Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C10H16N5O13P3 |
Molecular Weight | 507.181 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC=NC2=C1N=CN2[C@@H]3O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]3O
InChI
InChIKey=ZKHQWZAMYRWXGA-KQYNXXCUSA-N
InChI=1S/C10H16N5O13P3/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(26-10)1-25-30(21,22)28-31(23,24)27-29(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
Molecular Formula | C10H16N5O13P3 |
Molecular Weight | 507.181 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Adenosine triphosphate (ATP) is an adenine nucleotide containing three phosphate groups esterified to the sugar moiety. Adenosine triphosphate is the energy source in living cells. In physiological conditions, the average concentration varies from 3150 mM in mammalian cells to 1500–1900 mM in human blood cells. Extracellular adenosine and adenosine triphosphate (ATP) are involved in biological processes including neurotransmission, muscle contraction, cardiac function, platelet function, vasodilatation, signal transduction and secretion in a variety of cell types. A large family of membrane-bound receptors mediates cell signalling by ATP and adenosine. These purinergic receptors ultimately determine the variety of effects induced by extracellular ATP and adenosine. ATP and adenosine have strong negative chronotropic and dromotropic effects on the mammalian heart. The sensitivity of the sinus node and the atrioventricular node to ATP and adenosine manifests pronounced variability among species. For more than three decades, ATP has been used routinely in Europe in the acute therapy of paroxysmal supraventricular tachycardia. ATPace™, an injectable formulation of adenosine 5′-triphosphate (ATP), was developed by Cordex Pharma, Inc. (Cordex) as a diagnostic and therapeutic drug for the management of cardiac bradyarrhythmias. Extracellular ATP exerts multiple effects in various cell types by activating cell-surface receptors known as P2 receptors. In the heart, ATP suppresses the automaticity of cardiac pacemakers and atrioventricular (AV) nodal conduction via adenosine, the product of its degradation by ecto-enzymes, as well as by triggering a cardio-cardiac vagal reflex. ATP, given as a rapid intravenous bolus injection, has been used since the late 1940s as a highly effective and safe therapeutic agent for the acute termination of reentrant paroxysmal supraventricular tachycardia (PSVT) involving the AV node. In addition, preliminary studies have shown that ATP can also be used as a diagnostic agent for the identification of several cardiac disorders including sinus node dysfunction (sick sinus syndrome), dual AV nodal pathways, long QT syndrome, and bradycardic syncope. The US Food and Drug Administration has approved Cordex formulation for ATP as an Investigational New Drug and two pathways for its marketing approval; one therapeutic, i.e., acute termination of paroxysmal PSVT, and the other diagnostic, i.e., the identification of patients with bradycardic syncope who can benefit from pacemaker therapy. However later ATPace development for the treatment of bradycardia and paroxysmal supraventricular tachycardia was discontinued.
Originator
Sources: https://www.nndb.com/people/075/000249325/
Curator's Comment: German biochemist Karl Lohmann discovered adenosine triphosphate (ATP), the key source of energy in all living things, in 1929. He isolated ATP from muscle and liver extracts, and originally called his discovery "inosinic acid".
