5-Methoxy-2-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethanesulfinyl)-1H-benzoimidazole

ID: ALA1503

Cas Number: 73590-58-6

PubChem CID: 4594

Product Number: O118724, Order Now?

Max Phase: Approved

First Approval: 1989

Molecular Formula: C17H19N3O3S

Molecular Weight: 345.42

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Omeprazole | H 168/68 | H-168/68 | NSC-751450 | NSC-759192 | omeprazole|73590-58-6|Losec|Prilosec|Antra|Audazol|Omeprazon|Mopral|Omapren|Parizac|Ceprandal|Dizprazol|Emeproton|Epirazole|Gastrimut|Gastroloc|Inhibitron|Logastric|Peptilcer|Sanamidol|Secrepina|Ulcometion|Belmazol|Dudencer|Gibancer|Indurgan|Inhipump|Miracid|Omepral|Omeprol|Ompanyt|Pepticum|Prazidec|Ramezol|Ulceral|Ulcesep|Ulcozol|Zegerid|Desec|Elgam|Lomac|Mepral|Omezol|Omisec|Omizac|Ozoken|Prysma|Ulsen|Ultop|Zefxon|Zimor|Zoltum|Miol|OShow More⌵

Synonyms from Alternative Forms(9): Omeprazole magnesium salt | Omeprazole (as magnesium) | Omeprazole magnesium | H 168/68 MAGNESIUM | Prilosec | Prilosec otc | Omeprazole sodium | Omeprazole (as sodium) | H 168/68 SODIUM

Trade Names(9): Antra | Losec | Losec mups | Mezzopram | Mopral | Omeprazole | Omeran | Prilosec | Zanprol

Canonical SMILES:  COc1ccc2[nH]c([S+]([O-])Cc3ncc(C)c(OC)c3C)nc2c1

Standard InChI:  InChI=1S/C17H19N3O3S/c1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)

Standard InChI Key:  SUBDBMMJDZJVOS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    9.6972   -8.6108    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.6946   -7.7858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7843  -10.0026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5474   -6.5550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1657   -8.6832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5019   -9.8413    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5552   -9.0300    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7196   -9.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3093  -10.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4130   -9.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2684   -8.6153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5446   -9.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7240  -10.7234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2658   -7.7903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9840   -9.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9592  -10.0050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5500   -7.3801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5490  -10.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8368   -7.7948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8395   -8.6197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9790   -7.3756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1211   -7.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1990  -10.7157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8317   -6.1448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1 10  1  0
  1 15  1  0
  3 16  1  0
  3 23  1  0
  4 17  1  0
  4 24  1  0
  5  8  1  0
  5 10  2  0
  6  9  1  0
  6 10  1  0
  7 11  1  0
  7 20  2  0
  8  9  1  0
  8 12  2  0
  9 13  2  0
 11 14  2  0
 11 15  1  0
 12 16  1  0
 13 18  1  0
 14 17  1  0
 14 21  1  0
 16 18  2  0
 17 19  2  0
 19 20  1  0
 19 22  1  0
M  CHG  2   1   1   2  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1503

   Omeprazole

2. Alternative Forms:

   

   ALA1503

   Esomeprazole Magnesium
3. 

   ALA1503

   Omeprazole sodium

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: No

Availability: Yes

Prodrug: Yes

Calculated Properties

Molecular Weight: 345.42

Molecular Weight (Monoisotopic): 345.1147

AlogP: 2.90

#Rotatable Bonds: 5

Polar Surface Area: 83.09

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.68

CX Basic pKa: 4.77

CX LogP: 2.43

CX LogD: 2.43

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.72

Np Likeness Score: -0.69

References

1. Kohl B, Sturm E, Senn-Bilfinger J, Simon WA, Krüger U, Schaefer H, Rainer G, Figala V, Klemm K..  (1992)  (H+,K+)-ATPase inhibiting 2-[(2-pyridylmethyl)sulfinyl]benzimidazoles. 4. A novel series of dimethoxypyridyl-substituted inhibitors with enhanced selectivity. The selection of pantoprazole as a clinical candidate.,  35  (6): [PMID:1313110] [10.1021/jm00084a010]

2. Sih JC, Im WB, Robert A, Graber DR, Blakeman DP..  (1991)  Studies on (H(+)-K+)-ATPase inhibitors of gastric acid secretion. Prodrugs of 2-[(2-pyridinylmethyl)sulfinyl]benzimidazole proton-pump inhibitors.,  34  (3): [PMID:1848293] [10.1021/jm00107a026]

3. Matsuda H, Pongpiriyadacha Y, Morikawa T, Kishi A, Kataoka S, Yoshikawa M..  (2003)  Protective effects of steroid saponins from Paris polyphylla var. yunnanensis on ethanol- or indomethacin-induced gastric mucosal lesions in rats: structural requirement for activity and mode of action.,  13  (6): [PMID:12643921] [10.1016/s0960-894x(03)00052-0]

4. Adelstein GW, Yen CH, Haack RA, Yu S, Gullikson G, Price DV, Anglin C, Decktor DL, Tsai H, Keith RH..  (1988)  Substituted 2-[(2-benzimidazolylsulfinyl)methyl]anilines as potential inhibitors of H+/K+ ATPase.,  31  (6): [PMID:2836591] [10.1021/jm00401a024]

5. Lombardo F, Obach RS, Shalaeva MY, Gao F..  (2004)  Prediction of human volume of distribution values for neutral and basic drugs. 2. Extended data set and leave-class-out statistics.,  47  (5): [PMID:14971904] [10.1021/jm030408h]

6. Sanfilippo PJ, Urbanski M, Press JB, Hajos ZG, Shriver DA, Scott CK..  (1988)  Synthesis of (aryloxy)alkylamines. 1. Novel antisecretory agents with H+K+-ATPase inhibitory activity.,  31  (9): [PMID:2842503] [10.1021/jm00117a018]

7. Yoon SH, Seo S, Lee Y, Hwang S, Kim DY..  (1998)  Syntheses of 2-[(3,5-dimethyl-4-methoxypyridyl)alkyl]-benzothiazolidine derivatives as a potential gastric H+/K(+)-ATPase inhibitor.,  8  (14): [PMID:9873457] [10.1016/s0960-894x(98)00334-5]

8. Ife RJ, Dyke CA, Keeling DJ, Meenan E, Meeson ML, Parsons ME, Price CA, Theobald CJ, Underwood AH..  (1989)  2-[[(4-Amino-2-pyridyl)methyl]sulfinyl]benzimidazole H+/K+-ATPase inhibitors. The relationship between pyridine basicity, stability, and activity.,  32  (8): [PMID:2547073] [10.1021/jm00128a046]

9. Lombardo F, Shalaeva MY, Tupper KA, Gao F..  (2001)  ElogD(oct): a tool for lipophilicity determination in drug discovery. 2. Basic and neutral compounds.,  44  (15): [PMID:11448232] [10.1021/jm0100990]

10. Yoshida F, Topliss JG..  (2000)  QSAR model for drug human oral bioavailability.,  43  (13): [PMID:10891117] [10.1021/jm0000564]

11. Yum EK, Kang SK, Kim SS, Choi JK, Cheon HG..  (1999)  Synthesis and pharmacological profile of 1-aryl-3-substituted pyrrolo[3,2-c]quinolines.,  9  (19): [PMID:10522698] [10.1016/s0960-894x(99)00496-5]

12. Lombardo F, Obach RS, Shalaeva MY, Gao F..  (2002)  Prediction of volume of distribution values in humans for neutral and basic drugs using physicochemical measurements and plasma protein binding data.,  45  (13): [PMID:12061889] [10.1021/jm0200409]

13. Terauchi H, Tanitame A, Tada K, Nakamura K, Seto Y, Nishikawa Y..  (1997)  Nicotinamide derivatives as a new class of gastric H+/K(+)-ATPase inhibitors. 1. Synthesis and structure-activity relationships of N-substituted 2-(benzhydryl- and benzylsulfinyl)nicotinamides.,  40  (3): [PMID:9022797] [10.1021/jm9605593]

14. Seidler J, McGovern SL, Doman TN, Shoichet BK..  (2003)  Identification and prediction of promiscuous aggregating inhibitors among known drugs.,  46  (21): [PMID:14521410] [10.1021/jm030191r]

15. Weidmann K, Herling AW, Lang HJ, Scheunemann KH, Rippel R, Nimmesgern H, Scholl T, Bickel M, Metzger H..  (1992)  2-[(2-pyridylmethyl)sulfinyl]-1H-thieno[3,4-d]imidazoles. A novel class of gastric H+/K(+)-ATPase inhibitors.,  35  (3): [PMID:1310742] [10.1021/jm00081a004]

16. Kühler TC, Fryklund J, Bergman NA, Weilitz J, Lee A, Larsson H..  (1995)  Structure-activity relationship of omeprazole and analogues as Helicobacter pylori urease inhibitors.,  38  (25): [PMID:8523404] [10.1021/jm00025a008]

17. Brown TH, Ife RJ, Keeling DJ, Laing SM, Leach CA, Parsons ME, Price CA, Reavill DR, Wiggall KJ..  (1990)  Reversible inhibitors of the gastric (H+/K+)-ATPase. 1. 1-Aryl-4-methylpyrrolo[3,2-c]quinolines as conformationally restrained analogues of 4-(arylamino)quinolines.,  33  (2): [PMID:2153816] [10.1021/jm00164a010]

