ADENOSINE PHOSPHATE

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

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	MOL RATIO 1 MOL RATIO (average)

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

Description

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	Substrate 661
Adrenergic receptor 35	Agonist 2,752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Asthma 244	Diagnostic		Phase II 1,147	Unknown
Ischemia 16	Primary		Not Provided 511	Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B1 1,079 OATP1B3 961

Drug as perpetrator

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Target	Modality	Activity	Metabolite	Clinical evidence
OATP1B1 1,095	inhibitor 4,027	yes [Inhibition 10 uM]
OATP1B3 970	inhibitor 4,027	yes [Inhibition 10 uM]

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Sourcing

Sourcing

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

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PubMed

Show entries

Title	Date	PubMed
Effects of hyperprolactinemia on testosterone production in rat Leydig cells.	2001	11135360
Homo- and heterodimerization of somatostatin receptor subtypes. Inactivation of sst(3) receptor function by heterodimerization with sst(2A).	2001 Apr 27	11134004
Functional and molecular characterization of receptor subtypes mediating coronary microvascular dilation to adenosine.	2001 Feb	11162132
Adrenomedullin expression and growth inhibitory effects in distinct pulmonary artery smooth muscle cell subpopulations.	2001 Feb	11159051
PTH and PTH-related peptide enhance steroid secretion from human adrenocortical cells.	2001 Feb	11158922

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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.