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2094 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12213051 |
56.0 nM [EC50] | ||
Target ID: CHEMBL4398 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11985476 |
85.0 nM [EC50] | ||
Target ID: CHEMBL4630 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20608738 |
|||
Target ID: CHEMBL203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20608738 |
PubMed
Title | Date | PubMed |
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Identification of receptor tyrosine kinase (RTK) substrates by the cloning of receptor targets (CORT) strategy. | 2001 |
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Detection of phosphorylation-dependent interactions by far-western gel overlay. | 2001 |
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Protein histidine kinase. | 2001 |
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Cyclin-dependent kinases and cyclin-dependent kinase inhibitors. Detection methods and activity measurements. | 2001 |
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Assays for glycogen synthase kinase-3 (GSK-3). | 2001 |
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Assays for mitogen-activated protein kinase (MAPK) subtypes and MAPK activating protein kinase-2 (MAPKAP K-2) using a common cell lysate. | 2001 |
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Two-dimensional phosphoamino acid analysis. | 2001 |
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Use of a real-time, coupled assay to measure the ATPase activity of DNA topoisomerase II. | 2001 |
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Topoisomerase II-catalyzed ATP hydrolysis as monitored by thin-layer chromatography. | 2001 |
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Analyzing reverse gyrase activity. | 2001 |
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Assaying DNA topoisomerase I relaxation activity. | 2001 |
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Properties of native P2X receptors in rat trigeminal mesencephalic nucleus neurones: lack of correlation with known, heterologously expressed P2X receptors. | 2001 |
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ATP-dependent activation of the intermediate conductance, Ca2+-activated K+ channel, hIK1, is conferred by a C-terminal domain. | 2001 Apr 6 |
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Modulation of in vivo HSP70 chaperone activity by Hip and Bag-1. | 2001 Feb 16 |
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Leishmania plasma membrane Mg2+-ATPase is a H+/K+-antiporter involved in glucose symport. Studies with sealed ghosts and vesicles of opposite polarity. | 2001 Feb 23 |
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Noninvasive measurements of transmural myocardial metabolites using 3-D (31)P NMR spectroscopy. | 2001 Jan |
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Activation of the heat shock response: relationship to energy metabolites. A (31)P NMR study in rat hearts. | 2001 Jan |
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Protection of cardiac myocytes via delta(1)-opioid receptors, protein kinase C, and mitochondrial K(ATP) channels. | 2001 Jan |
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Myocardial oxygenation and high-energy phosphate levels during graded coronary hypoperfusion. | 2001 Jan |
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Role of mitochondrial and sarcolemmal K(ATP) channels in ischemic preconditioning of the canine heart. | 2001 Jan |
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Dual roles of mitochondrial K(ATP) channels in diazoxide-mediated protection in isolated rabbit hearts. | 2001 Jan |
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Minimal protection of the liver by ischemic preconditioning in pigs. | 2001 Jan |
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Short-term hibernation in adult cardiomyocytes is PO(2) dependent and Ca(2+) mediated. | 2001 Jan |
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Role of K(ATP)(+) channels in regulation of systemic, pulmonary, and coronary vasomotor tone in exercising swine. | 2001 Jan |
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Properties of ATP-dependent K(+) channels in adrenocortical cells. | 2001 Jan |
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Modulation of P2Z/P2X(7) receptor activity in macrophages infected with Chlamydia psittaci. | 2001 Jan |
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Impairment of endothelial nitric oxide production by acute glucose overload. | 2001 Jan |
|
Differential effects of bcl-2 on cell death triggered under ATP-depleting conditions. | 2001 Jan 1 |
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Novel properties of the protein kinase CK2-site-regulated nuclear- localization sequence of the interferon-induced nuclear factor IFI 16. | 2001 Jan 1 |
|
Energetics of growth and penicillin production in a high-producing strain of Penicillium chrysogenum. | 2001 Jan 20 |
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Glucose deprivation and chemical hypoxia: neuroprotection by P2 receptor antagonists. | 2001 Mar |
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Cystic fibrosis transmembrane conductance regulator gating requires cytosolic electrolytes. | 2001 Mar 2 |
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Cystic fibrosis transmembrane conductance regulator facilitates ATP release by stimulating a separate ATP release channel for autocrine control of cell volume regulation. | 2001 Mar 2 |
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Interleukin-3 withdrawal induces an early increase in mitochondrial membrane potential unrelated to the Bcl-2 family. Roles of intracellular pH, ADP transport, and F(0)F(1)-ATPase. | 2001 Mar 2 |
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Mitochondrial Hsp70 Ssc1: role in protein folding. | 2001 Mar 2 |
