Neca

HCID 448222

Basic information

CAS
35920-39-9
Standard SMILES
CCNC(=O)[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O
InChIKey
JADDQZYHOWSFJD-FLNNQWSLSA-N
Molecular formula
C12H16N6O4
Average molar mass
308.29 g/mol
Monoisotopic mass
308.12330299

Overview

N-ethyl-5'-carboxamidoadenosine is a derivative of adenosine in which the 5'-hydroxymethyl group is replaced by an N-ethylcarboxamido group. It has a role as an antineoplastic agent, a vasodilator agent, an EC 3.1.4.* (phosphoric diester hydrolase) inhibitor, an adenosine A1 receptor agonist and an adenosine A2A receptor agonist. It is a member of adenosines and a monocarboxylic acid amide. It is functionally related to an adenosine.

Names & identifiers

Preferred name
Neca
IUPAC
(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-N-ethyl-3,4-dihydroxyoxolane-2-carboxamide
English name
NECA
Molecular formula
C12H16N6O4
Molecular weight
308.29

Names & synonyms

NECAN-ethyl-5'-carboxamidoadenosine(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-N-ethyl-3,4-dihydroxyoxolane-2-carboxamide3WC8SJ5ZLJCHEBI:73284RefChem:109229935920-39-95'-N-Ethylcarboxamidoadenosine5'-Ethylcarboxamido AdenosineAdenosine-5'-(N-ethylcarboxamide)N-Ethylcarboxamidoadenosine[3H]NECA
Show more names
D-NECA744-96765-21B-744-96NECA USP/EP/BPNECA, adenosine agonist5'-ETHYLCARBOXAMIDOADENOSINE5’-EthylcarboxamidoAdenosineAdenosine-5'-ethylcarboxamide
MFCD000691951-(6-Amino-9H-purin-9-yl)-1-deoxy-N-ethyl-beta-D-ribofuranuronamide(2S,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-N-ethyl-3,4-dihydroxytetrahydrofuran-2-carboxamideMLS000069759CHEMBL464859Adenosine-5-(N-ethylcarboxamide)AC-27392C12H16N6O4

Database identifiers

CAS
35920-39-9、78647-50-4
PubChem CID
448222
DTXSID
DTXSID801017234
ChEMBL
CHEMBL464859
ChEBI
CHEBI:73284
UNII
3WC8SJ5ZLJ
EC Number
636-060-5、636-863-0
Nikkaji
J260.378K

Properties

Computed structural properties

XLogP
-0.7
Topological polar surface area
148 Ų
Hydrogen bond donors
4
Hydrogen bond acceptors
8
Rotatable bonds
3
Heavy atoms
22

Experimental & physicochemical properties

Solubility>46.2 [ug/mL] (The mean of the results at pH 7.4)

Physicochemical properties

Melting point
229 · 229-231°C
Density
1.87 · 1.87±0.1 g/cm3(Predicted)
storage temp.
2 · 2-8°C
solubility
45 % · 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 0.2 mg/mL Solutions may be stored for several days at 4°C.
pka
12.93 · 12.93±0.70(Predicted)
form
powder

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 1 notifications to the ECHA C&L Inventory.

Danger

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

Hazard information

Hazard Classes and Categories · 2 items

Acute Tox. 2 (100%)

Acute Tox. 2 (100%)

Safety data

wgk
3
rtecs
VJ2232000
ridadr
UN 2811 6.1/PG 2
hs_code
29349990
risk_code
28
Signal word
Danger

Chemistry & industry

Applications · 4 items

UsesA potent adenosine receptor agonist. Inhibits platelet aggregation and is centrally active in vivo

UsesPotent adenosine receptor agonist with some affinity at A1 and A2 receptors

Uses5′-(N-Ethylcarboxamido)adenosine has been used:for the purification of human adenosine A2Areceptor (A2AR) in decylmaltoside (DM)to determine nonspecific binding of adenosine receptorsto investigate adenosine 2B receptor (RA2B) mechanism of action by competition assay

General DescriptionA cell-permeable adenosine analog that acts a potent non-selective agonist of adenosine receptors (Ki = 14 nM, 20 nM, 2.4 μM and 6.2 nM for A1, A2A, A2B, A3, respectively). Increases intracellular cAMP production (EC50 = 3.1 μM in A2B expressing CHO cells). Shown to increase glucagon release in a dose-dependent manner and inhibit insulin release at low concentrations. Although at higher concentration some insulin release is observed. Also, displays a wide range adenosine-dependent effects, such as blocking platelet aggregation and inhibiting DNA synthesis. When administered at reperfusion, it is shown reduce infarction and block the formation of the mitochondrial permeability transition pore by activating p70S6 kinase.

Suppliers70 total

陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]
苏州道澜生物医药科技有限公司15952404857 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
武汉敬康恩生物医药科技有限公司13720134139 086-15871494362 13720134139 · [email protected]

Additional notes

DefinitionChEBI: A derivative of adenosine in which the 5'-hydroxymethyl group is replaced by an N-ethylcarboxamido group.

Related reactions

5 records

Compound notes

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