4-[1-(2,3-Dimethyl-phenyl)-ethyl]-1H-imidazole

ID: ALA778

Cas Number: 113775-47-6

PubChem CID: 5311068

Product Number: D129818, Order Now?

Max Phase: Approved

First Approval: 1999

Molecular Formula: C13H16N2

Molecular Weight: 200.28

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Dexmedetomidine | Medetomidine, (s)- | MPV-1440 | DEXMEDETOMIDINE|113775-47-6|Dexmedetomidinum|MPV 1440|4-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole|5-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole|Dexmedetomidina|(+)-4-((S)-alpha,2,3-Trimethylbenzyl)imidazole|MPV-1440|Medetomidine, (s)-|(S)-5-(1-(2,3-Dimethylphenyl)ethyl)-1H-imidazole|Precedex (TN)|CHEMBL778|67VB76HONO|CHEBI:4466|113775-47-6 (free base)|(S)-4-[1-(2,3-Dimethylphenyl)ethyl]-1H-imidazole|1H-Imidazole, 5-[(1S)-1-(2,3-dimethylShow More⌵

Synonyms from Alternative Forms(10): Dexmedetomidine hydrochloride | Cepedex | Dexdomitor | Dexdor | Dexmedetomidine hcl | Igalmi | Sedadex | Sileo | Dexmedetomidine accord | Precedex

Canonical SMILES:  Cc1cccc([C@H](C)c2c[nH]cn2)c1C

Standard InChI:  InChI=1S/C13H16N2/c1-9-5-4-6-12(10(9)2)11(3)13-7-14-8-15-13/h4-8,11H,1-3H3,(H,14,15)/t11-/m0/s1

Standard InChI Key:  CUHVIMMYOGQXCV-NSHDSACASA-N

Molfile:  

     RDKit          2D

 15 16  0  0  1  0  0  0  0  0999 V2000
    0.3625    0.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0708    0.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4458    0.5458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7292    0.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8583    0.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4083   -1.9292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3458   -0.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9958   -1.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417   -0.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1667   -1.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167    2.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8583    2.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542   -2.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7500   -1.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375    0.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0
  3  2  1  0
  4  1  1  0
  5  1  1  0
  6  8  1  0
  7  3  2  0
  8  2  2  0
  9  4  2  0
 10  1  2  0
 11  4  1  0
  5 12  1  1
 13 10  1  0
 14 13  2  0
 15  9  1  0
  9 14  1  0
  6  7  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA778

   Dexmedetomidine

2. Alternative Forms:

   

   ALA778

   Dexmedetomidine HCl

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: Yes

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: Yes

Prodrug: No

Calculated Properties

Molecular Weight: 200.28

Molecular Weight (Monoisotopic): 200.1313

AlogP: 3.18

#Rotatable Bonds: 2

Polar Surface Area: 28.68

Molecular Species: NEUTRAL

HBA: 1

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.54

CX LogP: 3.39

CX LogD: 3.34

Aromatic Rings: 2

Heavy Atoms: 15

QED Weighted: 0.79

Np Likeness Score: -0.44

References

1. Ross TM, Jetter MC, McDonnell ME, Boyd RE, Connelly CD, Martinez RP, Lewis MA, Codd EE, Raffa RB, Reitz AB..  (2000)  Alpha(2) adrenoceptor agonists as potential analgesic agents. 2. Discovery of 4-(4-imidazo)-1,3-dimethyl-6,7-dihydro-thianaphthene as a high-affinity ligand for the alpha(2D) adrenergic receptor.,  43  (7): [PMID:10753480] [10.1021/jm000128r]

2. Boyd RE, Press JB, Rasmussen CR, Raffa RB, Codd EE, Connelly CD, Bennett DJ, Kirifides AL, Gardocki JF, Reynolds B, Hortenstein JT, Reitz AB..  (1999)  Alpha(2) adrenoceptor agonists as potential analgesic agents. 1. (Imidazolylmethyl)oxazoles and -thiazoles.,  42  (25): [PMID:10602691] [10.1021/jm990005a]

3. Ross TM, Jetter MC, McDonnell ME, Boyd RE, Connelly CD, Martinez RP, Lewis MA, Codd EE, Raffa RB, Reitz AB..  (2000)  alpha(2) Adrenoceptor agonists as potential analgesic agents. 2. Discovery of 4-(4-Imidazo)-1,3-dimethyl-6,7-dihydrothianaphthene [corrected] as a high-affinity ligand for the alpha(2D) adrenergic receptor.,  43  (5): [PMID:10715142] [10.1021/jm990569e]

4. Boyd RE, Press JB, Rasmussen CR, Raffa RB, Codd EE, Connelly CD, Li QS, Martinez RP, Lewis MA, Almond HR, Reitz AB..  (2001)  Alpha(2) adrenoceptor agonists as potential analgesic agents. 3. Imidazolylmethylthiophenes.,  44  (6): [PMID:11300868] [10.1021/jm0003891]

5. Crassous PA, Cardinaletti C, Carrieri A, Bruni B, Di Vaira M, Gentili F, Ghelfi F, Giannella M, Paris H, Piergentili A, Quaglia W, Schaak S, Vesprini C, Pigini M..  (2007)  Alpha2-adrenoreceptors profile modulation. 3.1 (R)-(+)-m-nitrobiphenyline, a new efficient and alpha2C-subtype selective agonist.,  50  (16): [PMID:17630725] [10.1021/jm061487a]

6. PubChem BioAssay data set, 

7. Obach RS, Lombardo F, Waters NJ..  (2008)  Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.,  36  (7): [PMID:18426954] [10.1124/dmd.108.020479]

8. Sączewski F, Kornicka A, Hudson AL, Laird S, Scheinin M, Laurila JM, Rybczyńska A, Boblewski K, Lehmann A, Gdaniec M..  (2011)  3-[(Imidazolidin-2-yl)imino]indazole ligands with selectivity for the α(2)-adrenoceptor compared to the imidazoline I(1) receptor.,  19  (1): [PMID:21129985] [10.1016/j.bmc.2010.11.020]

9. Liu Z, Shi Q, Ding D, Kelly R, Fang H, Tong W..  (2011)  Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).,  7  (12): [PMID:22194678] [10.1371/journal.pcbi.1002310]

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

11. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

12. Vucicevic J, Srdic-Rajic T, Pieroni M, Laurila JM, Perovic V, Tassini S, Azzali E, Costantino G, Glisic S, Agbaba D, Scheinin M, Nikolic K, Radi M, Veljkovic N..  (2016)  A combined ligand- and structure-based approach for the identification of rilmenidine-derived compounds which synergize the antitumor effects of doxorubicin.,  24  (14): [PMID:27265687] [10.1016/j.bmc.2016.05.043]

13. WHO Anatomical Therapeutic Chemical Classification, 

14.  (2005)  Novel methods for identifying improved, non-sedating alpha-2 agonists, 

15. Chen M, Suzuki A, Thakkar S, Yu K, Hu C, Tong W..  (2016)  DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans.,  21  (4): [PMID:26948801] [10.1016/j.drudis.2016.02.015]

16. Unpublished dataset, 

17. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

18. Arora S, Joshi G, Chaturvedi A, Heuser M, Patil S, Kumar R..  (2022)  A Perspective on Medicinal Chemistry Approaches for Targeting Pyruvate Kinase M2.,  65  (2.0): [PMID:34726055] [10.1021/acs.jmedchem.1c00981]

19. Li X, Zhang J, Zhou C, Ling R, Gong D, Kang Y, Qi Q, Yang J..  (2023)  Design, Synthesis, and Bioevaluation of Dexmedetomidine Prodrug.,  14  (4): [PMID:37077377] [10.1021/acsmedchemlett.2c00449]

Source

Source(8):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names
• AstraZeneca Deposited Data
• Patent Bioactivity Data
• WHO Anatomical Therapeutic Chemical Classification
• Fraunhofer HDAC6