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CX-5461

HCID 25257557
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Basic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
1138549-36-6
Standard SMILES
Cc1cnc(CNC(=O)c2c(=O)c3ccc(N4CCCN(C)CC4)nc3n3c2sc2ccccc23)cn1
InChIKey
XGPBJCHFROADCK-UHFFFAOYSA-N
Molecular formula
C27H27N7O2S
Average molar mass
513.627 g/mol
Monoisotopic mass
513.1946941

Names & identifiers

Preferred name
CX-5461
IUPAC
2-(4-Methyl-1,4-diazepan-1-yl)-N-[(5-methylpyrazin-2-yl)methyl]-5-oxo-5H-[1,3]benzothiazolo[3,2-a][1,8]naphthyridine-6-carboxamide
English name
CX-5461
Molecular formula
C27H27N7O2S
Molecular weight
513.61

Names & synonyms

Pidnarulex (CX-5461)CS-1938CX-5461PidanrulexPidnarulexCX-5461 500MGCX-5461/CX5461CX-5461, >=98%CX-5461 USP/EP/BPCX-5461 Pidnarulex

Database identifiers

CAS
1138549-36-6
PubChem CID
25257557
DTXSID
DTXSID20150591
ChEMBL
CHEMBL4303309
ChEBI
CHEBI:156287
UNII
3R4C5YLB9I
Nikkaji
J3.418.866A

Properties

Physicochemical properties

Boiling point
739.9 · 739.9±60.0 °C(Predicted)
Density
1.45 · 1.45
storage temp.
2 C · +2C to +8C
solubility
2 O; · insoluble in H2O; insoluble in EtOH; insoluble in DMSO
form
Light beige powder
pka
8.53 · 8.53±0.20(Predicted)
color
White to yellow
InChIKey
XGPBJCHFROADCK-UHFFFAOYSA-N
SMILES
[s]1c2[n](c4nc(ccc4[c](c2C(=O)NCc6ncc(nc6)C)=O)N5CCN(CCC5)C)c3c1cccc3
FDA UNII
3 R4C5YLB9I · 3R4C5YLB9I
UNSPSC Code
12352200 · 12352200
NACRES
77 · NA.77
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H315-H319-H335
Precautionary statements
261 · P261-P305+P351+P338
WGK Germany
3 · WGK 3
Storage Class
11 · 11 - Combustible Solids

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

wgk
WGK 3
Signal word
Warning
Symbol(GHS)
GHS07
Storage Class
11 - Combustible Solids
Hazard statements
H302-H315-H319-H335
Precautionary statements
P261-P305+P351+P338

Chemistry & industry

Applications · 2 items

UsesA cell-permeable benzothiazole compound that selectively inhibits RNA polymerase I-mediated pre-rRNA transcription (IC50 = 142, 113, 54, and 74 nM in HCT-116, A375, MIA PaCa-2, and BJ-hTert cells, respectively), but not Pol II-mediated c-myc transcription, by preventing TAF (TATA Binding Protein-/TBP-Associated Factor) SL1 and rDNA association, effectively inhibiting Pol I-dependent proliferation among 39 cancer cell lines (IC50<1 µM) in vitro. While Pol I inhibition by CX-5461 is shown to result in p53-dependent apoptosis in cancer cells of hematopoietic origin, cell death by CX-5461 treatment in solid tumors-derived A375 and MIA PaCa-2 cultures are primarily due to autophagy and senescence, but not apoptosis, induction. Shown to suppress A375 (50 mg/kg/d p.o.) and MIA PaCa-2 (50 mg/kg/3d p.o.) tumor expansion, as well as selectively induce p53-mediated cell death of Eμ-Myc lymphoma, but not normal B cells, in mice (50 mg/kg p.o.) in vivo.

General DescriptionA cell-permeable benzothiazole compound that selectively inhibits RNA polymerase I-mediated pre-rRNA transcription (IC50 = 142 nM in HCT-116), but not Pol II-mediated c-myc transcription, by preventing TAF SL1 and rDNA association). Effectively inhibits Pol I-dependent proliferation among 39 cancer cell lines (IC50<1 μM) in vitro and suppresses A375 (50 mg/kg/d p.o.) and MIA PaCa-2 (50 mg/kg/3d p.o.) tumor expansion in vivo.