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High hydrostatic pressure can probe the effects of functionally related ligands on the quaternary structures of the chaperonins GroEL and GroES. | 2001 Mar 2 |
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Activation of the endothelial nitric-oxide synthase by tumor necrosis factor-alpha. A novel feedback mechanism regulating cell death. | 2001 Mar 2 |
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Reversible thermal transition in GrpE, the nucleotide exchange factor of the DnaK heat-shock system. | 2001 Mar 2 |
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Evidence for the selective population of FeMo cofactor sites in MoFe protein and its molecular recognition by the Fe protein in transition state complex analogues of nitrogenase. | 2001 Mar 2 |
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Impaired ATP synthase assembly associated with a mutation in the human ATP synthase subunit 6 gene. | 2001 Mar 2 |
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Correlation between steady-state ATP hydrolysis and vanadate-induced ADP trapping in Human P-glycoprotein. Evidence for ADP release as the rate-limiting step in the catalytic cycle and its modulation by substrates. | 2001 Mar 23 |
|
Rotavirus nonstructural protein NSP2 self-assembles into octamers that undergo ligand-induced conformational changes. | 2001 Mar 30 |
|
Dissection of the ATP-binding domain of the chaperone hsc70 for interaction with the cofactor Hap46. | 2001 Mar 30 |
|
Equilibrium binding of single-stranded DNA to the secondary DNA binding site of the bacterial recombinase RecA. | 2001 Mar 30 |
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ATP modulation of ATP-sensitive potassium channel ATP sensitivity varies with the type of SUR subunit. | 2001 Mar 9 |
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Functional relationships between capacitation-dependent cell signaling and compartmentalized metabolic pathways in murine spermatozoa. | 2001 Mar 9 |
|
Cytosolic phospholipase A2 is required for optimal ATP activation of BK channels in GH(3) cells. | 2001 Mar 9 |
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Transporters on demand: intrahepatic pools of canalicular ATP binding cassette transporters in rat liver. | 2001 Mar 9 |
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The dhb operon of Bacillus subtilis encodes the biosynthetic template for the catecholic siderophore 2,3-dihydroxybenzoate-glycine-threonine trimeric ester bacillibactin. | 2001 Mar 9 |
|
Molecular mechanism for functional interaction between DnaA protein and acidic phospholipids: identification of important amino acids. | 2001 Mar 9 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2807609
Forty-two episodes of spontaneous paroxysmal supraventricular tachycardia, observed in 33 patients (16 men and 17 women, mean age 51 years) were treated with intravenous boluses. These were given in 10 mg increments at increasing doses from 10 to 50 mg at intervals of three minutes if the arrhythmia persisted despite the previous dose. When using a dose less than or equal to 40 mg, tachycardia was terminated in 37 of 42 episodes in less than 50 seconds. More than half of the treated episodes of supraventricular tachycardia terminated with the minimal dose of 10 mg and 7.1% required 40 mg.
Route of Administration:
Intravenous
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:00:45 UTC 2023
by
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on
Fri Dec 15 15:00:45 UTC 2023
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Record UNII |
8L70Q75FXE
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Record Status |
Validated (UNII)
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Record Version |
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LOINC |
73675-1
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1721-0
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10557-7
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35135-3
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46701-9
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DSLD |
3264 (Number of products:65)
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Code System | Code | Type | Description | ||
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ADENOSINE TRIPHOSPHATE
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C209
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DTXSID6022559
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8L70Q75FXE
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318
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56-65-5
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m1413
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91
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8L70Q75FXE
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5957
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100000092008
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SUB12741MIG
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15422
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DB00171
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200-283-2
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D000255
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
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SUBSTRATE -> TARGET |
recAP has a dual mechanism of action via dephosphorylation of both lipopolysaccharides (LPS) and extracellular ATP.
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TRANSPORTER -> SUBSTRATE |
Principal exporter of ATP, and
increased Panx1 expression and stimulation are correlated with an increase in ATP efflux.
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INHIBITOR OF EXPRESSION->TARGET |
DNP decreases the formation of high-energy phosphate bonds in mitochondria and at the same time stimulates systemic oxygen consumption. This dissociative effect is known as uncoupling of oxidative phosphorylation. Weak uncoupler.
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METABOLIC ENZYME -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |