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Drug Details

General Information of the Drug (ID: DR2116)
Name
Lonidamine
Synonyms
lonidamine; 50264-69-2; 1-(2,4-Dichlorobenzyl)-1H-indazole-3-carboxylic acid; Diclondazolic acid; Doridamina; DICA; Lonidamina; Lonidaminum; Lonidamin; AF 1890; 1-[(2,4-dichlorophenyl)methyl]-1H-indazole-3-carboxylic acid; 1-(2,4-Dichlorbenzyl)-indazole-3-carboxylic acid; UNII-U78804BIDR; C15H10Cl2N2O2; 1-(2,4-dichlorobenzyl)indazole-3-carboxylic acid; 1-[(2,4-dichlorophenyl)methyl]indazole-3-carboxylic acid; AF-1890; MLS000028822; U78804BIDR; CHEBI:50138; 1H-Indazole-3-carboxylic acid, 1-[(2,4-dichlorophenyl)methyl]-; AF-1890;Diclondazolic Acid;DICA; MFCD00866285; NCGC00015609-03; SMR000058467; DSSTox_CID_782; DSSTox_RID_75787; DSSTox_GSID_20782; Lonidaminum [INN-Latin]; Lonidamina [INN-Spanish]; Doridamina (TN); Dichlondazolic acid; Lonidamine (INN); CAS-50264-69-2; CCRIS 3516; Lonidamine [INN:BAN]; SR-01000075961; EINECS 256-510-0; BRN 0894483; KN-228; TH-070; Tocris-1646; Lopac-L-4900; L 4900; SCHEMBL7134; Lopac0_000718; cid_39562; ZINC1632; CHEMBL1257030; DTXSID5020782; BDBM59775; 1H-Indazole-3-carboxylic acid, 1-(2,4-dichlorobenzyl)-; HMS2234H24; HMS3262O17; HMS3268K09; HMS3369I01; HMS3412P05; HMS3651F09; HMS3676P05; HMS3874D03; Pharmakon1600-01503225; 1H-Indazole-3-carboxylicacid, 1-[(2,4-dichlorophenyl)methyl]-; ACT02617; BCP06555; HY-B0486; Tox21_110181; Tox21_202306; Tox21_500718; NSC741419; NSC758419; s2610; AKOS012842739; Tox21_110181_1; AC-5626; CCG-204803; DB06266; LP00718; NSC 741419; NSC 758419; NSC-741419; NSC-758419; SDCCGSBI-0050696.P003; NCGC00015609-01; NCGC00015609-02; NCGC00015609-04; NCGC00015609-05; NCGC00015609-06; NCGC00015609-07; NCGC00015609-08; NCGC00015609-09; NCGC00015609-16; NCGC00025244-01; NCGC00025244-02; NCGC00025244-03; NCGC00259855-01; NCGC00261403-01; AS-11653; SBI-0050696.P002; AB0010495; AM20060642; EU-0100718; FT-0650359; SW219810-1; Lonidamine, mitochondrial hexokinase inhibitor; D07257; J90044; S-4929; AB00597141_08; AB00597141_10; 264L692; Q-201318; Q3836670; SR-01000075961-1; SR-01000075961-3; SR-01000075961-6; BRD-K78513633-001-03-3; BRD-K78513633-001-06-6; Z1741977188; 1-[(2,4-dichlorophenyl)methyl]-3-indazolecarboxylic acid; 1H-Indazole-3-carboxylic acid, 1-((2,4-dichlorophenyl)methyl)- (9CI)
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Molecular Type
Small molecule
Disease Prostate hyperplasia [ICD-11: GA90] Discontinued in Phase 3 [1]
Structure
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2D MOL

3D MOL

    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C15H10Cl2N2O2
PubChem CID
39562
Canonical SMILES
C1=CC=C2C(=C1)C(=NN2CC3=C(C=C(C=C3)Cl)Cl)C(=O)O
InChI
1S/C15H10Cl2N2O2/c16-10-6-5-9(12(17)7-10)8-19-13-4-2-1-3-11(13)14(18-19)15(20)21/h1-7H,8H2,(H,20,21)
InChIKey
WDRYRZXSPDWGEB-UHFFFAOYSA-N
CAS Number
CAS 50264-69-2
ChEBI ID
CHEBI:50138
TTD Drug ID
D09SIR
DrugBank ID
DB06266
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Arsenic trioxide      Realgar and orpiment     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Up-regulation Phosphorylation AKT1  Molecule Info 
Pathway MAP
Up-regulation Expression BCL-xL  Molecule Info 
Pathway MAP
Down-regulation Expression BID  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP3  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP8  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP9  Molecule Info 
Pathway MAP
Up-regulation Phosphorylation ERK1  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation JNK1  Molecule Info 
Pathway MAP
Down-regulation Expression MCL1  Molecule Info 
Pathway MAP
Up-regulation Phosphorylation S6K1  Molecule Info 
Pathway MAP
Down-regulation Expression XIAP  Molecule Info 
Pathway MAP
                    Biological
                    Regulation
Up-regulation Cytochrome c release
                    In-vitro Model HL-60 CVCL_0002 Adult acute myeloid leukemia Homo sapiens
U-937 CVCL_0007 Adult acute monocytic leukemia Homo sapiens
NB4 CVCL_0005 Acute promyelocytic leukemia Homo sapiens
RPMI-8866 CVCL_1668 Chronic myelogenous leukemia Homo sapiens
                    Experimental
                    Result(s)
lonidamine efficaciously cooperates with the anti-leukemic agent arsenic trioxide (ATO) to induce apoptosis in HL-60 and other human leukemia cell lines, with low toxicity in non-tumor peripheral blood lymphocytes.
References
Reference 1 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800022059)
Reference 2 Increased apoptotic efficacy of lonidamine plus arsenic trioxide combination in human leukemia cells. Reactive oxygen species generation and defensive protein kinase (MEK/ERK, Akt/mTOR) modulation. Biochem Pharmacol. 2011 Dec 1;82(11):1619-29.
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Cite NPCDR
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Correspondence

X. N. Sun, Y. T. Zhang, Y. Zhou, X. C. Lian, L. L. Yan, T. Pan, T. Jin, H. Xie, Z. M. Liang, W. Q. Qiu, J. X. Wang, Z. R. Li, F. Zhu*, X. B. Sui*. NPCDR: natural product-based drug combination and its disease-specific molecular regulation. Nucleic Acids Research. 50(D1): 1324-1333 (2020). PMID: 34664659

Prof. Feng ZHU  (zhufeng@zju.edu.cn)

College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, China


Prof. Xinbing SUI  (hzzju@hznu.edu.cn)

School of Pharmacy and Department of Medical Oncology, the Affiliated Hospital of Hangzhou Normal University, Hangzhou Normal University, Hangzhou, China