ADL5859 HCl

Alias: ADL5859 HCl; ADL-5859; ADL 5859; ADL5859 HCl

Cat No.:V1276 Purity: ≥98%

COA Product Data Instructions for use SDS

ADL5859 HCl (ADL 5859; ADL-5859),the hydrochloride salt of ADL5859, is a potent, orally bioavailable δ-opioid receptor agonist with important biological activity.

ADL5859 HCl Chemical Structure CAS No.: 850173-95-4
Product category: Opioid Receptor

This product is for research use only, not for human use. We do not sell to patients.

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5mg
10mg
25mg
50mg
100mg
250mg
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Other Forms of ADL5859 HCl:

ADL-5859

Official Supplier of:

Top Publications Citing lnvivochem Products

Nature 2021, 597(7874):119-125.

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J Am Chem Soc 2022,144:21831-21836.

Cell 2020,183:1202-1218.e25.

Science Adv 2022:8,eabm9427.

Nature 2021,597(7874):119-125.

Cell 2020,183:1202-1218.e25.

PNAS Nexus 2022,1(3):pgac063.

ACS Nano 2023,17(10):9110-9125.

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Purity & Quality Control Documentation

Current batch：

Purity: ≥98%

COA

MSDS

Instructions

Product Description
Bioactivity & Protocols
Physicochemical Properties
Solubility Data
Calculators
Clinical Trial Information
Biological Data

Product Description

ADL5859 HCl (ADL 5859; ADL-5859), the hydrochloride salt of ADL5859, is a potent, orally bioavailable δ-opioid receptor agonist with important biological activity. It has a Ki of 0.8 nM for δ-opioid receptor activation. ADL5859 demonstrated selectivity towards alternative opioid receptors, including κ and μ.

Biological Activity I Assay Protocols (From Reference)

Targets

δ Opioid Receptor/DOR

ln Vitro

In vitro activity: ADL-5859 (0-10 μM) hydrochloride inhibits 32% and 37% of the activities of the ε and κ opioid receptors, respectively, and exhibits activities to the δ opioid receptor with a Ki and an EC50 value of 0.84 and 20 nM[1].
ADL-5859 (0-100 μM) hydrochloride shows inhibitory activity to the hERG channel with an IC50 value of 78 μM[1].
ADL-5859 (0-100 μM) hydrochloride inhibits the activity of the drug metabolizing enzyme cytochrome P450 2D6 (CYP2D6) in vitro with an IC50 value of 43 μM[2].

ln Vivo

ADL-5859 (0.3–10 mg/kg; p.o. once) hydrochloride exhibits strong antidepressant-like effects and reverses hyperalgesia in rats with inflamed paws[1].

Animal Protocol

Suspended in 0.5% methyl cellulose solution or dissolved in 5% sorbitol; 10 mg/kg; oral or i.v. injection

Male ICR (CD-1) subjected to nociceptin-induced allodynia test or hot plate test, and Male SD rats subjected to formalin-induced paw-licking response

References

[1]. Potent, orally bioavailable delta opioid receptor agonists for the treatment of pain: discovery of N,N-diethyl-4-(5-hydroxyspiro[chromene-2,4'-piperidine]-4-yl)benzamide (ADL5859). J Med Chem. 2008 Oct 9;51(19):5893-6.

[2]. Spirocyclic delta opioid receptor agonists for the treatment of pain: discovery of N,N-diethyl-3-hydroxy-4-(spiro[chromene-2,4'-piperidine]-4-yl) benzamide (ADL5747).J Med Chem. 2009 Sep 24;52(18):5685-702.

These protocols are for reference only. InvivoChem does not independently validate these methods.

