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List of Chronobiotics



Name SMILES FDA Status Effects Targets Mechanisms Articles
CCOC(=O)C1=C(NC(=C(C1C2=C(C(=CC=C2)Cl)Cl)C(=O)OC)C)C Approved BMAL1 expression (induction) Bmal1, de-repressing BMAL1, BMAL1 expression modulation, BMAL1 expression modulation, 1,4-dihydropyridine calcium channel blocker Tamai, T.K., Nakane, Y., Ota, W., Kobayashi, A., Ishiguro, M., Kadofusa, N., Ikegami, K., Yagita, K., Shigeyoshi, Y., Sudo, M. and Nishiwaki‐Ohkawa, T., 2018. Identification of circadian clock modulators from existing drugs. EMBO molecular medicine, 10(5), p.e8724.
C1=CC(=C2C(=C1NCCNCCO)C(=O)C3=C(C=CC(=C3C2=O)O)O)NCCNCCO.Cl.Cl Approved CLOCK-BMAL1 , Arntl (gene) , BMAL1 expression (induction) BMAL1 expression modulation Tamai, T.K., Nakane, Y., Ota, W., Kobayashi, A., Ishiguro, M., Kadofusa, N., Ikegami, K., Yagita, K., Shigeyoshi, Y., Sudo, M. and Nishiwaki‐Ohkawa, T., 2018. Identification of circadian clock modulators from existing drugs. EMBO molecular medicine, 10(5), p.e8724.
C1=CC(=CC=C1CCCC(=O)O)N(CCCl)CCCl Approved CLOCK-BMAL1 , Arntl (gene) , BMAL1 expression (induction) Bmal1, BMAL1 expression modulation, BMAL1 expression modulation Tamai, T.K., Nakane, Y., Ota, W., Kobayashi, A., Ishiguro, M., Kadofusa, N., Ikegami, K., Yagita, K., Shigeyoshi, Y., Sudo, M. and Nishiwaki‐Ohkawa, T., 2018. Identification of circadian clock modulators from existing drugs. EMBO molecular medicine, 10(5), p.e8724.
C1=NC2=C(N=C(N=C2N1C3C(C(C(O3)CO)O)F)Cl)N Approved CLOCK-BMAL1 , Arntl (gene) , BMAL1 expression (induction) Bmal1, BMAL1 expression modulation, BMAL1 expression modulation Tamai, T.K., Nakane, Y., Ota, W., Kobayashi, A., Ishiguro, M., Kadofusa, N., Ikegami, K., Yagita, K., Shigeyoshi, Y., Sudo, M. and Nishiwaki‐Ohkawa, T., 2018. Identification of circadian clock modulators from existing drugs. EMBO molecular medicine, 10(5), p.e8724.
[O-2].[O-2].[O-2].[As+3].[As+3] None CLOCK-BMAL1 , Arntl (gene) , BMAL1 expression (induction) Bmal1, de-repressing BMAL1, BMAL1 expression modulation, BMAL1 expression modulation, "Inhibitor of nuclear factor kappa-B kinase subunit beta Thioredoxin reductase 1, cytoplasmic Transcription factor AP-1 G1/S- Tamai, T.K., Nakane, Y., Ota, W., Kobayashi, A., Ishiguro, M., Kadofusa, N., Ikegami, K., Yagita, K., Shigeyoshi, Y., Sudo, M. and Nishiwaki‐Ohkawa, T., 2018. Identification of circadian clock modulators from existing drugs. EMBO molecular medicine, 10(5), p.e8724.
CC1=C(C=CC=C1O)C(=O)N[C@@H](CSC2=CC=CC=C2)[C@@H](CN3C[C@H]4CCCC[C@H]4C[C@H]3C(=O)NC(C)(C)C)O.CS(=O)(=O)O Approved CLOCK-BMAL1 , Arntl (gene) , BMAL1 expression (induction) Bmal1, de-repressing BMAL1, BMAL1 expression modulation, BMAL1 expression modulation, HIV-1 protease binding Tamai, T.K., Nakane, Y., Ota, W., Kobayashi, A., Ishiguro, M., Kadofusa, N., Ikegami, K., Yagita, K., Shigeyoshi, Y., Sudo, M. and Nishiwaki‐Ohkawa, T., 2018. Identification of circadian clock modulators from existing drugs. EMBO molecular medicine, 10(5), p.e8724.
C1=CC(=C(C=C1Cl)Cl)CO/N=C(\CN2C=CN=C2)/C3=C(C=C(C=C3)Cl)Cl.[N+](=O)(O)[O-] Approved CLOCK-BMAL1 , Arntl (gene) , BMAL1 expression (induction) Bmal1, de-repressing BMAL1, BMAL1 expression modulation, BMAL1 expression modulation Tamai, T.K., Nakane, Y., Ota, W., Kobayashi, A., Ishiguro, M., Kadofusa, N., Ikegami, K., Yagita, K., Shigeyoshi, Y., Sudo, M. and Nishiwaki‐Ohkawa, T., 2018. Identification of circadian clock modulators from existing drugs. EMBO molecular medicine, 10(5), p.e8724.
C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3Cl)N4C=CN=C4 Approved CLOCK-BMAL1 , Arntl (gene) , BMAL1 expression (induction) Bmal1, BMAL1 expression modulation, BMAL1 expression modulation, Intermediate conductance calcium-activated potassium channel, protein 4 Nuclear receptor subfamily 1 group I member 2, 3 Tamai, T.K., Nakane, Y., Ota, W., Kobayashi, A., Ishiguro, M., Kadofusa, N., Ikegami, K., Yagita, K., Shigeyoshi, Y., Sudo, M. and Nishiwaki‐Ohkawa, T., 2018. Identification of circadian clock modulators from existing drugs. EMBO molecular medicine, 10(5), p.e8724.
C1[C@@H]([C@H](O[C@H]1N2C=NC3=C(N=C(N=C32)Cl)N)CO)O Approved CLOCK-BMAL1 , BMAL1 expression (induction) Bmal1, de-repressing BMAL1, BMAL1 expression modulation, BMAL1 expression modulation Tamai, T.K., Nakane, Y., Ota, W., Kobayashi, A., Ishiguro, M., Kadofusa, N., Ikegami, K., Yagita, K., Shigeyoshi, Y., Sudo, M. and Nishiwaki‐Ohkawa, T., 2018. Identification of circadian clock modulators from existing drugs. EMBO molecular medicine, 10(5), p.e8724.
CC(C1=CC=CC2=CC=CC=C21)NCCCC3=CC(=CC=C3)C(F)(F)F.Cl Approved CLOCK-BMAL1 , BMAL1 expression (induction) Bmal1, de-repressing BMAL1, BMAL1 expression modulation, BMAL1 expression modulation, calcimimetic and a P450 inhibitor Tamai, T.K., Nakane, Y., Ota, W., Kobayashi, A., Ishiguro, M., Kadofusa, N., Ikegami, K., Yagita, K., Shigeyoshi, Y., Sudo, M. and Nishiwaki‐Ohkawa, T., 2018. Identification of circadian clock modulators from existing drugs. EMBO molecular medicine, 10(5), p.e8724.
C1=CN(C(=O)N=C1N)CC(CO)OCP(=O)(O)O Not approved CLOCK-BMAL1 , Arntl (gene) , BMAL1 expression (induction) Bmal1, BMAL1 expression modulation, BMAL1 expression modulation Tamai, T.K., Nakane, Y., Ota, W., Kobayashi, A., Ishiguro, M., Kadofusa, N., Ikegami, K., Yagita, K., Shigeyoshi, Y., Sudo, M. and Nishiwaki‐Ohkawa, T., 2018. Identification of circadian clock modulators from existing drugs. EMBO molecular medicine, 10(5), p.e8724.
C[C@H]1[C@@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)O.Cl Approved CLOCK-BMAL1 , BMAL1 expression (induction) Bmal1, de-repressing BMAL1, BMAL1 expression modulation, BMAL1 expression modulation, DNA DNA topoisomerase 2-alpha, beta binding, targeting DNA and DNA topoisomerase 2-alpha. Tamai, T.K., Nakane, Y., Ota, W., Kobayashi, A., Ishiguro, M., Kadofusa, N., Ikegami, K., Yagita, K., Shigeyoshi, Y., Sudo, M. and Nishiwaki‐Ohkawa, T., 2018. Identification of circadian clock modulators from existing drugs. EMBO molecular medicine, 10(5), p.e8724.
CC1=CN=C(N1)C2=CN=C(N=C2C3=C(C=C(C=C3)Cl)Cl)NCCNC4=NC=C(C=C4)C#N Not approved GSK-3α/β Highly selective, ATP-competitive inhibition of GSK-3 (both α and β isoforms) Hirota, T., Lewis, W.G., Liu, A.C., Lee, J.W., Schultz, P.G. and Kay, S.A., 2008. A chemical biology approach reveals period shortening of the mammalian circadian clock by specific inhibition of GSK-3β. Proceedings of the National Academy of Sciences, 105(52), pp.20746-20751.
C1CC2=C(C=CC(=C2)F)OC1C(CNCC(C3CCC4=C(O3)C=CC(=C4)F)O)O.Cl Approved CLOCK-BMAL1 , Arntl (gene) , BMAL1 expression (induction) , Beta 1,2 adrenergic receptor Bmal1, de-repressing BMAL1, BMAL1 expression modulation, BMAL1 expression modulation, Beta-1, 2 adrenergic receptor binding Tamai, T.K., Nakane, Y., Ota, W., Kobayashi, A., Ishiguro, M., Kadofusa, N., Ikegami, K., Yagita, K., Shigeyoshi, Y., Sudo, M. and Nishiwaki‐Ohkawa, T., 2018. Identification of circadian clock modulators from existing drugs. EMBO molecular medicine, 10(5), p.e8724.
CC1=CC(=CC=C1)CN2CCN(CC2)C(C3=CC=CC=C3)C4=CC=C(C=C4)Cl.Cl.Cl Approved CLOCK-BMAL1 , Arntl (gene) , Histamine 1 receptor , BMAL1 expression (induction) Bmal1, de-repressing BMAL1, BMAL1 expression modulation, Histamine 1 blocker, BMAL1 expression modulation, Histamine H1 receptor, Nuclear receptor subfamily 1 group I member 3 Tamai, T.K., Nakane, Y., Ota, W., Kobayashi, A., Ishiguro, M., Kadofusa, N., Ikegami, K., Yagita, K., Shigeyoshi, Y., Sudo, M. and Nishiwaki‐Ohkawa, T., 2018. Identification of circadian clock modulators from existing drugs. EMBO molecular medicine, 10(5), p.e8724.
CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC(=O)O)C)C Approved CLOCK-BMAL1 , Arntl (gene) , BMAL1 expression (induction) , Retinoic acid receptor alpha Bmal1, de-repressing BMAL1, BMAL1 expression modulation, BMAL1 expression modulation, Binding retinoic acid receptor alpha Tamai, T.K., Nakane, Y., Ota, W., Kobayashi, A., Ishiguro, M., Kadofusa, N., Ikegami, K., Yagita, K., Shigeyoshi, Y., Sudo, M. and Nishiwaki‐Ohkawa, T., 2018. Identification of circadian clock modulators from existing drugs. EMBO molecular medicine, 10(5), p.e8724.
CCC1=C2CN3C(=CC4=C(C3=O)COC(=O)C4(CC)O)C2=NC5=C1C=C(C=C5)OC(=O)N6CCC(CC6)N7CCCCC7.Cl Approved CLOCK-BMAL1 , BMAL1 expression (induction) , Topoisomerase I Bmal1, de-repressing BMAL1, BMAL1 expression modulation, BMAL1 expression modulation, inhibits topoisomerase I Tamai, T.K., Nakane, Y., Ota, W., Kobayashi, A., Ishiguro, M., Kadofusa, N., Ikegami, K., Yagita, K., Shigeyoshi, Y., Sudo, M. and Nishiwaki‐Ohkawa, T., 2018. Identification of circadian clock modulators from existing drugs. EMBO molecular medicine, 10(5), p.e8724.
C1CN1P(=S)(N2CC2)N3CC3 Not approved CLOCK-BMAL1 , Arntl (gene) , BMAL1 expression (induction) Bmal1, de-repressing BMAL1, BMAL1 expression modulation, BMAL1 expression modulation, DNA alkylation Tamai, T.K., Nakane, Y., Ota, W., Kobayashi, A., Ishiguro, M., Kadofusa, N., Ikegami, K., Yagita, K., Shigeyoshi, Y., Sudo, M. and Nishiwaki‐Ohkawa, T., 2018. Identification of circadian clock modulators from existing drugs. EMBO molecular medicine, 10(5), p.e8724.
CC1=C(C=CN=C1CS(=O)C2=NC3=CC=CC=C3[N-]2)OCCCOC.[Na+] Approved CLOCK-BMAL1 , Arntl (gene) , BMAL1 expression (induction) , H+ K+ ATPase Bmal1, de-repressing BMAL1, BMAL1 expression modulation, BMAL1 expression modulation, Potassium-transporting ATPase alpha chain 1 binding activity Tamai, T.K., Nakane, Y., Ota, W., Kobayashi, A., Ishiguro, M., Kadofusa, N., Ikegami, K., Yagita, K., Shigeyoshi, Y., Sudo, M. and Nishiwaki‐Ohkawa, T., 2018. Identification of circadian clock modulators from existing drugs. EMBO molecular medicine, 10(5), p.e8724.
CCOC(=O)C1=CN=C(C=C1)C#CC2=CC3=C(C=C2)SCCC3(C)C Approved CLOCK-BMAL1 , Arntl (gene) , BMAL1 expression (induction) , Retinoic acid receptor alpha Bmal1, de-repressing BMAL1, BMAL1 expression modulation, BMAL1 expression modulation Tamai, T.K., Nakane, Y., Ota, W., Kobayashi, A., Ishiguro, M., Kadofusa, N., Ikegami, K., Yagita, K., Shigeyoshi, Y., Sudo, M. and Nishiwaki‐Ohkawa, T., 2018. Identification of circadian clock modulators from existing drugs. EMBO molecular medicine, 10(5), p.e8724.
COC1=CC(=CC(=C1OC)OC)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)O Approved CLOCK-BMAL1 , Arntl (gene) , BMAL1 expression (induction) Bmal1, de-repressing BMAL1, BMAL1 expression modulation, BMAL1 expression modulation, DNA DNA topoisomerase 2-alpha, beta binding, Tubulin alpha-4A, beta chain binding Tamai, T.K., Nakane, Y., Ota, W., Kobayashi, A., Ishiguro, M., Kadofusa, N., Ikegami, K., Yagita, K., Shigeyoshi, Y., Sudo, M. and Nishiwaki‐Ohkawa, T., 2018. Identification of circadian clock modulators from existing drugs. EMBO molecular medicine, 10(5), p.e8724.
CC[C@@H]1/C=C(/C[C@@H](C[C@@H]([C@@H]2[C@H](C[C@H]([C@@](O2)(C(=O)C(=O)N3CCCC[C@H]3C(=O)O[C@@H]([C@@H]([C@H](CC1=O)O)C)/C(=C/[C@@H]4CC[C@@H]([C@@H](C4)OC)Cl)/C)O)C)OC)OC)C)\C Approved CLOCK-BMAL1 , Arntl (gene) , BMAL1 expression (induction) BMAL1 expression modulation, BMAL1 expression modulation, Calcineurin Inhibitor Immunosuppressant Tamai, T.K., Nakane, Y., Ota, W., Kobayashi, A., Ishiguro, M., Kadofusa, N., Ikegami, K., Yagita, K., Shigeyoshi, Y., Sudo, M. and Nishiwaki‐Ohkawa, T., 2018. Identification of circadian clock modulators from existing drugs. EMBO molecular medicine, 10(5), p.e8724.
CC1(CCC2=C3C(=C(C=C2O1)OCC(=O)NC4=CC=CC=C4C(=O)N)C(=CC(=O)O3)C5=CC=CC=C5)C Not approved CLOCK-BMAL1 Interferes with CLOCK–BMAL1 Doruk, Y.U., Yarparvar, D., Akyel, Y.K., Gul, S., Taskin, A.C., Yilmaz, F., Baris, I., Ozturk, N., Türkay, M., Ozturk, N. and Okyar, A., 2020. A CLOCK-binding small molecule disrupts the interaction between CLOCK and BMAL1 and enhances circadian rhythm amplitude. Journal of Biological Chemistry, 295(11), pp.3518-3531.
C1C2=C(C3=C(C=CC=N3)NC1=O)NC4=C2C=C(C=C4)Br Not approved GSK-3α/β Dual inhibitor of Cyclin-dependent kinases (CDK) and Glycogen Synthase Kinase-3 (GSK-3) He, B. and Chen, Z., 2016. Molecular targets for small-molecule modulators of circadian clocks. Current drug metabolism, 17(5), pp.503-512.
CS(=O)(=O)N(CC1=CC=CO1)CC(CN2C3=CC=CC=C3C4=CC=CC=C42)O Not approved CRY1-PER2 complex , CRY1 , CRY1 Selective stabilizer of CRY1, Selectively stabilizes CRY2, Binds CRY1 FAD-binding Hirota, T., Lee, J.W., St. John, P.C., Sawa, M., Iwaisako, K., Noguchi, T., Pongsawakul, P.Y., Sonntag, T., Welsh, D.K., Brenner, D.A. and Doyle III, F.J., 2012. Identification of small molecule activators of cryptochrome. Science, 337(6098), pp.1094-1097 , Iida, M., Nakane, Y., Yoshimura, T. and Hirota, T., 2022. Effects of cryptochrome-modulating compounds on circadian behavioural rhythms in zebrafish. Journal of Biochemistry, 171(5), pp.501-507.