U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of ADENOSINE TRIPHOSPHATE

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

HIDE SMILES / InChI
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

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

PubMed

PubMed

TitleDatePubMed
An enhancement of nitric oxide production regulates energy metabolism in rat hepatocytes after a partial hepatectomy.
1999 May
Involvement of vanilloid receptors and purinoceptors in the Phoneutria nigriventer spider venom-induced plasma extravasation in rat skin.
2000 Mar 17
Dual regulation of leptin secretion: intracellular energy and calcium dependence of regulated pathway.
2000 May
Expression of P2X(7) purinoceptors on human lymphocytes and monocytes: evidence for nonfunctional P2X(7) receptors.
2000 Oct
Iron- and aluminum-induced carcinogenesis.
2000 Sep-Oct
ATP-dependent activation of the intermediate conductance, Ca2+-activated K+ channel, hIK1, is conferred by a C-terminal domain.
2001 Apr 6
The delta subunit of type 6 phosphodiesterase reduces light-induced cGMP hydrolysis in rod outer segments.
2001 Feb 16
Hexamminecobalt(III) chloride inhibits glucose-induced insulin secretion at the exocytotic process.
2001 Feb 2
Characterization of the biosynthesis of human immunodeficiency virus type 1 Env from infected T-cells and the effects of glucose trimming of Env on virion infectivity.
2001 Feb 23
The external calcium-dependent NADPH dehydrogenase from Neurospora crassa mitochondria.
2001 Feb 9
RNA passes through the hole of the protein hexamer in the complex with the Escherichia coli Rho factor.
2001 Feb 9
The molecular chaperone DnaJ is required for the degradation of a soluble abnormal protein in Escherichia coli.
2001 Feb 9
ATP-stimulated release of interleukin (IL)-1beta and IL-18 requires priming by lipopolysaccharide and is independent of caspase-1 cleavage.
2001 Feb 9
Low temperature molecular adaptation of the skeletal muscle sarco(endo)plasmic reticulum Ca2+-ATPase 1 (SERCA 1) in the wood frog (Rana sylvatica).
2001 Feb 9
Protection of cardiac myocytes via delta(1)-opioid receptors, protein kinase C, and mitochondrial K(ATP) channels.
2001 Jan
Role of mitochondrial and sarcolemmal K(ATP) channels in ischemic preconditioning of the canine heart.
2001 Jan
Dual roles of mitochondrial K(ATP) channels in diazoxide-mediated protection in isolated rabbit hearts.
2001 Jan
Minimal protection of the liver by ischemic preconditioning in pigs.
2001 Jan
Modulation of P2Z/P2X(7) receptor activity in macrophages infected with Chlamydia psittaci.
2001 Jan
Impairment of endothelial nitric oxide production by acute glucose overload.
2001 Jan
Actin dynamics.
2001 Jan
Novel properties of the protein kinase CK2-site-regulated nuclear- localization sequence of the interferon-induced nuclear factor IFI 16.
2001 Jan 1
Excluded volume effects on the refolding and assembly of an oligomeric protein. GroEL, a case study.
2001 Jan 12
The Lys1010-Lys1325 fragment of the Wilson's disease protein binds nucleotides and interacts with the N-terminal domain of this protein in a copper-dependent manner.
2001 Jan 19
A hybrid between Na+,K+-ATPase and H+,K+-ATPase is sensitive to palytoxin, ouabain, and SCH 28080.
2001 Jan 26
Kinetic basis for activation of CDK2/cyclin A by phosphorylation.
2001 Jan 5
Biochemical characterization of the DNA helicase activity of the escherichia coli RecQ helicase.
2001 Jan 5
Identification of UvrY as the cognate response regulator for the BarA sensor kinase in Escherichia coli.
2001 Jan 5
Altered cytokine production in mice lacking P2X(7) receptors.
2001 Jan 5
Indirubins inhibit glycogen synthase kinase-3 beta and CDK5/p25, two protein kinases involved in abnormal tau phosphorylation in Alzheimer's disease. A property common to most cyclin-dependent kinase inhibitors?
2001 Jan 5
Glucose deprivation and chemical hypoxia: neuroprotection by P2 receptor antagonists.
2001 Mar
Exogenous Mg-ATP induces a large inhibition of pyruvate kinase in intact rat hepatocytes.
2001 Mar 2
Impaired ATP synthase assembly associated with a mutation in the human ATP synthase subunit 6 gene.
2001 Mar 2
Residues within the conserved helicase motifs of UL9, the origin-binding protein of herpes simplex virus-1, are essential for helicase activity but not for dimerization or origin binding activity.
2001 Mar 2
Executioner caspase-3, -6, and -7 perform distinct, non-redundant roles during the demolition phase of apoptosis.
2001 Mar 9
Patents

Sample Use Guides

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
Name Type Language
ADENOSINE TRIPHOSPHATE
INCI   MART.   MI   VANDF   WHO-DD  
INCI  
Official Name English
ADENOSINE TRIPHOSPHATE [VANDF]
Common Name English
ADENOSINE TRIPHOSPHATE [MART.]
Common Name English
Adenosine triphosphate [WHO-DD]
Common Name English
ADENOSINE 5'-(TETRAHYDROGEN TRIPHOSPHATE)
Systematic Name English
ATP
Common Name English
ADENOSINE TRIPHOSPHATE [MI]
Common Name English
ADENOSINE 5'-TRIPHOSPHATE
Systematic Name English
ADENOSINE 5'-TRIPHOSPHORIC ACID
Common Name English
ADENOSINE TRIPHOSPHATE [INCI]
Common Name English
Classification Tree Code System Code
LOINC 73675-1
Created by admin on Fri Dec 15 15:00:45 GMT 2023 , Edited by admin on Fri Dec 15 15:00:45 GMT 2023
LOINC 1721-0
Created by admin on Fri Dec 15 15:00:45 GMT 2023 , Edited by admin on Fri Dec 15 15:00:45 GMT 2023
LOINC 10557-7
Created by admin on Fri Dec 15 15:00:45 GMT 2023 , Edited by admin on Fri Dec 15 15:00:45 GMT 2023
LOINC 35135-3
Created by admin on Fri Dec 15 15:00:45 GMT 2023 , Edited by admin on Fri Dec 15 15:00:45 GMT 2023
LOINC 46701-9
Created by admin on Fri Dec 15 15:00:45 GMT 2023 , Edited by admin on Fri Dec 15 15:00:45 GMT 2023
DSLD 3264 (Number of products:65)
Created by admin on Fri Dec 15 15:00:45 GMT 2023 , Edited by admin on Fri Dec 15 15:00:45 GMT 2023
Code System Code Type Description
WIKIPEDIA
ADENOSINE TRIPHOSPHATE
Created by admin on Fri Dec 15 15:00:45 GMT 2023 , Edited by admin on Fri Dec 15 15:00:45 GMT 2023
PRIMARY
NCI_THESAURUS
C209
Created by admin on Fri Dec 15 15:00:45 GMT 2023 , Edited by admin on Fri Dec 15 15:00:45 GMT 2023
PRIMARY
EPA CompTox
DTXSID6022559
Created by admin on Fri Dec 15 15:00:45 GMT 2023 , Edited by admin on Fri Dec 15 15:00:45 GMT 2023
PRIMARY
DAILYMED
8L70Q75FXE
Created by admin on Fri Dec 15 15:00:45 GMT 2023 , Edited by admin on Fri Dec 15 15:00:45 GMT 2023
PRIMARY
RXCUI
318
Created by admin on Fri Dec 15 15:00:45 GMT 2023 , Edited by admin on Fri Dec 15 15:00:45 GMT 2023
PRIMARY RxNorm
CAS
56-65-5
Created by admin on Fri Dec 15 15:00:45 GMT 2023 , Edited by admin on Fri Dec 15 15:00:45 GMT 2023
PRIMARY
MERCK INDEX
m1413
Created by admin on Fri Dec 15 15:00:45 GMT 2023 , Edited by admin on Fri Dec 15 15:00:45 GMT 2023
PRIMARY Merck Index
DRUG CENTRAL
91
Created by admin on Fri Dec 15 15:00:45 GMT 2023 , Edited by admin on Fri Dec 15 15:00:45 GMT 2023
PRIMARY
FDA UNII
8L70Q75FXE
Created by admin on Fri Dec 15 15:00:45 GMT 2023 , Edited by admin on Fri Dec 15 15:00:45 GMT 2023
PRIMARY
PUBCHEM
5957
Created by admin on Fri Dec 15 15:00:45 GMT 2023 , Edited by admin on Fri Dec 15 15:00:45 GMT 2023
PRIMARY
SMS_ID
100000092008
Created by admin on Fri Dec 15 15:00:45 GMT 2023 , Edited by admin on Fri Dec 15 15:00:45 GMT 2023
PRIMARY
EVMPD
SUB12741MIG
Created by admin on Fri Dec 15 15:00:45 GMT 2023 , Edited by admin on Fri Dec 15 15:00:45 GMT 2023
PRIMARY
CHEBI
15422
Created by admin on Fri Dec 15 15:00:45 GMT 2023 , Edited by admin on Fri Dec 15 15:00:45 GMT 2023
PRIMARY
DRUG BANK
DB00171
Created by admin on Fri Dec 15 15:00:45 GMT 2023 , Edited by admin on Fri Dec 15 15:00:45 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-283-2
Created by admin on Fri Dec 15 15:00:45 GMT 2023 , Edited by admin on Fri Dec 15 15:00:45 GMT 2023
PRIMARY
MESH
D000255
Created by admin on Fri Dec 15 15:00:45 GMT 2023 , Edited by admin on Fri Dec 15 15:00:45 GMT 2023
PRIMARY