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Encyclopedia > Vincristine
Vincristine
Systematic (IUPAC) name
 ?
Identifiers
CAS number 57-22-7
ATC code L01CA02
PubChem 5978
DrugBank APRD00495
Chemical data
Formula C46H56N4O10 
Mol. mass 824.958 g/mol
Pharmacokinetic data
Bioavailability n/a
Protein binding ~75%
Metabolism Hepatic
Half life 19 to 155 hours
Excretion Mostly biliary, 10% in urine
Therapeutic considerations
Pregnancy cat.

D(AU) D(US) Image File history File links Vincristin. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules. ... The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... For other uses, see Carbon (disambiguation). ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, symbol, number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, period, block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... A drugs efficacy may be affected by the degree to which it binds to the proteins within blood plasma. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... The liver is an organ present in vertebrates and some other animals. ... It has been suggested that Effective half-life be merged into this article or section. ... The kidneys are important excretory organs in vertebrates. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ... For other uses, see Australia (disambiguation). ... Motto: (Out Of Many, One) (traditional) In God We Trust (1956 to date) Anthem: The Star-Spangled Banner Capital Washington D.C. Largest city New York City None at federal level (English de facto) Government Federal constitutional republic  - President George Walker Bush (R)  - Vice President Dick Cheney (R) Independence from...

Legal status

Prescription only The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ...

Routes Exclusively intravenous

Vincristine (Oncovin®), also known as leurocristine, is a vinca alkaloid from the Madagascar periwinkle (Catharanthus roseus, formerly Vinca rosea and hence its name). It is a mitotic inhibitor, and is used in cancer chemotherapy. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body. ... Intravenous therapy or IV therapy is the giving of liquid substances directly into a vein. ... Chemical structure of ephedrine, a phenethylamine alkaloid An alkaloid is, strictly speaking, a naturally occurring amine produced by a plant,[1] but amines produced by animals and fungi are also called alkaloids. ... Species Catharanthus coriaceus Catharanthus lanceus Catharanthus longifolius Catharanthus ovalis Catharanthus pusillus Catharanthus roseus Catharanthus scitulus Catharanthus trichophyllus Madagascar Periwinkle (Catharanthus) is a genus of eight species of herbaceous perennial plants, seven endemic to the island of Madagascar, the eighth, , from Sri Lanka. ... A mitotic inhibitor is a type of drug used mainly to treat cancer. ... Chemotherapy is the use of chemical substances to treat disease. ...

Contents

Mode of action

Tubulin is a structural protein which polymerises to form microtubules. The cell cytoskeleton and mitotic spindle, amongst other things, are made of microtubules. Vincristine binds to tubulin dimers, inhibiting assembly of microtubule structures. Disruption of the microtubules arrests mitosis in metaphase. The vinca alkaloids therefore affect all rapidly dividing cell types including cancer cells, but also intestinal epithelium and bone marrow. Tubulin is the protein which makes up microtubules. ... A polymer (from Greek: πολυ, polu, many; and μέρος, meros, part) is a substance composed of molecules with large molecular mass composed of repeating structural units, or monomers, connected by covalent chemical bonds. ... Microtubules are one of the components of the cytoskeleton. ... The eukaryotic cytoskeleton. ... Micrograph showing condensed chromosomes in blue and the mitotic spindle in green during prometaphase of mitosis The mitotic spindle (a. ... Mitosis is the way that in which a cell duplicates its chromosomes to generate two identical nuclei. ... An image of a newt lung cell stained with flourescent dyes during metaphase. ... This article is about the epithelium as it relates to animal anatomy. ... This article does not cite any references or sources. ...


Uses

Vincristine, injected intravenously only, is used in various types of chemotherapy regimens. Its main uses are in non-Hodgkin's lymphoma as part of the chemotherapy regimen CHOP, Hodgkin's lymphoma as part of MOPP or COPP, or the less popular Stanford V chemotherapy regimen, and in acute lymphoblastic leukemia. It is occasionally used as an immunosuppressant, e.g. in thrombotic thrombocytopenic purpura (TTP). An intravenous drip in a hospital Intravenous therapy or IV therapy is the administration of liquid substances directly into a vein. ... Chemotherapy regimens are often identified with acronyms, identifying the agents used in combination. ... This article is about lymphoma in humans. ... Look up chop in Wiktionary, the free dictionary. ... Hodgkins lymphoma, also known as Hodgkins disease, is a type of lymphoma first described by Thomas Hodgkin in 1832. ... Stanford V is a chemotherapy regimen designed for Hodgkins lymphoma that consists of the following: Mechlorethamine Doxorubicin Vinblastine Vincristine Bleomycin Etoposide Prednisone It is a newer method than MOPP or ABVD, the two previous most common treatments for Hodgkins lymphoma. ... Acute lymphoblastic leukemia (ALL), also known as acute lymphocytic leukemia, is a form of leukemia, characterised by the overproduction and continuous multiplication of malignant and immature white blood cells (also known as lymphoblasts) in the bone marrow. ... Thrombotic thrombocytopenic purpura (TTP or Moschcowitz disease) is a rare disorder of the blood coagulation system. ...


Warnings

Accidental injection of vinca alkaloids into the spinal canal (intrathecal administration) is highly dangerous, with a mortality rate approaching 100%. The medical literature documents cases of ascending paralysis due to massive encephalopathy and spinal nerve demyelination, accompanied by intractable pain, almost uniformly leading to death; a handful of survivors were left with devastating neurological damage with no hope of recovery. Rescue treatments consist of washout of the cerebrospinal fluid and administration of protective medications.[1] Intrathecal: Delivered into the spinal canal (intrathecal space surrounding the spinal cord), as in a spinal anaesthesia. ... This article does not cite any references or sources. ... Encephalopathy literally means disease of the brain. ... In neuroscience, myelin is an electrically insulating fatty layer that surrounds the axons of many neurons, especially those in the peripheral nervous system. ... Cerebrospinal fluid (CSF), Liquor cerebrospinalis, is a clear bodily fluid that occupies the subarachnoid space in the brain (the space between the skull and the cerebral cortex—more specifically, between the arachnoid and pia layers of the meninges). ...


Side effects

The main side-effects of vincristine are peripheral neuropathy, hyponatremia, and constipation. Peripheral neuropathy is the term for damage to nerves of the peripheral nervous system, which may be caused either by diseases of the nerve or from the side-effects of systemic illness. ... The electrolyte disturbance hyponatremia or hyponatraemia exists in humans when the sodium level in the plasma falls below 135 mmol/l. ... Constipation or irregularity, is a condition of the digestive system where a person (or animal) experiences hard feces that are difficult to egest; it may be extremely painful, and in severe cases (fecal impaction) lead to symptoms of bowel obstruction. ...


Peripheral neuropathy can be severe, hence reason to avoid, reduce, or stop the use of vincristine. One of the first symptoms of peripheral neuropathy is foot drop: a person with a family history of foot drop and/or Charcot-Marie-Tooth disease (CMT) may benefit from genetic testing for CMT before taking vincristine.[2] An editor has expressed a concern that the subject of the article does not satisfy the notability guideline or one of the following guidelines for inclusion on Wikipedia: Biographies, Books, Companies, Fiction, Music, Neologisms, Numbers, Web content, or several proposals for new guidelines. ... Charcot-Marie-Tooth disease (CMT), known also as Hereditary Motor and Sensory Neuropathy (HMSN) or Peroneal Muscular Atrophy, is a heterogeneous inherited disorder of nerves (neuropathy) that is characterized by loss of muscle tissue and touch sensation, predominantly in the feet and legs but also in the hands and arms...


