Ethanesulfonic acid [3-(1H-imidazol-4-ylmethyl)-phenyl]-amide

ID: ALA326702

Chembl Id: CHEMBL326702

Cas Number: 258526-74-8

PubChem CID: 9838192

Max Phase: Preclinical

Molecular Formula: C12H15N3O2S

Molecular Weight: 265.34

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: ABT-866 | ABT-866|258526-74-8|ABT 866|Ethanesulfonamide, N-(3-(1H-imidazol-4-ylmethyl)phenyl)-|P7JGJ12E1W|CHEMBL326702|A-286666|N-(3-(1H-imidazol-4-ylmethyl)phenyl)ethanesulfonamide|Ethanesulfonamide, N-(3-(1H-imidazol-5-ylmethyl)phenyl)-|N-(3-((1H-Imidazol-5-yl)methyl)phenyl)ethanesulfonamide|UNII-P7JGJ12E1W|A 286666|SCHEMBL5612868|BDBM50118705|AKOS040750039|N-[3-(1H-imidazol-5-ylmethyl)phenyl]ethanesulfonamide|Q27286326|N-[3-(1H-imidazol-4-ylmethyl)-phenyl]ethanesulfonamide|N-(3-((1H-imidazol-Show More

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

Associated Targets(Human)

ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA1A Tclin Adrenergic receptors; alpha-1 A & B (290 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA1A Tclin Alpha adrenergic receptor (1a and 1d) (128 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA1B Tclin Alpha-1b adrenergic receptor (2912 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA1D Tclin Alpha-1d adrenergic receptor (4171 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Adra1a Alpha-1a adrenergic receptor (3346 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA1B Alpha-1b adrenergic receptor (201 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Adra1d Alpha-1d adrenergic receptor (1475 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Adra1b Alpha adrenergic receptor 1A and 1B (134 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Adra1d Alpha adrenergic receptor 1A and 1D (103 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA1A Alpha-1a adrenergic receptor (209 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Adra1b Alpha-1b adrenergic receptor (2470 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Adra2b Alpha-2b adrenergic receptor (94 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Adra2a Alpha-2a adrenergic receptor (204 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Canis familiaris (36305 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Oryctolagus cuniculus (11301 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 265.34Molecular Weight (Monoisotopic): 265.0885AlogP: 1.76#Rotatable Bonds: 5
Polar Surface Area: 74.85Molecular Species: NEUTRALHBA: 3HBD: 2
#RO5 Violations: HBA (Lipinski): 5HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: 10.17CX Basic pKa: 6.62CX LogP: 0.70CX LogD: 0.64
Aromatic Rings: 2Heavy Atoms: 18QED Weighted: 0.86Np 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