ID: ALA289480

Max Phase: Approved

First Approval: 1987

Molecular Formula: C10H16N2O

Molecular Weight: 180.25

Molecule Type: Small molecule

Representations

Synonyms (2): Hyperium | Rilmenidine
Synonyms from Alternative Forms(2):

Canonical SMILES:  C1COC(NC(C2CC2)C2CC2)=N1

Standard InChI:  InChI=1S/C10H16N2O/c1-2-7(1)9(8-3-4-8)12-10-11-5-6-13-10/h7-9H,1-6H2,(H,11,12)

Standard InChI Key:  CQXADFVORZEARL-UHFFFAOYSA-N

Molecule Features

Natural Product: Yes

Oral: Yes

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: 180.25

Molecular Weight (Monoisotopic): 180.1263

AlogP: 1.15

#Rotatable Bonds: 3

Polar Surface Area: 33.62

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 7.11

CX LogP: 1.58

CX LogD: 1.40

Aromatic Rings: 0

Heavy Atoms: 13

QED Weighted: 0.71

Np Likeness Score: -0.29

References

1. Schann S, Bruban V, Pompermayer K, Feldman J, Pfeiffer B, Renard P, Scalbert E, Bousquet P, Ehrhardt JD..  (2001)  Synthesis and biological evaluation of pyrrolinic isosteres of rilmenidine. Discovery of cis-/trans-dicyclopropylmethyl-(4,5-dimethyl-4,5-dihydro-3H-pyrrol-2-yl)-amine (LNP 509), an I1 imidazoline receptor selective ligand with hypotensive activity.,  44  (10): [PMID:11334568] [10.1021/jm001111b]

2. Touzeau F, Arrault A, Guillaumet G, Scalbert E, Pfeiffer B, Rettori MC, Renard P, Mérour JY..  (2003)  Synthesis and biological evaluation of new 2-(4,5-dihydro-1H-imidazol-2-yl)-3,4-dihydro-2H-1,4-benzoxazine derivatives.,  46  (10): [PMID:12723959] [10.1021/jm021050c]

3. Wong WC, Wang D, Forray C, Vaysse PJ, Branchek TA, Gluchowski C.  (1994)  A convenient synthesis of 2-amino-2-oxazolines and their pharmacological evaluation at cloned human adrenergic receptors,  4  (19): [10.1016/0960-894X(94)85032-1]

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10. PubChem BioAssay data set, 

11. PubChem BioAssay data set, 

12. PubChem BioAssay data set, 

13. PubChem BioAssay data set, 

14. PubChem BioAssay data set, 

15. PubChem BioAssay data set, 

16. Schann S, Greney H, Gasparik V, Dontenwill M, Rascente C, Lacroix G, Monassier L, Bruban V, Feldman J, Ehrhardt JD, Bousquet P..  (2012)  Methylation of imidazoline related compounds leads to loss of α₂-adrenoceptor affinity. Synthesis and biological evaluation of selective I₁ imidazoline receptor ligands.,  20  (15): [PMID:22750139] [10.1016/j.bmc.2012.06.008]

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

18. Nicolotti O, Carotti A, Carrieri A, Pigini M, Gentili F, Brasili L, Giannella M, Quaglia W, Piergentili A, Bousquet P, Dontenwill M.  (2004)  Alpha2-Adrenergic Receptors in Intestinal Epithelial Cells: Mechanisms of Signaling, Role, and Regulation,  13  (3): [10.1007/s00044-004-0023-9]

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20. PubChem BioAssay data set, 

21. PubChem BioAssay data set, 

22. Gasparik V, Greney H, Schann S, Feldman J, Fellmann L, Ehrhardt JD, Bousquet P..  (2015)  Synthesis and biological evaluation of 2-aryliminopyrrolidines as selective ligands for I1 imidazoline receptors: discovery of new sympatho-inhibitory hypotensive agents with potential beneficial effects in metabolic syndrome.,  58  (2): [PMID:25521963] [10.1021/jm501456p]

23. 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]

24. WHO Anatomical Therapeutic Chemical Classification, 

25. Unpublished dataset, 

26. Katie Heiser, Peter F. McLean, Chadwick T. Davis, Ben Fogelson, Hannah B. Gordon, Pamela Jacobson, Brett Hurst, Ben Miller, Ronald W. Alfa, Berton A. Earnshaw, Mason L. Victors, Yolanda T. Chong, Imran S. Haque, Adeline S. Low, Christopher C. Gibson.  (2020)  Identification of potential treatments for COVID-19 through artificial intelligence-enabled phenomic analysis of human cells infected with SARS-CoV-2,  [10.1101/2020.04.21.054387]

27. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

28. 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]

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Source

Source(8):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names
• WHO Anatomical Therapeutic Chemical Classification
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6