History

Having been used as a folk remedy for centuries, studies in the 1950s revealed that C. roseus contained 70 alkaloids, many of which are biologically active. While initial studies for its use in diabetes mellitus were disappointing, the discovery that it caused myelosuppression (decreased activity of the bone marrow) led to its study in mice with leukemia, whose lifespan was prolonged by the use of a vinca preparation. Treatment of the ground plant with Skelly-B defatting agent and an acid benzene extract led to a fraction termed "fraction A". This fraction was further treated with aluminium oxide, chromatography, trichloromethane, benz-dichloromethane and separation by pH to yield vincristine.[3] Binomial name (L.) G.Don Catharanthus roseus (Madagascar Periwinkle) is a species of Catharanthus native and endemic to Madagascar. ... For the disease characterized by excretion of large amounts of very dilute urine, see diabetes insipidus. ... Bone marrow suppression is a serious side effect of chemotherapy and certain drugs affecting the immune system such as azathioprine. ... Leukemia or leukaemia (see spelling differences) is a cancer of the blood or bone marrow and is characterized by an abnormal proliferation (production by multiplication) of blood cells, usually white blood cells (leukocytes). ... Aluminium oxide is an amphoteric oxide of aluminium with the chemical formula Al2O3. ... For the Second Person album, see Chromatography (album). ... R-phrases , , , S-phrases , Flash point Non-flammable U.S. Permissible exposure limit (PEL) 50 ppm (240 mg/m3) (OSHA) Supplementary data page Structure and properties n, εr, etc. ...


Vincristine was approved by the United States Food and Drug Administration (FDA) in July 1963 as Oncovin. The drug was initially marketed by Eli Lilly and Company. “FDA” redirects here. ... Eli Lilly and Company (NYSE: LLY) is a global pharmaceutical company and one of the worlds largest corporations. ...


Suppliers

Three generic drug makers supply vincristine in the United States - APP, Mayne, and Sicor (Teva). Teva Pharmaceutical Industries Ltd. ...


See also

A white Rosy Periwinkle flower The Rosy Periwinkle (catharanthus roseus) is a species of the Madagascar periwinkle genus in the apocynaceae and Kareen whoo go kareen!!ŹăĞĞfamily and is native to Madagascar. ...

References

  1. ^ Qweider M, Gilsbach JM, Rohde V (2007). "Inadvertent intrathecal vincristine administration: a neurosurgical emergency. Case report". J Neurosurg Spine 6 (3): 280–3. PMID 17355029. 
  2. ^ Graf WD, Chance PF, Lensch MW, Eng LJ, Lipe HP, Bird TD (1996). "Severe vincristine neuropathy in Charcot-Marie-Tooth disease type 1A". Cancer 77 (7): 1356–62. DOI:10.1002/(SICI)1097-0142(19960401)77:7%3C1356::AID-CNCR20%3E3.0.CO;2-%23. PMID 8608515. 
  3. ^ Johnson IS, Armstrong JG, Gorman M, Burnett JP (1963). "The vinca alkaloids: a new class of oncolytic agents". Cancer Res 23: 1390-427. PMID 14070392. 

A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ...

External links

  • Vincristine chemotherapy
  • Vincristine and vinblastine
  • Description and Natural History of the Periwinkle
  • The Boger Route to (-)-Vindoline

  Results from FactBites:
 
Oncovin Online, Description, Chemistry, Ingredients - Vincristine Sulfate - RxList Monographs (316 words)
Vincristine Sulfate Injection is the salt of an alkaloid obtained from a common flowering herb, the periwinkle plant (Vinca rosea Linn).
Vincristine sulfate is a white to off-white powder.
Vincristine Sulfate Injection, USP is a sterile, preservative-free, single use only solution available for intravenous use in 2 mL (1 mg and 2 mg) vials.
Oncology Nursing Society. (5121 words)
Vincristine sulfate is the salt of an alkaloid obtained from a flowering herb, the Madagascar periwinkle plant (Catharanthus roseus, formerly classified as Vinca rosea Linn, which caused it to be called a vinca alkaloid) (Greuter et al., 1999).
Vincristine inhibits microtubule formation in the mitotic spindle, resulting in the arrest of dividing cells at the metaphase stage and, because of this action, sometimes is referred to as an antimicrotubule agent.
Dispensing vincristine in small-volume infusion bags or diluting the dose to at least 10 ml to help differentiate it from intrathecal drugs, for which such a large volume is not given, may help to reduce the potential for inadvertent intrathecal vincristine administration.
  More results at FactBites »

 
 

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