IT8922520A1 - USE OF GUANIDINACETIC ACID TO INDUCE AN INCREASE IN THE MUSCLE CONTENT OF CREATINE - Google Patents
USE OF GUANIDINACETIC ACID TO INDUCE AN INCREASE IN THE MUSCLE CONTENT OF CREATINE Download PDFInfo
- Publication number
- IT8922520A1 IT8922520A1 IT1989A22520A IT2252089A IT8922520A1 IT 8922520 A1 IT8922520 A1 IT 8922520A1 IT 1989A22520 A IT1989A22520 A IT 1989A22520A IT 2252089 A IT2252089 A IT 2252089A IT 8922520 A1 IT8922520 A1 IT 8922520A1
- Authority
- IT
- Italy
- Prior art keywords
- acid
- guanidinacetic
- creatine
- methionine
- increase
- Prior art date
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- CVSVTCORWBXHQV-UHFFFAOYSA-N creatine Chemical compound NC(=[NH2+])N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-N 0.000 title claims description 42
- 239000006046 creatine Substances 0.000 title claims description 21
- 229960003624 creatine Drugs 0.000 title claims description 21
- 239000002253 acid Substances 0.000 title claims description 12
- BPMFZUMJYQTVII-UHFFFAOYSA-M guanidinoacetate Chemical compound NC(=N)NCC([O-])=O BPMFZUMJYQTVII-UHFFFAOYSA-M 0.000 title claims description 11
- 210000003205 muscle Anatomy 0.000 title claims description 10
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 12
- 229930182817 methionine Natural products 0.000 claims description 12
- 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 claims description 7
- 230000003834 intracellular effect Effects 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 230000037396 body weight Effects 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 230000003387 muscular Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound 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 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
- 235000005911 diet Nutrition 0.000 description 3
- 230000037213 diet Effects 0.000 description 3
- DRBBFCLWYRJSJZ-UHFFFAOYSA-N N-phosphocreatine Chemical compound OC(=O)CN(C)C(=N)NP(O)(O)=O DRBBFCLWYRJSJZ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000008602 contraction Effects 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
- 208000019423 liver disease Diseases 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 1
- 208000008784 apnea Diseases 0.000 description 1
- 235000019577 caloric intake Nutrition 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 210000004413 cardiac myocyte Anatomy 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
- 235000015872 dietary supplement Nutrition 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000010247 heart contraction Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 230000002045 lasting effect Effects 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
- 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
- 210000004165 myocardium Anatomy 0.000 description 1
- 238000006213 oxygenation reaction Methods 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 210000002363 skeletal muscle cell Anatomy 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
- 210000001519 tissue Anatomy 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
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)
Description
Domanda di Brevetto per Invenzione Industriale dal titolo: "Impiego dell'acido guanidinacetico per indurre un incremento del contenuto muscolare di creatina" Patent Application for Industrial Invention entitled: "Use of guanidinacetic acid to induce an increase in muscle creatine content"
RIASSUNTO SUMMARY
L'acido guanidinacetico, o un suo sale, da solo o in associazione con metionina o con solfoadenosilmetionina viene utilmente impiegato nelle affezioni e nelle condizioni fisiche che richiedono un incremento del contenuto intracellulare muscolare di creatina. Guanidinacetic acid, or one of its salt, alone or in association with methionine or with sulfoadenosylmethionine is usefully used in diseases and physical conditions that require an increase in the intracellular muscle content of creatine.
Tecnica nota Known technique
E' noto che nel tessuto muscolare esistono diversi composti biologici a contenuto energetico di cui il principale ? l'adenosina trifosfato (ATP). It is known that in muscle tissue there are several biological compounds with energy content, the main one of which? adenosine triphosphate (ATP).
Tra queste sostanze riveste una grande importanza la creatina fosfato la quale ? in rapporto con l'ATP nel senso che tra i due composti ha luogo uno scambio di gruppi fosfato. Among these substances, creatine phosphate is of great importance, which? in relation to ATP in the sense that an exchange of phosphate groups takes place between the two compounds.
L'importanza della creatina ? dimostrata dal fatto che in condizioni di ischemia del miocardio si ha 1' arresto della funzione contrattile del cuore al momento dell'esaurimento della creatina stessa mentre ? presente ancora il 90% dell'ATP. The importance of creatine? demonstrated by the fact that in conditions of myocardial ischemia there is the arrest of the contractile function of the heart at the time of exhaustion of the creatine itself while? 90% of ATP is still present.