Physicochemical Properties

Molecular Formula

C24H29CLN2O3

Molecular Weight

428.95

Exact Mass

428.19

Elemental Analysis

C, 67.20; H, 6.81; Cl, 8.26; N, 6.53; O, 11.19

CAS #

850173-95-4

Related CAS #

850305-06-5 (ADL 5859 free base)

Appearance

Solid powder

SMILES

CCN(CC)C(=O)C1=CC=C(C=C1)C2=CC3(CCNCC3)OC4=CC=CC(=C42)O.Cl

InChi Key

ZFNLSWREIULTDO-UHFFFAOYSA-N

InChi Code

InChI=1S/C24H28N2O3.ClH/c1-3-26(4-2)23(28)18-10-8-17(9-11-18)19-16-24(12-14-25-15-13-24)29-21-7-5-6-20(27)22(19)21;/h5-11,16,25,27H,3-4,12-15H2,1-2H3;1H

Chemical Name

N,N-diethyl-4-(5-hydroxyspiro[chromene-2,4'-piperidine]-4-yl)benzamide;hydrochloride

Synonyms

ADL5859 HCl; ADL-5859; ADL 5859; ADL5859 HCl

HS Tariff Code

2934.99.9001

Storage

Powder -20°C 3 years

4°C 2 years

In solvent -80°C 6 months

-20°C 1 month

Shipping Condition

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Solubility Data

Solubility (In Vitro)

DMSO: ~86 mg/mL (~200.5 mM)

Water: ~5 mg/mL (~11.6 mM)

Ethanol: ~1 mg/mL (~2.3 mM)

Solubility (In Vivo)

0.5% hydroxyethyl cellulose+0.1% Tween 80: 30 mg/mL

(Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.3313 mL	11.6564 mL	23.3127 mL
	5 mM	0.4663 mL	2.3313 mL	4.6625 mL
	10 mM	0.2331 mL	1.1656 mL	2.3313 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Mass

Concentration

Volume

Molecular Weight*

Calculate Reset

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

Calculate the Mass of a compound required to prepare a solution of known volume and concentration
Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume

See Example

An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?

Enter 350.26 in the Molecular Weight (MW) box
Enter 10 in the Concentration box and choose the correct unit (mM)
Enter 5 in the Volume box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Concentration (Start)

Volume (Start)

Concentration (End)

Volume (End)

Calculate Reset

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:

Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
Enter 25 into the Concentration (End) box and select the correct unit (mM)
Enter 25 into the Volume (End) box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box

Molecular formula

Total molecular weight

g/mol

Calculate Reset

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4 c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:

To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.

Definitions of molecular mass, molecular weight, molar mass and molar weight:

Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.

Volume (to add to vial)

Mass (in vial)

Desired Reconstitution Concentration

Calculate Reset

Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
Click the “Calculate” button
The answer appears in the Volume (to add to vial) box

In vivo Formulation Calculator (Clear solution)

Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)

Dosage mg/kg

Average weight of animals g

Dosing volume per animal μL

Number of animals

Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)

% DMSO

% Tween 80

% ddH₂O

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Calculation results

Working concentration： mg/mL；

Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH₂O，mix and clarify.

Note： (1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.

Clinical Trial Information

NCT Number	Recruitment	interventions	Conditions	Sponsor/Collaborators	Start Date	Phases
NCT00603265	Completed	Drug: ADL5859 Drug: Duloxetine	Peripheral Neuropathy Neuropathic Pain	Cubist Pharmaceuticals LLC, a subsidiary of Merck & Co., Inc. (Rahway, New Jersey USA)	November 2007	Phase 2

Biological Data

ADL5747-, ADL5859-, and SNC80-induced analgesia in CFA-induced inflammatory (A and B) or SNL-induced neuropathic (C) pain models in wild-type mice.J Pharmacol Exp Ther.2012 Sep;342(3):799-807.
Locomotor activity after administration of SNC80 and ADL compounds in naive mice.J Pharmacol Exp Ther.2012 Sep;342(3):799-807.
Confocal imaging of SNC80-, ADL5747-, and ADL5859-induced δ-receptor redistribution in DOR-eGFP mice.J Pharmacol Exp Ther.2012 Sep;342(3):799-807.