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WO2003030884A2 - Use of solasonine for the treatment of skin tumors - Google Patents

Use of solasonine for the treatment of skin tumors Download PDF

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Publication number
WO2003030884A2
WO2003030884A2 PCT/EP2002/011317 EP0211317W WO03030884A2 WO 2003030884 A2 WO2003030884 A2 WO 2003030884A2 EP 0211317 W EP0211317 W EP 0211317W WO 03030884 A2 WO03030884 A2 WO 03030884A2
Authority
WO
WIPO (PCT)
Prior art keywords
use
solasonine
use according
skin tumors
concentration
Prior art date
Application number
PCT/EP2002/011317
Other languages
French (fr)
Other versions
WO2003030884A3 (en
Inventor
Chris Lawson
Original Assignee
Glycomed Sciences Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to EP01124675.8 priority Critical
Priority to EP01124675 priority
Application filed by Glycomed Sciences Limited filed Critical Glycomed Sciences Limited
Publication of WO2003030884A2 publication Critical patent/WO2003030884A2/en
Publication of WO2003030884A3 publication Critical patent/WO2003030884A3/en

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/70Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom

Abstract

The present invention relates to the use of the triglycoside (22R, 25R)-spiro-5-en3β-yl-α-L-rhamnopyranosyl-(1→2gal)-O-p-D-glucopyranosyl-(1→3gal)-β-D-galactopyranose for the preparation of pharmaceutical compositions for treating skin tumors.

Description

USE OF SOLASONINE

The present invention relates to the use of the triglycoside solasonine (22R, 25R)- spiro-5-en-3β-yl-α-L-rhamnopyranosyl-(1→2gal)-0-p-D-glucopyranosyl-(1->3gal)-β- D-galactopyranose for the preparation of pharmaceutical compositions for treating skin tumors.

In particular the pharmaceutical compositions according to the invention are useful for the treatment of human skin tumors, like premalignant skin lesions, malignant skin lesions.malignant skin tumors like basal cell carcinomas (BCCs), squamous cell carcinomas (SCCs), Karposi's sarcoma and benign skin tumors like actinic keratosis, keratoses and keratoacanthomas.

It is well established that certain naturally occurring conjugate solasodine glycosides have potent antineoplastic properties (WO 91/10743, Cham, B. E. and Meares H.M.(1987) Cancer Letters, 36, 111-118, Cham et al. (1991) Cancer Letters, 59, 55- 58, Cham B.E. and Daunter B. (1990) Cancer Letters, 55, 221-225).

This findings however relate to the use of a crude extract of the fruits of S. sodomaeum, commonly referred to as BEC (Cham, B.E. and Wilson, L.(1987) Planta

Medica, 53, 9-62).

BEC is incorporated in small concentrations into an over the counter (OTC) topical formulation (Curaderm®), which is used to treat skin lesions such as sunspots and keratosis.

No investigations have been carried out regarding the nature of the pharmaceutical active component(s). The assumption being that all solasodine glycoside components in combination exhibit the antineoplastic effect. Contrary to this, in accordance with the present invention it was found that the triglycoside solasonine exhibits a potent antineoplastic effect on various human skin conditions.

Detailed description of the invention

The present invention is directed to the use of the solasodine triglycoside solasonine for the preparation of pharmaceutical compositions for treating skin tumors. Thus it has been unexpectedly found that not only the complex extract of S. sodomaeum, commonly referred to as BEC (Drug Future, 1988, rd 138, pages 714- 716) a crude mixture of solamargine (33%), solasonine (33 %) and of an undefined fraction of di-and monoglycosides (34 %), but the individual purified S. sodomaeum glycoside solasonine (formula 1 )

Figure imgf000003_0001

is highly effective in treating skin tumors, in particular malignant tumors such as basal cell carcinomas (BCCs), squamous cell carcinomas (SCCs) and Karposi's sarcoma and benign tumors.like actinic keratosis, keratoses and keratoacanthomas even in the absence of the other solasodine glycoside components. Since it is well recognized in the art that the effect of plant extract is very often caused by the often complex interactions and potentating effects of the individual compounds present in crude plant extracts comprising more than 1 potentially active component this finding was very unexpected.

Thus the invention provides a novel, more stable, fully characterized, effective pharmaceutical composition for treating skin tumors, benign as well as malignant tumors.

The compositions of the invention may be administered e. g. orally, parenterally, topically or via an implanted reservoir or therapeutic system, whereby parenteral or topical administration are preferred. Particularly preferred is the topical administration.

Parenterally as used herein includes subcutanous, intravenous, intramuscular, intra- articular, intrasynovial, intrastemal, intrathecal, intrahepatical, intralesional and intracranial injections or infusions. Sterile injectable compositions according to the invention may be aqueous or oleagious formulation.

These formulations may be formulated according to techniques well known in the art using suitable solvents, diluents or vehicles such as water for injection, Ringer's solution and isotonic sodium chloride solution. Optionally commonly adjuvants may also be used.

The pharmaceutical compositon of the invention may also be orally administered in any orally acceptable dosage form, including capsules, tablets, granules, suspensions or solutions, which are also formulated according techniques well known in the art.

For the particularly preferred topical administration route, the formulation may be in suitable formulations such as cremes, gels, ointments, liniments, lotions, emulsions and patches using suitable carriers and adjuvants well known in the art.

