VANOXERINE

ID: ALA281594

Max Phase: Phase

Molecular Formula: C28H32F2N2O

Molecular Weight: 450.57

Molecule Type: Small molecule

Associated Items:

Representations

Synonyms (3): Vanoxerine | GBR 12909 | GBR-12909
Synonyms from Alternative Forms(3):

    Canonical SMILES:  Fc1ccc(C(OCCN2CCN(CCCc3ccccc3)CC2)c2ccc(F)cc2)cc1

    Standard InChI:  InChI=1S/C28H32F2N2O/c29-26-12-8-24(9-13-26)28(25-10-14-27(30)15-11-25)33-22-21-32-19-17-31(18-20-32)16-4-7-23-5-2-1-3-6-23/h1-3,5-6,8-15,28H,4,7,16-22H2

    Standard InChI Key:  NAUWTFJOPJWYOT-UHFFFAOYSA-N

    Associated Targets(Human)

    Sigma opioid receptor 6358 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Monoamine transporters; serotonin & dopamine 417 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Monoamine transporters; Norepinephrine & dopamine 216 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Dopamine transporter 10535 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Serotonin transporter 12625 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Norepinephrine transporter 10102 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Prelamin-A/C 36751 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Nuclear factor NF-kappa-B p105 subunit 1459 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Huntingtin 19182 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Ras-related protein Rab-9A 22488 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Survival motor neuron protein 34246 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Thyroid stimulating hormone receptor 29986 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Serine/threonine-protein kinase mTOR 13850 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Tyrosyl-DNA phosphodiesterase 1 345557 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Cytochrome P450 2C19 29246 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Microtubule-associated protein tau 95507 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Hypoxia-inducible factor 1 alpha 6027 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Aldehyde dehydrogenase 1A1 77053 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    MAP kinase ERK2 25055 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Menin/Histone-lysine N-methyltransferase MLL 48157 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Niemann-Pick C1 protein 18985 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Thrombopoietin 834 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Cellular tumor antigen p53 48468 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Cytochrome P450 2D6 33882 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Cytochrome P450 3A4 53859 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Cytochrome P450 2C9 32119 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    ATPase family AAA domain-containing protein 5 122566 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Beta-glucocerebrosidase 14647 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Nuclear factor erythroid 2-related factor 2 95332 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    M-phase phosphoprotein 8 656 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 93046 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Chromobox protein homolog 1 92434 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Arachidonate 15-lipoxygenase, type II 7244 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Runt-related transcription factor 1/Core-binding factor subunit beta 7867 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Cytochrome P450 1A2 26471 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Ataxin-2 54410 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    DNA polymerase kappa 8653 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    HEK293 82097 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    SH-SY5Y 11521 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Ubiquitin carboxyl-terminal hydrolase 1 22556 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Cerebroside-sulfatase 655 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Histone deacetylase 6 20808 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Associated Targets(non-human)

    Dopamine transporter 6071 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Serotonin transporter 6087 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Monoamine transporters; serotonin & dopamine 1148 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Norepinephrine transporter 2222 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Monoamine transporters; Norepininephrine & dopamine 561 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Rattus norvegicus 775804 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Mus musculus 284745 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Histamine H2 receptor 1693 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Sigma opioid receptor 1607 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Monoamine transporters; Norepinephrine & serotonin 298 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Sigma-1 receptor 3326 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Transporter 332 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Saccharomyces cerevisiae 19171 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Nuclear receptor ROR-gamma 89407 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    4'-phosphopantetheinyl transferase ffp 24982 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Inositol monophosphatase 1 16203 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Anthrax lethal factor 7585 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Muscarinic acetylcholine receptor M1 3437 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Dopamine transporter 139 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Serotonin transporter 150 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Voltage-dependent L-type calcium channel subunit alpha-1C 242 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    SARS-CoV-2 38078 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Molecule Features

    Natural Product: YesOral: NoChemical Probe: NoParenteral: No
    Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
    Chirality: YesAvailability: NoProdrug: No

    Drug Indications

    MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

    Mechanisms of Action

    Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

    Properties

    Molecular Weight: 450.57Molecular Weight (Monoisotopic): 450.2483AlogP: 5.32#Rotatable Bonds: 10
    Polar Surface Area: 15.71Molecular Species: NEUTRALHBA: 3HBD: 0
    #RO5 Violations: 1HBA (Lipinski): 3HBD (Lipinski): 0#RO5 Violations (Lipinski): 1
    CX Acidic pKa: CX Basic pKa: 8.18CX LogP: 6.24CX LogD: 5.40
    Aromatic Rings: 3Heavy Atoms: 33QED Weighted: 0.42Np Likeness Score: -0.81

    References

    1. Ghorai SK, Cook C, Davis M, Venkataraman SK, George C, Beardsley PM, Reith ME, Dutta AK..  (2003)  High affinity hydroxypiperidine analogues of 4-(2-benzhydryloxyethyl)-1-(4-fluorobenzyl)piperidine for the dopamine transporter: stereospecific interactions in vitro and in vivo.,  46  (7): [PMID:12646032] [10.1021/jm020275k]
    2. Hsin LW, Dersch CM, Baumann MH, Stafford D, Glowa JR, Rothman RB, Jacobson AE, Rice KC..  (2002)  Development of long-acting dopamine transporter ligands as potential cocaine-abuse therapeutic agents: chiral hydroxyl-containing derivatives of 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine and 1-[2-(diphenylmethoxy)ethyl]-4-(3-phenylpropyl)piperazine.,  45  (6): [PMID:11882001] [10.1021/jm010430f]
    3. Lewis D, Zhang Y, Prisinzano T, Dersch CM, Rothman RB, Jacobson AE, Rice KC..  (2003)  Further exploration of 1-[2-[Bis-(4-fluorophenyl)methoxy]ethyl]piperazine (GBR 12909): role of N-aromatic, N-heteroaromatic, and 3-oxygenated N-phenylpropyl substituents on affinity for the dopamine and serotonin transporter.,  13  (7): [PMID:12657288] [10.1016/s0960-894x(03)00108-2]
    4. Greiner E, Prisinzano T, Johnson EM, Dersch CM, Marcus J, Partilla JS, Rothman RB, Jacobson AE, Rice KC..  (2003)  Structure-activity relationship studies of highly selective inhibitors of the dopamine transporter: N-benzylpiperidine analogues of 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine.,  46  (8): [PMID:12672246] [10.1021/jm020419v]
    5. Goodman MM, Kung MP, Kabalka GW, Kung HF, Switzer R..  (1994)  Synthesis and characterization of radioiodinated N-(3-iodopropen-1-yl)-2 beta-carbomethoxy-3 beta-(4-chlorophenyl)tropanes: potential dopamine reuptake site imaging agents.,  37  (10): [PMID:8182712] [10.1021/jm00036a020]
    6. Zhang S, Reith ME, Dutta AK..  (2003)  Design, synthesis, and activity of novel cis- and trans-3,6-disubstituted pyran biomimetics of 3,6-disubstituted piperidine as potential ligands for the dopamine transporter.,  13  (9): [PMID:12699762] [10.1016/s0960-894x(03)00169-0]
    7. Kolhatkar RB, Ghorai SK, George C, Reith ME, Dutta AK..  (2003)  Interaction of cis-(6-benzhydrylpiperidin-3-yl)benzylamine analogues with monoamine transporters: structure-activity relationship study of structurally constrained 3,6-disubstituted piperidine analogues of (2,2-diphenylethyl)-[1-(4-fluorobenzyl)piperidin-4-ylmethyl]amine.,  46  (11): [PMID:12747792] [10.1021/jm020561w]
    8. Newman AH, Allen AC, Izenwasser S, Katz JL..  (1994)  Novel 3 alpha-(diphenylmethoxy)tropane analogs: potent dopamine uptake inhibitors without cocaine-like behavioral profiles.,  37  (15): [PMID:8057273] [10.1021/jm00041a002]
