Cremophor EL
Encyclopedia
Cremophor EL is the registered trademark of BASF
Corp. for its version of polyethoxylated castor oil. It is prepared by reacting 35 moles of ethylene oxide
with each mole of castor oil
. The resulting product is a mixture (CAS number
61791-12-6): the major component is the material in which the hydroxyl groups of the castor oil triglyceride
have ethoxylated
with ethylene oxide to form polyethylene glycol
ethers. Minor components are the polyethyelene glycol esters of ricinoleic acid
, polyethyelene glycols and polyethyelene glycol ethers of glycerol
. Cremophor EL is a synthetic, nonionic surfactant
. Its utility comes from its ability to stabilize emulsions of nonpolar materials in aqueous systems.
Cremophor EL is an excipient
or additive in drugs. Therapeutically, modern drugs are rarely given in a pure chemical state, so most active ingredients are combined with excipients or additives such as Cremophor EL
Note that these should not be confused with the normal side effects of Taxol. The allergic reaction is usually immediate and is similar to severe allergic reactions of many other substances that trigger allergic reactions.
BASF
BASF SE is the largest chemical company in the world and is headquartered in Germany. BASF originally stood for Badische Anilin- und Soda-Fabrik . Today, the four letters are a registered trademark and the company is listed on the Frankfurt Stock Exchange, London Stock Exchange, and Zurich Stock...
Corp. for its version of polyethoxylated castor oil. It is prepared by reacting 35 moles of ethylene oxide
Ethylene oxide
Ethylene oxide, also called oxirane, is the organic compound with the formula . It is a cyclic ether. This means that it is composed of two alkyl groups attached to an oxygen atom in a cyclic shape . This colorless flammable gas with a faintly sweet odor is the simplest epoxide, a three-membered...
with each mole of castor oil
Castor oil
Castor oil is a vegetable oil obtained from the castor bean . Castor oil is a colorless to very pale yellow liquid with mild or no odor or taste. Its boiling point is and its density is 961 kg/m3...
. The resulting product is a mixture (CAS number
CAS registry number
CAS Registry Numbersare unique numerical identifiers assigned by the "Chemical Abstracts Service" toevery chemical described in the...
61791-12-6): the major component is the material in which the hydroxyl groups of the castor oil triglyceride
Triglyceride
A triglyceride is an ester derived from glycerol and three fatty acids. There are many triglycerides, depending on the oil source, some are highly unsaturated, some less so....
have ethoxylated
Ethoxylation
Ethoxylation is an industrial process in which ethylene oxide is added to alcohols and phenols to give surfactants. The invention of the process is attributed to Schöller and Wittwer at I.G. Farben industrie.-Production:...
with ethylene oxide to form polyethylene glycol
Polyethylene glycol
Polyethylene glycol is a polyether compound with many applications from industrial manufacturing to medicine. It has also been known as polyethylene oxide or polyoxyethylene , depending on its molecular weight, and under the tradename Carbowax.-Available forms:PEG, PEO, or POE refers to an...
ethers. Minor components are the polyethyelene glycol esters of ricinoleic acid
Ricinoleic acid
Ricinoleic acid is an unsaturated omega-9 fatty acid that naturally occurs in mature Castor plant seeds or in sclerotium of ergot . About 90% of the fatty acid content in castor oil is the triglyceride formed from ricinoleic acid...
, polyethyelene glycols and polyethyelene glycol ethers of glycerol
Glycerol
Glycerol is a simple polyol compound. It is a colorless, odorless, viscous liquid that is widely used in pharmaceutical formulations. Glycerol has three hydroxyl groups that are responsible for its solubility in water and its hygroscopic nature. The glycerol backbone is central to all lipids...
. Cremophor EL is a synthetic, nonionic surfactant
Surfactant
Surfactants are compounds that lower the surface tension of a liquid, the interfacial tension between two liquids, or that between a liquid and a solid...
. Its utility comes from its ability to stabilize emulsions of nonpolar materials in aqueous systems.
Cremophor EL is an excipient
Excipient
An excipient is generally a pharmacologically inactive substance used as a carrier for the active ingredients of a medication. In many cases, an "active" substance may not be easily administered and absorbed by the human body; in such cases the substance in question may be dissolved into or...
or additive in drugs. Therapeutically, modern drugs are rarely given in a pure chemical state, so most active ingredients are combined with excipients or additives such as Cremophor EL
Uses
- MiconazoleMiconazoleMiconazole is an imidazole antifungal agent, developed by Janssen Pharmaceutica, commonly applied topically to the skin or to mucus membranes to cure fungal infections. It works by inhibiting the synthesis of ergosterol, a critical component of fungal cell membranes...
, anti-fungal - PaclitaxelPaclitaxelPaclitaxel is a mitotic inhibitor used in cancer chemotherapy. It was discovered in a U.S. National Cancer Institute program at the Research Triangle Institute in 1967 when Monroe E. Wall and Mansukh C. Wani isolated it from the bark of the Pacific yew tree, Taxus brevifolia and named it taxol...
, anti-cancer - Docetaxel, anti-cancer
- Aci-Jel (acetic acid / oxyquinoline / ricinoleic acid - vaginal)
- Sandimmune (cyclosporine injection, USP)
- Nelfinavir mesylate, HIVHIVHuman immunodeficiency virus is a lentivirus that causes acquired immunodeficiency syndrome , a condition in humans in which progressive failure of the immune system allows life-threatening opportunistic infections and cancers to thrive...
protease inhibitor - PropofolPropofolPropofol is a short-acting, intravenously administered hypnotic agent. Its uses include the induction and maintenance of general anesthesia, sedation for mechanically ventilated adults, and procedural sedation. Propofol is also commonly used in veterinary medicine...
, intravenous anaesthetic agent, originally presented in Cremophor for trials; now presented in a lipid emulsion - DiazepamDiazepamDiazepam , first marketed as Valium by Hoffmann-La Roche is a benzodiazepine drug. Diazepam is also marketed in Australia as Antenex. It is commonly used for treating anxiety, insomnia, seizures including status epilepticus, muscle spasms , restless legs syndrome, alcohol withdrawal,...
injection; superseded by lipid emulsion alternative (Diazemuls) - Vitamin KVitamin KVitamin K is a group of structurally similar, fat soluble vitamins that are needed for the posttranslational modification of certain proteins required for blood coagulation and in metabolic pathways in bone and other tissue. They are 2-methyl-1,4-naphthoquinone derivatives...
injection - IxabepiloneIxabepiloneIxabepilone is an epothilone B analog developed by Bristol-Myers Squibb as a cancer drug.It is produced by Sorangium cellulosum.-Pharmacology:It acts to stabilize microtubules....
, anti-cancer
Side effects
Allergic reactions to Taxol are most often allergic reactions to Cremophor EL; symptoms include tightness in the chest, shortness of breath, and similar reactions consistent with severe anaphylactic reactions. Although many anti-allergens including corticosteroids and Benadryl may be administered before chemotherapy, they are not always sufficient to prevent the severe reaction to Cremophor.Note that these should not be confused with the normal side effects of Taxol. The allergic reaction is usually immediate and is similar to severe allergic reactions of many other substances that trigger allergic reactions.