The amount of incorporated solasonine in the composition will vary depending on the particular mode of administration as well as the nature of the condition to be treated, as well as the age, weight and condition of the patient.

Preferably the compositions, especially the compositions for topical administration should be formulated to comprise between 0.001 and 10% (w/w), 0.001 and 4% (w/w)) preferably between 0.001 and 1% (w/w) and most preferably between 0.001% and 0.5% (w/w) of the formulation.

However, it should also be understood that a specific dosage and treatment regimen will depended upon variety of factors such as e. g. age, bodyweight, general state of health, sex of the patient, severity of disease and concommitant medication.

Claims

Claims
1. Use of solasonine for the preparation of a pharmaceutical composition for treating skin tumors.
2. Use according to claim 2, wherein the skin tumor is selected from premalignant skin lesions, malignant skin lesions, basal cell carcinomas (BCCs), squamous cell carcinomas (SCCs), Karposi's sarcoma, benign skin tumors, actinic keratosis, keratoses and keratoacanthomas.
3. Use according to claim 1or 2, wherein the composition is formulated for topical use.
4. Use according to any one of claims 1-3, wherein the concentration in the compostion is between 0.001% and 10% (w/w).
5. Use according to any one of claims 1-4, wherein the concentration is between 0.001% and 4% (w/w).
6. Use according to any one of claims 1-5, wherein the concentration is between 0.001% and 1% (w/w).
7. Use according to any one of claims 1-6, wherein the concentration is between 0.001% and 0.5%.
PCT/EP2002/011317 2001-10-09 2002-10-09 Use of solasonine for the treatment of skin tumors WO2003030884A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP01124675.8 2001-10-09
EP01124675 2001-10-09

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
AU2002350513A AU2002350513A1 (en) 2001-10-09 2002-10-09 Use of solasonine for the treatment of skin tumors

Publications (2)

Publication Number Publication Date
WO2003030884A2 true WO2003030884A2 (en) 2003-04-17
WO2003030884A3 WO2003030884A3 (en) 2003-09-04

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2002/011317 WO2003030884A2 (en) 2001-10-09 2002-10-09 Use of solasonine for the treatment of skin tumors

Country Status (2)

Country Link
AU (1) AU2002350513A1 (en)
WO (1) WO2003030884A2 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005005449A2 (en) * 2003-07-08 2005-01-20 Glycomed Sciences Limited Steroid modified solatrioses
US8614196B2 (en) 2011-05-12 2013-12-24 G & E Herbal Biotechnology Co., Ltd. Treatment and/or prevention of inflammation and cutaneous photodamage and photoprotection of the skin with a water-soluble extract from plant of Solanum genus

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0020029A1 (en) * 1979-05-02 1980-12-10 Aruba (Qld.) Pty. Ltd. Pharmaceutical compositions comprising steroid alkaloids
WO1991010743A1 (en) * 1990-01-18 1991-07-25 Cura Nominees Pty Ltd Glycoalkaloids
WO2000061153A1 (en) * 1999-04-09 2000-10-19 Cura Nominees Pty. Ltd. Medicinal compositions and their method of preparation

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0020029A1 (en) * 1979-05-02 1980-12-10 Aruba (Qld.) Pty. Ltd. Pharmaceutical compositions comprising steroid alkaloids
WO1991010743A1 (en) * 1990-01-18 1991-07-25 Cura Nominees Pty Ltd Glycoalkaloids
WO2000061153A1 (en) * 1999-04-09 2000-10-19 Cura Nominees Pty. Ltd. Medicinal compositions and their method of preparation

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CHAM B E ET AL: "TOPICAL TREATMENT OF MALIGNANT AND PREMALIGNANT SKIN LESIONS BY VERY LOW CONCENTRATIONS OF A STANDARD MIXTURE (BEC) OF SOLASODINE GLYCOSIDES" CANCER LETTERS, NEW YORK, NY, US, vol. 59, 1991, pages 183-192, XP001077064 ISSN: 0304-3835 *
CHAM B E: "SOLASODINE GLYCOSIDES AS ANTI-CANCER AGENTS: PRE-CLINICAL AND CLINICAL STUDIES" ASIA PACIFIC JOURNAL OF PHARMACOLOGY, SINGAPORE UNIVERSITY PRESS, SG, vol. 9, 1994, pages 113-118, XP002950616 ISSN: 0217-9687 *
CHEM B E ET AL: "GLYCOALKALOIDS FROM SOLANUM SODOMAEUM ARE EFFECTIVE IN THE TREATMENT OF SKIN CANCERS IN MAN" CANCER LETTERS, NEW YORK, NY, US, vol. 36, 1987, pages 111-118, XP002950615 ISSN: 0304-3835 cited in the application *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005005449A2 (en) * 2003-07-08 2005-01-20 Glycomed Sciences Limited Steroid modified solatrioses
WO2005005449A3 (en) * 2003-07-08 2005-04-21 Glycomed Sciences Ltd Steroid modified solatrioses
US8614196B2 (en) 2011-05-12 2013-12-24 G & E Herbal Biotechnology Co., Ltd. Treatment and/or prevention of inflammation and cutaneous photodamage and photoprotection of the skin with a water-soluble extract from plant of Solanum genus

Also Published As

Publication number Publication date
AU2002350513A1 (en) 2003-04-22
WO2003030884A3 (en) 2003-09-04

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