anhydrovinblastine

ID: ALA553025

Cas Number: 71486-22-1

PubChem CID: 5311497

Product Number: V129738, Order Now?

Max Phase: Approved

First Approval: 1994

Molecular Formula: C45H54N4O8

Molecular Weight: 778.95

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Navelbin | Vinorelbine | Vinorelbine Base | NSC-760087 | vinorelbine|71486-22-1|Vinorelbine base|Vinorelbina|Vinorelbinum|Exelbine|Navelbine base|Navelbin|Nor-5'-anhydrovinblastine|Navelbine|KW 2307 base|Vinorelbinum [Latin]|KW-2307 base|Eunades|UNII-Q6C979R91Y|Vinorelbine (INN)|HSDB 7665|CHEBI:480999|Q6C979R91Y|5'-Noranhydrovinblastine|NSC-760087|Vinorelbina [Spanish]|Vinorelbin|C'-Norvincaleukoblastine, 3',4'-didehydro-4'-deoxy-|DTXSID8040640|Vinorelbinum (Latin)|NSC 760087|VINORELBINE [INN]|NShow More⌵

Synonyms from Alternative Forms(10): Vinorelbine ditartrate | Liposomal vinorelbine tartrate | Vinorelbine (as tartrate) | Vinorelbine Ditartarate | Vinorelbine liposomal | Vinorelbine tartrate | Vinorelbine tartrate (1:2) | TLC-178 | TLC178 | Navelbine

Canonical SMILES:  CCC1=C[C@@H]2CN(C1)Cc1c([nH]c3ccccc13)[C@@](C(=O)OC)(c1cc3c(cc1OC)N(C)[C@H]1[C@@](O)(C(=O)OC)[C@H](OC(C)=O)[C@]4(CC)C=CCN5CC[C@]31[C@@H]54)C2

Standard InChI:  InChI=1S/C45H54N4O8/c1-8-27-19-28-22-44(40(51)55-6,36-30(25-48(23-27)24-28)29-13-10-11-14-33(29)46-36)32-20-31-34(21-35(32)54-5)47(4)38-43(31)16-18-49-17-12-15-42(9-2,37(43)49)39(57-26(3)50)45(38,53)41(52)56-7/h10-15,19-21,28,37-39,46,53H,8-9,16-18,22-25H2,1-7H3/t28-,37-,38+,39+,42+,43+,44-,45-/m0/s1

Standard InChI Key:  GBABOYUKABKIAF-IELIFDKJSA-N

Molfile:  

     RDKit          2D

 60 68  0  0  0  0  0  0  0  0999 V2000
    6.7670   -6.9860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7869   -7.1156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7916   -3.9449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0806   -3.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5103   -8.0861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3644   -4.2921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0806   -5.1788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3651   -4.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4155   -8.0861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0633   -5.0534    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3393   -7.8099    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7236   -6.0909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1759   -4.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7341   -4.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0806   -6.8228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1056   -7.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5710   -5.5051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8803   -6.2539    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2765   -6.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6237   -8.5755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7916   -5.5804    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9370   -7.5088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1756   -5.3546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2339   -6.7391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3651   -3.9449    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7916   -4.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1508   -6.2790    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3651   -6.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2447   -4.7565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0806   -6.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6666   -6.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6483   -8.9101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3950   -5.5930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4405   -8.9101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9806   -6.7601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8803   -4.9153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6863   -4.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3848   -4.5557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6666   -5.1788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9804   -7.7849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5529   -7.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2763   -7.6385    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3950   -7.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3893   -5.5804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5112   -2.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5330   -4.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5777   -5.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3019   -5.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5097   -3.5321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8418   -8.0358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5984   -6.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0455   -6.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7665   -6.3794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5027   -6.7601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8995   -6.2163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4525   -6.2163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7364   -7.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9430   -3.9449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4099   -6.8479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1020   -8.3290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 43 35  1  0
 51 59  1  1
 11 41  1  0
 10 47  1  0
  4 25  1  0
  7 30  1  0
 22 24  2  0
  6 10  1  0
 18 31  1  0
 24 12  1  0
 55 51  1  0
  7 21  1  6
 38 23  1  0
 33 36  1  0
 47 19  1  0
 48 56  1  0
 35  1  1  0
 17 33  2  0
 29 14  2  0
 19 56  1  1
 20 11  1  0
  8  7  1  0
 51  2  1  0
  3 49  1  0
 44 47  1  0
 37 44  1  0
 54 53  2  0
 40  1  2  0
 57 51  1  0
 49 45  1  0
 26  7  1  0
 36 39  1  0
 55 44  1  0
 19 54  1  0
 39 31  2  0
 13 37  2  0
  2 11  1  0
  2 19  1  0
 48 10  1  0
 25  8  1  0
 46 36  2  0
 41 54  1  0
  2 42  1  1
 29 17  1  0
 44 23  1  6
 28  1  1  1
 14 46  1  0
  5 57  1  0
 32  5  1  0
 53 15  1  0
  3 26  2  0
 47 27  1  6
 13  6  1  0
 15 28  1  0
 55 12  1  1
 33 18  1  0
  4  3  1  0
 50 16  1  0
 58 39  1  0
 34  9  1  0
 41 50  2  0
 16 15  2  0
  9 16  1  0
 30 28  1  0
 52 24  1  0
 31 28  1  0
 58 25  1  0
 57 60  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA553025

   VINORELBINE

2. Alternative Forms:

   

   ALA553025

   VINORELBINE TARTRATE

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: Yes

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: Yes

Chirality: Yes

Availability: Yes

Prodrug: No

Calculated Properties

Molecular Weight: 778.95

Molecular Weight (Monoisotopic): 778.3942

AlogP: 4.75

#Rotatable Bonds: 7

Polar Surface Area: 133.87

Molecular Species: BASE

HBA: 11

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.87

CX Basic pKa: 8.66

CX LogP: 4.65

CX LogD: 2.86

Aromatic Rings: 3

Heavy Atoms: 57

QED Weighted: 0.20

Np Likeness Score: 1.55

References

1. Shao Y, Ding H, Tang W, Lou L, Hu L..  (2007)  Synthesis and structure-activity relationships study of novel anti-tumor carbamate anhydrovinblastine analogues.,  15  (15): [PMID:17544278] [10.1016/j.bmc.2007.05.045]

2. Shao Y, Ding H, Tang W, Lou L, Hu L..  (2007)  Synthesis and structure-activity relationships study of novel anti-tumor carbamate anhydrovinblastine analogues.,  15  (15): [PMID:17544278] [10.1016/j.bmc.2007.05.045]

3. Santana L, González-Díaz H, Quezada E, Uriarte E, Yáñez M, Viña D, Orallo F..  (2008)  Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.,  51  (21): [PMID:18834112] [10.1021/jm800656v]

4. Zhang HK, Shao Y, Ding H, Hu LH..  (2008)  Synthesis and structure-activity relationship studies of cytotoxic ester and ether anhydrovinblastine derivatives.,  71  (10): [PMID:18771244] [10.1021/np800284h]

5. Ngo QA, Roussi F, Cormier A, Thoret S, Knossow M, Guénard D, Guéritte F..  (2009)  Synthesis and biological evaluation of vinca alkaloids and phomopsin hybrids.,  52  (1): [PMID:19072542] [10.1021/jm801064y]

6. Ngo QA, Roussi F, Cormier A, Thoret S, Knossow M, Guénard D, Guéritte F..  (2009)  Synthesis and biological evaluation of vinca alkaloids and phomopsin hybrids.,  52  (1): [PMID:19072542] [10.1021/jm801064y]

7. Passarella D, Giardini A, Peretto B, Fontana G, Sacchetti A, Silvani A, Ronchi C, Cappelletti G, Cartelli D, Borlak J, Danieli B..  (2008)  Inhibitors of tubulin polymerization: synthesis and biological evaluation of hybrids of vindoline, anhydrovinblastine and vinorelbine with thiocolchicine, podophyllotoxin and baccatin III.,  16  (11): [PMID:18468444] [10.1016/j.bmc.2008.04.025]

8. Voss ME, Ralph JM, Xie D, Manning DD, Chen X, Frank AJ, Leyhane AJ, Liu L, Stevens JM, Budde C, Surman MD, Friedrich T, Peace D, Scott IL, Wolf M, Johnson R..  (2009)  Synthesis and SAR of vinca alkaloid analogues.,  19  (4): [PMID:19147348] [10.1016/j.bmcl.2008.12.077]

9. Varma MV, Feng B, Obach RS, Troutman MD, Chupka J, Miller HR, El-Kattan A..  (2009)  Physicochemical determinants of human renal clearance.,  52  (15): [PMID:19445515] [10.1021/jm900403j]

10. Shao Y, Zhang HK, Ding H, Quan HT, Lou LG, Hu LH..  (2009)  Synthesis and structure-activity relationship studies of cytotoxic anhydrovinblastine amide derivatives.,  72  (6): [PMID:19499938] [10.1021/np900157t]

11. Putey A, Popowycz F, Do QT, Bernard P, Talapatra SK, Kozielski F, Galmarini CM, Joseph B..  (2009)  Indolobenzazepin-7-ones and 6-, 8-, and 9-membered ring derivatives as tubulin polymerization inhibitors: synthesis and structure--activity relationship studies.,  52  (19): [PMID:19743863] [10.1021/jm900476c]

12. Toropov AA, Toropova AP, Raska I, Benfenati E..  (2010)  QSPR modeling of octanol/water partition coefficient of antineoplastic agents by balance of correlations.,  45  (4): [PMID:20106561] [10.1016/j.ejmech.2009.12.043]

13. Feng T, Li Y, Wang YY, Cai XH, Liu YP, Luo XD..  (2010)  Cytotoxic indole alkaloids from Melodinus tenuicaudatus.,  73  (6): [PMID:20462230] [10.1021/np100086x]

14. Prado-Prado FJ, García-Mera X, González-Díaz H..  (2010)  Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.,  18  (6): [PMID:20185316] [10.1016/j.bmc.2010.01.068]

15. PubChem BioAssay data set, 

16. 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]

17. Evans CA, Jolivette LJ, Nagilla R, Ward KW..  (2006)  Extrapolation of preclinical pharmacokinetics and molecular feature analysis of "discovery-like" molecules to predict human pharmacokinetics.,  34  (7): [PMID:16621936] [10.1124/dmd.105.006619]

18. 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]

19. Engel JC, Ang KK, Chen S, Arkin MR, McKerrow JH, Doyle PS..  (2010)  Image-based high-throughput drug screening targeting the intracellular stage of Trypanosoma cruzi, the agent of Chagas' disease.,  54  (8): [PMID:20547819] [10.1128/aac.01777-09]

20. Fourches D, Barnes JC, Day NC, Bradley P, Reed JZ, Tropsha A..  (2010)  Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.,  23  (1): [PMID:20014752] [10.1021/tx900326k]

21. Matthews EJ, Kruhlak NL, Weaver JL, Benz RD, Contrera JF..  (2004)  Assessment of the health effects of chemicals in humans: II. Construction of an adverse effects database for QSAR modeling.,  1  (4): [PMID:16472241] [10.2174/1570163043334794]

22.  (2008)  Casarett and Doull's Toxicology The Basic Science of Poisons, 7th edition, 

23. Xie F, Zhao H, Li D, Chen H, Quan H, Shi X, Lou L, Hu Y..  (2011)  Synthesis and biological evaluation of 2,4,5-substituted pyrimidines as a new class of tubulin polymerization inhibitors.,  54  (9): [PMID:21480626] [10.1021/jm101388d]

24. PubChem BioAssay data set, 

25. Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS..  (2001)  Rational use of in vitro P-glycoprotein assays in drug discovery.,  299  (2): [PMID:11602674]

26. Scott S. Auerbach, DrugMatrix¨ and ToxFX¨ Coordinator National Toxicology Program. DrugMatrix in vitro pharmacology data, 

27. 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]

28. La Regina G, Bai R, Rensen W, Coluccia A, Piscitelli F, Gatti V, Bolognesi A, Lavecchia A, Granata I, Porta A, Maresca B, Soriani A, Iannitto ML, Mariani M, Santoni A, Brancale A, Ferlini C, Dondio G, Varasi M, Mercurio C, Hamel E, Lavia P, Novellino E, Silvestri R..  (2011)  Design and synthesis of 2-heterocyclyl-3-arylthio-1H-indoles as potent tubulin polymerization and cell growth inhibitors with improved metabolic stability.,  54  (24): [PMID:22044164] [10.1021/jm2012886]

29. Song W, Hu L, Meng Y, Ma L, Guo D, Liu X, Hu L..  (2012)  The effect of vindoline C-16 substituents on the biomimetic coupling reaction: synthesis and cytotoxicity evaluation of the corresponding vinorelbine analogues.,  22  (10): [PMID:22525316] [10.1016/j.bmcl.2012.03.082]

30. Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS..  (2001)  Rational use of in vitro P-glycoprotein assays in drug discovery.,  299  (2): [PMID:11602674]

31. Brunhofer G, Fallarero A, Karlsson D, Batista-Gonzalez A, Shinde P, Gopi Mohan C, Vuorela P..  (2012)  Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.,  20  (22): [PMID:23062825] [10.1016/j.bmc.2012.09.040]

32. Song W, Lei M, Zhao K, Hu L, Meng Y, Guo D, Liu X, Hu L..  (2012)  Ceric ammonium nitrate-promoted oxidative coupling reaction for the synthesis and evaluation of a series of anti-tumor amide anhydrovinblastine analogs.,  22  (1): [PMID:22115594] [10.1016/j.bmcl.2011.10.114]

33. Hu L, Song W, Meng Y, Guo D, Liu X, Hu L..  (2012)  Synthesis and structure-activity relationship studies of cytotoxic vinorelbine amide analogues.,  22  (24): [PMID:23107481] [10.1016/j.bmcl.2012.10.024]

34. Schleicher KD, Sasaki Y, Tam A, Kato D, Duncan KK, Boger DL..  (2013)  Total synthesis and evaluation of vinblastine analogues containing systematic deep-seated modifications in the vindoline subunit ring system: core redesign.,  56  (2): [PMID:23252481] [10.1021/jm3014376]

35. La Regina G, Bai R, Rensen WM, Di Cesare E, Coluccia A, Piscitelli F, Famiglini V, Reggio A, Nalli M, Pelliccia S, Da Pozzo E, Costa B, Granata I, Porta A, Maresca B, Soriani A, Iannitto ML, Santoni A, Li J, Miranda Cona M, Chen F, Ni Y, Brancale A, Dondio G, Vultaggio S, Varasi M, Mercurio C, Martini C, Hamel E, Lavia P, Novellino E, Silvestri R..  (2013)  Toward highly potent cancer agents by modulating the C-2 group of the arylthioindole class of tubulin polymerization inhibitors.,  56  (1): [PMID:23214452] [10.1021/jm3013097]

36. Verones V, Flouquet N, Lecoeur M, Lemoine A, Farce A, Baldeyrou B, Mahieu C, Wattez N, Lansiaux A, Goossens JF, Berthelot P, Lebegue N..  (2013)  Synthesis, antiproliferative activity and tubulin targeting effect of acridinone and dioxophenothiazine derivatives.,  59  [PMID:23202849] [10.1016/j.ejmech.2012.10.051]

37. Genomics of Drug Sensitity in Cancer screening data, Wellcome Trust Sanger Institute,  [10.6019/CHEMBL1201861]

38. Gherbovet O, Coderch C, García Alvarez MC, Bignon J, Thoret S, Martin MT, Guéritte F, Gago F, Roussi F..  (2013)  Synthesis and biological evaluation of a new series of highly functionalized 7'-homo-anhydrovinblastine derivatives.,  56  (15): [PMID:23822556] [10.1021/jm4004347]

39. Biour M, Ben Salem C, Chazouillères O, Grangé JD, Serfaty L, Poupon R..  (2004)  [Drug-induced liver injury; fourteenth updated edition of the bibliographic database of liver injuries and related drugs].,  28  (8-9): [PMID:15646539] [10.1016/s0399-8320(04)95062-2]

40. Gherbovet O, Coderch C, García Alvarez MC, Bignon J, Thoret S, Guéritte F, Gago F, Roussi F..  (2014)  One-pot synthesis of vinca alkaloids-phomopsin hybrids.,  57  (12): [PMID:24871162] [10.1021/jm500530v]

41. La Regina G, Bai R, Coluccia A, Famiglini V, Pelliccia S, Passacantilli S, Mazzoccoli C, Ruggieri V, Sisinni L, Bolognesi A, Rensen WM, Miele A, Nalli M, Alfonsi R, Di Marcotullio L, Gulino A, Brancale A, Novellino E, Dondio G, Vultaggio S, Varasi M, Mercurio C, Hamel E, Lavia P, Silvestri R..  (2014)  New pyrrole derivatives with potent tubulin polymerization inhibiting activity as anticancer agents including hedgehog-dependent cancer.,  57  (15): [PMID:25025991] [10.1021/jm500561a]

42. Apel C, Gény C, Dumontet V, Birlirakis N, Roussi F, Pham VC, Doan Thi Mai H, Nguyen VH, Chau VM, Litaudon M..  (2014)  Endiandric acid analogues from Beilschmiedia ferruginea as dual inhibitors of Bcl-xL/Bak and Mcl-1/Bid interactions.,  77  (6): [PMID:24901800] [10.1021/np500170v]

43. Gherbovet O, La Spisa F, Thoret S, Alvarez MC, Levaique H, Bignon J, Roussi F..  (2015)  Synthesis and biological evaluation of C-13' substituted 7'-homo-anhydrovinblastine derivatives.,  25  (8): [PMID:25804719] [10.1016/j.bmcl.2015.02.045]

44. Liéby-Muller F, Heudré Le Baliner Q, Grisoni S, Fournier E, Guilbaud N, Marion F..  (2015)  Synthesis and activities towards resistant cancer cells of sulfone and sulfoxide griseofulvin derivatives.,  25  (10): [PMID:25872984] [10.1016/j.bmcl.2015.03.081]

45. Parrino B, Carbone A, Ciancimino C, Spanò V, Montalbano A, Barraja P, Cirrincione G, Diana P, Sissi C, Palumbo M, Pinato O, Pennati M, Beretta G, Folini M, Matyus P, Balogh B, Zaffaroni N..  (2015)  Water-soluble isoindolo[2,1-a]quinoxalin-6-imines: in vitro antiproliferative activity and molecular mechanism(s) of action.,  94  [PMID:25768699] [10.1016/j.ejmech.2015.03.005]

46. Lin X, Skolnik S, Chen X, Wang J..  (2011)  Attenuation of intestinal absorption by major efflux transporters: quantitative tools and strategies using a Caco-2 model.,  39  (2): [PMID:21051535] [10.1124/dmd.110.034629]

47. La Regina G, Bai R, Coluccia A, Famiglini V, Pelliccia S, Passacantilli S, Mazzoccoli C, Ruggieri V, Verrico A, Miele A, Monti L, Nalli M, Alfonsi R, Di Marcotullio L, Gulino A, Ricci B, Soriani A, Santoni A, Caraglia M, Porto S, Da Pozzo E, Martini C, Brancale A, Marinelli L, Novellino E, Vultaggio S, Varasi M, Mercurio C, Bigogno C, Dondio G, Hamel E, Lavia P, Silvestri R..  (2015)  New Indole Tubulin Assembly Inhibitors Cause Stable Arrest of Mitotic Progression, Enhanced Stimulation of Natural Killer Cell Cytotoxic Activity, and Repression of Hedgehog-Dependent Cancer.,  58  (15): [PMID:26132075] [10.1021/acs.jmedchem.5b00310]

48. Wang S, Fang K, Dong G, Chen S, Liu N, Miao Z, Yao J, Li J, Zhang W, Sheng C..  (2015)  Scaffold Diversity Inspired by the Natural Product Evodiamine: Discovery of Highly Potent and Multitargeting Antitumor Agents.,  58  (16): [PMID:26226379] [10.1021/acs.jmedchem.5b00910]

49. Ma LY, Zhou QL, Yang XW..  (2015)  New SIRT1 activator from alkaline hydrolysate of total saponins in the stems-leaves of Panax ginseng.,  25  (22): [PMID:26420067] [10.1016/j.bmcl.2015.09.039]

50. WHO Anatomical Therapeutic Chemical Classification, 

51. British National Formulary (72nd edition), 

52. Gherbovet O, García Alvarez MC, Bignon J, Roussi F..  (2016)  Original Vinca Derivatives: From P-Glycoprotein Substrates to P-Glycoprotein Inhibitors.,  59  (23): [PMID:27753480] [10.1021/acs.jmedchem.6b00525]

53. Spanò V, Pennati M, Parrino B, Carbone A, Montalbano A, Lopergolo A, Zuco V, Cominetti D, Diana P, Cirrincione G, Zaffaroni N, Barraja P..  (2016)  [1,2]Oxazolo[5,4-e]isoindoles as promising tubulin polymerization inhibitors.,  124  [PMID:27643641] [10.1016/j.ejmech.2016.09.013]

54. DrugMatrix,  [10.6019/CHEMBL3885881]

55. 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]

56. Capuzzi SJ, Sun W, Muratov EN, Martínez-Romero C, He S, Zhu W, Li H, Tawa G, Fisher EG, Xu M, Shinn P, Qiu X, García-Sastre A, Zheng W, Tropsha A..  (2018)  Computer-Aided Discovery and Characterization of Novel Ebola Virus Inhibitors.,  61  (8): [PMID:29624387] [10.1021/acs.jmedchem.8b00035]

57. La Regina G, Bai R, Coluccia A, Naccarato V, Famiglini V, Nalli M, Masci D, Verrico A, Rovella P, Mazzoccoli C, Da Pozzo E, Cavallini C, Martini C, Vultaggio S, Dondio G, Varasi M, Mercurio C, Hamel E, Lavia P, Silvestri R..  (2018)  New 6- and 7-heterocyclyl-1H-indole derivatives as potent tubulin assembly and cancer cell growth inhibitors.,  152  [PMID:29730191] [10.1016/j.ejmech.2018.04.042]

58. Unpublished dataset, 

59. Spanò V, Pennati M, Parrino B, Carbone A, Montalbano A, Cilibrasi V, Zuco V, Lopergolo A, Cominetti D, Diana P, Cirrincione G, Barraja P, Zaffaroni N..  (2016)  Preclinical Activity of New [1,2]Oxazolo[5,4-e]isoindole Derivatives in Diffuse Malignant Peritoneal Mesothelioma.,  59  (15): [PMID:27428868] [10.1021/acs.jmedchem.6b00777]

60. Cai S, Risinger AL, Petersen CL, Grkovic T, O'Keefe BR, Mooberry SL, Cichewicz RH..  (2019)  Anacolosins A-F and Corymbulosins X and Y, Clerodane Diterpenes from Anacolosa clarkii Exhibiting Cytotoxicity toward Pediatric Cancer Cell Lines.,  82  (4): [PMID:30830773] [10.1021/acs.jnatprod.8b01015]

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

62. Liu H,Fu Q,Lu Y,Zhang W,Yu P,Liu Z,Sun X.  (2020)  Anti-tubulin agent vinorelbine inhibits metastasis of cancer cells by regulating epithelial-mesenchymal transition.,  200  [PMID:32473523] [10.1016/j.ejmech.2020.112332]

63. Singh A,Chang TY,Kaur N,Hsu KC,Yen Y,Lin TE,Lai MJ,Lee SB,Liou JP.  (2021)  CAP rigidification of MS-275 and chidamide leads to enhanced antiproliferative effects mediated through HDAC1, 2 and tubulin polymerization inhibition.,  215  [PMID:33588178] [10.1016/j.ejmech.2021.113169]

64. 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]

65. Sutherland JJ, Yonchev D, Fekete A, Urban L..  (2023)  A preclinical secondary pharmacology resource illuminates target-adverse drug reaction associations of marketed drugs.,  14  (1): [PMID:37468498] [10.1038/s41467-023-40064-9]

Source

Source(10):

• Scientific Literature
• Sanger Institute Genomics of Drug Sensitivity in Cancer
• PubChem BioAssays
• Clinical Candidates
• DrugMatrix
• TP-search Transporter Database
• WHO Anatomical Therapeutic Chemical Classification
• British National Formulary
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6