(2S,3S,4R,5S)-2-(5,6-dichloro-2-(isopropylamino)-1H-benzo[d]imidazol-1-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

ID: ALA515408

Cas Number: 176161-24-3

PubChem CID: 471161

Product Number: M611736, Order Now?

Max Phase: Approved

First Approval: 2021

Molecular Formula: C15H19Cl2N3O4

Molecular Weight: 376.24

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Livtencity | Maribavir | 1263-W-94 | 1263W94 | BW-1263W94 | GW-257406X | Maribavir|176161-24-3|Benzimidavir|livtencity|1263W94|Camvia|(2S,3S,4R,5S)-2-(5,6-dichloro-2-(isopropylamino)-1H-benzo[d]imidazol-1-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol|BW-1263W94|UNII-PTB4X93HE1|PTB4X93HE1|GW-257406X|GW-1263|BW 1263W94|5,6-Dichloro-2-(isopropylamino)-1-beta-L-ribofuranosyl-1H-benzimidazole|(2S,3S,4R,5S)-2-[5,6-dichloro-2-(propan-2-ylamino)benzimidazol-1-yl]-5-(hydroxymethyl)oxolane-3,4-diol|DTXSIDShow More⌵

Trade Names(1): Livtencity

Canonical SMILES:  CC(C)Nc1nc2cc(Cl)c(Cl)cc2n1[C@H]1O[C@@H](CO)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C15H19Cl2N3O4/c1-6(2)18-15-19-9-3-7(16)8(17)4-10(9)20(15)14-13(23)12(22)11(5-21)24-14/h3-4,6,11-14,21-23H,5H2,1-2H3,(H,18,19)/t11-,12-,13-,14-/m0/s1

Standard InChI Key:  KJFBVJALEQWJBS-XUXIUFHCSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  1  0  0  0  0  0999 V2000
    0.0542    0.1500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5375    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3042   -0.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7458    0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417    1.4958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0875   -0.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1833   -1.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7458    1.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0875   -1.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4583   -0.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3042   -1.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4625    1.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542    0.8333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1750    0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1708    1.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7542   -0.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7542   -2.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875   -0.0042    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875    1.6458    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0500   -2.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667    1.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6042   -3.3542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5917    1.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542    2.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  6
  4  1  1  0
  5  2  2  0
  6  3  1  0
  7  3  1  0
  8  4  1  0
  9  6  1  0
 10  4  2  0
 11  7  1  0
 12  8  2  0
 13  2  1  0
 14 10  1  0
 15 14  2  0
  6 16  1  1
  9 17  1  1
 18 14  1  0
 19 15  1  0
 11 20  1  6
 21 13  1  0
 22 20  1  0
 23 21  1  0
 24 21  1  0
  8  5  1  0
 11  9  1  0
 12 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA515408

   maribavir

Molecule Features

Natural Product: Yes

Oral: Yes

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: Yes

Black Box: No

Chirality: Yes

Availability: Yes

Prodrug: No

Calculated Properties

Molecular Weight: 376.24

Molecular Weight (Monoisotopic): 375.0753

AlogP: 1.77

#Rotatable Bonds: 4

Polar Surface Area: 99.77

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.45

CX Basic pKa: 6.38

CX LogP: 1.84

CX LogD: 1.80

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.65

Np Likeness Score: 0.14

References

1. Prado-Prado FJ, Martinez de la Vega O, Uriarte E, Ubeira FM, Chou KC, González-Díaz H..  (2009)  Unified QSAR approach to antimicrobials. 4. Multi-target QSAR modeling and comparative multi-distance study of the giant components of antiviral drug-drug complex networks.,  17  (2): [PMID:19112024] [10.1016/j.bmc.2008.11.075]

2. Goldwater DR, Dougherty C, Schumacher M, Villano SA..  (2008)  Effect of ketoconazole on the pharmacokinetics of maribavir in healthy adults.,  52  (5): [PMID:18316526] [10.1128/aac.00951-07]

3. Chou S..  (2009)  Diverse cytomegalovirus UL27 mutations adapt to loss of viral UL97 kinase activity under maribavir.,  53  (1): [PMID:18981262] [10.1128/aac.01177-08]

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

5. WHO Anatomical Therapeutic Chemical Classification, 

6. Kharitonova MI, Denisova AO, Andronova VL, Kayushin AL, Konstantinova ID, Kotovskaya SK, Galegov GA, Charushin VN, Miroshnikov AI..  (2017)  New modified 2-aminobenzimidazole nucleosides: Synthesis and evaluation of their activity against herpes simplex virus type 1.,  27  (11): [PMID:28408228] [10.1016/j.bmcl.2017.03.100]

7. Unpublished dataset, 

8. Bernhard Ellinger, Denisa Bojkova, Andrea Zaliani, Jindrich Cinatl, Carsten Claussen, Sandra Westhaus, Jeanette Reinshagen, Maria Kuzikov, Markus Wolf, Gerd Geisslinger, Philip Gribbon, Sandra Ciesek.  (2020)  Identification of inhibitors of SARS-CoV-2 in-vitro cellular toxicity in human (Caco-2) cells using a large scale drug repurposing collection,  [10.21203/rs.3.rs-23951/v1]

9. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]

10. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]

11. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of MMV (CH) - Pandemic Response Box,  [10.6019/CHEMBL4513161]

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

13. 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]

14. Unpublished dataset, 

15. European Medicines Agency, 

Source

Source(10):

• Scientific Literature
• Clinical Candidates
• FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book)
• USP Dictionary of USAN and International Drug Names
• CO-ADD antimicrobial screening data
• WHO Anatomical Therapeutic Chemical Classification
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6
• European Medicines Agency