ChemicalBook >> CAS DataBase List >>(1S,4Z,7S,10S,11E,20R)-4-ethylidene-7,20-dipropan-2-yl-9-oxa-15,16-dit hia-3,6,18,21-tetrazabicyclo[8.7.6]tricos-11-ene-2,5,8,19,22-pentone

(1S,4Z,7S,10S,11E,20R)-4-ethylidene-7,20-dipropan-2-yl-9-oxa-15,16-dit hia-3,6,18,21-tetrazabicyclo[8.7.6]tricos-11-ene-2,5,8,19,22-pentone

(1S,4Z,7S,10S,11E,20R)-4-ethylidene-7,20-dipropan-2-yl-9-oxa-15,16-dit hia-3,6,18,21-tetrazabicyclo[8.7.6]tricos-11-ene-2,5,8,19,22-pentone structure

CAS No.: 128517-07-7

Chemical Name:: (1S,4Z,7S,10S,11E,20R)-4-ethylidene-7,20-dipropan-2-yl-9-oxa-15,16-dit hia-3,6,18,21-tetrazabicyclo[8.7.6]tricos-11-ene-2,5,8,19,22-pentone

Synonyms: Romidepsin;FK228;depsipeptide;Romidisin;CS-972;GS-002;GS-003;istodax;GSI-001;FR 901228

CBNumber:: CB31260794

Molecular Formula:: C24H36N4O6S2

Molecular Weight:: 540.7

MDL Number:: MFCD18433404

MOL File:: 128517-07-7.mol

MSDS File:: SDS

TDS File:: TDS

Last updated:2026-07-17 09:03:53

Product description	Number	Pack Size	Price
Romidepsin ≥98% (HPLC)	SML1175	1mg	$361
Romidepsin ≥98%	17130	500μg	$121
Romidepsin ≥98%	17130	1mg	$204
Romidepsin ≥98%	17130	5mg	$597
Romidepsin ≥98%	17130	500μg	$110
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(1S,4Z,7S,10S,11E,20R)-4-ethylidene-7,20-dipropan-2-yl-9-oxa-15,16-dit hia-3,6,18,21-tetrazabicyclo[8.7.6]tricos-11-ene-2,5,8,19,22-pentone Properties

Melting point	219-224°C
Boiling point	942.8±65.0 °C(Predicted)
Density	1.174
storage temp.	-20°C
solubility	Soluble in DMSO (up to 10 mg/ml).
form	powder
pka	11.33±0.60(Predicted)
color	white to beige
Stability	Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month.
InChIKey	OHRURASPPZQGQM-RGTIDSFYNA-N
SMILES	[C@@]12([H])NC(=O)[C@@]([H])(C(C)C)NC(=O)C[C@@]([H])(C=CCCSSC1)OC(=O)[C@H](C(C)C)NC(=O)/C(=C/C)/NC2=O \|c:16,&1:0,5,14,26,r\|
NCI Dictionary of Cancer Terms	depsipeptide; FR901228; Istodax; romidepsin
FDA UNII	CX3T89XQBK
NCI Drug Dictionary	Istodax
ATC code	L01XH02
UNSPSC Code	12352200
NACRES	NA.77

SAFETY

Risk and Safety Statements

Symbol(GHS)

GHS08,GHS09,GHS06

Signal word

Danger

Hazard statements

H301-H341-H317-H410

Precautionary statements

P201-P202-P281-P308+P313-P405-P501-P264-P270-P301+P310-P321-P330-P405-P501-P261-P272-P280-P302+P352-P333+P313-P321-P363-P501-P273-P391-P501

WGK Germany

WGK 3

RTECS

YV9399000

HS Code

29349990

Storage Class

11 - Combustible Solids

Toxicity

mouse,LD50,intraperitoneal,6400ug/kg (6.4mg/kg),Journal of Antibiotics. Vol. 47, Pg. 301, 1994.