    9. Bradley AL, Izenwasser S, Wade D, Klein-Stevens C, Zhu N, Trudell ML..  (2002)  Synthesis and dopamine transporter binding affinities of 3alpha-benzyl-8-(diarylmethoxyethyl)-8-azabicyclo[3.2.1]octanes.,  12  (17): [PMID:12161139] [10.1016/s0960-894x(02)00464-x]
    10. Hanson RN, Choi S, Elmaleh DR, Fischman AJ.  (1997)  Synthesis and evaluation of novel-N-[2-(bis-aryl-methoxy)ethyl-N-aralkyl-,-alkanediamines as potent and selective dopamine reuptake inhibitors: Seco analogs of GBR12935 and GBR12909,  (20): [10.1016/S0960-894X(97)10053-1]
    11. Cao J, Kulkarni SS, Husbands SM, Bowen WD, Williams W, Kopajtic T, Katz JL, George C, Newman AH..  (2003)  Dual probes for the dopamine transporter and sigma1 receptors: novel piperazinyl alkyl-bis(4'-fluorophenyl)amine analogues as potential cocaine-abuse therapeutic agents.,  46  (13): [PMID:12801223] [10.1021/jm030008u]
    12. Zimmermann K, Hengerer B..  (1998)  Design and synthesis of a biotinylated dopamine transporter ligand for the purification and labeling of dopaminergic neurons.,  (3): [PMID:9871666] [10.1016/s0960-894x(98)00003-1]
    13. Bucholtz EC, Brown RL, Tropsha A, Booth RG, Wyrick SD..  (1999)  Synthesis, evaluation, and comparative molecular field analysis of 1-phenyl-3-amino-1,2,3,4-tetrahydronaphthalenes as ligands for histamine H(1) receptors.,  42  (16): [PMID:10447948] [10.1021/jm980428x]
    14. Cao J, Husbands SM, Kopajtic T, Katz JL, Newman AH..  (2001)  [3-cis-3,5-Dimethyl-(1-piperazinyl)alkyl]-bis-(4'-fluorophenyl)amine analogues as novel probes for the dopamine transporter.,  11  (24): [PMID:11720867] [10.1016/s0960-894x(01)00662-x]
    15. Dutta AK, Xu C, Reith ME..  (1998)  Tolerance in the replacement of the benzhydrylic O atom in 4-[2-(diphenylmethoxy)ethyl]-1-benzylpiperidine derivatives by an N atom: development of new-generation potent and selective N-analogue molecules for the dopamine transporter.,  41  (17): [PMID:9703474] [10.1021/jm980066t]
    16. Newman AH, Kline RH, Allen AC, Izenwasser S, George C, Katz JL..  (1995)  Novel 4'-substituted and 4',4"-disubstituted 3 alpha-(diphenylmethoxy)tropane analogs as potent and selective dopamine uptake inhibitors.,  38  (20): [PMID:7562926] [10.1021/jm00020a006]
    17. Zhang Y, Joseph DB, Bowen WD, Flippen-Anderson JL, Dersch CM, Rothman RB, Jacobson AE, Rice KC..  (2001)  Synthesis and biological evaluation of tropane-like 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine (GBR 12909) analogues.,  44  (23): [PMID:11689080] [10.1021/jm0101592]
    18. Myers AM, Charifson PS, Owens CE, Kula NS, McPhail AT, Baldessarini RJ, Booth RG, Wyrick SD..  (1994)  Conformational analysis, pharmacophore identification, and comparative molecular field analysis of ligands for the neuromodulatory sigma 3 receptor.,  37  (24): [PMID:7990111] [10.1021/jm00050a008]
    19. Hoffman BT, Kopajtic T, Katz JL, Newman AH..  (2000)  2D QSAR modeling and preliminary database searching for dopamine transporter inhibitors using genetic algorithm variable selection of Molconn Z descriptors.,  43  (22): [PMID:11063611] [10.1021/jm990472s]
    20. Dutta AK, Coffey LL, Reith ME..  (1997)  Highly selective, novel analogs of 4-[2-(diphenylmethoxy)ethyl]- 1-benzylpiperidine for the dopamine transporter: effect of different aromatic substitutions on their affinity and selectivity.,  40  (1): [PMID:9016326] [10.1021/jm960638e]
    21. Prisinzano T, Greiner E, Johnson EM, Dersch CM, Marcus J, Partilla JS, Rothman RB, Jacobson AE, Rice KC..  (2002)  Piperidine analogues of 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine (GBR 12909): high affinity ligands for the dopamine transporter.,  45  (19): [PMID:12213078] [10.1021/jm020264r]
    22. Husbands SM, Izenwasser S, Kopajtic T, Bowen WD, Vilner BJ, Katz JL, Newman AH..  (1999)  Structure-activity relationships at the monoamine transporters and sigma receptors for a novel series of 9-[3-(cis-3, 5-dimethyl-1-piperazinyl)propyl]carbazole (rimcazole) analogues.,  42  (21): [PMID:10543888] [10.1021/jm9902943]
    23. Matecka D, Rothman RB, Radesca L, de Costa BR, Dersch CM, Partilla JS, Pert A, Glowa JR, Wojnicki FH, Rice KC..  (1996)  Development of novel, potent, and selective dopamine reuptake inhibitors through alteration of the piperazine ring of 1-[2-(diphenylmethoxy)ethyl]-and 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazines (GBR 12935 and GBR 12909).,  39  (24): [PMID:8941383] [10.1021/jm960305h]
    24. Zhang Y, Rothman RB, Dersch CM, de Costa BR, Jacobson AE, Rice KC..  (2000)  Synthesis and transporter binding properties of bridged piperazine analogues of 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine (GBR 12909).,  43  (25): [PMID:11123994] [10.1021/jm000300r]
    25. Lewis DB, Matecka D, Zhang Y, Hsin LW, Dersch CM, Stafford D, Glowa JR, Rothman RB, Rice KC..  (1999)  Oxygenated analogues of 1-[2-(Diphenylmethoxy)ethyl]- and 1-[2-[Bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazines (GBR 12935 and GBR 12909) as potential extended-action cocaine-abuse therapeutic agents.,  42  (24): [PMID:10585212] [10.1021/jm990291q]
    26. Neumeyer JL, Tamagnan G, Wang S, Gao Y, Milius RA, Kula NS, Baldessarini RJ..  (1996)  N-substituted analogs of 2 beta-carbomethoxy-3 beta- (4'-iodophenyl)tropane (beta-CIT) with selective affinity to dopamine or serotonin transporters in rat forebrain.,  39  (2): [PMID:8558525] [10.1021/jm9505324]
    27. Bradley AL, Izenwasser S, Wade D, Cararas S, Trudell ML..  (2003)  Synthesis of dopamine transporter selective 3-[2-(diarylmethoxyethylidene)]-8-alkylaryl-8-azabicyclo[3.2.1]octanes.,  13  (4): [PMID:12639545] [10.1016/s0960-894x(02)01051-x]
    28. Xing D, Chen P, Keil R, Kilts CD, Shi B, Camp VM, Malveaux G, Ely T, Owens MJ, Votaw J, Davis M, Hoffman JM, BaKay RA, Subramanian T, Watts RL, Goodman MM..  (2000)  Synthesis, biodistribution, and primate imaging of fluorine-18 labeled 2beta-carbo-1'-fluoro-2-propoxy-3beta-(4-chlorophenyl)tr opanes. Ligands for the imaging of dopamine transporters by positron emission tomography.,  43  (4): [PMID:10691690] [10.1021/jm9902234]
    29. Dutta AK, Davis MC, Fei XS, Beardsley PM, Cook CD, Reith ME..  (2002)  Expansion of structure-activity studies of piperidine analogues of 1-[2-(diphenylmethoxy)ethyl]-4-(3-phenylpropyl)piperazine (GBR 12935) compounds by altering substitutions in the N-benzyl moiety and behavioral pharmacology of selected molecules.,  45  (3): [PMID:11806716] [10.1021/jm010316x]
