(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 Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung

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.

Chemische Eigenschaften

Pale Yellow Solid

Verwenden

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.

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.

(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 Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte

(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 Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Firmenname	Telefon	E-Mail	Land	Produktkatalog	Edge Rate
ATK CHEMICAL COMPANY LIMITED	+undefined-21-51877795	ivan@atkchemical.com	China	32480	60
career henan chemical co	+86-0371-86658258	sales@coreychem.com	China	29914	58
Biochempartner	0086-13720134139	candy@biochempartner.com	CHINA	967	58
Cangzhou Wanyou New Material Technology Co.,Ltd	18631714998	sales@czwytech.com	CHINA	906	58
Hubei xin bonus chemical co. LTD	86-13657291602	linda@hubeijusheng.com	CHINA	22968	58
BOC Sciences	+1-631-485-4226	inquiry@bocsci.com	United States	19553	58
Chongqing Chemdad Co., Ltd	+86-023-61398051 +8613650506873	sales@chemdad.com	China	39916	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
Fuxin Pharmaceutical	+86-021-021-50872116 +8613122107989	contact@fuxinpharm.com	China	10297	58

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• 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
• Romidepsin
• FK228
• depsipeptide
• 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
• 128517-07-7
• 128517-07-8
• C24H36N4O6S2
• API
• Inhibitor
• Heterocycles
• Inhibitors
• Intermediates & Fine Chemicals
• Pharmaceuticals