NFPA 704

	0
2		0

(1S,4Z,7S,10S,11E,20R)-4-ethylidene-7,20-dipropan-2-yl-9-oxa-15,16-dit hia-3,6,18,21-tetrazabicyclo[8.7.6]tricos-11-ene-2,5,8,19,22-pentone price More Price(71)

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
Sigma-Aldrich	SML1175	Romidepsin ≥98% (HPLC)	128517-07-7	1mg	$361	2026-04-30	Buy
Cayman Chemical	17130	Romidepsin ≥98%	128517-07-7	500μg	$121	2026-04-30	Buy
Cayman Chemical	17130	Romidepsin ≥98%	128517-07-7	1mg	$204	2026-04-30	Buy
Cayman Chemical	17130	Romidepsin ≥98%	128517-07-7	5mg	$597	2026-04-30	Buy
Cayman Chemical	17130	Romidepsin ≥98%	128517-07-7	500μg	$110	2024-03-01	Buy

Product number	Packaging	Price	Buy
SML1175	1mg	$361	Buy
17130	500μg	$121	Buy
17130	1mg	$204	Buy
17130	5mg	$597	Buy
17130	500μg	$110	Buy

(1S,4Z,7S,10S,11E,20R)-4-ethylidene-7,20-dipropan-2-yl-9-oxa-15,16-dit hia-3,6,18,21-tetrazabicyclo[8.7.6]tricos-11-ene-2,5,8,19,22-pentone Chemical Properties,Uses,Production

Description

The U.S. FDA approved romidepsin (also referredto as FK228) in 2009 for the treatment of cutaneous T-cell lymphoma (CTCL) for patients who received at least one systemic therapy. Romidepsin is a natural product that was first isolated from the fermentation broth of C. violaceum. Romidepsin is the second histone deacetylase (HDAC) inhibitor approved for CTCL, the other being vorinostat,whichwas approved by the FDA in 2006. Unlike vorinostat which is a pan-HDAC inhibitor, romidepsin shows modest selectivity for class I HDACs in in vitro assays. It has been shown that after romidepsin enters the cytoplasm, the disulfide bond is cleaved by glutathione to release the sulfhydryl groupwhich chelateswith the activesite zinc of class IHDACs and inhibits the enzymatic activity at nanomolar concentrations. Although romidepsin inhibits class I HDACs, it is 17–23 times less potent as the parent than the corresponding reduced form at each isozyme. For example, the IC₅₀ of romidepsin at HDAC1 is 36±16nM while that of the reduced form is IC₅₀=1.6± 0.9nM.Romidepsinhasalsobeenshownto induce cell cycle arrest, differentiation, and apoptosis in tumor cells by mechanisms that cannot be completely explained by HDAC inhibition alone.

Chemical Properties

Pale Yellow Solid

Originator

Fujisawa (Astellas Pharma) (Japan)

Uses

Romidepsin is a histone deacetylase inhibitor that can alter chromatin structure and gene transcription leading to multiple changes in cellular protein production. This may result in cell cycle arrest and tumor growth inhibition. Romidepsin has shown anti-proliferative activity in vitro against multiple mouse and human tumor cell lines and in vivo in human tumor xenograft models. Romidepsin can be administered with a second agent, such as a cytotoxic agent, a steroidal agent, a proteasome inhibitor, or a kinase inhibitor.

Uses

Labelled Romidepsin (R425060). Romidepsin is a histone deacetylase inhibitor that can alter chromatin structure and gene transcription leading to multiple changes in cellular protein production. This may result in cell cycle arrest and tumor growth inhibition. Romidepsin has shown anti-proliferative activity in vitro against multiple mouse and human tumor cell lines and in vivo in human tumor xeno graft models. Romidepsin can be administered with a second agent, such as a cytotoxic agent, a steroidal agent, a proteasome inhibitor, or a kinase inhibitor.

Definition

ChEBI: A cyclodepsipeptide consisting of the cyclic disulfide of (2Z)-2-aminobut-2-enoyl, L-valyl, (3S,4E)-3-hydroxy-7-sulfanylhept-4-enoyl, D-valyl and D-cystei yl residues coupled in sequence and cyclised head-to tail.

brand name

Chromadax (Gloucester);Istodax.

