ADENOSINE PHOSPHATE

US Previously Marketed

First approved in 1949

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H14N5O7P
Molecular Weight	347.2212
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC=NC2=C1N=CN2[C@@H]3O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]3O

InChI

InChIKey=UDMBCSSLTHHNCD-KQYNXXCUSA-N

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

HIDE SMILES / InChI

Molecular Formula	C10H14N5O7P
Molecular Weight	347.2212
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://books.google.ru/books?id=BVpDI7n2M9gC&pg=PA87
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
5'-nucleotidase 7 Target ID: P21589 Gene ID: 4907.0 Gene Symbol: NT5E Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/1194267	Substrate 661
Adrenergic receptor 35 Target ID: CHEMBL2331074 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12614440	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Asthma 241 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12614440	Diagnostic		Phase II 1132	Unknown Approved Use Unknown
Ischemia 16 Sources: https://clinicaltrials.gov/ct2/show/NCT00179010	Primary		Not Provided 504	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B1 788 OATP1B3 706

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
OATP1B1 803	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDc1MiJ9fQ%3D%3D	yes [Inhibition 10 uM]
OATP1B3 715	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDc1MiJ9fQ%3D%3D	yes [Inhibition 10 uM]

Sourcing

Vendor/Aggregator	ID	URL
BLD Pharm	BD756296	http://www.bldpharm.com/products/134296-35-8.html
BLD Pharm	BD01225746	http://www.bldpharm.com/products/26763-19-9.html
PubChem	66927421	https://pubchem.ncbi.nlm.nih.gov/compound/66927421