18. Pajeva IK, Wiese M..  (2002)  Pharmacophore model of drugs involved in P-glycoprotein multidrug resistance: explanation of structural variety (hypothesis).,  45  (26): [PMID:12477351] [10.1021/jm020941h]

19. Pajeva IK, Wiese M..  (2002)  Pharmacophore model of drugs involved in P-glycoprotein multidrug resistance: explanation of structural variety (hypothesis).,  45  (26): [PMID:12477351] [10.1021/jm020941h]

20. Pajeva IK, Wiese M..  (2002)  Pharmacophore model of drugs involved in P-glycoprotein multidrug resistance: explanation of structural variety (hypothesis).,  45  (26): [PMID:12477351] [10.1021/jm020941h]

21. Yamada M, Yura T, Morimoto M, Harada T, Yamada K, Honma Y, Kinoshita M, Sugiura M..  (1996)  2-[(2-Aminobenzyl)sulfinyl]-1-(2-pyridyl)-1,4,5,6-tetrahydrocyclopent[d]imidazoles as a novel class of gastric H+/K+-ATPase inhibitors.,  39  (2): [PMID:8558532] [10.1021/jm950610n]

22. Meinke PT..  (2001)  Perspectives in animal health: old targets and new opportunities.,  44  (5): [PMID:11262075] [10.1021/jm990564h]

23. Afzelius L, Zamora I, Masimirembwa CM, Karlén A, Andersson TB, Mecucci S, Baroni M, Cruciani G..  (2004)  Conformer- and alignment-independent model for predicting structurally diverse competitive CYP2C9 inhibitors.,  47  (4): [PMID:14761192] [10.1021/jm030972s]

24. Donadel OJ, Guerreiro E, María AO, Wendel G, Enriz RD, Giordano OS, Tonn CE..  (2005)  Gastric cytoprotective activity of ilicic aldehyde: structure-activity relationships.,  15  (15): [PMID:15963720] [10.1016/j.bmcl.2005.05.053]

25. Wang YH, Li Y, Li YH, Yang SL, Yang L..  (2005)  Modeling K(m) values using electrotopological state: substrates for cytochrome P450 3A4-mediated metabolism.,  15  (18): [PMID:15990295] [10.1016/j.bmcl.2005.06.015]

26. Vidaillac C, Guillon J, Arpin C, Forfar-Bares I, Ba BB, Grellet J, Moreau S, Caignard DH, Jarry C, Quentin C..  (2007)  Synthesis of omeprazole analogues and evaluation of these as potential inhibitors of the multidrug efflux pump NorA of Staphylococcus aureus.,  51  (3): [PMID:17101679] [10.1128/aac.01306-05]

27. Sharma P, Singh S, Siddiqui TI, Singh VS, Kundu B, Prathipati P, Saxena AK, Dikshit DK, Rastogi L, Dixit C, Gupta MB, Patnaik GK, Dikshit M..  (2007)  alpha-Amino acid derivatives as proton pump inhibitors and potent anti-ulcer agents.,  42  (3): [PMID:17045703] [10.1016/j.ejmech.2006.08.016]

28. Jain KS, Shah AK, Bariwal J, Shelke SM, Kale AP, Jagtap JR, Bhosale AV..  (2007)  Recent advances in proton pump inhibitors and management of acid-peptic disorders.,  15  (3): [PMID:17150362] [10.1016/j.bmc.2006.07.068]

29. Mishina YV, Krishna S, Haynes RK, Meade JC..  (2007)  Artemisinins inhibit Trypanosoma cruzi and Trypanosoma brucei rhodesiense in vitro growth.,  51  (5): [PMID:17339374] [10.1128/aac.01544-06]

30. Morikawa T, Li N, Nagatomo A, Matsuda H, Li X, Yoshikawa M..  (2006)  Triterpene saponins with gastroprotective effects from tea seed (the seeds of Camellia sinensis).,  69  (2): [PMID:16499314] [10.1021/np058097w]

31. Pedersen JM, Matsson P, Bergström CA, Norinder U, Hoogstraate J, Artursson P..  (2008)  Prediction and identification of drug interactions with the human ATP-binding cassette transporter multidrug-resistance associated protein 2 (MRP2; ABCC2).,  51  (11): [PMID:18457386] [10.1021/jm7015683]

32. Wassvik CM, Holmén AG, Draheim R, Artursson P, Bergström CA..  (2008)  Molecular characteristics for solid-state limited solubility.,  51  (10): [PMID:18396854] [10.1021/jm701587d]

33. Carlton DL, Collin-Smith LJ, Daniels AJ, Deaton DN, Goetz AS, Laudeman CP, Littleton TR, Musso DL, Morgan RJ, Szewczyk JR, Zhang C..  (2008)  Discovery of small molecule agonists for the bombesin receptor subtype 3 (BRS-3) based on an omeprazole lead.,  18  (20): [PMID:18818070] [10.1016/j.bmcl.2008.09.033]

34. 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]

35. Roy K, Pratim Roy P..  (2009)  Comparative chemometric modeling of cytochrome 3A4 inhibitory activity of structurally diverse compounds using stepwise MLR, FA-MLR, PLS, GFA, G/PLS and ANN techniques.,  44  (7): [PMID:19128860] [10.1016/j.ejmech.2008.12.004]

36. Varma MV, Obach RS, Rotter C, Miller HR, Chang G, Steyn SJ, El-Kattan A, Troutman MD..  (2010)  Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.,  53  (3): [PMID:20070106] [10.1021/jm901371v]

37. Lee PH, Conradi R, Shanmugasundaram V..  (2010)  Development of an in silico model for human skin permeation based on a Franz cell skin permeability assay.,  20  (1): [PMID:19963379] [10.1016/j.bmcl.2009.11.039]

38. Sui X, Sun J, Li H, Wang Y, Liu J, Liu X, Zhang W, Chen L, He Z..  (2009)  Prediction of volume of distribution values in human using immobilized artificial membrane partitioning coefficients, the fraction of compound ionized and plasma protein binding data.,  44  (11): [PMID:19586686] [10.1016/j.ejmech.2009.06.004]

39. 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]

40. PubChem BioAssay data set, 

41. PubChem BioAssay data set, 

42. PubChem BioAssay data set, 

43. PubChem BioAssay data set, 

44. 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]

45. Suzuki H, Nishizawa T, Muraoka H, Hibi T..  (2009)  Sitafloxacin and garenoxacin may overcome the antibiotic resistance of Helicobacter pylori with gyrA mutation.,  53  (4): [PMID:19188389] [10.1128/aac.00049-09]

46. Puiac S, Negrea A, Richter-Dahlfors A, Plant L, Rhen M..  (2009)  Omeprazole antagonizes virulence and inflammation in Salmonella enterica-infected RAW264.7 cells.,  53  (6): [PMID:19307359] [10.1128/aac.01483-08]

47. Azevedo-Vethacke M, Garten D, Groll C, Schreiber S..  (2009)  Specific therapeutic schemes of omeprazole affect the orientation of Helicobacter pylori.,  53  (8): [PMID:19487446] [10.1128/aac.00158-09]

48. 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]

49. 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]

50. Kruhlak NL, Choi SS, Contrera JF, Weaver JL, Willard JM, Hastings KL, Sancilio LF..  (2008)  Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models.,  18  (2): [PMID:20020916] [10.1080/15376510701857262]

51. Unpublished dataset, 

52. PubChem BioAssay data set, 

53.  (2008)  Casarett and Doull's Toxicology The Basic Science of Poisons, 7th edition, 

54.  (2008)  Casarett and Doull's Toxicology The Basic Science of Poisons, 7th edition, 

55. Yan Y, Liu Z, Zhang J, Xu R, Hu X, Liu G..  (2011)  A reverse method for diversity introduction of benzimidazole to synthesize H(+)/K(+)-ATP enzyme inhibitors.,  21  (14): [PMID:21684741] [10.1016/j.bmcl.2011.05.080]

56. Zhang LY, Yang F, Shi WQ, Zhang P, Li Y, Yin SF..  (2011)  Synthesis and antigastric ulcer activity of novel 5-isoproyl-3,8-dimethylazulene derivatives.,  21  (19): [PMID:21885274] [10.1016/j.bmcl.2011.08.018]

57. PubChem BioAssay data set, 

58. PubChem BioAssay data set, 

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

60. 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]

61. Pérez-Villanueva J, Romo-Mancillas A, Hernández-Campos A, Yépez-Mulia L, Hernández-Luis F, Castillo R..  (2011)  Antiprotozoal activity of proton-pump inhibitors.,  21  (24): [PMID:22047694] [10.1016/j.bmcl.2011.10.028]

62. PubChem BioAssay data set, 

63. Sakatis MZ, Reese MJ, Harrell AW, Taylor MA, Baines IA, Chen L, Bloomer JC, Yang EY, Ellens HM, Ambroso JL, Lovatt CA, Ayrton AD, Clarke SE..  (2012)  Preclinical strategy to reduce clinical hepatotoxicity using in vitro bioactivation data for >200 compounds.,  25  (10): [PMID:22931300] [10.1021/tx300075j]

64. Breedveld P, Zelcer N, Pluim D, Sönmezer O, Tibben MM, Beijnen JH, Schinkel AH, van Tellingen O, Borst P, Schellens JH..  (2004)  Mechanism of the pharmacokinetic interaction between methotrexate and benzimidazoles: potential role for breast cancer resistance protein in clinical drug-drug interactions.,  64  (1): [PMID:15313923] [10.1158/0008-5472.can-03-4062]

65. Pauli-Magnus C, Rekersbrink S, Klotz U, Fromm MF..  (2001)  Interaction of omeprazole, lansoprazole and pantoprazole with P-glycoprotein.,  364  (1): [PMID:11770010] [10.1007/s00210-001-0489-7]

66. Hitzl M, Klein K, Zanger UM, Fritz P, Nüssler AK, Neuhaus P, Fromm MF..  (2003)  Influence of omeprazole on multidrug resistance protein 3 expression in human liver.,  304  (1): [PMID:12538803] [10.1124/jpet.102.043547]

67. Derbyshire ER, Prudêncio M, Mota MM, Clardy J..  (2012)  Liver-stage malaria parasites vulnerable to diverse chemical scaffolds.,  109  (22): [PMID:22586124] [10.1073/pnas.1118370109]

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

69. PubChem BioAssay data set, 

70. PubChem BioAssay data set, 

71. Karlgren M, Vildhede A, Norinder U, Wisniewski JR, Kimoto E, Lai Y, Haglund U, Artursson P..  (2012)  Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions.,  55  (10): [PMID:22541068] [10.1021/jm300212s]

72. Dudhe PB, Jain KS, Raskar VK, Deodhe AS, Patel JG, Phoujdar MS, Kathiravan MK.  (2013)  Synthesis and biological evaluation of novel condensed pyrimidinylmethylsulfinylbenzimidazoles as antiulcer agent,  22  (8): [10.1007/s00044-012-0358-6]

73. El-Nezhawy AO, Biuomy AR, Hassan FS, Ismaiel AK, Omar HA..  (2013)  Design, synthesis and pharmacological evaluation of omeprazole-like agents with anti-inflammatory activity.,  21  (7): [PMID:23453216] [10.1016/j.bmc.2013.01.070]

74. Sharma A, Suhas R, Chandana KV, Banu SH, Channe Gowda D..  (2013)  tert-Butyl 1,5-bis(4-(benzo[d]isothiazol-3-yl)piperazin-1-yl)-1,5-dioxopentan-2-ylcarbamate urea/thiourea derivatives as potent H+/K(+)-ATPase inhibitors.,  23  (14): [PMID:23756367] [10.1016/j.bmcl.2013.05.043]

75. Unpublished dataset, 

76. Unpublished dataset, 

77. Unpublished dataset, 

78. Unpublished dataset, 

79. Hu S, Huang Y, Wu YJ, He H, Grant-Young KA, Bertekap RL, Whiterock V, Brassil P, Lentz K, Sivaprakasam P, Langley DR, Westphal RS, Scola PM..  (2014)  Structure activity relationship studies of 3-arylsulfonyl-pyrido[1,2-a]pyrimidin-4-imines as potent 5-HT₆ antagonists.,  22  (5): [PMID:24495863] [10.1016/j.bmc.2014.01.003]

80. Shea TA, Burburan PJ, Matubia VN, Ramcharan SS, Rosario I, Parkin DW, Stockman BJ..  (2014)  Identification of proton-pump inhibitor drugs that inhibit Trichomonas vaginalis uridine nucleoside ribohydrolase.,  24  (4): [PMID:24468412] [10.1016/j.bmcl.2014.01.014]

81. 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]

82. PubChem BioAssay data set, 

83. PubChem BioAssay data set, 

84. PubChem BioAssay data set, 

85. Kaiser M, Mäser P, Tadoori LP, Ioset JR, Brun R.. Antiprotozoal Activity Profiling of Approved Drugs: A Starting Point toward Drug Repositioning,  [10.6019/CHEMBL3392926]

86. Bharate SS, Vishwakarma RA..  (2015)  Thermodynamic equilibrium solubility measurements in simulated fluids by 96-well plate method in early drug discovery.,  25  (7): [PMID:25740159] [10.1016/j.bmcl.2015.02.013]

87. Fako VE, Wu X, Pflug B, Liu JY, Zhang JT..  (2015)  Repositioning proton pump inhibitors as anticancer drugs by targeting the thioesterase domain of human fatty acid synthase.,  58  (2): [PMID:25513712] [10.1021/jm501543u]

88. Loi CM, Smith DA, Dalvie D..  (2013)  Which metabolites circulate?,  41  (5): [PMID:23454828] [10.1124/dmd.112.050278]

89. Lutz JD, Isoherranen N..  (2012)  Prediction of relative in vivo metabolite exposure from in vitro data using two model drugs: dextromethorphan and omeprazole.,  40  (1): [PMID:22010218] [10.1124/dmd.111.042200]

