MedKoo Cat#: 319749 | Name: Irdabisant free base

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Irdabisant, also known as CEP-26401, is a potent, selective histamine H3 receptor inverse agonist. High affinity of CEP-26401 for H₃R was demonstrated in radioligand binding displacement assays in rat brain membranes (K(i) = 2.7 ± 0.3 nM) and recombinant rat and human H₃R-expressing systems (K(i) = 7.2 ± 0.4 and 2.0 ± 1.0 nM, respectively). CEP-26401 displayed potent antagonist and inverse agonist activities in [³⁵S]guanosine 5'-O-(γ-thio)triphosphate binding assays. CEP-26401 may also have therapeutic utility in treating schizophrenia or as adjunctive therapy to approved antipsychotics.

Chemical Structure

Irdabisant free base
Irdabisant free base
CAS#1005402-19-6 (free base)

Theoretical Analysis

MedKoo Cat#: 319749

Name: Irdabisant free base

CAS#: 1005402-19-6 (free base)

Chemical Formula: C18H23N3O2

Exact Mass: 313.1790

Molecular Weight: 313.40

Elemental Analysis: C, 68.98; H, 7.40; N, 13.41; O, 10.21

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Synonym
CEP-26401; CEP 26401; CEP26401; Irdabisant
IUPAC/Chemical Name
(R)-6-(4-(3-(2-methylpyrrolidin-1-yl)propoxy)phenyl)pyridazin-3(2H)-one
InChi Key
XUKROCVZGZNGSI-CQSZACIVSA-N
InChi Code
InChI=1S/C18H23N3O2/c1-14-4-2-11-21(14)12-3-13-23-16-7-5-15(6-8-16)17-9-10-18(22)20-19-17/h5-10,14H,2-4,11-13H2,1H3,(H,20,22)/t14-/m1/s1
SMILES Code
O=C1C=CC(C2=CC=C(OCCCN3[C@H](C)CCC3)C=C2)=NN1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 313.40 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Hudkins RL, Becknell NC, Lyons JA, Aimone LD, Olsen M, Haltiwanger RC, Mathiasen JR, Raddatz R, Gruner JA. 3,4-Diaza-bicyclo[4.1.0]hept-4-en-2-one phenoxypropylamine analogs of irdabisant (CEP-26401) as potent histamine-3 receptor inverse agonists with robust wake-promoting activity. Eur J Med Chem. 2015 May 5;95:349-56. doi: 10.1016/j.ejmech.2015.03.054. Epub 2015 Mar 24. PubMed PMID: 25827402. 2: Hudkins RL, Josef KA, Becknell NC, Aimone LD, Lyons JA, Mathiasen JR, Gruner JA, Raddatz R. Discovery of (1R,6S)-5-[4-(1-cyclobutyl-piperidin-4-yloxy)-phenyl]-3,4-diaza-bicyclo[4.1.0]hep t-4-en-2-one (R,S-4a): histamine H(3) receptor inverse agonist demonstrating potent cognitive enhancing and wake promoting activity. Bioorg Med Chem Lett. 2014 Mar 1;24(5):1303-6. doi: 10.1016/j.bmcl.2014.01.061. Epub 2014 Jan 30. PubMed PMID: 24513042. 3: Josef KA, Aimone LD, Lyons J, Raddatz R, Hudkins RL. Synthesis of constrained benzocinnolinone analogues of CEP-26401 (irdabisant) as potent, selective histamine H3 receptor inverse agonists. Bioorg Med Chem Lett. 2012 Jun 15;22(12):4198-202. doi: 10.1016/j.bmcl.2012.04.001. Epub 2012 Apr 26. PubMed PMID: 22617490. 4: Becknell NC, Lyons JA, Aimone LD, Gruner JA, Mathiasen JR, Raddatz R, Hudkins RL. Synthesis and evaluation of pyridone-phenoxypropyl-R-2-methylpyrrolidine analogues as histamine H3 receptor antagonists. Bioorg Med Chem Lett. 2011 Dec 1;21(23):7076-80. doi: 10.1016/j.bmcl.2011.09.091. Epub 2011 Sep 29. PubMed PMID: 22014551. 5: Raddatz R, Hudkins RL, Mathiasen JR, Gruner JA, Flood DG, Aimone LD, Le S, Schaffhauser H, Duzic E, Gasior M, Bozyczko-Coyne D, Marino MJ, Ator MA, Bacon ER, Mallamo JP, Williams M. CEP-26401 (irdabisant), a potent and selective histamine H₃ receptor antagonist/inverse agonist with cognition-enhancing and wake-promoting activities. J Pharmacol Exp Ther. 2012 Jan;340(1):124-33. doi: 10.1124/jpet.111.186585. Epub 2011 Oct 14. PubMed PMID: 22001260. 6: Hudkins RL, Raddatz R, Tao M, Mathiasen JR, Aimone LD, Becknell NC, Prouty CP, Knutsen LJ, Yazdanian M, Moachon G, Ator MA, Mallamo JP, Marino MJ, Bacon ER, Williams M. Discovery and characterization of 6-{4-[3-(R)-2-methylpyrrolidin-1-yl)propoxy]phenyl}-2H-pyridazin-3-one (CEP-26401, irdabisant): a potent, selective histamine H3 receptor inverse agonist. J Med Chem. 2011 Jul 14;54(13):4781-92. doi: 10.1021/jm200401v. Epub 2011 Jun 2. PubMed PMID: 21634396.