Terameprocol
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MedKoo CAT#: 202880

CAS#: 24150-24-1

Description: Terameprocol, also known as EM-1421, is a semi-synthetic tetra-methylated derivative of nordihydroguaiaretic acid (NDGA) and transcriptional inhibitor with potential antiviral, antiangiogenic, and antineoplastic activities. Terameprocol competes with the transcription factor Sp1 for specific Sp1 DNA binding domains within gene promoter regions during DNA synthesis. In virally-infected cells, blocking of the Sp1 binding site suppresses Sp1-regulated viral promoter activity and gene expression, thereby inhibiting viral transcription and replication.


Chemical Structure

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Terameprocol
CAS# 24150-24-1

Theoretical Analysis

MedKoo Cat#: 202880
Name: Terameprocol
CAS#: 24150-24-1
Chemical Formula: C22H30O4
Exact Mass: 358.21441
Molecular Weight: 358.47
Elemental Analysis: C, 73.71; H, 8.44; O, 17.85

Size Price Shipping out time Quantity
1g USD 90 Same day
2g USD 160 Same day
5g USD 350 Same day
10g USD 630 Same day
20g USD 1130 Same day
50g USD 2250 Same day
Inquire bulk and customized quantity

Pricing updated 2021-02-26. Prices are subject to change without notice.

Terameprocol, purity > 98%, is in stock. The same day shipping out after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide). Shipping fee: from $30.00 (USA); from $45.00 (Canada); from $70.00 (international).

Synonym: tetramethyl-nordihydroguaiaretic acid; tetra-O-methyl nordihydroguaiaretic acid. Abbreviations: M4N; tetramethyl-NDGA; TMNDGA; Code name: EM1421; EM-1421; EM 1421.

IUPAC/Chemical Name: (2R,3S)-2,3-dimethyl-1,4-bis(3,4-bimethoxylphenyl)-butane

InChi Key: ORQFDHFZSMXRLM-IYBDPMFKSA-N

InChi Code: InChI=1S/C22H30O4/c1-15(11-17-7-9-19(23-3)21(13-17)25-5)16(2)12-18-8-10-20(24-4)22(14-18)26-6/h7-10,13-16H,11-12H2,1-6H3/t15-,16+

SMILES Code: COC1=CC=C(C[C@H](C)[C@H](C)CC2=CC=C(OC)C(OC)=C2)C=C1OC

Appearance:
white solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 358.47 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Ho SS, Go ML. Restraining the flexibility of the central linker in terameprocol results in constrained analogs with improved growth inhibitory activity. Bioorg Med Chem Lett. 2013 Nov 15;23(22):6127-33. doi: 10.1016/j.bmcl.2013.09.014. Epub 2013 Sep 13. PubMed PMID: 24080463.

2: Grossman SA, Ye X, Peereboom D, Rosenfeld MR, Mikkelsen T, Supko JG, Desideri S; Adult Brain Tumor Consortium. Phase I study of terameprocol in patients with recurrent high-grade glioma. Neuro Oncol. 2012 Apr;14(4):511-7. doi: 10.1093/neuonc/nor230. Epub 2012 Feb 8. PubMed PMID: 22323663; PubMed Central PMCID: PMC3309850.

3: Oyegunwa AO, Sikes ML, Wilson JR, Scholle F, Laster SM. Tetra-O-methyl nordihydroguaiaretic acid (Terameprocol) inhibits the NF-κB-dependent transcription of TNF-α and MCP-1/CCL2 genes by preventing RelA from binding its cognate sites on DNA. J Inflamm (Lond). 2010 Dec 7;7:59. doi: 10.1186/1476-9255-7-59. PubMed PMID: 21138578; PubMed Central PMCID: PMC3002343.

4: Sun Y, Giacalone NJ, Lu B. Terameprocol (tetra-O-methyl nordihydroguaiaretic acid), an inhibitor of Sp1-mediated survivin transcription, induces radiosensitization in non-small cell lung carcinoma. J Thorac Oncol. 2011 Jan;6(1):8-14. doi: 10.1097/JTO.0b013e3181fa646a. PubMed PMID: 21107289; PubMed Central PMCID: PMC3010256.

5: Pollara JJ, Laster SM, Petty IT. Inhibition of poxvirus growth by Terameprocol, a methylated derivative of nordihydroguaiaretic acid. Antiviral Res. 2010 Dec;88(3):287-95. doi: 10.1016/j.antiviral.2010.09.017. Epub 2010 Oct 1. PubMed PMID: 20888364.

6: Eads D, Hansen R, Oyegunwa A, Cecil C, Culver C, Scholle F, Petty I, Laster S. Terameprocol, a methylated derivative of nordihydroguaiaretic acid, inhibits production of prostaglandins and several key inflammatory cytokines and chemokines. J Inflamm (Lond). 2009 Jan 8;6:2. doi: 10.1186/1476-9255-6-2. PubMed PMID: 19133137; PubMed Central PMCID: PMC2631502.

7: Khanna N, Dalby R, Connor A, Church A, Stern J, Frazer N. Phase I clinical trial of repeat dose terameprocol vaginal ointment in healthy female volunteers. Sex Transm Dis. 2008 Jun;35(6):577-82. doi: 10.1097/OLQ.0b013e31816766af. PubMed PMID: 18418294.

8: Smolewski P. Terameprocol, a novel site-specific transcription inhibitor with anticancer activity. IDrugs. 2008 Mar;11(3):204-14. Review. PubMed PMID: 18311658.

9: Khanna N, Dalby R, Tan M, Arnold S, Stern J, Frazer N. Phase I/II clinical safety studies of terameprocol vaginal ointment. Gynecol Oncol. 2007 Dec;107(3):554-62. Epub 2007 Oct 1. PubMed PMID: 17905420.

10: Lopez RA, Goodman AB, Rhodes M, Blomberg JA, Heller J. The anticancer activity of the transcription inhibitor terameprocol (meso-tetra-O-methyl nordihydroguaiaretic acid) formulated for systemic administration. Anticancer Drugs. 2007 Sep;18(8):933-9. PubMed PMID: 17667599.