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Pinometostat

Pinometostat structure

CAS No:
1380288-87-8
Formula:
C30H42N8O3
Chemical Name:
Pinometostat
Synonyms:
Adenosine,5′-deoxy-5′-[[cis-3-[2-[6-(1,1-dimethylethyl)-1H-benzimidazol-2-yl]ethyl]cyclobutyl](1-methylethyl)amino]-;5′-Deoxy-5′-[[cis-3-[2-[6-(1,1-dimethylethyl)-1H-benzimidazol-2-yl]ethyl]cyclobutyl](1-methylethyl)amino]adenosine;Pinometostat;EPZ 005676;EPZ 5676;(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-((((lr,3S)-3-(2-(5-(tert-butyl)-lH-benzo[d]imidazol2yl)ethyl)cyclobutyl)(isopropyl)amino)methyl)tetrahydrofuran-3,4-diol;2: PN: US20150212088 SEQID: 5 claimed sequence;(2R,3R,4S,5R)-2-(6-Amino-9H-purin-9-yl)-5-((((lr,3S)-3-(2-(5-(tert-butyl)-lH-benzo[d]imidazol2yl)ethyl)cyclobutyl)(isopropyl)amino)methyl)tetrahydrofuran-3,4-diol
Categories:
Biochemical Engineering > Inhibitors

Description

Pinometostat (EPZ-5676) is a potent DOT1L histone methyltransferase inhibitor with a Ki of 80 pM.

(2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-[[[3-[2-(6-tert-butyl-1H-benzimidazol-2-yl)ethyl]cyclobutyl]-propan-2-ylamino]methyl]oxolane-3,4-diol is a 5'-deoxyribonucleoside.|Pinometostat has been used in trials studying the treatment of Leukemia, Acute Leukemias, Acute Myeloid Leukemia, Myelodysplastic Syndrome, and Acute Lymphocytic Leukemia, among others.|Pinometostat is a small molecule inhibitor of histone methyltransferase with potential antineoplastic activity. Upon intravenous administration, pinometostat specifically blocks the activity of the histone lysine-methyltransferase DOT1L, thereby inhibiting the methylation of nucleosomal histone H3 on lysine 79 (H3K79) that is bound to the mixed lineage leukemia (MLL) fusion protein which targets genes and blocks the expression of leukemogenic genes. This eventually leads to an induction of apoptosis in the leukemic cells bearing the MLL gene translocations. DOT1L, a non-SET domain-containing histone methyltransferase, specifically methylates H3K79 and plays a key role in normal cell differentiation and in the development of leukemia with MLL gene rearrangement on chromosome 11 and promotes the expression of leukemia-causing genes.

Pinometostat Basic Attributes

Molecular Weight：

562.70628

Exact Mass：

562.71

EC Number：

-0

UNII：

8V9YR09EF3|F66X4M38G5

DSSTox ID：

DTXSID20720950

NCI Thesaurus Code：

C103179

Characteristics

PSA：

151

XLogP3：

4.3

Density：

1.45±0.1 g/cm3(Predicted)

Boiling Point：

835.3±75.0 °C(Predicted)

Flash Point：

459.0±37.1 °C

Refractive Index：

1.722

Drug Information

MeSH Entry Terms：

(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-((((1r,3S)-3-(2-(5-(tert-butyl)-1H-benzo(d)imidazol-2-yl)ethyl)cyclobutyl)(isopropyl)amino)methyl)tetrahydrofuran-3,4-diol

Computed Properties

Molecular Weight:562.7
XLogP3:4.3
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:9
Exact Mass:562.33798723
Monoisotopic Mass:562.33798723
Topological Polar Surface Area:151
Heavy Atom Count:41
Complexity:884
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes