 Home > Encyclopedia > (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
Formula:
C24H36N4O6S2
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:
(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;FR 901228;Romidepsin;istodax;RoMidepsin/Depsipeptide(FK-228, NSC-63017);[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
Categories:
Biochemical Engineering > Inhibitors

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Description

Pale Yellow SolidChEBI: 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.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

Romidepsin is an intravenously administered histone deacetylase inhibitor and antineoplastic agent that is approved for use in refractory or relapsed cutaneous and peripheral T cell lymphomas. Romidepsin is associated with modest rate of minor serum enzyme elevations during therapy but has not been linked to cases of clinically apparent liver injury, although it has been reported to cause reactivation of hepatitis B.

(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 Basic Attributes

Molecular Weight：

540.69600

Exact Mass：

540.207642

DSSTox ID：

DTXSID8048579

HScode：

29349990

Characteristics

PSA：

193.30000

XLogP3：

2.74480

Density：

1.174

Melting Point：

219-224°C

Boiling Point：

942.8±65.0 °C(Predicted)

Flash Point：

524.0±34.3 °C

Refractive Index：

1.529

Storage Conditions：

Amber Vial, -20°C Freezer, Under Inert Atmosphere

Vapor Pressure：

0mmHg at 25°C

Safety Information

Transport codes：

NONH for all modes of transport

RTECS Number：

YV9399000

GHS Classification：

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P261, P264, P270, P272, P273, P280, P281, P301+P310, P302+P352, P308+P313, P321, P330, P333+P313, P363, P391, P405, and P501|Aggregated GHS information provided by 158 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Hepatotoxicity：

In clinical trials of romidepsin in patients with CTLC and PTLC, the rates of serum enzyme elevations during therapy ranged from 7% to 20%, but the abnormalities were usually transient and mild and did not require dose modifications. Serum ALT elevations above 5 times ULN occurred in 6% of patients. In the preregistration clinical trials of romidepsin, there were no reports of hepatitis, jaundice or clinically apparent liver injury among the treated subjects. Romidepsin has had limited clinical use, but there is no evidence that it is associated with significant liver injury.

Drug Information

LiverTox Summary：

Drug Classes：

Antineoplastic Agents

(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 Use and Manufacturing

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 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.

Computed Properties

Molecular Weight:540.7
XLogP3:2.2
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:2
Exact Mass:540.20762723
Monoisotopic Mass:540.20762723
Topological Polar Surface Area:193
Heavy Atom Count:36
Complexity:905
Undefined Atom Stereocenter Count:4
Undefined Bond Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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CAS No.: 128517-07-7

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Guide of (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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(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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