA 885 55
Shanghai Zheyan Biotech Co., Ltd.
18017610038
zheyansh@163.com CHINA 3619 58
career henan chemical co
+86-0371-86658258 +8613203830695
sales@coreychem.com China 29880 58
Chengdu Biopurify Phytochemicals Ltd.
+8618080483897
sales@biopurify.com China 3772 58
Nanjing Dolon Biotechnology Co.,Ltd.
18905173768
sales@dolonchem.com CHINA 2972 58
Hubei xin bonus chemical co. LTD
86-13657291602
linda@hubeijusheng.com CHINA 22963 58
Chongqing Chemdad Co., Ltd
+86-023-6139-8061 +86-86-13650506873
sales@chemdad.com China 39894 58
CONIER CHEM AND PHARMA LIMITED
+8618523575427
sales@conier.com China 49374 58

57-22-7(Vincristin)Verwandte Suche:


  • Vincaleukoblastine, 22-oxo-
  • LCR
  • Leucristine
  • Leurocristine (7CI, 8CI)
  • Vincaleukoblastine, 22-oxo- (9CI)
  • VINCRISTINE
  • Vincristine (base and/or unspecified salts)
  • Vincristine ,VCR, NSC-67574, Oncovin
  • (2'β)-22-Oxovincaleukoblastine
  • 10MG/50MG/50G
  • Cristovin
  • Leucid
  • Pericristine
  • Vincosid
  • 99% purity Raw Vincristine powder for chemotherapy use
  • Vincristine (free base)
  • Vincristine USP/EP/BP
  • 57-22-7 Vincristine
  • methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(1R,13S,15R,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0,12.0,1]nonadeca-4(12),5(10),6,8-tetraen-13-yl]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0
  • (+)-Vincristine
  • 57-22-7
  • C46H56N4O10
  • chemical reagent
  • pharmaceutical intermediate
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract
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