JPH0212931B2 - - Google Patents

Description

[Detailed description of the invention]

INDUSTRIAL APPLICATION FIELD The present invention relates to an anticancer agent containing an ethylene oxide adduct of p-menthanylphenol as an active ingredient. Prior Art Ethylene oxide adducts of p-menthanylphenol are known to have surface-active properties, and in particular, ethylene oxide adducts of p-menthanylphenol (average number of moles added: 8.8)
Known by its generic name Menfegol, it has been widely used as a vaginal spermicide. However, other medicinal uses of ethylene oxide adducts of p-menthanylphenol are not yet known. Purpose of the Invention The purpose of the present invention is to provide a novel and useful anticancer agent containing an ethylene oxide adduct of p-menthanylphenol (p-menthanyl phenyl polyoxyethylene ether; hereinafter referred to as the active substance) as an active ingredient. There is a particular thing. Structure of the Invention The active substance of the present invention is produced by using, for example, turpentine oil as a starting material, obtaining p-menthanylphenol via p-mentadiene and p-menthene, and reacting this with ethylene oxide in the presence of an alkali catalyst. It can be manufactured by
In this case, by appropriately adjusting the amount of ethylene oxide used, it is possible to obtain products with different average numbers of added moles of ethylene oxide (K.FURUSE; Parfumerie Cosmetic Savon). Coseme´tique
Savons), 10 , 342 (1967)]. The anticancer activity of the active substance of the present invention was confirmed by the following animal experiment. Test compound A: Ethylene oxide (6.0) adduct of p-menthanylphenol B: Ethylene oxide (8.0) adduct of p-menthanylphenol C: Ethylene oxide (8.8) adduct of p-menthanylphenol D: p - Ethylene oxide (9.0) adduct of menthanylphenol E: Ethylene oxide (11.2) adduct of p-menthanylphenol The value in brackets indicates the average number of moles of ethylene oxide added. ICR-SP female rats consisting of 5 rats per group (body weight
19.5-28.5 g) of Sarcoma 180 (obtained from the National Cancer Center) or 0.2 ml of saline containing 1 x ¹⁰⁶ each of Ehrlitsu ascites carcinoma cells.
Each was injected intraperitoneally. Test compound solutions were prepared such that each dose was contained in 0.2 ml of saline. 0.2 ml of the test compound solution was intraperitoneally administered once a day for 7 days, the first time being 24 hours after the cancer cell inoculation. Rats in the control group were similarly administered 0.2 ml of physiological saline instead of the test compound solution for 7 days. Record the number of days each mouse survived;
The life extension rate (T/C%) was calculated according to the following formula. T/C%=average survival days of test group/average survival days of control group×100 The results obtained are shown in Tables 1 and 2 below.

【table】

[Table] From the results shown in Tables 1 and 2, it is clear that the ethylene oxide adduct of p-menthanylphenol according to the present invention has excellent anticancer activity. The acute toxicity of the active substances of the invention is shown in mice as _an example of the ethylene oxide (8.8) adduct of p-menthanylphenol.
mg/Kg (intraperitoneal) and 8000 mg/Kg (oral). The active substances of the invention are usually administered by parenteral routes, with subcutaneous, intramuscular or intravenous administration being particularly preferred. Intravenous infusion is also a preferred method of administration.
Injectable formulations may be manufactured by conventional techniques in the pharmaceutical field. For example, it may be provided in the form of a unit dose ampoule or a multi-dose vial. The formulation may contain conventional excipients such as stabilizers, osmotic agents, etc. The dosage of the active agent of the invention will vary depending on various factors such as the patient's condition, the particular compound selected, the route of administration, or the number of doses per day, but will generally be within the range of 1 to 500 mg per day, and preferably
20-200mg. Examples regarding the formulations of the present invention are shown below. Example 1 Injection (Ampoule) Ethylene oxide (8.8) adduct of p-menthanylphenol 2.0g Glucose (pharmacopoeia) 50.0g Distilled water for injection (pharmacopoeia) Appropriate amount Total volume 1000ml Production method: P-menthanylphenol 2.0 g of ethylene oxide (8.8) adduct was dissolved in 500 ml of hot distilled water with stirring, and then 50.0 g of glucose was added thereto, stirred, and dissolved. After the resulting solution was cooled to room temperature, the total volume was adjusted to 1000 ml with distilled water and sterilized. The obtained solution was filled into ampoules (2 ml each) and sterilized. The resulting ampoule contains active substance 4
Contains mg. Example 2 Injection (vial) Ethylene oxide (8.8) adduct of p-menthanylphenol 40g Glucose (pharmacopoeia) 500g Distilled water for injection (pharmacopoeia) Appropriate amount Total amount 10 Production method: Same as Example 1, A sterile aqueous solution of the active substance was prepared, filled into 500 ml vials and sterilized.

Claims (1)

[Scope of Claims] 1. An anticancer agent containing an ethylene oxide adduct of p-menthanylphenol as an active ingredient. 2. An anticancer agent according to claim 1 in the form of an injection.