Suppliers100 total

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
湖北威德利化学试剂有限公司186-02735115 18062128043 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
武汉敬康恩生物医药科技有限公司13720134139 086-15871494362 13720134139 · [email protected]

Related reactions

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Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
上海麦克林生化科技股份有限公司
021-50706066 15221275939 · [email protected]
成都彼样生物科技有限公司18108052721 · [email protected]
杭州品高化工有限公司0571-87658025 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
普善实业(陕西)有限公司029-81310890 18165209495 · [email protected]
上海冬洋生物科技有限公司0512-13601744364 13601744364 · [email protected]
湖北科乐精细化工有限公司027-59101668 19945030958 · [email protected]
上海波以尔化工有限公司[email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
InvivoChem中国13549236410 · [email protected]
上海浦洛凯医药科技有限公司17269768198 · [email protected]
銳迪國際科技有限公司18024082417 · [email protected]
学研惠(武汉)科技有限公司15727060112 · [email protected]
武汉永璨生物科技有限公司17702719238 · [email protected]
Zhejiang J&C Biological Technology Co.,Limited+1-2135480471 · [email protected]
上海瀚香生物科技有限公司177-54423994 17754423994 · [email protected]
湖北魏氏化学试剂股份有限公司17771898297 13125137661 · [email protected]
ChemeGen 中国18818260767 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
AdooQ BioScience, LLC+1 (866) 930-6790 · [email protected]
Wuhan NCE Biomedical Co.,Ltd.4000-027-021 |24 +86-13986109188 | +86-15623472865 | +81-08033611988
上海偕腾生物科技有限公司+86-021-58975553 · [email protected]
Shanghai Witofly Chemical Co.,Ltd[email protected]
郑州鸿尚科技有限公司0371-55932928 18937192232 · [email protected]
上海昶衍化工科技有限公司021-20242659 18930833303 · [email protected]
上海喀露蓝科技有限公司18149758185 18149758185 · [email protected]
上海毕得医药科技股份有限公司400-164-7117 18317119277 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
南京百鑫德诺生物科技有限公司025-58849295 · [email protected]
上海孚一生物科技有限公司+86 (21) 61124340
上海楼岚生物科技有限公司021-52996696,15000506266 15000506266
上海蓓琅生物科技有限公司17764003753 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
上海东苍生物科技有限公司+86-21-58447131 · [email protected]
武汉天植生物技术有限公司18607101326 15172504745 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
斯派螺(武汉)药物研发有限公司[email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
上海德轩医药科技有限公司[email protected] · [email protected]
南通全益生物科技有限公司0513-66337626 18051384581 · [email protected]
武汉多普乐生物医药有限公司+86-02787215551 19945035818 · [email protected]
药渡经纬信息科技(北京)有限公司+86-400-851-9921 · [email protected]
上海思言生物科技有限公司021-50908862,442785678,326799392 18721037013 · [email protected]
北京华威锐科化工科技有限公司89508211 18501085097 · [email protected]
Additional notes · 1 item

DefinitionChEBI: CX-5461 is an organic heterotetracyclic compound that is 5-oxo-5H-[1,3]benzothiazolo[3,2-a][1,8]naphthyridine-6-carboxylic acid substituted by a 4-methyl-1,4-diazepan-1-yl group at position 2 and in which the carboxy group at position 6 is substituted by a [(5-methylpyrazin-2-yl)methyl]nitrilo group. An inhibitor of ribosomal RNA (rRNA) synthesis which specifically inhibits RNA polymerase I-driven transcription of rRNA in several cancer cell lines. It is currently in phase I/II clinical trials for advanced hematologic malignancies and triple-negative breast cancer with BRCA1/2 mutation. It has a role as an antineoplastic agent, an apoptosis inducer and an EC 2.7.7.6 (RNA polymerase) inhibitor. It is a diazepine, an organic heterotetracyclic compound, a member of pyrazines, a secondary carboxamide and a naphthyridine derivative.