Vipadenant (formerly BIIB-014; CEB-4520; V-2006; VER-11135) is a novel potent, selective and orally bioactive antagonist of adenosine A2A receptor with immunomodulatory and antidegenerative effects. The use of vitexenant as a Parkinson's disease treatment is being studied. Clinical trials in phase II evaluated dipademant. Vipadenant exhibited good selectivity against A3 (Ki = 1005 nM), but only modest selectivity against A1 and A2B (Ki = 63 nM). It also demonstrated excellent binding affinity for A2A. 44 demonstrated a minimum effective dose of 0.1 mg/kg in the mouse and 1 mg/kg in the rat haloperidol-induced hypolocomotion models when tested in vivo.

Physicochemical Properties

Molecular Formula	C16H15N7O
Molecular Weight	321.34
Exact Mass	321.134
Elemental Analysis	C, 59.80; H, 4.71; N, 30.51; O, 4.98
CAS #	442908-10-3
Related CAS #	442908-10-3
PubChem CID	21874557
Appearance	White to off-white solid powder
LogP	2.513
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	3
Heavy Atom Count	24
Complexity	439
Defined Atom Stereocenter Count	0
SMILES	O1C([H])=C([H])C([H])=C1C1=C2C(=NC(N([H])[H])=N1)N(C([H])([H])C1C([H])=C([H])C(=C(C([H])([H])[H])C=1[H])N([H])[H])N=N2
InChi Key	HQSBCDPYXDGTCL-UHFFFAOYSA-N
InChi Code	InChI=1S/C16H15N7O/c1-9-7-10(4-5-11(9)17)8-23-15-14(21-22-23)13(19-16(18)20-15)12-3-2-6-24-12/h2-7H,8,17H2,1H3,(H2,18,19,20)
Chemical Name	3-[(4-amino-3-methylphenyl)methyl]-7-(furan-2-yl)triazolo[4,5-d]pyrimidin-5-amine
Synonyms	CEB-4520; VER-11135; CEB4520; BIIB014; BIIB 014; V-2006; VER-A00-11; VER-A00049; CEB 4520; BIIB-014; V2006; V 2006; VER-ADO-49
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)

Biological Activity

Targets	A2A ( Ki = 1.3 nM ); A1 ( Ki = 68 nM ); A3 ( Ki = 1005 nM )
ln Vivo	Vipadenant (0.3-30 mg/kg) causes a decrease in catalepsy that is dose-dependent. In rats with 6-OHDA lesions, pupadenant (10 mg/kg) does not cause any statistically significant dyskinetic episodes over the course of a 19-day dosage regimen[1]. The minimum effective dose of vipadenant in the mouse and rat models of haloperidol-induced hypolocomotion is 0.1 mg/kg and 1 mg/kg, respectively. In rats with 6-OHDA lesions, vivadenant (3 and 10 mg/kg, p.o.) can enhance contralateral rotations[2].
References	[1]. A2A receptor antagonists do not induce dyskinesias in drug-naive or L-dopa sensitized rats. Brain Res Bull. 2013 Sep;98:163-9. [2]. Adenosine A2A Receptor Antagonists and Parkinson’s Disease. ACS Chem Neurosci. 2011 Oct 19; 2(10): 555-567.
Additional Infomation	Drug Indication Investigated for use/treatment in parkinson's disease.

Solubility Data

Solubility (In Vitro)

DMSO: ~31 mg/mL (~96.5 mM) Water: N/A Ethanol: N/A

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.1120 mL	15.5598 mL	31.1197 mL
	5 mM	0.6224 mL	3.1120 mL	6.2239 mL
	10 mM	0.3112 mL	1.5560 mL	3.1120 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.