EP0455770A1 - Use of guanidinoacetic acid to induce an increase of the creatine contents in muscles - Google Patents
Use of guanidinoacetic acid to induce an increase of the creatine contents in musclesInfo
- Publication number
- EP0455770A1 EP0455770A1 EP90917057A EP90917057A EP0455770A1 EP 0455770 A1 EP0455770 A1 EP 0455770A1 EP 90917057 A EP90917057 A EP 90917057A EP 90917057 A EP90917057 A EP 90917057A EP 0455770 A1 EP0455770 A1 EP 0455770A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- creatine
- guanidinoacetic acid
- methionine
- gaa
- same
- 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.)
- Withdrawn
Links
- BPMFZUMJYQTVII-UHFFFAOYSA-N guanidinoacetic acid Chemical compound NC(=N)NCC(O)=O BPMFZUMJYQTVII-UHFFFAOYSA-N 0.000 title claims abstract description 58
- CVSVTCORWBXHQV-UHFFFAOYSA-N creatine Chemical compound NC(=[NH2+])N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-N 0.000 title claims abstract description 44
- 229960003624 creatine Drugs 0.000 title claims abstract description 22
- 239000006046 creatine Substances 0.000 title claims abstract description 22
- 210000003205 muscle Anatomy 0.000 title abstract description 6
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims abstract description 12
- 229930182817 methionine Natural products 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 230000003387 muscular Effects 0.000 claims description 8
- 230000037396 body weight Effects 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 230000003834 intracellular effect Effects 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical group C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 description 8
- ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 8
- 241000700159 Rattus Species 0.000 description 6
- 235000005911 diet Nutrition 0.000 description 5
- 230000037213 diet Effects 0.000 description 5
- DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000008602 contraction Effects 0.000 description 3
- FVSFGYXQNHBRHP-TWBCTODHSA-N (2S)-2-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl-sulfoamino]-4-methylsulfanylbutanoic acid Chemical compound O[C@@H]1[C@H](O)[C@@H](CN([C@@H](CCSC)C(O)=O)S(O)(=O)=O)O[C@H]1N1C2=NC=NC(N)=C2N=C1 FVSFGYXQNHBRHP-TWBCTODHSA-N 0.000 description 2
- DRBBFCLWYRJSJZ-UHFFFAOYSA-N N-phosphocreatine Chemical group OC(=O)CN(C)C(=N)NP(O)(O)=O DRBBFCLWYRJSJZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229940109239 creatinine Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000002360 explosive Substances 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 208000028867 ischemia Diseases 0.000 description 2
- 208000017169 kidney disease Diseases 0.000 description 2
- 208000019423 liver disease Diseases 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 1
- 208000008784 apnea Diseases 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000019577 caloric intake Nutrition 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 230000008828 contractile function Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000007620 mathematical function Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- 230000000063 preceeding effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 235000000891 standard diet Nutrition 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
Definitions
- creatine phosphate which is in relationship with ATP in the sense that between the two compounds there is an exchange of phospate groups.
- the importance of creatine is demonstrated by the fact that in conditions of myocardial ischemia there is an arrest of the contractile function of the heart at the moment of the depletion of the creatine itself while 30% of the ATP is still present. This is due to the fact that the ATP available to give immediate energy for the contraction is only a small part of the ATP present, which functions as a reserve.
- the duty of creatine is to recharge the ATP until it can give energy for the contraction. From these considerations an important problem clearly emerges, that is, the problem of increasing, when necessary, the amount of creatine in the muscle.
- said substance is of great interest both in the medical and sports field: one only has to think, for example, of how many lives could be saved in case of myocardial infarct if it would be possible to make the cardial contractions continue in conditions of ischemia until a correct oxigenation of the infarcted tissue is restored or, in the case of sports activity, how well an athlete could perform in a sport with such an explosive type of effort, as in the 100 meter race, where the athlete carries out his performance in apnea.
- Such an administration brings an increase of the intercellular muscular content of creatine and therefore • increases the availibility of energy for both the skeletal and cardiacal muscular cells.
- GAA guanidinoacetic acid
- SAMe sulpho-adenosyl-methionine
- the experimentation with GAA was realized in two stages each of a week's duration, and intervalled by a period of three days between the first and second stage.
- the creatininuria was monitored in the rats fed with a diet which contained methionine in an amount equal to the one needed by the rat plus an amount of methionine of 1.7 mg/kg of body weight, which corresponds to the one necessary to activate the GAA which will be added in the successive weeks.
- the rats were fed with the diet of the preceding week supplemented with GAA in quantity of 1.7 mg/kg of body weight.
- Such substances are also usefully administered to athletes who practice sports which require explosive efforts.
- the adminsitration of GAA and of the GAA-methionine or GAA-SAMe association can be 5 made orally or parenterally employing said substances in a pure state or in the form of compositions comprising diluents and pharmacologically acceptable excipients.
- GAA can be used as such or in the form of salt with a pharmacologically acceptable cation.
- the daily dose of GAA to be administered is comprised between 10 0.0001 to 5 mg/kg of body weight in several daily doses.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT02252089A IT1237519B (it) | 1989-11-27 | 1989-11-27 | Impiego dell'acido guanidinacetico per indurre un incremento del contenuto muscolare di creatina |
| IT2252089 | 1989-11-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0455770A1 true EP0455770A1 (en) | 1991-11-13 |
Family
ID=11197371
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP90917057A Withdrawn EP0455770A1 (en) | 1989-11-27 | 1990-11-26 | Use of guanidinoacetic acid to induce an increase of the creatine contents in muscles |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0455770A1 (it) |
| AU (1) | AU6732190A (it) |
| IT (1) | IT1237519B (it) |
| WO (1) | WO1991007954A1 (it) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0601001B1 (en) * | 1991-08-26 | 1997-04-16 | PHARMACIA & UPJOHN COMPANY | Liquid food product containing 3-guanidinopropionic acid |
| CA2078019C (en) * | 1991-09-13 | 2002-08-27 | Siegbert Heinrich Bissbort | Substance or composition and uses thereof |
| GB9215746D0 (en) * | 1992-07-24 | 1992-09-09 | Hultman Eric | A method of increasing creatine supply depot |
| WO1994026261A1 (en) * | 1993-05-14 | 1994-11-24 | Amira, Inc. | Treating body parts susceptible to ischemia using creatine analogs |
| DE19537494C2 (de) * | 1995-09-25 | 1997-10-02 | Desitin Arzneimittel Gmbh | Kreatin zum Schutz von neuralem Gewebe |
| WO2004000297A1 (en) * | 2002-06-19 | 2003-12-31 | N.V. Nutricia | Nutritional or pharmaceutical compositions for increasing the creatine response of organisms |
| BRPI0511842B1 (pt) | 2004-06-09 | 2014-08-12 | Alzchem Trostberg Gmbh | Uso de ácido guanidino acético como aditivo para ração animal |
| US8536222B2 (en) | 2005-03-04 | 2013-09-17 | Alzchem Ag | Addition compounds of guanidinoacetic acid |
| DE102005009990A1 (de) * | 2005-03-04 | 2006-09-07 | Degussa Ag | Salze, Anlagerungs- und Komplexverbindungen der Guanidinoessigsäure |
| US20090297656A1 (en) * | 2005-08-02 | 2009-12-03 | Thomas Gastner | Liquid Formulation Based On a Guanidinoacetic Acid Component |
| DE102006009373A1 (de) * | 2006-03-01 | 2007-09-06 | Degussa Gmbh | Fertigfutter für Haustiere |
| DE102007004781A1 (de) | 2007-01-31 | 2008-08-07 | Alzchem Trostberg Gmbh | Verwendung von Guanidinoessigsäure(-Salzen) zur Herstellung eines gesundheitsfördernden Mittels |
| DE102007034102A1 (de) * | 2007-07-21 | 2009-01-22 | Alzchem Trostberg Gmbh | Abriebfeste und rieselfähige Glycocyamin-haltige Formlinge und Verfahren zu deren Herstellung |
-
1989
- 1989-11-27 IT IT02252089A patent/IT1237519B/it active IP Right Grant
-
1990
- 1990-11-26 AU AU67321/90A patent/AU6732190A/en not_active Abandoned
- 1990-11-26 EP EP90917057A patent/EP0455770A1/en not_active Withdrawn
- 1990-11-26 WO PCT/EP1990/002015 patent/WO1991007954A1/en not_active Ceased
Non-Patent Citations (1)
| Title |
|---|
| See references of WO9107954A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| IT8922520A1 (it) | 1991-05-27 |
| IT1237519B (it) | 1993-06-08 |
| AU6732190A (en) | 1991-06-26 |
| IT8922520A0 (it) | 1989-11-27 |
| WO1991007954A1 (en) | 1991-06-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE CH DE DK ES FR GB GR IT LI LU NL SE |
|
| 17P | Request for examination filed |
Effective date: 19911205 |
|
| 17Q | First examination report despatched |
Effective date: 19930208 |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
| 18D | Application deemed to be withdrawn |
Effective date: 19930619 |