Ci? ? dovuto al fatto che l'ATP disponibile per cedere immediatamente energia per la contrazione ? solamente una piccola parte dell?ATP presente il quale funziona da riserva. E' compito della creatina ricaricare l'ATP affinch? possa cedere energia per la contrazione. There? ? due to the fact that the ATP available to immediately release energy for the contraction? only a small part of the present ATP which functions as a reserve. It is the creatine's job to recharge the ATP so that? can release energy for contraction.
Da queste considerazioni emerge chiaramente un problema importante cio? il problema di aumentare,quando necessario, la creatina nel muscolo. Ci? consentirebbe una efficienza pi? prolungata e pi? potente del muscolo sia cardiaco che scheletrico. From these considerations, an important problem clearly emerges, that is? the problem of increasing creatine in the muscle when needed. There? would allow an efficiency more? prolonged and more? powerful of both cardiac and skeletal muscle.
Infatti, mentre la riserva di ATP ? facilmente rifornibile sia in aerobiosi che in anaerobiosi, la performance contrattile, specie in anaerobiosi, ? funzione della quantit? di creatina presente. Indeed, while the reserve of ATP? easily replenished both in aerobiosis and in anaerobiosis, the contractile performance, especially in anaerobiosis,? function of the quantity? of creatine present.
Perci? tale sostanza ? di grandissimo interesse sia in campo medico che sportivo: basta pensare ad esempio a quante vite si potrebbero salvare nell?infarto del miocardio se si riuscisse a fare continuare le contrazioni cardiache in condizioni di ischemia fino alla ripresa di una corretta ossigenazione del tessuto infartuato oppure nell'attivit? sportiva quanto potrebbe rendere un atleta in uno sport con sforzo di tipo esplosivo, come i 100 metri, laddove l'atleta compie la sua performance in apnea. So? such substance? of great interest both in the medical and sports fields: just think, for example, of how many lives could be saved in myocardial infarction if it were possible to make cardiac contractions continue in conditions of ischemia until the resumption of proper oxygenation of the infarcted tissue or in activity as sporty as an athlete could make in a sport with an explosive type of effort, such as 100 meters, where the athlete performs his performance in apnea.
D'altra parte si deve tenere presente che la creatina viene sintetizzata principalmente nel rene e nel fegato per cui si avr? una carenza nel corso di tutte le nefropatie ed epatopatie con compromissione parenchimale. On the other hand, it must be borne in mind that creatine is synthesized mainly in the kidney and liver for which it will have? a deficiency in all renal and hepatopathies with parenchymal compromise.
Purtroppo la somministrazione di creatina esogena non porta ad alcun risultato positivo in quanto la creatina esogena inibisce la sintesi di creatina endogena per una quantit? pari alla quantit? di creatina somministrata. Unfortunately, the administration of exogenous creatine does not lead to any positive result as exogenous creatine inhibits the synthesis of endogenous creatine for a quantity? equal to the quantity? of creatine administered.
Sommario Summary
Ora noi abbiamo trovato che i problemi della tecnica anteriore possono essere superati mediante la somministrazione di acido guanidinacetico, o di un suo sale, da solo o in associazione con metionina o con solfoadenosil-metionina. We have now found that the problems of the prior art can be overcome by administering guanidinacetic acid, or one of its salt, alone or in combination with methionine or sulfoadenosyl-methionine.
Detta somministrazione porta ad un incremento del contenuto intracellulare muscolare di creatina e quindi aumenta la disponibilit? di energia per le cellule muscolari sia scheletriche che cardiache. This administration leads to an increase in the intracellular muscle content of creatine and therefore increases the availability? of energy for both skeletal and cardiac muscle cells.
Descrizione dettagliata dell'invenzione Detailed description of the invention
Gli effetti ed i vantaggi della somministrazione di acido guanidinacetico (AGA) da solo o in associazione con metionina o solfoadenosil-metionina (SAME) allo scopo di incrementare il contenuto intracellulare muscolare di creatina saranno maggiormente illustrati nel corso della seguente descrizione dettagliata. The effects and advantages of administering guanidinacetic acid (AGA) alone or in combination with methionine or sulfoadenosyl-methionine (SAME) in order to increase the intracellular muscle content of creatine will be further illustrated in the course of the following detailed description.
In una sperimentazione condotta sui ratti ? stato somministrato AGA come supplementazione ad una dieta standard. Per la determinazione dell'aumento del contenuto intracellulare muscolare della creatina sono state raccolte le urine escrete nelle 24 ore ed ? stata dosata la concentrazione di creatinina. Questo dosaggio ? una misura del tutto affidabile del contenuto intracellulare della creatina in quanto, come noto, l'eliminazione renale della creatinina ? funzione matematica della concentrazione intracellulare di creatina e non dipende da alcun altro parametro come ad esempio l'esercizio muscolare o l?introduzione calorica. In a rat experiment? AGA was given as a supplement to a standard diet. Urine excreted within 24 hours and? the creatinine concentration was measured. This dosage? a completely reliable measure of the intracellular content of creatine since, as is known, the renal elimination of creatinine? mathematical function of the intracellular concentration of creatine and does not depend on any other parameter such as muscle exercise or caloric intake.
La sperimentazione con AGA ? stata realizzata in due stadi della durata di una settimana ciascuno, intervallati da un periodo di tre giorni tra il primo stadio ed il secondo stadio. Nella settimana precedente la sperimentazione con AGA veniva monitorizzata la creatininuria nei ratti alimentati con una dieta che conteneva metionina in quantit? pari al fabbisogno del ratto, pi? una quantit? di metionina pari a 1,7 mg/kg di peso corporeo, quantit? pari a quella necessaria per attivare l'AGA che sar? aggiunto nelle settimane successive. Experimentation with AGA? it was carried out in two stages lasting one week each, interspersed with a period of three days between the first stage and the second stage. In the week preceding the AGA experiment, creatininuria was monitored in rats fed a diet that contained methionine in quantities. equal to the needs of the rat, more? a quantity? of methionine equal to 1.7 mg / kg of body weight, quantity? equal to that necessary to activate the AGA which will be? added in the following weeks.
Nel 1? stadio della sperimentazione con AGA i ratti vennero alimentati con la dieta della settimana precedente supplementata con AGA in quantit? di 1,7 mg/Kg di peso corporeo. In the 1? stage of the experiment with AGA the rats were fed the previous week's diet supplemented with AGA in quantity. of 1.7 mg / kg of body weight.
Dopo una settimana ? stata sospesa per 3 giorni la supplementazione della dieta con AGA. After a week? Dietary supplementation with AGA was suspended for 3 days.
Dopo questa sospensione i ratti sono stati alimentati con dieta supplementata con AGA ancora per una settimana (2? stadio). After this suspension, the rats were fed an AGA supplemented diet for another week (2nd stage).
I risultati ottenuti sono riportati nella tabella 1. The results obtained are shown in table 1.
C'? da osservare che nel procedimento di sintesi della creatina a partire da AGA c?? il pericolo di sottrarre metionina ad altri procedimenti metabolici. Per questo motivo la presente invenzione prevede anche di associare la metionina o la SAME all'AGA con un rapporto molare fra metionina o SAME ed AGA compreso fra 0,5:1 e 3:1? There? it should be noted that in the creatine synthesis process starting from AGA c ?? the danger of removing methionine from other metabolic processes. For this reason, the present invention also envisages associating methionine or SAME with AGA with a molar ratio between methionine or SAME and AGA between 0.5: 1 and 3: 1?
La somministrazione dell'AGA e dell'associazione AGA-metionina o AGA-SAME trova quindi una importantissima indicazione in tutte quelle condizioni in cui ? necessario o opportuno aumentare la concentrazione intramuscolare di creatina, e particolarmente nelle nefropatie ed epatopatie con compromissione parenchinale, nelle persone anziane, nelle condizioni di iponutrizione e nella ischemia cronica e acuta del muscolo miocardico. The administration of AGA and the AGA-methionine or AGA-SAME association therefore finds a very important indication in all those conditions in which? It is necessary or appropriate to increase the intramuscular concentration of creatine, and particularly in renal and hepatopathies with parenchinal compromise, in the elderly, in conditions of hyponutrition and in chronic and acute ischemia of the myocardial muscle.
Dette sostanze sono inoltre utilmente somministrabili ad atleti che praticano sport che richiedono sforzi di tipo esplosivo. La somministrazione dell'AGA e dell'associazione AGA-metionina o AGA-SAME pu? essere effettuata per via orale o per via parenterale Impiegando dette sostanze allo stato puro oppure sotto forma di composizioni comprendenti diluenti ed eccipienti farmacologicamente accettabili. Said substances can also be usefully administered to athletes who practice sports that require explosive efforts. The administration of the AGA and the association AGA-methionine or AGA-SAME can? be carried out orally or parenterally using said substances in their pure state or in the form of compositions comprising pharmacologically acceptable diluents and excipients.
L'AQA pu? essere impiegato tal quale oppure sotto forma di sale con un catione farmacologicamente accettabile. The AQA can be used as such or in the form of a salt with a pharmacologically acceptable cation.
La quantit? giornaliera di AGA da somministrare ? compresa nel campo da 0,0001 a 5 mg/Kg di peso corporeo in pi? somministrazioni giornaliere. The quantity daily of AGA to be administered? included in the range from 0.0001 to 5 mg / kg of body weight in pi? daily administrations.
Claims (2)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT02252089A IT1237519B (en) | 1989-11-27 | 1989-11-27 | USE OF GUANIDINACETIC ACID TO INDUCE AN INCREASE IN THE CREATINE MUSCLE CONTENT |
| PCT/EP1990/002015 WO1991007954A1 (en) | 1989-11-27 | 1990-11-26 | Use of guanidinoacetic acid to induce an increase of the creatine contents in muscles |
| EP90917057A EP0455770A1 (en) | 1989-11-27 | 1990-11-26 | Use of guanidinoacetic acid to induce an increase of the creatine contents in muscles |
| AU67321/90A AU6732190A (en) | 1989-11-27 | 1990-11-26 | Use of guanidinoacetic acid to induce an increase of the creatine contents in muscles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT02252089A IT1237519B (en) | 1989-11-27 | 1989-11-27 | USE OF GUANIDINACETIC ACID TO INDUCE AN INCREASE IN THE CREATINE MUSCLE CONTENT |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| IT8922520A0 IT8922520A0 (en) | 1989-11-27 |
| IT8922520A1 true IT8922520A1 (en) | 1991-05-27 |
| IT1237519B IT1237519B (en) | 1993-06-08 |
Family
ID=11197371
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IT02252089A IT1237519B (en) | 1989-11-27 | 1989-11-27 | USE OF GUANIDINACETIC ACID TO INDUCE AN INCREASE IN THE CREATINE MUSCLE CONTENT |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0455770A1 (en) |
| AU (1) | AU6732190A (en) |
| IT (1) | IT1237519B (en) |
| WO (1) | WO1991007954A1 (en) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993003724A1 (en) * | 1991-08-26 | 1993-03-04 | The Upjohn Company | Pharmaceutical composition containing 3-guanidinopropionic acid and pioglitazone glibenclamide or glimepiride |
| AP387A (en) * | 1991-09-13 | 1995-07-31 | Siegbert Heinrich Bissbort | Therapeutical uses of L-methionine and compositions 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 (en) * | 1995-09-25 | 1997-10-02 | Desitin Arzneimittel Gmbh | Creatine to protect neural tissue |
| US20050287204A1 (en) * | 2002-06-19 | 2005-12-29 | Hageman Robert J J | Nutritional or pharmaceutical compositions for increasing the creatine response of organisms |
| WO2005120246A1 (en) | 2004-06-09 | 2005-12-22 | Degussa Ag | Guanidino acetic acid used as an animal food additive |
| US8536222B2 (en) | 2005-03-04 | 2013-09-17 | Alzchem Ag | Addition compounds of guanidinoacetic acid |
| DE102005009990A1 (en) * | 2005-03-04 | 2006-09-07 | Degussa Ag | Salts, addition and complex compounds of guanidinoacetic acid |
| JP5284088B2 (en) * | 2005-08-02 | 2013-09-11 | アルツケム アクチエンゲゼルシャフト | Liquid formulations based on guanidinoacetic acid components |
| DE102006009373A1 (en) * | 2006-03-01 | 2007-09-06 | Degussa Gmbh | Ready-made food for pets |
| DE102007004781A1 (en) | 2007-01-31 | 2008-08-07 | Alzchem Trostberg Gmbh | Use of guanidinoacetic acid (salts) for the preparation of a health-promoting agent |
| DE102007034102A1 (en) * | 2007-07-21 | 2009-01-22 | Alzchem Trostberg Gmbh | Abrasion-resistant and free-flowing glycocyamine-containing moldings and process for their preparation |
-
1989
- 1989-11-27 IT IT02252089A patent/IT1237519B/en active IP Right Grant
-
1990
- 1990-11-26 WO PCT/EP1990/002015 patent/WO1991007954A1/en not_active Application Discontinuation
- 1990-11-26 AU AU67321/90A patent/AU6732190A/en not_active Abandoned
- 1990-11-26 EP EP90917057A patent/EP0455770A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| EP0455770A1 (en) | 1991-11-13 |
| AU6732190A (en) | 1991-06-26 |
| WO1991007954A1 (en) | 1991-06-13 |
| IT1237519B (en) | 1993-06-08 |
| IT8922520A0 (en) | 1989-11-27 |
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| Date | Code | Title | Description |
|---|---|---|---|
| 0001 | Granted |