90. Wang H, An N, Wang H, Gao Y, Liu D, Bian T, Zhu J, Chen C..  (2011)  Evaluation of the effects of 20 nonsynonymous single nucleotide polymorphisms of CYP2C19 on S-mephenytoin 4'-hydroxylation and omeprazole 5'-hydroxylation.,  39  (5): [PMID:21325430] [10.1124/dmd.110.037549]

91. Ren S, Zeng J, Mei Y, Zhang JZ, Yan SF, Fei J, Chen L..  (2013)  Discovery and characterization of novel, potent, and selective cytochrome P450 2J2 inhibitors.,  41  (1): [PMID:23033255] [10.1124/dmd.112.048264]

92. Lee CA, Jones JP, Katayama J, Kaspera R, Jiang Y, Freiwald S, Smith E, Walker GS, Totah RA..  (2012)  Identifying a selective substrate and inhibitor pair for the evaluation of CYP2J2 activity.,  40  (5): [PMID:22328583] [10.1124/dmd.111.043505]

93. Foti RS, Pearson JT, Wong SL, Zalikowski JA, Boudreaux MD, Prokop SP, Davis JA, Banfield C, Emery MG, Rock DA, Wahlstrom JL, Wienkers LC, Amore BM..  (2012)  Predicting the drug interaction potential of AMG 853, a dual antagonist of the D-prostanoid and chemoattractant receptor-homologous molecule expressed on T helper 2 cells receptors.,  40  (12): [PMID:22930276] [10.1124/dmd.112.047928]

94. Zahanich I, Kondratov I, Naumchyk V, Kheylik Y, Platonov M, Zozulya S, Krasavin M..  (2015)  Phenoxymethyl 1,3-oxazoles and 1,2,4-oxadiazoles as potent and selective agonists of free fatty acid receptor 1 (GPR40).,  25  (16): [PMID:26096679] [10.1016/j.bmcl.2015.06.018]

95. Krasavin M, Lukin A, Zhurilo N, Kovalenko A, Zahanich I, Zozulya S, Moore D, Tikhonova IG..  (2016)  Novel free fatty acid receptor 1 (GPR40) agonists based on 1,3,4-thiadiazole-2-carboxamide scaffold.,  24  (13): [PMID:27229618] [10.1016/j.bmc.2016.04.065]

96. WHO Anatomical Therapeutic Chemical Classification, 

97. British National Formulary (72nd edition), 

98. Rackelmann N, Matter H, Englert H, Follmann M, Maier T, Weston J, Arndt P, Heyse W, Mertsch K, Wirth K, Bialy L..  (2016)  Discovery and Optimization of 1-Phenoxy-2-aminoindanes as Potent, Selective, and Orally Bioavailable Inhibitors of the Na+/H+ Exchanger Type 3 (NHE3).,  59  (19): [PMID:27606885] [10.1021/acs.jmedchem.6b00624]

99.  (2014)  Dimethylarginine Dimethylaminohydrolase inhibitors and methods of use thereof, 

100. Open TG-GATES,  [10.6019/CHEMBL3885861]

101. DrugMatrix,  [10.6019/CHEMBL3885881]

102. DailyMed|setid=93ec1327-22b1-4a5d-a793-e014f6dffd33 | OMEPRAZOLE - omeprazole capsule, delayed release|STAT Rx USA LLC, 

103. Morgan RE, Trauner M, van Staden CJ, Lee PH, Ramachandran B, Eschenberg M, Afshari CA, Qualls CW, Lightfoot-Dunn R, Hamadeh HK..  (2010)  Interference with bile salt export pump function is a susceptibility factor for human liver injury in drug development.,  118  (2): [PMID:20829430] [10.1093/toxsci/kfq269]

104. Li B, Ni S, Mao F, Chen F, Liu Y, Wei H, Chen W, Zhu J, Lan L, Li J..  (2018)  Novel Terminal Bipheny-Based Diapophytoene Desaturases (CrtN) Inhibitors as Anti-MRSA/VISR/LRSA Agents with Reduced hERG Activity.,  61  (1): [PMID:29243920] [10.1021/acs.jmedchem.7b01300]

105. Morgan RE, van Staden CJ, Chen Y, Kalyanaraman N, Kalanzi J, Dunn RT, Afshari CA, Hamadeh HK..  (2013)  A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development.,  136  (1): [PMID:23956101] [10.1093/toxsci/kft176]

106. 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]

107. Bi Y, Might M, Vankayalapati H, Kuberan B..  (2017)  Repurposing of Proton Pump Inhibitors as first identified small molecule inhibitors of endo-β-N-acetylglucosaminidase (ENGase) for the treatment of NGLY1 deficiency, a rare genetic disease.,  27  (13): [PMID:28512024] [10.1016/j.bmcl.2017.05.010]

108. Bala V, Chhonker YS..  (2018)  Recent developments in anti-Trichomonas research: An update review.,  143  [PMID:29175675] [10.1016/j.ejmech.2017.11.029]

109. Gu ZS, Xiao Y, Zhang QW, Li JQ..  (2017)  Synthesis and antidepressant activity of a series of arylalkanol and aralkyl piperazine derivatives targeting SSRI/5-HT1A/5-HT7.,  27  (24): [PMID:29138029] [10.1016/j.bmcl.2017.11.007]

110. Rajesh R, Manikandan A, Sivakumar A, Ramasubbu C, Nagaraju N..  (2017)  Substituted methoxybenzyl-sulfonyl-1H-benzo[d]imidazoles evaluated as effective H+/K+-ATPase inhibitors and anti-ulcer therapeutics.,  139  [PMID:28818769] [10.1016/j.ejmech.2017.08.001]

111. Xie Y, Dahlin JL, Oakley AJ, Casarotto MG, Board PG, Baell JB..  (2018)  Reviewing Hit Discovery Literature for Difficult Targets: Glutathione Transferase Omega-1 as an Example.,  61  (17): [PMID:29652143] [10.1021/acs.jmedchem.8b00318]

112. Gu ZS, Zhou AN, Xiao Y, Zhang QW, Li JQ..  (2018)  Synthesis and antidepressant-like activity of novel aralkyl piperazine derivatives targeting SSRI/5-HT1A/5-HT7.,  144  [PMID:29291438] [10.1016/j.ejmech.2017.12.063]

113. Wang SM, Zha GF, Rakesh KP, Darshini N, Shubhavathi T, Vivek HK, Mallesha N, Qin HL..  (2017)  Synthesis of benzo[d]thiazole-hydrazone analogues: molecular docking and SAR studies of potential H⁺/K⁺ ATPase inhibitors and anti-inflammatory agents.,  8  (6): [PMID:30108827] [10.1039/C7MD00111H]

114. Unpublished dataset, 

115. Franck Touret, Magali Gilles, Karine Barral, Antoine Nougairède, Etienne Decroly, Xavier de Lamballerie, Bruno Coutard.  (2020)  In vitro screening of a FDA approved chemical library reveals potential inhibitors of SARS-CoV-2 replication,  [10.1101/2020.04.03.023846]

116. 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]

117. Leroux F, Bosc D, Beghyn T, Hermant P, Warenghem S, Landry V, Pottiez V, Guillaume V, Charton J, Herledan A, Urata S, Liang W, Sheng L, Tang WJ, Deprez B, Deprez-Poulain R..  (2019)  Identification of ebselen as a potent inhibitor of insulin degrading enzyme by a drug repurposing screening.,  179  [PMID:31276900] [10.1016/j.ejmech.2019.06.057]

118. Gu ZS, Wang WT, Qian H, Zhou AN, Sun HB, Zhang QW, Li JQ..  (2019)  Synthesis and antidepressant effect of novel aralkyl piperazine and piperidine derivatives targeting SSRI/5-HT1A/5-HT7.,  29  (23): [PMID:31627993] [10.1016/j.bmcl.2019.126703]

119. Wang WT, Qian H, Wu JW, Chen XW, Li JQ..  (2019)  Synthesis and antidepressant-like activity of novel alkoxy-piperidine derivatives targeting SSRI/5-HT1A/5-HT7.,  29  (24): [PMID:31699607] [10.1016/j.bmcl.2019.126769]

120.  (2018)  INHIBITORS OF SARM1 NADase ACTIVITY AND USES THEREOF, 

121. 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]

122. 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]

123. 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 NIH (USA) - Clinical Collection,  [10.6019/CHEMBL4513141]

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

125. Xu JW,Qi YL,Wu JW,Yuan RX,Chen XW,Li JQ.  (2021)  Synthesis and biological evaluation of novel antipsychotic trans-4-(2-(1,2,4,5-tetrahydro-3H-benzo[d]azepin-3-yl)ethyl)cyclohexan-1-amine derivatives targeting dopamine/serotonin receptor subtypes.,  31  [PMID:33189775] [10.1016/j.bmcl.2020.127681]

126. Chen WL,Li DD,Chen X,Wang YZ,Xu JJ,Jiang ZY,You QD,Guo XK.  (2020)  Proton pump inhibitors selectively suppress MLL rearranged leukemia cells via disrupting MLL1-WDR5 protein-protein interaction.,  188  [PMID:31923859] [10.1016/j.ejmech.2019.112027]

127. Riches A,Hart CJS,Trenholme KR,Skinner-Adams TS.  (2020)  Anti-Giardia Drug Discovery: Current Status and Gut Feelings.,  63  (22.0): [PMID:32869995] [10.1021/acs.jmedchem.0c00910]

128. 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]

129. Chen LZ, Shu HY, Wu J, Yu YL, Ma D, Huang X, Liu MM, Liu XH, Shi JB..  (2021)  Discovery and development of novel pyrimidine and pyrazolo/thieno-fused pyrimidine derivatives as potent and orally active inducible nitric oxide synthase dimerization inhibitor with efficacy for arthritis.,  213  [PMID:33515864] [10.1016/j.ejmech.2021.113174]

130. Pérez-Villanueva J, Yépez-Mulia L, Rodríguez-Villar K, Cortés-Benítez F, Palacios-Espinosa JF, Soria-Arteche O..  (2021)  The giardicidal activity of lobendazole, fabomotizole, tenatoprazole and ipriflavone: A ligand-based virtual screening and in vitro study.,  211  [PMID:33360795] [10.1016/j.ejmech.2020.113110]

131. Ma C, Li Q, Zhao M, Fan G, Zhao J, Zhang D, Yang S, Zhang S, Gao D, Mao L, Zhu L, Li W, Xu G, Jiang Y, Ding Q..  (2021)  Discovery of 1-Amino-1H-imidazole-5-carboxamide Derivatives as Highly Selective, Covalent Bruton's Tyrosine Kinase (BTK) Inhibitors.,  64  (21.0): [PMID:34672559] [10.1021/acs.jmedchem.1c01559]

132.  (2021)  CXCL10 Inhibitors, 

133. Fallot LB, Suresh RR, Fisher CL, Salmaso V, O'Connor RD, Kaufman N, Gao ZG, Auchampach JA, Jacobson KA..  (2022)  Structure-Activity Studies of 1H-Imidazo[4,5-c]quinolin-4-amine Derivatives as A₃ Adenosine Receptor Positive Allosteric Modulators.,  65  (22.0): [PMID:36367749] [10.1021/acs.jmedchem.2c01170]

134. Zattoni IF, Delabio LC, Dutra JP, Kita DH, Scheiffer G, Hembecker M, Pereira GDS, Moure VR, Valdameri G..  (2022)  Targeting breast cancer resistance protein (BCRP/ABCG2): Functional inhibitors and expression modulators.,  237  [PMID:35483322] [10.1016/j.ejmech.2022.114346]

135. Ma Z, He S, Yuan Y, Zhuang Z, Liu Y, Wang H, Chen J, Xu X, Ding C, Molodtsov V, Lin W, Robertson GT, Weiss WJ, Pulse M, Nguyen P, Duncan L, Doyle T, Ebright RH, Lynch AS..  (2022)  Design, Synthesis, and Characterization of TNP-2198, a Dual-Targeted Rifamycin-Nitroimidazole Conjugate with Potent Activity against Microaerophilic and Anaerobic Bacterial Pathogens.,  65  (6.0): [PMID:35175750] [10.1021/acs.jmedchem.1c02045]

136. Huang J, Zhang J, Luo B, Qiao W, Qiu Z, Song R, Dai Z, Sui J, Xu X, Ruan S, Li C, Luo Y, Yang T..  (2022)  Discovery of a Novel Series of Imipridone Compounds as Homo sapiens Caseinolytic Protease P Agonists with Potent Antitumor Activities In Vitro and In Vivo.,  65  (11.0): [PMID:35609303] [10.1021/acs.jmedchem.1c02071]

137. Pillaiyar T, Meenakshisundaram S, Manickam M, Sankaranarayanan M..  (2020)  A medicinal chemistry perspective of drug repositioning: Recent advances and challenges in drug discovery.,  195  [PMID:32283298] [10.1016/j.ejmech.2020.112275]

138. 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]

139. Zimmermann M, Zimmermann-Kogadeeva M, Wegmann R, Goodman AL..  (2019)  Mapping human microbiome drug metabolism by gut bacteria and their genes.,  570  (7762): [PMID:31158845] [10.1038/s41586-019-1291-3]

140. Fraunhofer Institute for Translational Medicine and Pharmacology - Discovery Research – ScreeningPort.  (2022)  ECBD screening data for assay EOS300041,  [10.6019/EOS300041]

141. Fraunhofer Institute for Translational Medicine and Pharmacology - Discovery Research – ScreeningPort.  (2022)  ECBD screening data for assay EOS300044,  [10.6019/EOS300044]

Source

Source(21):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book)
• Open TG-GATEs
• USP Dictionary of USAN and International Drug Names
• Drugs for Neglected Diseases Initiative (DNDi)
• DrugMatrix
• TP-search Transporter Database
• Harvard Malaria Screening
• Gene Expression Atlas Compounds
• Patent Bioactivity Data
• Curated Drug Pharmacokinetic Data
• CO-ADD antimicrobial screening data
• WHO Anatomical Therapeutic Chemical Classification
• British National Formulary
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6
• EU-OPENSCREEN dataset
• Zimmerman Lab Biotransformation data Dec 2023