Biochem/physiol Actions

Romidepsin is a very potent natural prodrug inhibitor of HDAC1 and HDAC2 that is converted to active form by glutathione. Romidepsin has IC50 values of 36 nM and 47 nM for HDAC1 and HDAC2, respectively. Romidepsin kills lymphoma cell lines overexpressing Bcl-2 and Bcl-XL, and has been approved for the treatment for cutaneous T-cell lymphoma (CTCL) and peripheral T-cell lymphoma, and a variety of other cancers.

Clinical Use

Romidepsin, a histone deacetylase inhibitor, originally developed by Fujisawa (now Astellas Pharma), causes cell cycle arrest, differentiation, and apoptosis in various cancer cells. In 2004, the FDA granted fast-track designation for romidepsin as monotherapy for the treatment of cutaneous Tcell lymphoma (CTCL) in patients who have relapsed following, or become refractory to, other systemic therapies. The FDA designated romidepsin as an orphan drug and it was approved in 2009 for this indication and it was commercialized in 2010. In 2007, another fast-track designation was granted for the product as monotherapy of previously treated peripheral T-cell lymphoma. Romidepsin (FR901228) was originally discovered and isolated from the fermentation broth of Chromobacterium violaceum No. 968. It was identified through efforts in the search for novel agents which selectively reverse the morphological phenotype of Ras oncogene-transformed cells since the Ras signaling pathway plays a critical role in cancer development. Therefore, the drug could also have multiple molecular targets for its anticancer activity besides HDAC. FR901228 is a bicyclic depsipeptide which is structurally unrelated to any known class of cyclic peptides with an unusual disulfide bond connecting a thiol and Dcysteine.

Synthesis

Romidepsin is commercially produced by fermentation; however its interesting and novel structure warrants examination of its synthesis within the context of this review. The synthesis of romidepsin described is based on the total synthesis reported by the Williams and Simon groups. L-Valine methyl ester (134) was coupled to N-Fmoc-L-threonine in the presence of the BOP reagent in 95% yield. The N-Fmoc protecting group was removed with Et2NH and the corresponding free amine was coupled to N-alloc-(S-triphenylmethyl)-D-cysteine with 1-ethyl-3- (3-dimethylaminopropyl)carbodiimide (EDCI) and HOBT in DMF and CH2Cl2 to yield the tripeptide 135 in good yield. The threonine residue of tripeptide 135 was then subjected to dehydrating conditions to give alkene 136 in 95% yield. The N-alloc protecting group of the dehydrated tripeptide 136 was removed with palladium and tin reagents and the corresponding free amine was subsequently coupled with N-Fmoc-D-valine to give tetrapeptide 137 in 83% yield. After removal of the N-Fmoc protecting group of compound 137 with Et2NH amine 138 was obtained in quantitative yield. The acid coupling partner 145 for amine 138 was prepared as follows: methyl 3,3-dimethoxypropionate (139) was converted to its corresponding Weinreb amide by standard conditions and reacted with lithium acetylide 140 to give propargylic ketone 141 in 75% yield. Noyoriˉs asymmetric reduction of ketone 141 using ruthenium catalyst 142 gave the (R)-propargylic alcohol in 98% ee. This was followed by Red-Al reduction of the alkyne to selectively yield (E)-alkene 143 in 58% yield for the two steps. Liberation of the primary alcohol with tetrabutylammonium fluoride (TBAF) followed by selective tosylation gave 144 in 70% yield in two steps. Hydrolysis of the dimethyl acetal of 144 with LiBF4 was followed by a Pinnick oxidation to give the corresponding carboxylic acid. The tosylate was displaced with trityl mercaptan in the presence of tert-butyl alcohol to give allylic alcohol 145 in 65% yield for the three steps. Aminoamide 138 was then coupled to acid 145 using BOP to give peptide 146 in quantitative yield. The methyl ester of compound 146 was hydrolyzed with lithium hydroxide to provide the free carboxylic acid which underwent macrolactonization under Mitsunobu conditions in the presence of diisopropyl azodicarboxylate (DIAD) and triphenylphosine to give macrocycle 147 in 24% yield. Finally, the disulfide linkage was formed by treating bis-tritylsulfane 147 with iodine in methanol at room temperature to give romidepsin (XIII) in 81% yield.

Synthesis_128517-07-7

storage

-20°C

References

[1] FK228 (depsipeptide) as a natural prodrug that inhibits class I histone deacetylases
[2] JYOTI PANICKER. Romidepsin (FK228/depsipeptide) controls growth and induces apoptosis in neuroblastoma tumor cells.[J]. Cell Cycle, 2010, 9 9: 1830-1838. DOI:10.4161/cc.9.9.11543
[3] H UEDA. FR901228, a novel antitumor bicyclic depsipeptide produced by Chromobacterium violaceum No. 968. III. Antitumor activities on experimental tumors in mice.[J]. Journal of Antibiotics, 1994, 47 3: 315-323. DOI:10.7164/antibiotics.47.315
[4] KAREN M VANDERMOLEN. Romidepsin (Istodax, NSC 630176, FR901228, FK228, depsipeptide): a natural product recently approved for cutaneous T-cell lymphoma[J]. Journal of Antibiotics, 2011, 64 8: 525-531. DOI:10.1038/ja.2011.35

(1S,4Z,7S,10S,11E,20R)-4-ethylidene-7,20-dipropan-2-yl-9-oxa-15,16-dit hia-3,6,18,21-tetrazabicyclo[8.7.6]tricos-11-ene-2,5,8,19,22-pentone Preparation Products And Raw materials

Raw materials

Preparation Products

(1S,4Z,7S,10S,11E,20R)-4-ethylidene-7,20-dipropan-2-yl-9-oxa-15,16-dit hia-3,6,18,21-tetrazabicyclo[8.7.6]tricos-11-ene-2,5,8,19,22-pentone Suppliers

Global( 235)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
Chongqing Qiantai Pharma Co., Ltd.	17864179792	richardchan@bright-gene.com	China	95	58
ATK CHEMICAL COMPANY LIMITED	+undefined-21-51877795	ivan@atkchemical.com	China	33024	60
career henan chemical co	+86-0371-86658258	sales@coreychem.com	China	29812	58
Biochempartner	0086-13720134139	candy@biochempartner.com	CHINA	965	58
Cangzhou Wanyou New Material Technology Co.,Ltd	18631714998	sales@czwytech.com	CHINA	904	58
Shenzhen Excellent Biotech Co., Ltd.	13480692018	ramyan@ex-biotech.com	CHINA	954	58
Jurong Coupling Biotechnology Co., Ltd.	13656108824	coupling278191416@hotmail.com	CHINA	184	58
Antai Fine Chemical Technology Co.,Limited	18503026267	info@antaichem.com	CHINA	9636	58
TargetMol Chemicals Inc.	+1-781-999-5354; +1-00000000000	marketing@targetmol.com	United States	32468	58
HANGZHOU CLAP TECHNOLOGY CO.,LTD	86-571-88216897,88216896 13588875226	sales@hzclap.com	CHINA	6312	58

Supplier	Advantage
Chongqing Qiantai Pharma Co., Ltd.	58
ATK CHEMICAL COMPANY LIMITED	60
career henan chemical co	58
Biochempartner	58
Cangzhou Wanyou New Material Technology Co.,Ltd	58
Shenzhen Excellent Biotech Co., Ltd.	58
Jurong Coupling Biotechnology Co., Ltd.	58
Antai Fine Chemical Technology Co.,Limited	58
TargetMol Chemicals Inc.	58
HANGZHOU CLAP TECHNOLOGY CO.,LTD	58

View Lastest Price from (1S,4Z,7S,10S,11E,20R)-4-ethylidene-7,20-dipropan-2-yl-9-oxa-15,16-dit hia-3,6,18,21-tetrazabicyclo[8.7.6]tricos-11-ene-2,5,8,19,22-pentone manufacturers

Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
2026-07-17	Romidepsin 128517-07-7	$88.00-225.00		99.99%	10g	TargetMol Chemicals Inc.
2019-07-31	Romidepsin 128517-07-7	$1.00	1g	99%	2000kg	Cangzhou Wanyou New Material Technology Co.,Ltd
2019-07-06	(1S,4Z,7S,10S,11E,20R)-4-ethylidene-7,20-dipropan-2-yl-9-oxa-15,16-dit hia-3,6,18,21-tetrazabicyclo[8.7.6]tricos-11-ene-2,5,8,19,22-pentone 128517-07-7	$1.00	1G	98%	100KG	Career Henan Chemical Co

Romidepsin
128517-07-7
$88.00-225.00
99.99%
TargetMol Chemicals Inc.

Romidepsin
128517-07-7
$1.00
99%
Cangzhou Wanyou New Material Technology Co.,Ltd

(1S,4Z,7S,10S,11E,20R)-4-ethylidene-7,20-dipropan-2-yl-9-oxa-15,16-dit hia-3,6,18,21-tetrazabicyclo[8.7.6]tricos-11-ene-2,5,8,19,22-pentone
128517-07-7
$1.00
98%
Career Henan Chemical Co

(1S,4Z,7S,10S,11E,20R)-4-ethylidene-7,20-dipropan-2-yl-9-oxa-15,16-dit hia-3,6,18,21-tetrazabicyclo[8.7.6]tricos-11-ene-2,5,8,19,22-pentone Spectrum

(1S,4Z,7S,10S,11E,20R)-4-ethylidene-7,20-dipropan-2-yl-9-oxa-15,16-dit hia-3,6,18,21-tetrazabicyclo[8.7.6]tricos-11-ene-2,5,8,19,22-pentone(128517-07-7)¹HNMR

128517-07-7((1S,4Z,7S,10S,11E,20R)-4-ethylidene-7,20-dipropan-2-yl-9-oxa-15,16-dit hia-3,6,18,21-tetrazabicyclo[8.7.6]tricos-11-ene-2,5,8,19,22-pentone)Related Search:

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1of4

FK228 RoMidepsin 5)-disulfide Cyclo[(2Z)-2-aMino-2-butenoyl-L-valyl-(3S,4E)-3-hydroxy-7-Mercapto-4-heptenoyl-D-valyl-D-cysteinyl],cyclic (3® (1S,4Z,7S,10S,11E,20R)-4-ethylidene-7,20-dipropan-2-yl-9-oxa-15,16-dit hia-3,6,18,21-tetrazabicyclo[8.7.6]tricos-11-ene-2,5,8,19,22-pentone RoMidepsin (FK228, Depsipeptide) Romidepsin Antibiotic FR 901228 Romidepsin, >=98% (1S,4Z,7S,10S,11E,20R)-4-ethylidene-7,20-dipropan-2-yl-9-oxa-15,16-dit hia-3,6,18,21-tetrazabicyclo[ FR 901228 istodax RoMidepsin/Depsipeptide(FK-228, NSC-63017) (1S,4Z,7S,10S,11E,20R)-4-ethylidene-7,20-dipropan-2-yl-9-oxa-15,16-dit hia-3,6,18,21-tetrazabicyclo[8.7.6]tricos-11-ene-2,5,8,19,22-pentone RoMidepsin (FK228 ,Depsipeptide) [S-(E)]-N-(3-Hydroxy-7-Mercapto-1-oxo-4- heptenyl)-D-valyl-D-cysteinyl-(Z)-2,3-didehydro-2-aMinobutanoyl- Cyclo[(2Z)-2-aMino-2-butenoyl-L-valyl-(3S,4E)-3-hydroxy-7-Mercapto-4-heptenoyl-D-valyl-D-cysteinyl] Cyclic (35)-Disulfide Cyclo[(2Z)-2-aMino-2-butenoyl-L-valyl-(3S,4E)-3-hydroxy-7-Mercapto-4-heptenoyl-D-valyl-D-cysteinyl]-d8 Cyclic (35)-Disulfide RoMidepsin-d8 NSC 630176 Antibiotic FR 901228 Chromadax RoMidepsin(FK228) FK 228;? FR 901228;? NSC 630176;? DEPSIPEPTIDE;FK228 CS-972 Romidepsin (FK228, Depsipeptide, FR1228) Romidepsin, 98%, a potent HDAC1 and HDAC2 inhibitor (1S,4Z,7S,10S,11E,20R)-4-ethylidene-7,20-dipropan-2-yl-9-oxa-15,16-dit hia-3,6,18,21-tetrazabicyclo[8.7.6]tricos-11-ene-2,5,8,19,23-pentone (1S,4Z,7S,10S,11E,20R)-4-ethylidene-7,20-dipropan-2-yl-9-oxa-15,16-dit hia-3,6,18,21-tetrazabicyclo[8.7.6]tricos-11-ene-2,5,8,19,22-pentone USP/EP/BP Romidepsin (FK228, FR901228, Depsipeptide, NSC630176) FK228, Depsipeptide Romidepsin D7Q: What is Romidepsin D7 Q: What is the CAS Number of Romidepsin D7 Q: What is the storage condition of Romidepsin D7 Q: What are the applications of Romidepsin D7 Romidisin (1S,4S,7Z,10S,16E,21R)-7-Ethylidene-4,21-diisopropyl-2-oxa-12,13-dithia-5,8,20,23-tetraazabicyclo[8.7.6]tricos-16-ene-3,6,9,19,22-pentaone (1S,4Z,7S,10S,11E,20R)-4-ethylidene-7,20-dipropan-2-yl-9-oxa-15,16-dit hia-3,6,18, FK228 Romidepsin FK-228 (1S,4Z,7S,10S,11E,20R)-4-ethylidene-7 Romidixin GS-002 GS-003 GSI-001 Romidepsin - Bio-X ? depsipeptide FK228 Romidepsin 128517-07-7 128517-07-8 C24H36N4O6S2 API Inhibitor Heterocycles Inhibitors Intermediates & Fine Chemicals Pharmaceuticals

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(1S,4Z,7S,10S,11E,20R)-4-ethylidene-7,20-dipropan-2-yl-9-oxa-15,16-dit hia-3,6,18,21-tetrazabicyclo[8.7.6]tricos-11-ene-2,5,8,19,22-pentone

(1S,4Z,7S,10S,11E,20R)-4-ethylidene-7,20-dipropan-2-yl-9-oxa-15,16-dit hia-3,6,18,21-tetrazabicyclo[8.7.6]tricos-11-ene-2,5,8,19,22-pentone Properties

SAFETY

Risk and Safety Statements

(1S,4Z,7S,10S,11E,20R)-4-ethylidene-7,20-dipropan-2-yl-9-oxa-15,16-dit hia-3,6,18,21-tetrazabicyclo[8.7.6]tricos-11-ene-2,5,8,19,22-pentone price More Price(71)

(1S,4Z,7S,10S,11E,20R)-4-ethylidene-7,20-dipropan-2-yl-9-oxa-15,16-dit hia-3,6,18,21-tetrazabicyclo[8.7.6]tricos-11-ene-2,5,8,19,22-pentone Chemical Properties,Uses,Production

Description

Chemical Properties

Originator

Uses

Uses

Definition

brand name

Biochem/physiol Actions

Clinical Use

Synthesis

storage

References

(1S,4Z,7S,10S,11E,20R)-4-ethylidene-7,20-dipropan-2-yl-9-oxa-15,16-dit hia-3,6,18,21-tetrazabicyclo[8.7.6]tricos-11-ene-2,5,8,19,22-pentone Preparation Products And Raw materials

Raw materials

Preparation Products

(1S,4Z,7S,10S,11E,20R)-4-ethylidene-7,20-dipropan-2-yl-9-oxa-15,16-dit hia-3,6,18,21-tetrazabicyclo[8.7.6]tricos-11-ene-2,5,8,19,22-pentone Suppliers

View Lastest Price from (1S,4Z,7S,10S,11E,20R)-4-ethylidene-7,20-dipropan-2-yl-9-oxa-15,16-dit hia-3,6,18,21-tetrazabicyclo[8.7.6]tricos-11-ene-2,5,8,19,22-pentone manufacturers

(1S,4Z,7S,10S,11E,20R)-4-ethylidene-7,20-dipropan-2-yl-9-oxa-15,16-dit hia-3,6,18,21-tetrazabicyclo[8.7.6]tricos-11-ene-2,5,8,19,22-pentone Spectrum

128517-07-7((1S,4Z,7S,10S,11E,20R)-4-ethylidene-7,20-dipropan-2-yl-9-oxa-15,16-dit hia-3,6,18,21-tetrazabicyclo[8.7.6]tricos-11-ene-2,5,8,19,22-pentone)Related Search: