ID: ALA1829335

Max Phase: Phase

Molecular Formula: C18H23N3O2

Molecular Weight: 313.40

Molecule Type: Small molecule

Representations

Synonyms (4): Cep 26401 | Irdabisant | CEP-26401 | CEP26401
Synonyms from Alternative Forms(4):

Canonical SMILES:  C[C@@H]1CCCN1CCCOc1ccc(-c2ccc(=O)[nH]n2)cc1

Standard InChI:  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

Standard InChI Key:  XUKROCVZGZNGSI-CQSZACIVSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Properties

Molecular Weight: 313.40

Molecular Weight (Monoisotopic): 313.1790

AlogP: 2.69

#Rotatable Bonds: 6

Polar Surface Area: 58.22

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.43

CX Basic pKa: 9.57

CX LogP: 1.81

CX LogD: -0.13

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.83

Np Likeness Score: -1.58

References

1. 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..  (2011)  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.,  54  (13): [PMID:21634396] [10.1021/jm200401v]

2. Hudkins RL, Aimone LD, Bailey TR, Bendesky RJ, Dandu RR, Dunn D, Gruner JA, Josef KA, Lin YG, Lyons J, Marcy VR, Mathiasen JR, Sundar BG, Tao M, Zulli AL, Raddatz R, Bacon ER..  (2011)  Identification of pyridazin-3-one derivatives as potent, selective histamine H₃ receptor inverse agonists with robust wake activity.,  21  (18): [PMID:21782432] [10.1016/j.bmcl.2011.06.108]

3. Tao M, Raddatz R, Aimone LD, Hudkins RL..  (2011)  Synthesis and structure-activity relationships of 4,5-fused pyridazinones as histamine H₃ receptor antagonists.,  21  (20): [PMID:21906941] [10.1016/j.bmcl.2011.08.045]

4. Dandu RR, Gruner JA, Mathiasen JR, Aimone LD, Hostetler G, Benfield C, Bendesky RJ, Marcy VR, Raddatz R, Hudkins RL..  (2011)  Synthesis and evaluation of pyridazinone-phenethylamine derivatives as selective and orally bioavailable histamine H3 receptor antagonists with robust wake-promoting activity.,  21  (21): [PMID:21944855] [10.1016/j.bmcl.2011.08.104]

5. Tao M, Aimone LD, Huang Z, Mathiasen J, Raddatz R, Lyons J, Hudkins RL..  (2012)  Optimization of 5-pyridazin-3-one phenoxypropylamines as potent, selective histamine H₃ receptor antagonists with potent cognition enhancing activity.,  55  (1): [PMID:22107017] [10.1021/jm201295j]

6. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

7. Hudkins RL, Josef KA, Becknell NC, Aimone LD, Lyons JA, Mathiasen JR, Gruner JA, Raddatz R..  (2014)  Discovery of (1R,6S)-5-[4-(1-cyclobutyl-piperidin-4-yloxy)-phenyl]-3,4-diaza-bicyclo[4.1.0]hept-4-en-2-one (R,S-4a): histamine H(3) receptor inverse agonist demonstrating potent cognitive enhancing and wake promoting activity.,  24  (5): [PMID:24513042] [10.1016/j.bmcl.2014.01.061]

8. Hudkins RL, Becknell NC, Lyons JA, Aimone LD, Olsen M, Haltiwanger RC, Mathiasen JR, Raddatz R, Gruner JA..  (2015)  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.,  95  [PMID:25827402] [10.1016/j.ejmech.2015.03.054]

9. Unpublished dataset, 

Source

Source(3):

• Scientific Literature
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names