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SML1175

Romidepsin

≥98% (HPLC), powder, histone deacetylase inhibitor

Synonym(s):

Cyclo[(2Z)-2-amino-2-butenoyl-L-valyl-(3S,4E)-3-hydroxy-7-mercapto-4-heptenoyl-D-valyl-D-cysteinyl] cyclic (35)-disulfide, Depsipeptide, FK228, FR901228, L-Valine, N-((3S,4E)-3-hydroxy-7-mercapto-1-oxo-4-heptenyl)-D-valyl-D-cysteinyl-(2Z)-2-amino-2-butenoxyl-, (4-1)-lactone, cyclic (1-2)-disulfide

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About This Item

Empirical Formula (Hill Notation):
C24H36N4O6S2
CAS Number:
128517-07-7
Molecular Weight:
540.70
UNSPSC Code:
12352200
PubChem Substance ID:
329825701
NACRES:
NA.77
MDL number:
MFCD18433404
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100
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Product Name

Romidepsin, ≥98% (HPLC)

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 25 mg/mL, clear

storage temp.

−20°C

SMILES string

O=C(N/C(C(N[C@@H](C(C)C)C(O[C@@]1([H])CC2=O)=O)=O)=C\C)[C@@H](CSSCC/C=C/1)NC([C@H](N2)C(C)C)=O

InChI

1S/C24H36N4O6S2/c1-6-16-21(30)28-20(14(4)5)24(33)34-15-9-7-8-10-35-36-12-17(22(31)25-16)26-23(32)19(13(2)3)27-18(29)11-15/h6-7,9,13-15,17,19-20H,8,10-12H2,1-5H3,(H,25,31)(H,26,32)(H,27,29)(H,28,30)/b9-7+,16-6-/t15-,17-,19-,20+/m1/s1

InChI key

OHRURASPPZQGQM-GCCNXGTGSA-N

Gene Information

human ... HDAC1(3065), HDAC10(83933), HDAC11(79885), HDAC2(3066), HDAC3(8841), HDAC4(9759), HDAC5(10014), HDAC6(10013), HDAC7(51564), HDAC8(55869), HDAC9(9734)

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.
Romidepsin is a very potent natural prodrug inhibitor of HDAC1 and HDAC2; antineoplastic.
Romidepsin promotes apoptosis, while hindering tumor growth in glioma models.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000209809
0000209809
0000178117
0000173871
0000173871

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Anna Otte et al.
International journal of oncology, 49(6), 2453-2463 (2016-10-18)
Chemotherapeutic drug testing of SCCOHT-1 and BIN-67 tumor cells revealed synergistic growth-inhibition of >95% in vitro with a combination of foretinib and FK228. Application of this drug combination in vivo in NODscid mice-induced SCCOHT-1GFP tumors was associated with ~6-fold reduction in
A phase I/II trial of the histone deacetylase inhibitor romidepsin for adults with recurrent malignant glioma: North American Brain Tumor Consortium Study 03-03.
Iwamoto F M, et al.
Neuro-Oncology, 13(5), 509-516 (2011)
YiHan Wu et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 84, 462-469 (2016-09-30)
Temozolomide is a novel cytotoxic agent currently used as first-line chemotherapy for glioblastoma multiforme (GBM). Romidepsin (FK228), a histone deacetylase inhibitor, is a promising new class of antineoplastic agent with the capacity to induce growth arrest and/or apoptosis of cancer
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