ID: ALA326702

Max Phase: Preclinical

Molecular Formula: C12H15N3O2S

Molecular Weight: 265.34

Molecule Type: Small molecule

Representations

Synonyms (1): ABT-866
Synonyms from Alternative Forms(1):

Canonical SMILES:  CCS(=O)(=O)Nc1cccc(Cc2c[nH]cn2)c1

Standard InChI:  InChI=1S/C12H15N3O2S/c1-2-18(16,17)15-11-5-3-4-10(6-11)7-12-8-13-9-14-12/h3-6,8-9,15H,2,7H2,1H3,(H,13,14)

Standard InChI Key:  ROUIPNDCVDWYEH-UHFFFAOYSA-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: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 265.34

Molecular Weight (Monoisotopic): 265.0885

AlogP: 1.76

#Rotatable Bonds: 5

Polar Surface Area: 74.85

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.17

CX Basic pKa: 6.62

CX LogP: 0.70

CX LogD: 0.64

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.86

Np Likeness Score: -1.39

References

1. Altenbach RJ, Khilevich A, Kolasa T, Rohde JJ, Bhatia PA, Patel MV, Searle XB, Yang F, Bunnelle WH, Tietje K, Bayburt EK, Carroll WA, Meyer MD, Henry R, Buckner SA, Kuk J, Daza AV, Milicic IV, Cain JC, Kang CH, Ireland LM, Carr TL, Miller TR, Hancock AA, Nakane M, Esbenshade TA, Brune ME, O'Neill AB, Gauvin DM, Katwala SP, Holladay MW, Brioni JD, Sullivan JP..  (2004)  Synthesis and structure-activity studies on N-[5-(1H-imidazol-4-yl)-5,6,7,8-tetrahydro-1-naphthalenyl]methanesulfonamide, an imidazole-containing alpha(1A)-adrenoceptor agonist.,  47  (12): [PMID:15163201] [10.1021/jm030551a]

2. Altenbach RJ, Khilevich A, Meyer MD, Buckner SA, Milicic I, Daza AV, Brune ME, O'Neill AB, Gauvin DM, Cain JC, Nakane M, Holladay MW, Williams M, Brioni JD, Sullivan JP..  (2002)  N-[3-(1H-imidazol-4-ylmethyl)phenyl]ethanesulfonamide (ABT-866, 1),(1) a novel alpha(1)-adrenoceptor ligand with an enhanced in vitro and in vivo profile relative to phenylpropanolamine and midodrine.,  45  (20): [PMID:12238918] [10.1021/jm025550h]

3. Whitlock GA, Conlon K, McMurray G, Roberts LR, Stobie A, Thurlow RJ..  (2008)  Novel 2-imidazoles as potent and selective alpha1A adrenoceptor partial agonists.,  18  (9): [PMID:18400496] [10.1016/j.bmcl.2008.03.070]

4. Jain KS, Bariwal JB, Kathiravan MK, Phoujdar MS, Sahne RS, Chauhan BS, Shah AK, Yadav MR..  (2008)  Recent advances in selective alpha1-adrenoreceptor antagonists as antihypertensive agents.,  16  (9): [PMID:18378462] [10.1016/j.bmc.2008.02.091]

5. Carroll WA, Altenbach RJ, Buckner SA, Brioni JD, Brune ME, Kolasa T, Meyer MD, Sullivan JP.  (2004)  In Vitro and In Vivo Characterization of Alpha-1A Selective Agonists and Their Utility for Stress Incontience,  13  (3): [10.1007/s00044-004-0020-z]

Source

Source(1):

• Scientific Literature