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Adenosine phosphate

Adenosine monophosphate is a key cellular metabolite that regulates energy homeostasis and signal transduction.
Adenosine phosphate
Adenosine phosphate Chemical Structure CAS No.: 61-19-8
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Adenosine monophosphate is a key cellular metabolite that regulates energy homeostasis and signal transduction.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
The result of numerous enzymatic processes, many of which are dysregulated in pathological situations, is adenosine monophosphate [1].
ADME/Pharmacokinetics
Absorption, Distribution and Excretion
AMP ADMIN TO RATS ORALLY WAS RECOVERED INTACT IN BLOOD. IT APPEARED RAPIDLY IN BLOOD (IN 15-30 MIN) & WAS ALSO RAPIDLY DISTRIBUTED, SINCE PLASMA CONCN WAS DECR BY FACTOR OF 5 IN 2 HR.
References
[1]. Mondal S, et al. Utility of Adenosine Monophosphate Detection System for Monitoring the Activities of Diverse Enzyme Reactions. Assay Drug Dev Technol. 2017 Oct/Nov;15(7):330-341.
Additional Infomation
Adenosine 5'-monophosphate is a purine ribonucleoside 5'-monophosphate having adenine as the nucleobase. It has a role as an EC 3.1.3.11 (fructose-bisphosphatase) inhibitor, an EC 3.1.3.1 (alkaline phosphatase) inhibitor, an adenosine A1 receptor agonist, a nutraceutical, a micronutrient, a fundamental metabolite and a cofactor. It is an adenosine 5'-phosphate and a purine ribonucleoside 5'-monophosphate. It is a conjugate base of an adenosine 5'-monophosphate(1+). It is a conjugate acid of an adenosine 5'-monophosphate(2-).
Adenosine phosphate, or adenylic acid, is an adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position. Adenosine phosphate was withdrawn by the FDA since it was considered neither safe nor effective for its intended uses as a vasodilator and an anti-inflammatory.
Adenosine monophosphate is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).
Adenosine monophosphate has been reported in Drosophila melanogaster, Bombyx mori, and other organisms with data available.
Adenosine monophosphate is a metabolite found in or produced by Saccharomyces cerevisiae.
Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position.
See also: Poly A-U (monomer of).
Drug Indication
For nutritional supplementation, also for treating dietary shortage or imbalance
Mechanism of Action
Nucleotides such as Adenosine-5'-Monophosphate affect a number of immune functions, including the reversal of malnutrition and starvation-induced immunosuppression, the enhancement of T-cell maturation and function, the enhancement of natural killer cell activity, the improvement of delayed cutaneous hypersensitivity, helping resistance to such infectious agents as Staphylococcus aureus and Candida albicans, and finally the modulation of T-cell responses toward type 1 CD4 helper lymphocytes or Th1 cells. Studies have shown that mice fed a nucleotide-free diet have both impaired humoral and cellular immune responses. The addition of dietary nucleotides normalizes both types of responses. RNA, a delivery form of nucleotides, and ribonucleotides were used in these studies. The mechanism of the immune-enhancing activity of nucleic acids/nucleotides is not clear.
Therapeutic Uses
ENERGY-RICH PHOSPHATES REPRESENT "ENERGY POOL" FROM WHICH CELLS OBTAIN THEIR ENERGY REQUIREMENTS. IN PATHOLOGICAL SITUATIONS, WHERE METABOLISM IS ALTERED, SPECIFIC DETERMINATION OF NUCLEOTIDES IS OF DIAGNOSTIC VALUE & IS INCREASINGLY USED IN HEART, LIVER & KIDNEY DISEASES.
Pharmacodynamics
Adenosine monophosphate, also known as 5'-adenylic acid and abbreviated AMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside adenosine. AMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase adenine. AMP is used as a dietary supplement to boost immune activity, and is also used as a substitute sweetener to aid in the maintenance of a low-calorie diet.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C10H14N5O7P
Molecular Weight
347.2212
Exact Mass
347.063
CAS #
61-19-8
Related CAS #
24937-83-5
PubChem CID
6083
Appearance
CRYSTALS FROM WATER + ACETONE
POWDER, NEEDLES FROM WATER & DIL ALC
Density
2.3±0.1 g/cm3
Boiling Point
798.5±70.0 °C at 760 mmHg
Melting Point
178-185 °C
Flash Point
436.7±35.7 °C
Vapour Pressure
0.0±3.0 mmHg at 25°C
Index of Refraction
1.905
LogP
-0.22
Hydrogen Bond Donor Count
5
Hydrogen Bond Acceptor Count
11
Rotatable Bond Count
4
Heavy Atom Count
23
Complexity
481
Defined Atom Stereocenter Count
4
SMILES
P(=O)(O[H])(O[H])OC([H])([H])[C@]1([H])[C@]([H])([C@]([H])([C@]([H])(N2C([H])=NC3=C(N([H])[H])N=C([H])N=C23)O1)O[H])O[H]
InChi Key
UDMBCSSLTHHNCD-KQYNXXCUSA-N
InChi Code
InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
Chemical Name
[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~16.67 mg/mL (~48.01 mM)
H2O : ~1.67 mg/mL (~4.81 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 1.67 mg/mL (4.81 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 16.7 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 1.67 mg/mL (4.81 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 16.7 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 1.67 mg/mL (4.81 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 16.7 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


Solubility in Formulation 4: 3.33 mg/mL (9.59 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication (<60°C).

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.8800 mL 14.4001 mL 28.8002 mL
5 mM 0.5760 mL 2.8800 mL 5.7600 mL
10 mM 0.2880 mL 1.4400 mL 2.8800 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT00679250 Completed Drug: levocetirizine
Drug: placebo to levocetirizine
Allergic Rhinitis Brian J Lipworth November 2005 Phase 4
NCT01939587 Completed Drug: PBF-680 5 mg
Drug: PBF-680 20 mg
Asthma Fundació Institut de Recerca de
l'Hospital de la Santa Creu i Sant Pau
December 2013 Phase 2
NCT02318043 Completed Drug: inhaled corticosteroids (usually
budesonide/fomorterol 160/4.5mcg;
fluticasone/salmeterol 250/50mcg)
Asthma Guangzhou Institute of Respiratory
Disease
January 2007 Not Applicable
NCT00179010 Terminated Has Results Drug: Adenosine
Drug: Adenosine Mono Phosphate (AMP)
Ischemia Vanderbilt University Medical Center October 2003 Phase 1
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