AU2002367451A1 - Composition based on ethyl ester of linoleic acid and triethyl ester of citric acid for topical use in the treatment of seborrhoea and acne - Google Patents
Composition based on ethyl ester of linoleic acid and triethyl ester of citric acid for topical use in the treatment of seborrhoea and acneInfo
- Publication number
- AU2002367451A1 AU2002367451A1 AU2002367451A AU2002367451A AU2002367451A1 AU 2002367451 A1 AU2002367451 A1 AU 2002367451A1 AU 2002367451 A AU2002367451 A AU 2002367451A AU 2002367451 A AU2002367451 A AU 2002367451A AU 2002367451 A1 AU2002367451 A1 AU 2002367451A1
- Authority
- AU
- Australia
- Prior art keywords
- acid
- acne
- composition
- triethylcitrate
- weight
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
Description
"COMPOSITION BASED ON ETYLLINOLEATE AND TRTETHYLCITRATE FOR THE TREATMENT OF SEBOR HEA AND ACNE"
FIELD OF INVENTION
This invention concerns a new product for pharmaceutical and/or cosmetic use in the treatment of acne, acne rosacea and seborrhoea. PRIOR ART
A very large number of people suffer from acne which has a pathological cutaneous picture characterised by a morphological and functional alteration of the pilosebaceous organ with appearance of whiteheads (closed comedo), blackheads
(open comedo), papules and in the more serious forms, pustules, nodules, cysts and scars.
Acne affects about 80% of the population between the ages of 12 and 30 and, above all in women, may persist even to a more advanced age.
The etiopathogenesis of acne is in close relationship with:
• an increase in the production of sebum (seborrhoea) • an anomalous keratinisation of the pilosebaceous duct
• a bacterial colonization
Seborrhoea is a consequence of an exasperated reaction of the sebaceous gland to the action of androgen hormones, to be more exact the action of dihydrotestosterone caused by the reduction of testosterone caused by the enzyme 5 - α reductase.
Anomalous keratinisation of the pilosebaceous duct is the direct cause of formation of a keratic plug, cause of formation of microcomedo and later of acne lesions. Due to the increase in production of sebum, and prior to the formation of microcomedo, there is an anomalous growth of cutaneous saprophyte bacteria, such as Propionilbacterium Acnes. The latter, due to the release of lytic enzymes (protease and lipase), capable of destroying the protein structure of the sebaceous gland and to hydrolyse the triglycerides normally contained in the sebum (which besides is produced in larger quantities due to the action of dihydrotestosterone) releasing fatty acids and glycerol. The fatty acids released in this way are characterised by their
comedogenic action and are therefore oxidised, forming chemical compounds favouring inflammation.
The therapy used up to now in the pharmaceutical treatment of acne or cosmetic treatment of the seborreha has been mainly based on the action of keratolytic and/or anti-biotic substances, or other active principles, for example, retinoids
Among these substances may be mentioned for example salycilic acid, tartaric acid, glycolic acid, resorcin, phenol etc., all capable of carrying out their action aimed at clinically improving the acneic picture through a keratolytic type mechanism. Among the antibiotic substances used up until now to keep the increase of
Propionilbacterium Acnes under control worthy of mention are clindamycine, minocycline, eritromycin, metronidazole, etc.
Other active principles used in treating acne are trans-retinoic acid, found to be efficacious, but characterised by being highly toxic, photo-toxic and teratogenic. OBJECT AND SUMMARY OF THE INVENTION
The object of the invention is to provide a new product characterised by being highly efficacious with excellent cutaneous tolerability, in particular in the treatment of seborrhoea, acne and acne rosacea.
The object is achieved, according to the invention, with a composition, which is characterised by the fact that it contains as an active ingredient a mixture including the ethyl ester of linoleic acid (ethyllinoleate) and triethylester of citric acid (triethylcitrate).
This composition results as being able, among other things, to inhibit the activity of specific enzymes, such as for example, 5-alpha reductase, lipase and esterase, enabling a control of the seborrhoea and in general the evolution of the acneic and rosacea picture. DETAILED DESCRIPTION OF THE INVENTION
According to this invention, ethyllinoleate and triethylcitrate can be contained in a composition each in a quantity in weight from between 0.1 to 99.9%, preferably in equal quantities from between 1.00 and 40% each, based on the final weight of the composition.
Furthermore, the composition based on ethyllinoleate and triethylcitrate can also contain various active ingredients, which for descriptive simplicity will be defined as synergists.
The synergists can be chosen from between acetic acid, lactic acid, salicylic acid, tartaric acid, glycolic acid, clindamycin, eritromycin, metronidazole, amoxycillin, triclosan, capryloyl glcine, azelaic acid, zinc hydroxide, zinc chloride, trans-retinoic acid, resorcinol, hyaluronic acid, gentamicin, meclocycline, phenol, ascorbic acid, tocopherol, lipoic acid, phosphatidylcholine, phosphatidylserine, chlorhexidine, irgasan, adapalene, phospholipids in general, in all the dextrorotary, levorotary forms, recemic mixtures, cis forms, trans forms and relative salts, esters and amides and formulated together with particular additives and excipients for external use.
These synergists may be present in the composition, individually or combined, in two or more, together with ethyllinoleate and triethylcitrate. These synergists may be contained in variable weight quantities from between
0.001 to 70%o, preferably from 0.5 to 15% based on the final formulation when the proportions of ethyllinoleate and triethylcitrate are each from between 0.5 to 90.5% in weight.
The clinical efficacy and safety of use are the consequence of an original mechanism of action characterised by the fact that both ethyllinoleate and triethylcitrate, which in themselves behave as inert substances, are transformed into active principles once in contact with the skin. This transformation, from an inert substance into an active principle is a result of the hydrolysis, which takes place through specific cutaneous enzymes or bacteria (lipase and esterase) capable of releasing ethyl alcohol and respectively linolenic acid, diethyl citrate then monoethyl citrate and finally citric acid.
The action mechanism of the composition of the invention can be described more in detail as follows.
Ethyllinoleate and triethylcitrate synergically are able to reduce seborrhoea and hyper keratinisation of the pilosebaceous duct; this action is achieved through the release of the respective acid forms, through hydrolysis of the esters by the action of the lipase bacteria.
In this invention it has been proven that hydrolysis of ethyllinoleate and triethylcitrate carried out by lipase bacteria is to be preferred to hydrolysis of the triglycerides (lipid component of sebum) carried out by the same lipase bacteria, consequently avoiding an irritative condition due to the release of fatty acids achieved through hydrolysis of the triglycerides.
In relation to hyper keratinisation of the pilosebaceous duct, the combined action of ethyllinoleate and triethylcitrate is innovative in that the former prevents hyper-keratinisation whereas the latter cures it, behaving as a keratolytic. This combined action results in higher efficacy compared with the effect of the two components taken individually.
In relation to seborrhoea the combined action of ethyllinoleate and triethylcitrate is innovative in that it results in a decrease in the sebum levels achieved by inhibiting the 5 -alpha reductase enzyme, an enzyme which as stated above is the cause of the reduction of testosterone to dihydrotestosterone whose action is capable of increasing the production of sebum. Once ethyllinoleate is hydrolysed into linoleic acid, it is able to inhibit the activity of 5-alpha reductase by a direct mechanism, whereas triethylcitrate, once hydrolysed into citric acid, acts in an indirect way, creating an environment where the activity of the aforementioned enzyme is obstructed. In other words, lipase bacteria recognise the ethyllinoleate and triethylcitrate mixture as the preferential substratum rather than the triglycerides of the sebum and so do not interfere with the structure of these triglycerides, thus reducing the inflammatory pathologies of seborrhoea and acne. EFFECTS OF THE INVENTION IN RELATION TO TESTS RESERVED ON SAMPLES.
Based on the present invention, tests were carried out to evaluate experimentally the action of two products, a lotion and a cream, for the treatment of acne through a clinical test using a sebumetric measuring device. Aim The test is able to evaluate if the products being tested are a valid help in the treatment against acne and if they are able to mitigate reddening due to the presence of acne focus.
Test specimen
Five female volunteers from between 15 and 28 years of age with greasy skin and suffering from acne. Preparation of samples The samples must be applied, on the basis of their use characteristics, as they are. Method of application of samples
The samples must be applied uniformly on specific parts of the face, according to the indications given on the description card handed to the volunteer. The lotion on the right side of the face; the cream on the left side of the face.
Carrying out the test
After finding the volunteers for the test, the following instrumental evaluations are carried out: basic sebum measurement using an authorized sebumetric device in compliance with EEC regulations (SKIN LAB®) Basic hydration using an authorized instrument in compliance with EEC regulations (SKXN LAB®) Basic TEWL using an authorized instrument in compliance with EEC regulations (Tewameter®) - only on the left side of the face > Acquisition of micro photographs using a video camera with polarised light -
VΓDEOCAP - with 20x enlargements and, when possible, 200x. The micro images are necessary to visualise in depth the slight blemishes due to acne and to highlight any improvements during the treatment under examination. Acquisition of macro photographs with Mini DV. The photographs are useful in defining the general start situation and to document any macroscopic improvements during the use of the products.
Furthermore the volunteers are supplied with a card on which to register daily observations about the cosmetic agreeable nature of the products and their performance. Each volunteer is given a card describing how she must apply the various products being tested. To facilitate the task, the first application is carried out on the premises.
The following controls are carried out after seven days (t7), fourteen days (tl4), twenty one days (t21) and twenty eight days (t28) of treatment with a lotion and a cream.
Following the above experiment, the difference between the sebumetric, keratic and TEWL values measured before and after the application of the products using the polarised light video camera and with the Mini DV the variations of the furuncles and acne pustules was evaluated.
The sebumetric, keratic and TEWL values are registered, elaborated and graphically presented together with the results in the following tables.
TABLES AND GRAPHIC REPRESENTATION OF THE RESULTS Sebometric values after prolonged use
LOTION
% Decrease in sebum on the skin
Hydration indexes after prolonged use
Sebometric values after prolonged use
Hydration indexes after prolonged use
TEWL values after prolonged use
EXAMPLES of FORMULATION
Here following are some examples of formulations according to the present invention.
Preparation 01 - oleolita
N° Description % w/w
01 Ethyllinoleate 20.00
02 Triethylcitrate 80.00 Method of preparation: mix 01 in 02
Preparation 02 - alcoholic solution
N° Description %w/w
01 Ethyllinoleate 20.00 02 triethylcitrate 20.00
03 salicylic acid 2.00
04 ethyl acid 58.00 Method of preparation: dissolve 03 in 04; to the solution mix 01 + 02
Preparation 03 - emulsion
N ° Description %w/w PHASE A
01 Ethyllinoleate 5.00
02 triethylcitrate 5.00 03 Ascorbil palmitate 1.50
04 Ppg - 15 stearyl ether 10.00
05 Capryloyl glycine 4.00
06 Steareth -2 3.00
07 Steareth - 21 2.00 PHASE B
08 Preservatives as req.
09 Glycerol 3.00
10 Water as req.
Method of preparation: Phase A, mix 01 + 02 + 03 + 04 + 05 + 06 + 07 and heat to 75°C; Phase B, mix 08 + 09 + 10 and heat the pre-mix to + 75%C, then add under agitation the Phase B to Phase A. Cool to room temperature always agitating.
Preparation 04 - Alcoholic solution
N° Description %w/w
01 Ethyllinoleate 20.00
02 Triethylcitrate 20.00
03 Erythromycin 10.00 04 ethyl acid 50.00
Method of preparation: dissolve 03 in 04, mix 01 + 02 in the solution
Preparation 05 - Alcoholic solution
N° Description %wΛv 01 Trans-retinoic 0.025
02 ethyllinoleate 5.00
03 triethylcitrate 20.00
04 ethylic acid as req. Method of preparation: dissolve 01 + 02 + 03 + in 04
Preparation 06 - Alcoholic solution
N° Description %wΛv
01 clindamycin 1.00
02 ethyllinoleate 5.00 03 triethylcitrate 20.00
04 ethyl acid as.req.
Method of preparation: mix 02 + 03 + 04 then dissolve 01 in it.
It has therefore been proved that the action of ethyllinoleate and triethylcitrate, described in the treatment of acne, greasy skin and seborrhoea, in consideration of the particular biological, pharmacological, physiological and biochemical action mechanism, has been found to be wider and is addressed to the treatment of several other cutaneous pathologies such as for example atopic
dermatitis, dermatitis seborrheica, exfoliative dermatitis, stasis dermatitis, neurodermatitis, acne, acne rosacea, alopecia areata, scarring alopecia, female alopecia, anagen effluviam, Hippocratic alopecia, psoriasis, Lichen, ichthyosis, xerodermia, keratosis pilaris, decubital ulcer, trophic ulcer, torpid sores, angioma nevus or vascular bundle, hemangioma, granuloma telangiectaticum, keratosis seborrhoea, etc.
The use of ethyllinoleate and triethylcitrate, also combined with opportune synergists, due to its particular action mechanism on the skin is innovative even as regards to its cosmetic use, such as: anti-aging composition aimed at improving the aesthetic conditions of the skin and to prevent signs of cutaneous aging; anti -wrinkle; moisturiser; the treatment of cutaneous hyper-pigmentation; cosmetic treatment of seborrhoea with tendency to develop into acne.
Claims (8)
1. Composition for topical use for treating and improving the aesthetic conditions of the skin comprising, as an active ingredient, a mixture of ethyllinoleate and triethylcitrate.
2. Composition for topical use according to claim 1, characterised in that the ethyllinoleate is contained in a quantity from 0.1 to 99% weight/weight and the triethylcitrate in a quantity from 99% to 0.1 % weight / weight.
3. Composition for topical use according to claims 1 and 2, which contains in addition active ingredients, used singularly or in combination, such as acetic acid, lactic acid, salicylic acid, tartaric acid, glycolic acid, clindamycin, minocycline, eritromycin, metronidazole, amoxycillin, triclosan, capryloyl glcine, azelaic acid, zinc hydroxide, zinc chloride, vitamin A trans-retinoic acid, resorcinol, hyaluronic acid, gentamicin, meclocycline, phenol, ascorbic acid, tocopherol, lipoic acid, phosphatidylcholine, phosphatidylserine, chlorhexidine, irgasan, adapalene, phospholipids in general, in all the dextrorotary, levorotary forms, recemic mixtures, cis forms, trans forms and relative salts, esters and amides and formulated in a base of particular additives and excipients for external use.
4. Composition for topical use according to claim 3, wherein the active added ingredients are contained in a quantity from 0,001 to 90%> weight/weight, preferably from 0.5 to 15%) weight/weight.
5. Composition for topical use according to claims 1 and 2, which is prepared in formulations for external use, such as water emulsions in oil, oil emulsions in water, mono-phase solutions, dual-phase pseudo-solutions, mono-phase gels, dual-phase gels or sub-micelle gels, anhydrous ointments, powder sprinklers, alcoholates, alcohol solutions, hydro-alcoholic solutions.
6. Use of composition according to claims 1 and 2 for the treatment of seborrhoea, acne and acne rosacea.
7. A method for the treatment of the skin, in particular for the treatment of seborrhoea, acne and acne rosacea comprising the steps of using a composition
containing a mixture of ethyllinoleate and triethylcitrate and applying the composition locally on the parts of the skin affected by seborrhoea, acne and acne rosacea, for a period of time and in quantities sufficient for a preservation of the structural integrity of the triglycerides of the sebum, whereby the composition provide a preferential substratum for the action of the lipase bacteria or the cutaneous esterase so as to decrease the pre-digestion of triglycerides on the part of lipase bacteria and cutaneous esterase.
8. The method of claim 7, according to which the composition containing the ethyllinoleate and triethylcitrate mixture is applied on the skin for a transformation of the ethyllinoleate and triethylcitrate into their respective acid forms by means of lipase bacteria or cutaneous esterase so as to form an active component able to act directly and indirectly against the causes of seborrhoea , acne and acne rosacea.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT2001BS000111A ITBS20010111A1 (en) | 2001-12-20 | 2001-12-20 | COMPOSITION FOR TOPICAL USE BASED ON THE ETHYL ESTER OF LINOLEIC ACID AND OF THE TRIETYL ESTER OF CITRIC ACID ASSOCIATED WITH OPPORTUN |
ITBS2001A000111 | 2001-12-20 | ||
PCT/IT2002/000791 WO2003061766A1 (en) | 2001-12-20 | 2002-12-13 | Composition based on etyllinoleate and triethylcitrate for the treatment of seborrhea and acne |
Publications (3)
Publication Number | Publication Date |
---|---|
AU2002367451A1 true AU2002367451A1 (en) | 2003-09-18 |
AU2002367451B2 AU2002367451B2 (en) | 2009-02-26 |
AU2002367451B8 AU2002367451B8 (en) | 2009-03-26 |
Family
ID=11440808
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU2002367451A Ceased AU2002367451B8 (en) | 2001-12-20 | 2002-12-13 | Composition based on ethyl ester of linoleic acid and triethyl ester of citric acid for topical use in the treatment of seborrhoea and acne |
Country Status (14)
Country | Link |
---|---|
US (1) | US7169811B2 (en) |
EP (1) | EP1455899B1 (en) |
JP (1) | JP5257913B2 (en) |
KR (1) | KR101057848B1 (en) |
CN (1) | CN100374109C (en) |
AT (1) | ATE515253T1 (en) |
AU (1) | AU2002367451B8 (en) |
CA (1) | CA2470199C (en) |
ES (1) | ES2368815T3 (en) |
IT (1) | ITBS20010111A1 (en) |
NZ (1) | NZ533530A (en) |
PL (1) | PL210279B1 (en) |
RU (1) | RU2313338C2 (en) |
WO (1) | WO2003061766A1 (en) |
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US7689225B2 (en) * | 2002-01-28 | 2010-03-30 | Ntt Docomo, Inc. | Method and apparatus for dormant mode support with paging |
ITBS20020078A1 (en) * | 2002-09-02 | 2004-03-03 | Paoli Ambrosi Gianfranco De | COMPOSITION BASED ON TRIETYL CITRATE IN THE TREATMENT OF INFECTIONS OF BACTERIAL ORIGIN OF THE SKIN. |
US20040248982A1 (en) * | 2003-06-09 | 2004-12-09 | Dyer Gordon Wayne | Use of compounds for the inhibition of proteins and UV protection |
US20100204323A1 (en) * | 2004-12-09 | 2010-08-12 | The Dial Corporation | Antimicrobial compositions comprising organic acid esters and methods for reducing virus and bacterial populations using such compositions |
ITBS20050154A1 (en) * | 2005-12-06 | 2007-06-07 | Paoli Ambrosi Gianfranco De | COMPOSITION BASED ON TRIETHYL CITRATE IN THE PREVENTION OF ENZYMATIC HYDROLYSIS OF TRIGLYCERIDES |
US7687650B2 (en) | 2006-02-03 | 2010-03-30 | Jr Chem, Llc | Chemical compositions and methods of making them |
KR101324578B1 (en) | 2006-02-03 | 2013-11-01 | 제이알 켐, 엘엘씨 | Anti-aging treatment using copper and zinc compositions |
US7897800B2 (en) | 2006-02-03 | 2011-03-01 | Jr Chem, Llc | Chemical compositions and methods of making them |
US8647682B2 (en) * | 2006-06-30 | 2014-02-11 | Audrey Kunin | Composition and method for treating keratosis pilaris |
US7867522B2 (en) | 2006-09-28 | 2011-01-11 | Jr Chem, Llc | Method of wound/burn healing using copper-zinc compositions |
US8273791B2 (en) | 2008-01-04 | 2012-09-25 | Jr Chem, Llc | Compositions, kits and regimens for the treatment of skin, especially décolletage |
CA2717899A1 (en) * | 2008-03-17 | 2009-09-24 | Glenmark Pharmaceuticals Limited | Stable fixed dose topical formulation |
US20160184354A1 (en) | 2009-01-23 | 2016-06-30 | Jr Chem, Llc | Rosacea treatments and kits for performing them |
FR2954124B1 (en) * | 2009-12-18 | 2012-04-06 | Fabre Pierre Dermo Cosmetique | USE OF 2,3-DIHYDROXYPROPYL DODECANOATE FOR THE TREATMENT OF SEBORRHEA |
US8952057B2 (en) | 2011-01-11 | 2015-02-10 | Jr Chem, Llc | Compositions for anorectal use and methods for treating anorectal disorders |
TR201816243T4 (en) * | 2011-01-31 | 2018-11-21 | Lucolas M D Ltd | Combinations of aromatase inhibitors and antioxidants. |
RU2519330C2 (en) * | 2011-10-31 | 2014-06-10 | Открытое Акционерное Общество "Татхимфармпрепараты" | Topical composition possessing anti-inflammatory, analgesic, antirheumatic and antibacterial activity and method for preparing it |
ITBS20120126A1 (en) * | 2012-08-01 | 2014-02-02 | Paoli Ambrosi Gianfranco De | ANTIBACTERIAL COMPOSITION FOR TOPICAL USE |
CN105997775A (en) * | 2016-05-10 | 2016-10-12 | 赫尔森江苏医药有限公司 | Pearl acne removing cream and preparing technology thereof |
EP3700504A4 (en) * | 2017-10-24 | 2021-07-28 | Glenmark Pharmaceuticals Limited | Topical pharmaceutical composition of adapalene and minocycline |
EP3717655A1 (en) | 2017-11-28 | 2020-10-07 | c-LEcta GmbH | Method for producing trehalose employing a trehalose phosphorylase variant |
KR102170815B1 (en) * | 2019-11-11 | 2020-10-29 | 대봉엘에스 주식회사 | Composition for moisturizing or anti-atopic comprising fatty acid or fatty acid derivatives |
CN113456570A (en) * | 2021-07-23 | 2021-10-01 | 完美(广东)日用品有限公司 | Acne-removing composition, acne-removing gel and preparation method thereof |
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DE2452119A1 (en) * | 1974-11-02 | 1976-05-13 | Henkel & Cie Gmbh | Cosmetic preparations against acne - contg. neutral esters of hydroxycarboxylic acids and alcohols |
JPH01110610A (en) * | 1987-10-22 | 1989-04-27 | Lion Corp | Preventive for pimple |
US6063762A (en) * | 1997-12-05 | 2000-05-16 | Chong Kun Dang Corp. | Cyclosporin-containing microemulsion preconcentrate composition |
US6028067A (en) * | 1997-12-05 | 2000-02-22 | Chong Kun Dang Corp. | Cyclosporin-containing microemulsion preconcentrate composition |
WO1999029335A1 (en) * | 1997-12-05 | 1999-06-17 | Chong Kun Dang Corp. | Pharmaceutical composition containing cyclosporin |
US6267985B1 (en) * | 1999-06-30 | 2001-07-31 | Lipocine Inc. | Clear oil-containing pharmaceutical compositions |
ITBS20010046A1 (en) * | 2001-06-20 | 2002-12-20 | Paoli Ambrosi Gianfranco De | COMPOSITION FOR TOPICAL USE BASED ON THE ETHYL ESTER OF LINOLEIC ACID AND CITRIC ACID TRIETYL ESTER ASSOCIATED WITH OPPORT |
-
2001
- 2001-12-20 IT IT2001BS000111A patent/ITBS20010111A1/en unknown
-
2002
- 2002-12-13 AU AU2002367451A patent/AU2002367451B8/en not_active Ceased
- 2002-12-13 CA CA2470199A patent/CA2470199C/en not_active Expired - Fee Related
- 2002-12-13 AT AT02806573T patent/ATE515253T1/en active
- 2002-12-13 KR KR1020047009506A patent/KR101057848B1/en active IP Right Grant
- 2002-12-13 RU RU2004118419/15A patent/RU2313338C2/en not_active IP Right Cessation
- 2002-12-13 JP JP2003561703A patent/JP5257913B2/en not_active Expired - Lifetime
- 2002-12-13 NZ NZ533530A patent/NZ533530A/en unknown
- 2002-12-13 CN CNB028255534A patent/CN100374109C/en not_active Expired - Fee Related
- 2002-12-13 WO PCT/IT2002/000791 patent/WO2003061766A1/en active IP Right Grant
- 2002-12-13 PL PL370795A patent/PL210279B1/en unknown
- 2002-12-13 EP EP02806573A patent/EP1455899B1/en not_active Expired - Lifetime
- 2002-12-13 ES ES02806573T patent/ES2368815T3/en not_active Expired - Lifetime
- 2002-12-16 US US10/322,566 patent/US7169811B2/en active Active
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