    30. Dutta AK, Coffey LL, Reith ME..  (1998)  Potent and selective ligands for the dopamine transporter (DAT): structure-activity relationship studies of novel 4-[2-(diphenylmethoxy)ethyl]-1-(3-phenylpropyl)piperidine analogues.,  41  (5): [PMID:9513598] [10.1021/jm970595h]
    31. Matecka D, Lewis D, Rothman RB, Dersch CM, Wojnicki FH, Glowa JR, DeVries AC, Pert A, Rice KC..  (1997)  Heteroaromatic analogs of 1-[2-(diphenylmethoxy)ethyl]- and 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazines (GBR 12935 and GBR 12909) as high-affinity dopamine reuptake inhibitors.,  40  (5): [PMID:9057857] [10.1021/jm9606599]
    32. Dutta AK, Xu C, Reith ME..  (1996)  Structure-activity relationship studies of novel 4-[2-[bis(4-fluorophenyl)methoxy]ethyl]-1-(3-phenylpropyl)piperidine analogs: synthesis and biological evaluation at the dopamine and serotonin transporter sites.,  39  (3): [PMID:8576918] [10.1021/jm9506581]
    33. Dutta AK, Fei XS, Beardsley PM, Newman JL, Reith ME..  (2001)  Structure-activity relationship studies of 4-[2-(diphenylmethoxy)ethyl]-1-benzylpiperidine derivatives and their N-analogues: evaluation of O-and N-analogues and their binding to monoamine transporters.,  44  (6): [PMID:11300876] [10.1021/jm000311k]
    34. Carroll FI, Lewin AH, Boja JW, Kuhar MJ..  (1992)  Cocaine receptor: biochemical characterization and structure-activity relationships of cocaine analogues at the dopamine transporter.,  35  (6): [PMID:1552510] [10.1021/jm00084a001]
    35. Zhang S, Zhen J, Reith ME, Dutta AK..  (2005)  Discovery of novel trisubstituted asymmetric derivatives of (2S,4R,5R)-2-benzhydryl-5-benzylaminotetrahydropyran-4-ol, exhibiting high affinity for serotonin and norepinephrine transporters in a stereospecific manner.,  48  (15): [PMID:16033275] [10.1021/jm049021k]
    36. Lapa GB, Byrd GD, Lapa AA, Budygin EA, Childers SR, Jones SR, Harp JJ..  (2005)  The synthesis and biological evaluation of dopamine transporter inhibiting activity of substituted diphenylmethoxypiperidines.,  15  (22): [PMID:16165350] [10.1016/j.bmcl.2005.08.028]
    37. Zhang S, Fernandez F, Hazeldine S, Deschamps J, Zhen J, Reith ME, Dutta AK..  (2006)  Further structural exploration of trisubstituted asymmetric pyran derivatives (2S,4R,5R)-2-benzhydryl-5-benzylamino-tetrahydropyran-4-ol and their corresponding disubstituted (3S,6S) pyran derivatives: a proposed pharmacophore model for high-affinity interaction with the dopamine, serotonin, and norepinephrine transporters.,  49  (14): [PMID:16821783] [10.1021/jm0601699]
    38. Cao J, Lever JR, Kopajtic T, Katz JL, Pham AT, Holmes ML, Justice JB, Newman AH..  (2004)  Novel azido and isothiocyanato analogues of [3-(4-phenylalkylpiperazin-1-yl)propyl]bis(4-fluorophenyl)amines as potential irreversible ligands for the dopamine transporter.,  47  (25): [PMID:15566284] [10.1021/jm049670w]
    39. Gilbert KM, Boos TL, Dersch CM, Greiner E, Jacobson AE, Lewis D, Matecka D, Prisinzano TE, Zhang Y, Rothman RB, Rice KC, Venanzi CA..  (2007)  DAT/SERT selectivity of flexible GBR 12909 analogs modeled using 3D-QSAR methods.,  15  (2): [PMID:17127069] [10.1016/j.bmc.2006.09.070]
    40. Mishra M, Kolhatkar R, Zhen J, Parrington I, Reith ME, Dutta AK..  (2008)  Further structural optimization of cis-(6-benzhydryl-piperidin-3-yl)-benzylamine and 1,4-diazabicyclo[3.3.1]nonane derivatives by introducing an exocyclic hydroxyl group: interaction with dopamine, serotonin, and norepinephrine transporters.,  16  (6): [PMID:18249549] [10.1016/j.bmc.2008.01.009]
    41. Grice CA, Tays KL, Savall BM, Wei J, Butler CR, Axe FU, Bembenek SD, Fourie AM, Dunford PJ, Lundeen K, Coles F, Xue X, Riley JP, Williams KN, Karlsson L, Edwards JP..  (2008)  Identification of a potent, selective, and orally active leukotriene a4 hydrolase inhibitor with anti-inflammatory activity.,  51  (14): [PMID:18588282] [10.1021/jm701575k]
    42. Hsin LW, Chang LT, Rothman RB, Dersch CM, Jacobson AE, Rice KC..  (2008)  Design and synthesis of 2- and 3-substituted-3-phenylpropyl analogs of 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine and 1-[2-(diphenylmethoxy)ethyl]-4-(3-phenylpropyl)piperazine: role of amino, fluoro, hydroxyl, methoxyl, methyl, methylene, and oxo substituents on affinity for the dopamine and serotonin transporters.,  51  (9): [PMID:18393401] [10.1021/jm701270n]
    43. Cao J, Kopajtic T, Katz JL, Newman AH..  (2008)  Dual DAT/sigma1 receptor ligands based on 3-(4-(3-(bis(4-fluorophenyl)amino)propyl)piperazin-1-yl)-1-phenylpropan-1-ol.,  18  (19): [PMID:18774292] [10.1016/j.bmcl.2008.08.065]
    44. White JD, Juniku R, Huang K, Yang J, Wong DT..  (2009)  Synthesis of 1,1-[1-naphthyloxy-2-thiophenyl]-2-methylaminomethylcyclopropanes and their evaluation as inhibitors of serotonin, norepinephrine, and dopamine transporters.,  52  (19): [PMID:19791802] [10.1021/jm900847b]
    45. Hojahmat M, Horton DB, Norrholm SD, Miller DK, Grinevich VP, Deaciuc AG, Dwoskin LP, Crooks PA..  (2010)  Lobeline esters as novel ligands for neuronal nicotinic acetylcholine receptors and neurotransmitter transporters.,  18  (2): [PMID:20036131] [10.1016/j.bmc.2009.12.002]
    46. PubChem BioAssay data set, 
    47. PubChem BioAssay data set, 
    48. PubChem BioAssay data set, 
    49. PubChem BioAssay data set, 
    50. PubChem BioAssay data set, 
    51. Hayashi S, Nakata E, Morita A, Mizuno K, Yamamura K, Kato A, Ohashi K..  (2010)  Discovery of {1-[4-(2-{hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl}-1H-benzimidazol-1-yl)piperidin-1-yl]cyclooctyl}methanol, systemically potent novel non-peptide agonist of nociceptin/orphanin FQ receptor as analgesic for the treatment of neuropathic pain: design, synthesis, and structure-activity relationships.,  18  (21): [PMID:20875743] [10.1016/j.bmc.2010.07.034]
    52. Nencetti S, Mazzoni MR, Ortore G, Lapucci A, Giuntini J, Orlandini E, Banti I, Nuti E, Lucacchini A, Giannaccini G, Rossello A..  (2011)  Synthesis, molecular docking and binding studies of selective serotonin transporter inhibitors.,  46  (3): [PMID:21272963] [10.1016/j.ejmech.2010.12.018]
    53. Lebar MD, Hahn KN, Mutka T, Maignan P, McClintock JB, Amsler CD, van Olphen A, Kyle DE, Baker BJ..  (2011)  CNS and antimalarial activity of synthetic meridianin and psammopemmin analogs.,  19  (19): [PMID:21907583] [10.1016/j.bmc.2011.08.033]
    54. PubChem BioAssay data set, 
    55. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 
    56. PubChem BioAssay data set, 
    57. Han M, Song C, Jeong N, Hahn HG..  (2014)  Exploration of 3-Aminoazetidines as Triple Reuptake Inhibitors by Bioisosteric Modification of 3-α-Oxyazetidine.,  (9): [PMID:25221656] [10.1021/ml500187a]
    58. Xu R, Lord SA, Peterson RM, Fergason-Cantrell EA, Lever JR, Lever SZ..  (2015)  Ether modifications to 1-[2-(3,4-dimethoxyphenyl)ethyl]-4-(3-phenylpropyl)piperazine (SA4503): effects on binding affinity and selectivity for sigma receptors and monoamine transporters.,  23  (1): [PMID:25468036] [10.1016/j.bmc.2014.11.007]
    59. Wiśniowska B, Mendyk A, Fijorek K, Glinka A, Polak S..  (2012)  Predictive model for L-type channel inhibition: multichannel block in QT prolongation risk assessment.,  32  [PMID:22761000] [10.1002/jat.2784]
    60. Cao J, Slack RD, Bakare OM, Burzynski C, Rais R, Slusher BS, Kopajtic T, Bonifazi A, Ellenberger MP, Yano H, He Y, Bi GH, Xi ZX, Loland CJ, Newman AH..  (2016)  Novel and High Affinity 2-[(Diphenylmethyl)sulfinyl]acetamide (Modafinil) Analogues as Atypical Dopamine Transporter Inhibitors.,  59  (23): [PMID:27933960] [10.1021/acs.jmedchem.6b01373]
    61. Paudel S, Acharya S, Yoon G, Kim KM, Cheon SH..  (2017)  Design, synthesis and in vitro activity of 1,4-disubstituted piperazines and piperidines as triple reuptake inhibitors.,  25  (7): [PMID:28274674] [10.1016/j.bmc.2017.02.051]
    62. Paudel S, Min X, Acharya S, Khadka DB, Yoon G, Kim KM, Cheon SH..  (2017)  Triple reuptake inhibitors: Design, synthesis and structure-activity relationship of benzylpiperidine-tetrazoles.,  25  (20): [PMID:28807575] [10.1016/j.bmc.2017.07.046]
    63. Felts AS, Rodriguez AL, Morrison RD, Bollinger KA, Venable DF, Blobaum AL, Byers FW, Thompson Gray A, Daniels JS, Niswender CM, Jones CK, Conn PJ, Lindsley CW, Emmitte KA..  (2017)  Discovery of imidazo[1,2-a]-, [1,2,4]triazolo[4,3-a]-, and [1,2,4]triazolo[1,5-a]pyridine-8-carboxamide negative allosteric modulators of metabotropic glutamate receptor subtype 5.,  27  (21): [PMID:28958625] [10.1016/j.bmcl.2017.09.042]
    64. Unpublished dataset, 
    65. Sun H, Shi M, Zhang W, Zheng YM, Xu YZ, Shi JJ, Liu T, Gunosewoyo H, Pang T, Gao ZB, Yang F, Tang J, Yu LF..  (2016)  Development of Novel Alkoxyisoxazoles as Sigma-1 Receptor Antagonists with Antinociceptive Efficacy.,  59  (13): [PMID:27309376] [10.1021/acs.jmedchem.6b00571]
    66. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]
    67. 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]
    68. Mehr-Un-Nisa, Munawar MA, Rankin D, Hruby VJ, Porreca F, Lee YS..  (2021)  C-terminal modified Enkephalin-like tetrapeptides with enhanced affinities at the kappa opioid receptor and monoamine transporters.,  51  [PMID:34798381] [10.1016/j.bmc.2021.116509]
    69. Hubert J. Sijben; Wieke M. van Oostveen; Peter B. R. Hartog; Laura Stucchi; Andrea Rossignoli; Giovanna Maresca; Lia Scarabottolo; Adriaan P. IJzerman; Laura H. Heitman.  (2021)  Label-free high-throughput screening assay for the identification of norepinephrine transporter (NET/SLC6A2) inhibitors,  11  (1): [PMID:34112854] [10.1038/s41598-021-91700-7]