Payload Information

General Information of This Payload

Payload ID	PAY0ZZCOD
Name	Panobinostat
Synonyms	Panobinostat; 404950-80-7; LBH589; LBH-589; Farydak; Panobinostat (LBH589); Faridak; LBH 589; (E)-N-Hydroxy-3-(4-(((2-(2-methyl-1H-indol-3-yl)ethyl)amino)methyl)phenyl)acrylamide; NVP-LBH589; NVP-LBH-589; Panobinostat [INN]; LBH-589B; Panobinostat(LBH589); Panobinostat [USAN:INN]; UNII-9647FM7Y3Z; (2E)-N-hydroxy-3-[4-({[2-(2-methyl-1H-indol-3-yl)ethyl]amino}methyl)phenyl]prop-2-enamide; CHEBI:85990; 9647FM7Y3Z; 404950-80-7 (free base); (E)-N-HYDROXY-3-(4-{[2-(2-METHYL-1H-INDOL-3-YL)-ETHYLAMINO]-METHYL}-PHENYL)-ACRYLAMIDE; (E)-N-hydroxy-3-[4-[[2-(2-methyl-1H-indol-3-yl)ethylamino]methyl]phenyl]prop-2-enamide; Farydak (TN); (2E)-N-hydroxy-3-[4-({[2-(2-methyl-1H-indol-3-yl)ethyl]amino}methyl)phenyl]acrylamide; (2E)-N-Hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2-propenamide; 2-Propenamide, N-hydroxy-3-(4-(((2-(2-methyl-1H-indol-3-yl)ethyl)amino)methyl)phenyl)-, (2E)-; 2-Propenamide, N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-, (2E)-; PANOBINOSTAT [MI]; LBH589 - Panobinostat; Panobinostat (USAN/INN); D0E3SH; PANOBINOSTAT [USAN]; N-Hydroxy-3-[4-[2-(2-methyl-1H-indol-3-yl)ethylaminomethyl]phenyl]-2(E)-propenamide; PANOBINOSTAT [MART.]; MLS006011216; NVP-LBH 589; PANOBINOSTAT [WHO-DD]; SCHEMBL164801; SCHEMBL183197; CHEMBL483254; GTPL7489; SCHEMBL22773814; BDBM29589; CHEBI:93774; DTXSID40193506; EX-A169; FPOHNWQLNRZRFC-ZHACJKMWSA-N; N-hydroxy-3-[4-[[2-(2-methyl-1H-indol-3-yl)ethylamino]methyl]phenyl]-2-propenamide; BCPP000187; BDBM198124; BCP01816; LBH58,9NVP-LBH589,Panobinostat; (LBH-589); MFCD09833242; NSC761190; s1030; AKOS005146046; BCP9000844; CCG-208762; CS-0267; DB06603; EX-8456; NSC-761190; (E)-3-[4-[[2-(2-methyl-1H-indol-3-yl)ethylamino]methyl]phenyl]prop-2-enehydroxamic acid; (E)-N-hydroxy-3-(4-((2-(2-methyl-1H-indol-3-yl)ethylamino)methyl)phenyl)acrylamide; Panobinostat, NVP-LBH589, LBH589; NCGC00263117-05; NCGC00263117-07; 2-Propenamide, N-hydroxy-3-(4-(((2-(2-methyl-1H-indol-3-yl)ethyl)amino) methyl)phenyl)-, (2E)-; AC-28652; AM808102; AS-17046; HY-10224; SMR004702978; SW219369-1; EC-000.2287; A25218; D10319; EN300-7395075; J-523585; Q7131441; BRD-K02130563-001-07-2; (E)-N-Hydroxy-3-[4-[[[2-(2-methyl-1H-indole-3-yl)ethyl]amino]methyl]phenyl]acrylamide; N-hydroxy-3 -[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide; N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide; Panobinostat;(E)-N-hydroxy-3-(4-((2-(2-methyl-1H-indol-3-yl)ethylamino)methyl)phenyl)acrylamide Click to Show/Hide
Target(s)	Histone deacetylase 1 (HDAC1)			Target Info
Structure
Structure	3D MOL		2D MOL
Formula	C21H23N3O2
Isosmiles	CC1=C(C2=CC=CC=C2N1)CCNCC3=CC=C(C=C3)/C=C/C(=O)NO
PubChem CID	6918837
InChI	InChI=1S/C21H23N3O2/c1-15-18(19-4-2-3-5-20(19)23-15)12-13-22-14-17-8-6-16(7-9-17)10-11-21(25)24-26/h2-11,22-23,26H,12-14H2,1H3,(H,24,25)/b11-10+
InChIKey	FPOHNWQLNRZRFC-ZHACJKMWSA-N
IUPAC Name	(E)-N-hydroxy-3-[4-[[2-(2-methyl-1H-indol-3-yl)ethylamino]methyl]phenyl]prop-2-enamide
Pharmaceutical Properties	Molecule Weight	349.4	Polar area	77.2
	Complexity	474	xlogp Value	3
	Heavy Count	26	Rot Bonds	7
	Hbond acc	3	Hbond Donor	4

The activity data of This Payload

Standard Type	Value	Units	Cell line	Disease Model	Cell line ID	Reference
Half Maximal Inhibitory Concentration (IC50)	0.83	nM	HeLa cells	Endocervical adenocarcinoma	CVCL_0030	[1]
Half Maximal Inhibitory Concentration (IC50)	1	nM	Sf9 cells	Normal	CVCL_0549	[2]
Half Maximal Inhibitory Concentration (IC50)	1.26	nM	Sf9 cells	Normal	CVCL_0549	[1]
Half Maximal Inhibitory Concentration (IC50)	1.673	nM	Sf9 cells	Normal	CVCL_0549	[3]
Half Maximal Inhibitory Concentration (IC50)	1.926	nM	Sf9 cells	Normal	CVCL_0549	[3]
Half Maximal Inhibitory Concentration (IC50)	10.9	nM	CAL-27 cells	Tongue adenosquamous carcinom	CVCL_1107	[4]
Half Maximal Inhibitory Concentration (IC50)	<100	nM	Hep-G2 cells	Hepatoblastoma	CVCL_0027	[5]
Half Maximal Inhibitory Concentration (IC50)	<100	nM	CAL-148 cells	Breast carcinoma	CVCL_1106	[5]
Half Maximal Inhibitory Concentration (IC50)	1000	nM	PANC-1 cells	Pancreatic ductal adenocarcinoma	CVCL_0480	[6]
Half Maximal Inhibitory Concentration (IC50)	>10000	nM	Sf9 cells	Normal	CVCL_0549	[1]
Half Maximal Inhibitory Concentration (IC50)	>10000	nM	Sf9 cells	Normal	CVCL_0549	[1]
Half Maximal Inhibitory Concentration (IC50)	11	nM	HEK293 cells	Normal	CVCL_0045	[7]
Half Maximal Inhibitory Concentration (IC50)	13	nM	Sf21 cells	Normal	CVCL_0518	[7]
Half Maximal Inhibitory Concentration (IC50)	150	nM	KM3/BTZ cells	Multiple myeloma	CVCL_GZ66	[8]
Half Maximal Effective Concentration (EC50)	150.71	nM	A2780 cells	Ovarian endometrioid adenocarcinoma	CVCL_0134	[1]
Half Maximal Effective Concentration (EC50)	169.5	nM	A2780 cells	Ovarian endometrioid adenocarcinoma	CVCL_0134	[1]
Half Maximal Inhibitory Concentration (IC50)	17.51	nM	NCI-H1975 cells	Lung adenocarcinoma	CVCL_1511	[9]
Half Maximal Inhibitory Concentration (IC50)	18	nM	COLO 205 cells	Colon adenocarcinoma	CVCL_0218	[10]
Half Maximal Inhibitory Concentration (IC50)	190.3	nM	Sf9 cells	Normal	CVCL_0549	[1]
Half Maximal Inhibitory Concentration (IC50)	>19952.62	nM	Vero C1008 cells	Normal	CVCL_0574	[11]
Half Maximal Inhibitory Concentration (IC50)	2	nM	Sf9 cells	Normal	CVCL_0549	[2]
Half Maximal Inhibitory Concentration (IC50)	2	nM	Sf9 cells	Normal	CVCL_0549	[2]
Half Maximal Inhibitory Concentration (IC50)	2.059	nM	Sf9 cells	Normal	CVCL_0549	[3]
Half Maximal Inhibitory Concentration (IC50)	2.097	nM	Sf9 cells	Normal	CVCL_0549	[3]
Half Maximal Inhibitory Concentration (IC50)	2.1	nM	HEK293 cells	Normal	CVCL_0045	[7]
Half Maximal Inhibitory Concentration (IC50)	2.1	nM	Sf9 cells	Normal	CVCL_0549	[3]
Half Maximal Inhibitory Concentration (IC50)	2.27	nM	Sf9 cells	Normal	CVCL_0549	[1]
Half Maximal Inhibitory Concentration (IC50)	2.5	nM	HEK293 cells	Normal	CVCL_0045	[7]
Half Maximal Inhibitory Concentration (IC50)	2.97	nM	MV4-11 cells	Childhood acute monocytic leukemia	CVCL_0064	[1]
Half Maximal Inhibitory Concentration (IC50)	20	nM	A-549 cells	Lung adenocarcinoma	CVCL_0023	[5]
Half Maximal Inhibitory Concentration (IC50)	20	nM	BC1 cells	Primary effusion lymphoma	CVCL_1079	[12]
Half Maximal Inhibitory Concentration (IC50)	20.1	nM	KM3/BTZ cells	Multiple myeloma	CVCL_GZ66	[8]
Half Maximal Inhibitory Concentration (IC50)	200	nM	HEK293 cells	Normal	CVCL_0045	[7]
Half Maximal Inhibitory Concentration (IC50)	>20000	nM	Sf9 cells	Normal	CVCL_0549	[9]
Half Maximal Inhibitory Concentration (IC50)	>20000	nM	Sf9 cells	Normal	CVCL_0549	[9]
Half Maximal Inhibitory Concentration (IC50)	>20000	nM	Sf9 cells	Normal	CVCL_0549	[9]
Half Maximal Inhibitory Concentration (IC50)	>20000	nM	Vero C1008 cells	Normal	CVCL_0574	[11]
Half Maximal Inhibitory Concentration (IC50)	21.28	nM	Bel-7402 cells	Hepatoma	CVCL_5492	[9]
Half Maximal Inhibitory Concentration (IC50)	22	nM	HeLa cells	Endocervical adenocarcinoma	CVCL_0030	[13]
Half Maximal Inhibitory Concentration (IC50)	231	nM	Sf9 cells	Normal	CVCL_0549	[2]
Half Maximal Inhibitory Concentration (IC50)	24	nM	PC-3 cells	Prostate carcinoma	CVCL_0035	[10]
Half Maximal Inhibitory Concentration (IC50)	2680	nM	Sf9 cells	Normal	CVCL_0549	[2]
Half Maximal Inhibitory Concentration (IC50)	27.85	nM	EBC-1 cells	Lung squamous cell carcinoma	CVCL_2891	[9]
Half Maximal Inhibitory Concentration (IC50)	280	nM	Sf9 cells	Normal	CVCL_0549	[7]
Half Maximal Inhibitory Concentration (IC50)	2830	nM	Sf9 cells	Normal	CVCL_0549	[2]
Half Maximal Inhibitory Concentration (IC50)	29.13	nM	MDA-MB-231 cells (5T4 overexpression)	Breast adenocarcinoma	CVCL_0062	[9]
Half Maximal Inhibitory Concentration (IC50)	3.28	nM	Sf9 cells	Normal	CVCL_0549	[1]
Half Maximal Inhibitory Concentration (IC50)	3.36	nM	HCT 116 cells	Colon carcinoma	CVCL_0291	[1]
Half Maximal Inhibitory Concentration (IC50)	30	nM	HeLa cells	Endocervical adenocarcinoma	CVCL_0030	[14]
Half Maximal Effective Concentration (EC50)	<30	nM	MV4-11 cells	Childhood acute monocytic leukemia	CVCL_0064	[15]
Half Maximal Inhibitory Concentration (IC50)	337.8	nM	Sf9 cells	Normal	CVCL_0549	[1]
Half Maximal Inhibitory Concentration (IC50)	35	nM	A2780 cells	Ovarian endometrioid adenocarcinoma	CVCL_0134	[10]
Half Maximal Inhibitory Concentration (IC50)	37.55	nM	HT-29 cells	Colon adenocarcinoma	CVCL_0320	[9]
Half Maximal Inhibitory Concentration (IC50)	373	nM	Sf9 cells	Normal	CVCL_0549	[2]
Half Maximal Inhibitory Concentration (IC50)	4.16	nM	Sf9 cells	Normal	CVCL_0549	[1]
Half Maximal Effective Concentration (EC50)	4.3	nM	HuT 78 cells	T lymphocytic leukemia	CVCL_0337	[16]
Half Maximal Inhibitory Concentration (IC50)	4.45	nM	Sf9 cells	Normal	CVCL_0549	[1]
Half Maximal Inhibitory Concentration (IC50)	4.86	nM	Sf9 cells	Normal	CVCL_0549	[1]
Half Maximal Inhibitory Concentration (IC50)	4112	nM	Sf9 cells	Normal	CVCL_0549	[1]
Half Maximal Inhibitory Concentration (IC50)	4354	nM	Sf9 cells	Normal	CVCL_0549	[1]
Half Maximal Inhibitory Concentration (IC50)	46	nM	MED-MEB-8A cells	Medulloblastoma	CVCL_M137	[17]
Half Maximal Inhibitory Concentration (IC50)	48	nM	HCT 116 cells	Colon carcinoma	CVCL_0291	[10]
Half Maximal Effective Concentration (EC50)	5.2	nM	MV4-11 cells	Childhood acute monocytic leukemia	CVCL_0064	[3]
Half Maximal Inhibitory Concentration (IC50)	54	nM	UW228 cells	Medulloblastoma	CVCL_8585	[17]
Half Maximal Inhibitory Concentration (IC50)	54.8	nM	A2780 cells	Ovarian endometrioid adenocarcinoma	CVCL_0134	[4]
Half Maximal Inhibitory Concentration (IC50)	6.98	nM	T-47D cells	Invasive breast carcinoma	CVCL_0553	[9]
Half Maximal Inhibitory Concentration (IC50)	67	nM	UW426 cells	Medulloblastoma	CVCL_DH82	[17]
Half Maximal Inhibitory Concentration (IC50)	7.67	nM	A2780 cells	Ovarian endometrioid adenocarcinoma	CVCL_0134	[4]
Half Maximal Inhibitory Concentration (IC50)	70	nM	NFF Fibroblast cells	Normal	Undisclosed	[18]
Half Maximal Inhibitory Concentration (IC50)	70	nM	NFF Fibroblast cells	Normal	Undisclosed	[19]
Half Maximal Inhibitory Concentration (IC50)	70	nM	HEK293 cells	Normal	CVCL_0045	[18]
Half Maximal Inhibitory Concentration (IC50)	70	nM	HEK293 cells	Normal	CVCL_0045	[19]
Half Maximal Inhibitory Concentration (IC50)	8.32	nM	A2780 cells	Ovarian endometrioid adenocarcinoma	CVCL_0134	[1]
Half Maximal Inhibitory Concentration (IC50)	8.42	nM	NCI-N87 cells	Gastric tubular adenocarcinoma	CVCL_1603	[9]
Half Maximal Inhibitory Concentration (IC50)	887.8	nM	Sf9 cells	Normal	CVCL_0549	[1]
Half Maximal Inhibitory Concentration (IC50)	9	nM	MCF7-F (fulvestrant resistant) cells	Invasive breast carcinoma	CVCL_0031	[9]
Half Maximal Inhibitory Concentration (IC50)	92	nM	Sf9 cells	Normal	CVCL_0549	[2]

Each Antibody-drug Conjugate Related to This Payload

References

Ref 1	Development of Purine-Based Hydroxamic Acid Derivatives: Potent Histone Deacetylase Inhibitors with Marked in Vitro and in Vivo Antitumor Activities. J Med Chem. 2016 Jun 9;59(11):5488-504. doi: 10.1021/acs.jmedchem.6b00579. Epub 2016 May 24.
Ref 2	Kinetic and structural insights into the binding of histone deacetylase 1 and 2 (HDAC1, 2) inhibitors. Bioorg Med Chem. 2016 Sep 15;24(18):4008-4015. doi: 10.1016/j.bmc.2016.06.040. Epub 2016 Jun 22.
Ref 3	Design of Hydrazide-Bearing HDACIs Based on Panobinostat and Their p53 and FLT3-ITD Dependency in Antileukemia Activity. J Med Chem. 2020 May 28;63(10):5501-5525. doi: 10.1021/acs.jmedchem.0c00442. Epub 2020 May 6.
Ref 4	Novel ,-unsaturated hydroxamic acid derivatives overcome cisplatin resistance. Bioorg Med Chem. 2019 Oct 1;27(19):115036. doi: 10.1016/j.bmc.2019.07.052. Epub 2019 Aug 7.
Ref 5	Discovery of novel 9H-purin derivatives as dual inhibitors of HDAC1 and CDK2. Bioorg Med Chem Lett. 2019 Aug 15;29(16):2136-2140. doi: 10.1016/j.bmcl.2019.06.059. Epub 2019 Jun 29.
Ref 6	Design and evaluation of 1,2,3-dithiazoles and fused 1,2,4-dithiazines as anti-cancer agents. Bioorg Med Chem Lett. 2021 Jul 1;43:128078. doi: 10.1016/j.bmcl.2021.128078. Epub 2021 May 2.
Ref 7	Biocatalytic synthesis and structure elucidation of cyclized metabolites of the deacetylase inhibitor panobinostat (LBH589). Drug Metab Dispos. 2012 May;40(5):1041-50. doi: 10.1124/dmd.111.043620. Epub 2012 Feb 16.
Ref 8	Discovery of Peptide Boronate Derivatives as Histone Deacetylase and Proteasome Dual Inhibitors for Overcoming Bortezomib Resistance of Multiple Myeloma. J Med Chem. 2020 May 14;63(9):4701-4715. doi: 10.1021/acs.jmedchem.9b02161. Epub 2020 Apr 23.
Ref 9	Synthesis and in Vitro and in Vivo Biological Evaluation of Tissue-Specific Bisthiazole Histone Deacetylase (HDAC) Inhibitors. J Med Chem. 2020 Jan 23;63(2):804-815. doi: 10.1021/acs.jmedchem.9b01792. Epub 2020 Jan 7.
Ref 10	Discovery of (2E)-3-{2-butyl-1-[2-(diethylamino)ethyl]-1H-benzimidazol-5-yl}-N-hydroxyacrylamide (SB939), an orally active histone deacetylase inhibitor with a superior preclinical profile. J Med Chem. 2011 Jul 14;54(13):4694-720. doi: 10.1021/jm2003552. Epub 2011 Jun 16.
Ref 11	Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity.
Ref 12	Evaluation of the potential cancer chemotherapeutic efficacy of natural product isolates employing in vivo hollow fiber tests. J Nat Prod. 2002 Jun;65(6):842-50. doi: 10.1021/np010322w.
Ref 13	Exploring hydroxamic acid inhibitors of HDAC1 and HDAC2 using small molecule tools and molecular or homology modelling. Bioorg Med Chem Lett. 2019 Sep 15;29(18):2581-2586. doi: 10.1016/j.bmcl.2019.08.002. Epub 2019 Aug 2.
Ref 14	Design, synthesis and biological evaluation of indeno[1,2-d]thiazole derivatives as potent histone deacetylase inhibitors. Bioorg Med Chem Lett. 2013 Jun 1;23(11):3200-3. doi: 10.1016/j.bmcl.2013.04.004. Epub 2013 Apr 11.
Ref 15	Development of Allosteric Hydrazide-Containing Class I Histone Deacetylase Inhibitors for Use in Acute Myeloid Leukemia. J Med Chem. 2016 Nov 10;59(21):9942-9959. doi: 10.1021/acs.jmedchem.6b01385. Epub 2016 Oct 26.
Ref 16	Squaramides as novel class I and IIB histone deacetylase inhibitors for topical treatment of cutaneous t-cell lymphoma. Bioorg Med Chem Lett. 2018 Sep 15;28(17):2985-2992. doi: 10.1016/j.bmcl.2018.06.029. Epub 2018 Jun 18.
Ref 17	Medulloblastoma drugs in development: Current leads, trials and drawbacks. Eur J Med Chem. 2021 Apr 5;215:113268. doi: 10.1016/j.ejmech.2021.113268. Epub 2021 Feb 8.
Ref 18	Lysine Deacetylase Inhibitors in Parasites: Past, Present, and Future Perspectives. J Med Chem. 2017 Jun 22;60(12):4780-4804. doi: 10.1021/acs.jmedchem.6b01595. Epub 2017 Mar 15.
Ref 19	One-pot, multi-component synthesis and structure-activity relationships of peptoid-based histone deacetylase (HDAC) inhibitors targeting malaria parasites. Eur J Med Chem. 2018 Oct 5;158:801-813. doi: 10.1016/j.ejmech.2018.09.018. Epub 2018 Sep 7.

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Correspondence

Prof. Feng ZHU (zhufeng@zju.edu.cn)

Prof. Xiaowu DONG (dongxw@zju.edu.cn)

Prof. Luo FANG (fangluo@zjcc.org.cn)