PubMed

Title	Date	PubMed
Adenine-induced selective apoptosis toward HIV chronically infected cells in vitro.	2000 Jul 14	10891366
Functional and molecular characterization of receptor subtypes mediating coronary microvascular dilation to adenosine.	2001 Feb	11162132
The phosphodiesterase inhibitors pentoxifylline and rolipram suppress macrophage activation and nitric oxide production in vitro and in vivo.	2001 Feb	11161985
ST14A cells have properties of a medium-size spiny neuron.	2001 Feb	11161610
Maintaining methylation activities during salt stress. The involvement of adenosine kinase.	2001 Feb	11161043
Characterization of a G protein-coupled receptor for nicotinic acid.	2001 Feb	11160872
Partial agonist clonidine mediates alpha(2)-AR subtypes specific regulation of cAMP accumulation in adenylyl cyclase II transfected DDT1-MF2 cells.	2001 Feb	11160870
Differential actions of PKA and PKC in the regulation of glutamate release by group III mGluRs in the entorhinal cortex.	2001 Feb	11160494
Peptones stimulate intestinal cholecystokinin gene transcription via cyclic adenosine monophosphate response element-binding factors.	2001 Feb	11159844
Regulation of phosphate uptake in primary cultured rabbit renal proximal tubule cells by glucocorticoids: evidence for nongenomic as well as genomic mechanisms.	2001 Feb	11159843
Autoradiographic localization of specific binding of meiosis-activating sterol to cumulus-oocyte complexes from marmoset, cow, and mouse.	2001 Feb	11159355
Beta,gamma-methylene ATP-induced cAMP formation in C6Bu-1 cells: involvement of local metabolism and subsequent stimulation of adenosine A2B receptor.	2001 Feb	11158259
GH mRNA levels are elevated by forskolin but not GH releasing hormone in GHRH receptor-expressing MtT/S somatotroph cell line.	2001 Feb 14	11165046
Polymorphic deletion of three intracellular acidic residues of the alpha 2B-adrenergic receptor decreases G protein-coupled receptor kinase-mediated phosphorylation and desensitization.	2001 Feb 16	11056163
Mechanisms of hydrogen peroxide-induced relaxation in rabbit mesenteric small artery.	2001 Feb 2	11166293
C-type natriuretic peptide has a negative inotropic effect on cardiac myocytes.	2001 Feb 2	11166282
Expression of type I adenylyl cyclase in intrinsic pathways of the hippocampal formation of the macaque (Macaca nemestrina).	2001 Feb 23	11165765
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	11164809
Prostaglandin E2 and vasoactive intestinal peptide increase vascular endothelial cell growth factor mRNAs in lung cancer cells.	2001 Feb-Mar	11165399
Involvement of endogenous PACAP expression in the activity-dependent survival of mouse cerebellar granule cells.	2001 Jan	11164256
G protein and cAMP-dependent protein kinase mediate amyloid beta-peptide inhibition of neuronal glucose uptake.	2001 Jan	11161593
Activity of adenosine diphosphates and triphosphates on a P2Y(T) -type receptor in brain capillary endothelial cells.	2001 Jan	11156575
Peptidergic modulation of an insect Na(+) current: role of protein kinase A and protein kinase C.	2001 Jan	11152737
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	11145997
Tubulin stimulates adenylyl cyclase activity in C6 glioma cells by bypassing the beta-adrenergic receptor: a potential mechanism of G protein activation.	2001 Jan	11145991
Glucose enhances adenylyl cyclase responses in normal but not diabetic GK rat islets.	2001 Jan	11138973
Effects of cilostazol on late lumen loss and repeat revascularization after Palmaz-Schatz coronary stent implantation.	2001 Jan	11136497
Dexamethasone inhibits luteinizing hormone-induced synthesis of steroidogenic acute regulatory protein in cultured rat preovulatory follicles.	2001 Jan	11133671
Nitric oxide attenuates H(2)O(2)-induced endothelial barrier dysfunction: mechanisms of protection.	2001 Jan	11133501
Differential alterations in cardiac adrenergic signaling in chronic hypoxia or norepinephrine infusion.	2001 Jan	11124161
Lymphocytes from spontaneously hypertensive rats exhibit enhanced adenylyl cyclase-Gi protein signaling.	2001 Jan	11121816
An isoform-specific interaction of the membrane anchors affects mammalian adenylyl cyclase type V activity.	2001 Jan	11121109
VIP and PACAP inhibit Fas ligand-mediated bystander lysis by CD4(+) T cells.	2001 Jan 1	11108936
Effects of the nitric oxide/cGMP system compared with the cAMP system on airway mucus secretion in the rat.	2001 Jan 12	11164391
Phentolamine inhibits exocytosis of glucagon by Gi2 protein-dependent activation of calcineurin in rat pancreatic alpha -cells.	2001 Jan 12	10995774
Adenosine receptor subtypes modulate two major functional pathways for hippocampal serotonin release.	2001 Jan 15	11160442
Cloning and sequence of the LYS2 homologue gene from the osmotolerant yeast Pichia sorbitophila.	2001 Jan 15	11124702
Expression and purification of polyhistidine-tagged firefly luciferase in insect cells--a potential alternative for process scale-up.	2001 Jan 23	11164962
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	11164779
Acylation of lysine 983 is sufficient for toxin activity of Bordetella pertussis adenylate cyclase. Substitutions of alanine 140 modulate acylation site selectivity of the toxin acyltransferase CyaC.	2001 Jan 5	11031260
The regulation of type 7 adenylyl cyclase by its C1b region and Escherichia coli peptidylprolyl isomerase, SlyD.	2001 Mar 16	11113152
Neurohormonal regulation of secretion from isolated rat stomach ECL cells: a critical reappraisal.	2001 Mar 2	11164953
The human VPAC1 receptor: three-dimensional model and mutagenesis of the N-terminal domain.	2001 Mar 30	11124960
Stimulation of extracellular signal-regulated kinases and proliferation in rat osteoblastic cells by parathyroid hormone is protein kinase C-dependent.	2001 Mar 9	11108712

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 `Sat Dec 16 17:55:11 GMT 2023` Edited by `admin` on `Sat Dec 16 17:55:11 GMT 2023`
Record UNII	415SHH325A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ADENOSINE PHOSPHATE

Official Name

English

A 5MP

Code

English

adenosine phosphate [INN]

Common Name

English

NSC-20264

Code

English

ADENOSINE 5'-(DIHYDROGEN PHOSPHATE).

Common Name

English

Adenosine phosphate [WHO-DD]

Common Name

English

ADENOSINE 5'-MONOPHOSPHATE

Systematic Name

English

5'-ADENYLIC ACID [USP-RS]

Common Name

English

ADENOSINE PHOSPHATE [INCI]

Common Name

English

A-5MP

Code

English

ADENOSINE PHOSPHATE [MART.]

Common Name

English

ADENOSINE PHOSPHATE [USAN]

Common Name

English

ADENOSINE PHOSPHATE [VANDF]

Common Name

English

5'-ADENYLIC ACID

Systematic Name

English

ADENOSINE PHOSPHATE [HSDB]

Common Name

English

ADENOSINE 5'-MONOPHOSPHORIC ACID

Common Name

English

AMP

Common Name

English

5'-ADENYLIC ACID [MI]

Common Name

English

5'-ADENYLIC ACID [FCC]

Common Name

English

ADENYL

Brand Name

English

ADENOSINE MONOPHOSPHATE

Systematic Name

English

Classification Tree Code System Code

DSLD

3633 (Number of products:8)