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List of Chronobiotics



Name SMILES FDA Status Effects Targets Mechanisms Articles
CCCC(C)C1(C(=O)NC(=O)NC1=O)CC=C None GABAA receptors GABA A receptor binding, GABAergic system influence Brunet, R., Caza, N. and Cyr, A., 1996. Food intake and circadian rhythms of activity of red-winged blackbirds (Agelaius phoeniceus). A time-course study on the effects of alpha-chloralose and secobarbital. Biological Rhythm Research, 27(2), pp.227-240.
CC1=NN=C2N1C3=C(C=C(C=C3)Cl)C(=NC2)C4=CC=CC=C4Cl Approved GABAA receptors GABA A receptor binding, GABAergic system influence Seidel, W.F., Cohen, S.A., Bliwise, N.G., Roth, T. and Dement, W.C., 1986. Dose‐related effects of triazolam and flurazepam on a circadian rhythm insomnia. Clinical Pharmacology & Therapeutics, 40(3), pp.314-320. , Turek, F.W. and Losee-Olson, S.H., 1987. Dose response curve for the phase-shifting effect of triazolam on the mammalian circadian clock. Life sciences, 40(11), pp.1033-1038.
CCN(CC)CCN1C(=O)CN=C(C2=C1C=CC(=C2)Cl)C3=CC=CC=C3F Approved GABAA receptors GABAergic system influence Seidel, W.F., Cohen, S.A., Bliwise, N.G., Roth, T. and Dement, W.C., 1986. Dose‐related effects of triazolam and flurazepam on a circadian rhythm insomnia. Clinical Pharmacology & Therapeutics, 40(3), pp.314-320. , Crowley, T.J. and Hydinger-Macdonald, M., 1979. Bedtime flurazepam and the human circadian rhythm of spontaneous motility. Psychopharmacology, 62, pp.157-161.
CC1=C(C2=CC3=NC(=CC4=NC(=CC5=C(C(=C(N5)C=C1N2)C=C)C)C(=C4CCC(=O)O)C)C(=C3C)CCC(=O)O)C=C None CLOCK-BMAL1 Core clock 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=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)OC.[Cl-] Not approved CLOCK-BMAL1 , REV-ERBα , Rev-erb expression , NLRP3 inflammasome BMAL1 expression modulation, Rev-erb expression modulation, NLRP3 inflammasome 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. , Zhou, Z., Lin, Y., Gao, L., Yang, Z., Wang, S. and Wu, B., 2020. Circadian pharmacological effects of berberine on chronic colitis in mice: role of the clock component Rev-erbα. Biochemical pharmacology, 172, p.113773. , Ye, C., Zhang, Y., Lin, S., Chen, Y., Wang, Z., Feng, H., Fang, G. and Quan, S., 2023. Berberine ameliorates metabolic-associated fatty liver disease mediated metabolism disorder and redox homeostasis by upregulating clock genes: Clock and Bmal1 expressions. Molecules, 28(4), p.1874.
CN1CCN(CC1)/C=C\2/C(=O)N3C(=N2)CN=C(C4=C3C=CC(=C4)[N+](=O)[O-])C5=CC=CC=C5Cl Not approved GABAA receptors GABA A receptor binding, GABAergic system influence De Crescenzo, F., D'Alò, G.L., Ostinelli, E.G., Ciabattini, M., Di Franco, V., Watanabe, N., Kurtulmus, A., Tomlinson, A., Mitrova, Z., Foti, F. and Del Giovane, C., 2022. Comparative effects of pharmacological interventions for the acute and long-term management of insomnia disorder in adults: a systematic review and network meta-analysis. The Lancet, 400(10347), pp.170-184.
C1C(=O)NC2=C(C=C(C=C2)[N+](=O)[O-])C(=N1)C3=CC=CC=C3 Not approved GABAA receptors GABA A receptor binding, GABAergic system influence Turek, F.W. and Van Reeth, O., 1989. Use of benzodiazepines to manipulate the circadian clock regulating behavioral and endocrine rhythms. Hormone Research in Paediatrics, 31(1-2), pp.59-65.
CN1C2=C(C=C(C=C2)Cl)C(=NC(C1=O)O)C3=CC=CC=C3Cl Not approved GABAA receptors GABA A receptor binding, GABAergic system influence https://pubmed.ncbi.nlm.nih.gov/35052310/
C1=CC2=C(C=CC(=C2N=C1)O)[N+](=O)[O-] Approved 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.
CN(CCCOC1=C(C=C(C=C1)Cl)Cl)CC#C.Cl Approved CLOCK-BMAL1 , Arntl (gene) , BMAL1 expression (induction) , Monoamine oxidase A Bmal1, de-repressing BMAL1, BMAL1 expression modulation, BMAL1 expression modulation, Monoamine oxidase A 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.
CN1CC(CC2C1CC3=CN(C4=CC=CC2=C34)C)CNC(=O)OCC5=CC=CC=C5 Approved CLOCK-BMAL1 , Arntl (gene) , BMAL1 expression (induction) 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.
CC1CCC2=C3N1C=C(C(=O)C3=CC(=C2N4CCC(CC4)O)F)C(=O)O Approved CLOCK-BMAL1 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. , Jacob, H., Curtis, A.M. and Kearney, C.J., 2020. Therapeutics on the clock: circadian medicine in the treatment of chronic inflammatory diseases. Biochemical pharmacology, 182, p.114254.
C1=CC2=C(C(=C1)Cl)SC=C2COC(CN3C=CN=C3)C4=C(C=C(C=C4)Cl)Cl Approved CLOCK-BMAL1 , Arntl (gene) , BMAL1 expression (induction) BMAL1 expression modulation, Myosin-9 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(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C)O Approved CLOCK-BMAL1 , BMAL1 expression (induction) , Glyceraldehyde-3-phosphate dehydrogenase Glyceraldehyde-3-phosphate dehydrogenase 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]1CC[C@H]2[C@H]([C@H](O[C@H]3[C@@]24[C@H]1CC[C@](O3)(OO4)C)O)C Approved BMAL1 expression (induction) BMAL1 expression modulation, "Peptidyl-prolyl cis-trans isomerase A Peroxiredoxin-1 60S ribosomal protein L10, L14, L18, L23a, L35, L4 40S ribosomal prote 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.
CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)C)O)N)O.Cl 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
CC1=CC(=C(C(=C1/C=C/C(=C/C=C/C(=C/C(=O)O)/C)/C)C)C)OC 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.
CC(C)CC1C(=O)N2CCCC2C3(N1C(=O)C(O3)(C(C)C)NC(=O)C4CN(C5CC6=C(NC7=CC=CC(=C67)C5=C4)Br)C)O Approved CLOCK-BMAL1 , D2R (dopamine receptor) , BMAL1 expression (induction) Dopamine receptor binding, Bmal1, de-repressing BMAL1, Dopamine receptor binding, Dopamine receptor agonist, 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.
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.