Table 1. The chemical structures and applications of imidazole drugs in cancer chemotherapy.

S. no	Drugs	Structures and chemical names	Brand names	Market status	Applications
1	Acadesine	5-Amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-imidazole-4-carboxamide	—	Phase III	Acute lymphoblastic leukemia
2	Azathioprine	6-[(1-Methyl-4-nitro-1H-imidazol-5-yl)sulfanyl]-7H-purine	Imuran	Phase I	Childhood acute lymphoblastic leukemia
3	Bleomycin	(3-{[(2′-{(5S,8S,9S,10R,13S)-15-{6-Amino-2-[(1S)-3-amino-1-{[(2S)-2,3-diamino-3-oxopropyl]amino}-3-oxo propyl]-5-methylpyrimidin-4-yl}-13-[{[(2R,3S,4S,5S,6S)-3-{[(2R,3S,4S, 5R,6R)-4-(carbamoyloxy)-3,5-dihydr oxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}(1H-imidazol-5-yl)methyl]-9-hydroxy-5-[(1R)-1-hydr oxyethyl]-8,10-dimethyl-4,7,12,15-tetraoxo-3,6,11,14-tetraazapentadec-1-yl}-2,4′-bi-1,3-thiazol-4-yl)carbon yl]amino}propyl)dimethylsulfonium	Blenoxane	US-FDA approval in 1973	Hodgkin's lymphoma, non-Hodgkin's lymphoma, testicular, ovarian and cervical cancer
4	Bendamustine	4-[5-[Bis(2-chloroethyl)amino]-1-met hylbenzimidazol-2-yl]butanoic acid	Treanda	US-FDA approval in 2008	Chronic lymphocytic leukemia and lymphomas
5	Bombesin	Pyr-Gln-Arg-Leu-Gly-Asn-Gln-Trp-Ala-Val-Gly-His-Leu-Met-NH2	—	Phase-III	Small cell carcinoma of lung, gastric, pancreatic and neuroblastoma
6	Dacarbazine	Fig. 1 5-(3,3-Dimethyl-1-triazenyl)imidazole-4-carboxamide	DTIC-Dome	US-FDA approval in 1975	Malignant melanoma, Hodgkin's lymphoma, sarcoma and islet cell carcinoma of the pancreas
7	Mitozolomide	3-(2-Chloroethyl)-4-oxo-3,4-dihydr oimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide	—	Discontinued during phase II	—
8	Mercaptopurine	Fig. 1 3,7-Dihydropurine-6-thione	Purinethol	Phase I	Acute lymphocytic leukemia
9	Nilotinib	Fig. 1 4-Methyl-N-[3-(4-methyl-1H-imid azol-1-yl)-5-(trifluoromethyl)phenyl]-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]benzamide	Tasigna	US-FDA approval in 2009	Philadelphia chromosome(Ph+)-positive chronic myelogenous leukaemia
10	Pilocarpine	3-Ethyl-4-((1-methyl-1H-imidazol-5-yl)methyl)dihydrofuran-2(3H)-one	Salagen	Under clinic	As a side effect of radiation therapy for head and neck cancer
11	Plinabulin	3-Benzylidene-6-{[5-(2-methyl-2-propanyl)-1H-imidazol-4-yl]methylene}-2,5-piperazinedione		Phase I and II	Non-small cell lung cancer
12	Radotinib	4-Methyl-N-[3-(4-methylimidazol-1-yl)-5-(trifluoromethyl)phenyl]-3-[(4-pyrazin-2-ylpyrimidin-2-yl)amino]benzamide	Supect	Phase II	Chronic myeloid leukemia
13	SB-431542	4-(4-Benzo[1,3]dioxol-5-yl-5-pyridin-2-yl-1H-imidazol-2-yl)-benzamide	—	No clinical trials	It suppress the TGF-beta-induced proliferation of osteosarcoma cells in humans
14	Tipifarnib	Fig. 1 6-[Amino(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methyl]-4-(3-chlor ophenyl)-1-methylquinolin-2(1H)-one	Zarnestra	US-FDA disapproval in 2005	Acute myeloid leukemia
15	Temozolomide	Fig. 1 4-Methyl-5-oxo-2,3,4,6,8-pentaza bicyclo[4.3.0]nona-2,7,9-triene-9-carboxamide	Temodar		Astrocytoma and glioblastoma multiforme
16	Zoledronic acid	Fig. 1 1-Hydroxy-2-(1H-imidazol-1-yl)ethane-1,1-diyl]bis(phosphonic acid)	Zometa	Under clinic	In management of patients with multiple myeloma and prostate cancer
17	Indimitecan		—	Phase I	Topoisomerase-I inhibitor
18	Fadrozole	4-(5,6,7,8-Tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile	Afema	Under clinic	Breast cancer