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HDAC-Inhibitoren >(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
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- CAS-Nr.
- 128517-07-7
- Englisch 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
- Synonyma:
- Romidepsin;FK228;Romidisin;depsipeptide;CS-972;istodax;FR 901228;Chromadax;Romidixin;NSC 630176
- CBNumber:
- CB31260794
- Summenformel:
- C24H36N4O6S2
- Molgewicht:
- 540.7
- MOL-Datei:
- 128517-07-7.mol
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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 Eigenschaften
- Schmelzpunkt:
- 219-224°C
- Siedepunkt:
- 942.8±65.0 °C(Predicted)
- Dichte
- 1.174
- storage temp.
- -20°C
- L?slichkeit
- Soluble in DMSO (up to 10 mg/ml).
- pka
- 11.33±0.60(Predicted)
- Aggregatzustand
- powder
- Farbe
- white to beige
- Stabilit?t:
- Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month.
Sicherheit
- Risiko- und Sicherheitserkl?rung
- Gefahreninformationscode (GHS)
RTECS-Nr. |
YV9399000 |
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HS Code |
29349990 |
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Toxizit?t |
mouse,LD50,intraperitoneal,6400ug/kg (6.4mg/kg),Journal of Antibiotics. Vol. 47, Pg. 301, 1994. |
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Bildanzeige (GHS) |
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Alarmwort |
Achtung |
Gefahrenhinweise |
Code |
Gefahrenhinweise |
Gefahrenklasse |
Abteilung |
Alarmwort |
Symbol |
P-Code |
H301 |
Giftig bei Verschlucken. |
Akute Toxizit?t oral |
Kategorie 3 |
Achtung |
src="/GHS06.jpg" width="20" height="20" /> |
P264, P270, P301+P310, P321, P330,P405, P501 |
H317 |
Kann allergische Hautreaktionen verursachen. |
Sensibilisierung der Haut |
Kategorie 1A |
Warnung |
src="/GHS07.jpg" width="20" height="20" /> |
P261, P272, P280, P302+P352,P333+P313, P321, P363, P501 |
H341 |
Kann vermutlich genetische Defekte verursachen. |
Keimzellmutagenit?t |
Kategorie 2 |
Warnung |
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P201,P202, P281, P308+P313, P405,P501 |
H410 |
Sehr giftig für Wasserorganismen mit langfristiger Wirkung. |
Langfristig (chronisch) gew?ssergef?hrdend |
Kategorie 1 |
Warnung |
src="/GHS09.jpg" width="20" height="20" /> |
P273, P391, P501 |
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Sicherheit |
P201 |
Vor Gebrauch besondere Anweisungen einholen. |
P202 |
Vor Gebrauch alle Sicherheitshinweise lesen und verstehen. |
P261 |
Einatmen von Staub vermeiden. |
P264 |
Nach Gebrauch gründlich waschen. |
P264 |
Nach Gebrauch gründlich waschen. |
P270 |
Bei Gebrauch nicht essen, trinken oder rauchen. |
P272 |
Kontaminierte Arbeitskleidung nicht au?erhalb des Arbeitsplatzes tragen. |
P280 |
Schutzhandschuhe/Schutzkleidung/Augenschutz tragen. |
P281 |
Vorgeschriebene pers?nliche Schutzausrüstung verwenden. |
P301+P310 |
BEI VERSCHLUCKEN: Sofort GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen. |
P302+P352 |
BEI BERüHRUNG MIT DER HAUT: Mit viel Wasser/... (Hersteller kann, falls zweckm??ig, ein Reinigungsmittel angeben oder, wenn Wasser eindeutig ungeeignet ist, ein alternatives Mittel empfehlen) waschen. |
P308+P313 |
BEI Exposition oder falls betroffen: ?rztlichen Rat einholen/?rztliche Hilfe hinzuziehen. |
P321 |
Besondere Behandlung |
P330 |
Mund ausspülen. |
P405 |
Unter Verschluss aufbewahren. |
P501 |
Inhalt/Beh?lter ... (Entsorgungsvorschriften vom Hersteller anzugeben) zuführen. |
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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 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 IC
50 of romidepsin at HDAC1 is 36±16nM while that of the reduced form is IC
50=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 H?ndler.
Global( 188)Lieferanten
- 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
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