Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C10H12N5O7P.2K |
| Molecular Weight | 423.4019 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[K+].[K+].NC1=NC=NC2=C1N=CN2[C@@H]3O[C@H](COP([O-])([O-])=O)[C@@H](O)[C@H]3O
InChI
InChIKey=OYERHOIFBRDTSU-IDIVVRGQSA-L
InChI=1S/C10H14N5O7P.2K/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);;/q;2*+1/p-2/t4-,6-,7-,10-;;/m1../s1
| Molecular Formula | C10H12N5O7P |
| Molecular Weight | 345.2053 |
| Charge | -2 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | K |
| Molecular Weight | 39.0983 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/12614440 |
https://clinicaltrials.gov/ct2/show/NCT00179010
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/12614440 |
https://clinicaltrials.gov/ct2/show/NCT00179010
Adenosine monophosphate (AMP) is a nucleotide, consisting of a phosphate group, the sugar ribose, and the nucleobase adenine. AMP is an activator of several enzymes in the tissues. In the glycolytic pathway, the enzyme phosphofructokinase is inhibited by ATP but the inhibition is reversed by AMP, the deciding factor for the reaction being the ratio between ATP and AMP. In medicine, AMP is used mainly as an alternative to adenosine for treatment of ischemia and as a tool compound to measure hyperresponsiveness of airways.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P21589 Gene ID: 4907.0 Gene Symbol: NT5E Target Organism: Homo sapiens (Human) |
|||
Target ID: CHEMBL2331074 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Diagnostic | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Functional and molecular characterization of receptor subtypes mediating coronary microvascular dilation to adenosine. | 2001 Feb |
|
| The phosphodiesterase inhibitors pentoxifylline and rolipram suppress macrophage activation and nitric oxide production in vitro and in vivo. | 2001 Feb |
|
| ST14A cells have properties of a medium-size spiny neuron. | 2001 Feb |
|
| Maintaining methylation activities during salt stress. The involvement of adenosine kinase. | 2001 Feb |
|
| Characterization of a G protein-coupled receptor for nicotinic acid. | 2001 Feb |
|
| Partial agonist clonidine mediates alpha(2)-AR subtypes specific regulation of cAMP accumulation in adenylyl cyclase II transfected DDT1-MF2 cells. | 2001 Feb |
|
| Differential actions of PKA and PKC in the regulation of glutamate release by group III mGluRs in the entorhinal cortex. | 2001 Feb |
|
| Peptones stimulate intestinal cholecystokinin gene transcription via cyclic adenosine monophosphate response element-binding factors. | 2001 Feb |
|
| Regulation of phosphate uptake in primary cultured rabbit renal proximal tubule cells by glucocorticoids: evidence for nongenomic as well as genomic mechanisms. | 2001 Feb |
|
| Autoradiographic localization of specific binding of meiosis-activating sterol to cumulus-oocyte complexes from marmoset, cow, and mouse. | 2001 Feb |
|
| Adrenomedullin expression and growth inhibitory effects in distinct pulmonary artery smooth muscle cell subpopulations. | 2001 Feb |
|
| Regulation of G protein-coupled receptor-adenylyl cyclase responsiveness in human airway smooth muscle by exogenous and autocrine adenosine. | 2001 Feb |
|
| PTH and PTH-related peptide enhance steroid secretion from human adrenocortical cells. | 2001 Feb |
|
| Beta,gamma-methylene ATP-induced cAMP formation in C6Bu-1 cells: involvement of local metabolism and subsequent stimulation of adenosine A2B receptor. | 2001 Feb |
|
| C2-ceramide and reactive oxygen species inhibit pituitary adenylate cyclase activating polypeptide (PACAP)-induced cyclic-AMP-dependent signalling pathway. | 2001 Feb |
|
| Construction of gene therapy vectors targeting thyroid cells: enhancement of activity and specificity with histone deacetylase inhibitors and agents modulating the cyclic adenosine 3',5'-monophosphate pathway and demonstration of activity in follicular and anaplastic thyroid carcinoma cells. | 2001 Feb |
|
| Orexin A stimulates cortisol secretion from human adrenocortical cells through activation of the adenylate cyclase-dependent signaling cascade. | 2001 Feb |
|
| Leptin-induced lipolysis opposes the tonic inhibition of endogenous adenosine in white adipocytes. | 2001 Feb |
|
| Structural analysis of adenylate cyclases from Trypanosoma brucei in their monomeric state. | 2001 Feb 1 |
|
| Brief treatments with forskolin enhance s-phase entry in balance epithelia from the ears of rats. | 2001 Feb 1 |
|
| GH mRNA levels are elevated by forskolin but not GH releasing hormone in GHRH receptor-expressing MtT/S somatotroph cell line. | 2001 Feb 14 |
|
| Mechanisms of hydrogen peroxide-induced relaxation in rabbit mesenteric small artery. | 2001 Feb 2 |
|
| C-type natriuretic peptide has a negative inotropic effect on cardiac myocytes. | 2001 Feb 2 |
|
| Expression of type I adenylyl cyclase in intrinsic pathways of the hippocampal formation of the macaque (Macaca nemestrina). | 2001 Feb 23 |
|
| Does the developmental neurotoxicity of chlorpyrifos involve glial targets? Macromolecule synthesis, adenylyl cyclase signaling, nuclear transcription factors, and formation of reactive oxygen in C6 glioma cells. | 2001 Feb 9 |
|
| Prostaglandin E2 and vasoactive intestinal peptide increase vascular endothelial cell growth factor mRNAs in lung cancer cells. | 2001 Feb-Mar |
|
| Involvement of endogenous PACAP expression in the activity-dependent survival of mouse cerebellar granule cells. | 2001 Jan |
|
| G protein and cAMP-dependent protein kinase mediate amyloid beta-peptide inhibition of neuronal glucose uptake. | 2001 Jan |
|
| Nitrogen-dependent accumulation of cytokinins in root and the translocation to leaf: implication of cytokinin species that induces gene expression of maize response regulator. | 2001 Jan |
|
| Differential coupling of the human P2Y(11) receptor to phospholipase C and adenylyl cyclase. | 2001 Jan |
|
| Activity of adenosine diphosphates and triphosphates on a P2Y(T) -type receptor in brain capillary endothelial cells. | 2001 Jan |
|
| Peptidergic modulation of an insect Na(+) current: role of protein kinase A and protein kinase C. | 2001 Jan |
|
| cAMP-dependent presynaptic regulation of spontaneous glycinergic IPSCs in mechanically dissociated rat spinal cord neurons. | 2001 Jan |
|
| Effects of prostaglandin E2 and cAMP elevating drugs on GM-CSF release by cultured human airway smooth muscle cells. Relevance to asthma therapy. | 2001 Jan |
|
| Regulation of TNF-alpha-induced eotaxin release from cultured human airway smooth muscle cells by beta2-agonists and corticosteroids. | 2001 Jan |
|
| Extracellular ATP formation on vascular endothelial cells is mediated by ecto-nucleotide kinase activities via phosphotransfer reactions. | 2001 Jan |
|
| A novel transverse push-pull microprobe: in vitro characterization and in vivo demonstration of the enzymatic production of adenosine in the spinal cord dorsal horn. | 2001 Jan |
|
| Tubulin stimulates adenylyl cyclase activity in C6 glioma cells by bypassing the beta-adrenergic receptor: a potential mechanism of G protein activation. | 2001 Jan |
|
| AgRP(83-132) acts as an inverse agonist on the human-melanocortin-4 receptor. | 2001 Jan |
|
| Localization and mechanisms of action of cannabinoid receptors at the glutamatergic synapses of the mouse nucleus accumbens. | 2001 Jan 1 |
|
| Role of stimulatory guanine nucleotide binding protein (GSalpha) in proliferation of PC-3M prostate cancer cells. | 2001 Jan 1 |
|
| Chemical coding of intrinsic and extrinsic nerves in the guinea pig gallbladder: distributions of PACAP and orphanin FQ. | 2001 Jan 1 |
|
| Pituitary adenylate cyclase activating peptide (PACAP) in the enteropancreatic innervation. | 2001 Jan 1 |
|
| Effects of the nitric oxide/cGMP system compared with the cAMP system on airway mucus secretion in the rat. | 2001 Jan 12 |
|
| Adenosine receptor subtypes modulate two major functional pathways for hippocampal serotonin release. | 2001 Jan 15 |
|
| Expression and purification of polyhistidine-tagged firefly luciferase in insect cells--a potential alternative for process scale-up. | 2001 Jan 23 |
|
| Cerebroprotective action of a Na+/Ca2+ channel blocker NS-7. I. Effect on the cerebral infarction and edema at the acute stage of permanent middle cerebral artery occlusion in rats. | 2001 Jan 26 |
|
| Estrogen modulates norepinephrine-induced accumulation of adenosine cyclic monophosphate in a subpopulation of immortalized luteinizing hormone-releasing hormone secreting neurons from the mouse hypothalamus. | 2001 Jan 26 |
|
| Hypothalamic orexin-A binding sites are downregulated by chronic nicotine treatment in the rat. | 2001 Jan 26 |
|
| Neurohormonal regulation of secretion from isolated rat stomach ECL cells: a critical reappraisal. | 2001 Mar 2 |
Patents
Sample Use Guides
In clinical studies for treatment of Ichemia, adenosine monophosphate is administered by intraaterial infusion of AMP at 3 different doses for 15 minutes each (at equimolar doses as adenosine). As a tool to measure hyperresponsiveness of airways, AMP was administered internasally.
Route of Administration:
Other
To measure activity of 5’-nucleotidase, lymphocytes from peripheral blood were incubated with [G-3H]adenosine 5'-monophosphate. Aliquots were removed after 0, 15, 30, and 60 min of incubation without shaking. The cells were washed twice with phosphate buffered saline. The cells were dissolved in 7 ml of Aquasol, and the radioactivity was determined in a scintillation counter.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 17:15:10 GMT 2023
by
admin
on
Fri Dec 15 17:15:10 GMT 2023
|
| Record UNII |
225M14T7DD
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Systematic Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
225M14T7DD
Created by
admin on Fri Dec 15 17:15:10 GMT 2023 , Edited by admin on Fri Dec 15 17:15:10 GMT 2023
|
PRIMARY | |||
|
66927421
Created by
admin on Fri Dec 15 17:15:10 GMT 2023 , Edited by admin on Fri Dec 15 17:15:10 GMT 2023
|
PRIMARY | |||
|
100000078854
Created by
admin on Fri Dec 15 17:15:10 GMT 2023 , Edited by admin on Fri Dec 15 17:15:10 GMT 2023
|
PRIMARY | |||
|
SUB00299MIG
Created by
admin on Fri Dec 15 17:15:10 GMT 2023 , Edited by admin on Fri Dec 15 17:15:10 GMT 2023
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
PARENT -> SALT/SOLVATE |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |