terameprocol

Names

[ Name ]:
terameprocol

[Synonym ]:
terameprocol
tetramethyl Nordihydroguaiaretic Acid Exclusive
4-[(2R,3S)-4-(3,4-Dimethoxyphenyl)-2,3-dimethylbutyl]-1,2-dimethoxybenzene
tetramethyl Nordihydroguaiaretic Acid
Benzene, 4-[(2R,3S)-4-(3,4-dimethoxyphenyl)-2,3-dimethylbutyl]-1,2-dimethoxy-

Biological Activity

[Description]:

Terameprocol is a synthetic derivative of Nordihydroguaiaretic acid and a non-selective lipoxygenase inhibitor. Terameprocol has antiviral and antitumor effects[1][2][3].

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Infection

Signaling Pathways >> Metabolic Enzyme/Protease >> 5-Lipoxygenase

[References]

[1]. Hwu JR, et al. Antiviral activities of methylated nordihydroguaiaretic acids. 1. Synthesis, structure identification, and inhibition of tat-regulated HIV transactivation. J Med Chem. 1998 Jul 30;41(16):2994-3000.

[2]. Chen H, et al. Antiviral activities of methylated nordihydroguaiaretic acids. 2. Targeting herpes simplex virus replication by the mutation insensitive transcription inhibitor tetra-O-methyl-NDGA. J Med Chem. 1998 Jul 30;41(16):3001-7.

[3]. Park R, et al. Systemic treatment with tetra-O-methyl nordihydroguaiaretic acid suppresses the growth of human xenograft tumors. Clin Cancer Res. 2005 Jun 15;11(12):4601-9.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
458.5±40.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₂H₃₀O₄

[ Molecular Weight ]:
358.471

[ Flash Point ]:
108.8±34.2 °C

[ Exact Mass ]:
358.214417

[ PSA ]:
36.92000

[ LogP ]:
5.86

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.522

Safety Information

[ Symbol ]:

GHS09

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H410

[ Precautionary Statements ]:
P273-P501

[ RIDADR ]:
UN 3077 9 / PGIII

Precursor & DownStream

Precursor

DownStream

Articles

Terameprocol, a novel site-specific transcription inhibitor with anticancer activity.

Drugs 3rd ed., 11 , 204-214, (2008)

Terameprocol, a novel, semisynthetic derivative of a naturally occurring plant lignan, is under development by Erimos Pharmaceuticals LLC for the potential treatment of cancer. The antitumor activity ...

Tetra-O-Methyl Nordihydroguaiaretic Acid Broadly Suppresses Cancer Metabolism and Synergistically Induces Strong Anticancer Activity in Combination with Etoposide, Rapamycin and UCN-01.

PLoS ONE 11 , e0148685, (2016)

The ability of Tetra-O-methyl nordihydroguaiaretic acid (M4N) to induce rapid cell death in combination with Etoposide, Rapamycin, or UCN-01 was examined in LNCaP cells, both in cell culture and anima...

Synthesis of apolipoprotein B lipoparticles to deliver hydrophobic/amphiphilic materials.

ACS Appl. Mater. Interfaces 5 , 7509-16, (2013)

To develop a drug delivery system (DDS), it is critical to address challenging tasks such as the delivery of hydrophobic and amphiphilic compounds, cell uptake, and the metabolic fate of the drug deli...