TERAMEPROCOL

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H30O4
Molecular Weight	358.4712
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=ORQFDHFZSMXRLM-IYBDPMFKSA-N

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+

HIDE SMILES / InChI

Molecular Formula	C22H30O4
Molecular Weight	358.4712
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://clinicaltrials.gov/ct2/show/NCT00664677 | https://www.drugbank.ca/drugs/DB12226 | https://www.ncbi.nlm.nih.gov/pubmed/15329416 | http://adisinsight.springer.com/drugs/800020885 | https://www.ncbi.nlm.nih.gov/pubmed/1368832

Temperocol is an investigative anti-cancer drug that inhibits the expression of survivin and CDK-1; discovered at Johns Hopkins University and under development by Erimos Pharmaceuticals. It has been tested in phase I/II clinical trials for Leukemia, and several forms of neoplasms including gliomas. Results of these clinical trials have shown promise, however treatment regimes produce several toxic side effects that need to be balanced against efficacy. Temperocol is a fully methylated derivative of the natural product Nordihydroguaiaretic acid.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Baculoviral IAP repeat-containing protein 5 3 Target ID: O15392\|\|\|Q75SP2 Gene ID: 332.0 Gene Symbol: BIRC5 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21107289 \| https://www.ncbi.nlm.nih.gov/pubmed/23299390	Antagonist 2849
Cyclin-dependent kinase 1 27 Target ID: P06493 Gene ID: 983.0 Gene Symbol: CDK1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/11454698 \| https://www.ncbi.nlm.nih.gov/pubmed/18311658	Antagonist 2849

Conditions

Condition	Modality	Highest Phase	Product
Leukemia 72 Sources: https://clinicaltrials.gov/ct2/show/NCT00664677	Primary	Phase I 438	Unknown Approved Use Unknown
Refractory solid tumor 1 Sources: https://clinicaltrials.gov/ct2/show/NCT00664586	Primary	Phase I 438	Unknown Approved Use Unknown
Glioma 25 Sources: https://clinicaltrials.gov/ct2/show/NCT00404248	Primary	Phase II 1147	Unknown Approved Use Unknown
Cervical intraepithelial neoplasia 1 Sources: https://clinicaltrials.gov/ct2/show/NCT00154089	Primary	Phase II 1147	Unknown Approved Use Unknown
Head and neck cancer 50 Sources: https://clinicaltrials.gov/ct2/show/NCT00057512	Primary	Phase I 438	Unknown Approved Use Unknown

T_1/2

Value	Dose	Co-administered	Analyte	Population
17.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18418294	750 mg 1 times / day multiple, intravenous dose: 750 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:		TERAMEPROCOL serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00BERJ	https://www.1pchem.com/search?query=1P00BERJ
AK Scientific	2065AH	https://aksci.com/item_detail.php?cat=2065AH
ApexBio Technology	C4630	https://www.apexbt.com/catalogsearch/result/?q=C4630
BOC Sciences	24150-24-1	http://www.bocsci.com/description.asp?cas=24150-24-1
Cayman Chemical	70302	http://www.caymanchem.com/app/template/Product.vm/catalog/70302
eMolecules	300458592	https://orderbb.emolecules.com/search/#?query=300458592
eMolecules	30155148	https://orderbb.emolecules.com/search/#?query=30155148
eMolecules	45918466	https://orderbb.emolecules.com/search/#?query=45918466
mcule	MCULE-1808905202	https://mcule.com/MCULE-1808905202/
MolPort	MolPort-009-018-732	https://www.molport.com/shop/molecule-link/MolPort-009-018-732
MuseChem	R025422	https://www.musechem.com/product/R025422.html

PubMed

Title	Date	PubMed
Phase I study of the novel Cdc2/CDK1 and AKT inhibitor terameprocol in patients with advanced leukemias.	2015-04	25523151
Tetra-O-methyl nordihydroguaiaretic acid, an inhibitor of Sp1-mediated survivin transcription, induces apoptosis and acts synergistically with chemo-radiotherapy in glioblastoma cells.	2013-08	23299390
Phase I study of terameprocol in patients with recurrent high-grade glioma.	2012-04	22323663
Terameprocol (tetra-O-methyl nordihydroguaiaretic acid), an inhibitor of Sp1-mediated survivin transcription, induces radiosensitization in non-small cell lung carcinoma.	2011-01	21107289
Lignans with anti-HIV activity from Schisandra propinqua var. sinensis.	2009-06	19413342
New nordihydroguaiaretic acid derivatives as anti-HIV agents.	2008-03-15	18321703
Terameprocol, a novel site-specific transcription inhibitor with anticancer activity.	2008-03	18311658
Tetra-O-methyl nordihydroguaiaretic acid induces growth arrest and cellular apoptosis by inhibiting Cdc2 and survivin expression.	2004-09-07	15329416
Tetra-O-methyl nordihydroguaiaretic acid induces G2 arrest in mammalian cells and exhibits tumoricidal activity in vivo.	2001-07-15	11454698
Antiviral activities of methylated nordihydroguaiaretic acids. 1. Synthesis, structure identification, and inhibition of tat-regulated HIV transactivation.	1998-07-30	9685238
Suppression of hydrogen peroxide-induced mammalian cytotoxicity by nordihydroguaiaretic acid.	1992-07	1368832

Patents

Sample Use Guides

In Vivo Use Guide

Terameprocol (EM-1421) was given as a single intravenous dose over 6 hours three times a week in a 3-week cycle of 2 weeks on, and one week off. Dosing began with 1000 mg and will be adjusted up or down to 500, 1500, and 2200 mg. Patients will continue in subsequent cycles until disease progression or until severe toxicities occur outweighing any benefits. Partial remission and transfusion independence were achieved in the 1500 mg cohort.

Route of Administration: Intravenous

In Vitro Use Guide

HCC2429 and H460 lung cancer cells were transfected with pLuc2931 luciferase reporter under the control of human survivin promoter fragment and pLuc control. Cells were cultured in RPMI1640 supplemented with 10% fetal bovine serum and 1% penicillin-streptomycin and incubated in a 5% CO2 atmosphere at 37 deg-C. Cells were treated with 10 microM terameprocol and incubated for up to 48 hours. Downregulation of survivin transcription was noted at 24 hours and continued to increase to 48 hours.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:46:59 GMT 2025` Edited by `admin` on `Mon Mar 31 18:46:59 GMT 2025`
Record UNII	53YET703F2
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TERAMEPROCOL

Official Name

English

EM1421

Preferred Name

English

TERAMEPROCOL [USAN]

Common Name

English

MESO-TETRA-O-METHYL NORDIHYDROGUAIARETIC ACID

Common Name

English

Terameprocol [WHO-DD]

Common Name

English

TETRA-O-METHYL NORDIHYDROGUAIARETIC ACID

Common Name

English

terameprocol [INN]

Common Name

English

1,4-BIS(3,4-DIMETHOXYPHENYL)-2,3-DIMETHYL-, MESO-

Common Name

English

1,1'-((2R*,3S*)-2,3-DIMETHYLBUTANE-1,4-DIYL)BIS(3,4-DIMETHOXYBENZENE)

Systematic Name

English

EM-1421

Code

English

BENZENE, 4-((2R,3S)-4-(3,4-DIMETHOXYPHENYL)-2,3-DIMETHYLBUTYL)-1,2-DIMETHOXY-, REL-

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1742

Created by admin on Mon Mar 31 18:46:59 GMT 2025 , Edited by admin on Mon Mar 31 18:46:59 GMT 2025

NCI_THESAURUS

C2161

Created by admin on Mon Mar 31 18:46:59 GMT 2025 , Edited by admin on Mon Mar 31 18:46:59 GMT 2025

Code System Code Type Description

NCI_THESAURUS

C61441

Created by admin on Mon Mar 31 18:46:59 GMT 2025 , Edited by admin on Mon Mar 31 18:46:59 GMT 2025

PRIMARY

MESH

C076852

Created by admin on Mon Mar 31 18:46:59 GMT 2025 , Edited by admin on Mon Mar 31 18:46:59 GMT 2025

PRIMARY

PUBCHEM

476861

Created by admin on Mon Mar 31 18:46:59 GMT 2025 , Edited by admin on Mon Mar 31 18:46:59 GMT 2025

PRIMARY

FDA UNII

53YET703F2

Created by admin on Mon Mar 31 18:46:59 GMT 2025 , Edited by admin on Mon Mar 31 18:46:59 GMT 2025

PRIMARY

DRUG BANK

DB12226

Created by admin on Mon Mar 31 18:46:59 GMT 2025 , Edited by admin on Mon Mar 31 18:46:59 GMT 2025

PRIMARY

SMS_ID

300000034412

Created by admin on Mon Mar 31 18:47:00 GMT 2025 , Edited by admin on Mon Mar 31 18:47:00 GMT 2025

PRIMARY

ChEMBL

CHEMBL90983

Created by admin on Mon Mar 31 18:46:59 GMT 2025 , Edited by admin on Mon Mar 31 18:46:59 GMT 2025

PRIMARY

INN

8860

Created by admin on Mon Mar 31 18:46:59 GMT 2025 , Edited by admin on Mon Mar 31 18:46:59 GMT 2025

PRIMARY

USAN

SS-63

Created by admin on Mon Mar 31 18:47:00 GMT 2025 , Edited by admin on Mon Mar 31 18:47:00 GMT 2025

PRIMARY

CAS

24150-24-1

Created by admin on Mon Mar 31 18:46:59 GMT 2025 , Edited by admin on Mon Mar 31 18:46:59 GMT 2025

PRIMARY

Related Record Type Details


					3AU321J2HF

SURVIVIN

TARGET->INHIBITOR OF EXPRESSION

Amount:

Related Record Type Details


					53YET703F2

TERAMEPROCOL

ACTIVE MOIETY

Amount:

Details

SMILES

InChI

DescriptionSources: https://clinicaltrials.gov/ct2/show/NCT00664677 | https://www.drugbank.ca/drugs/DB12226 | https://www.ncbi.nlm.nih.gov/pubmed/15329416 | http://adisinsight.springer.com/drugs/800020885 | https://www.ncbi.nlm.nih.gov/pubmed/1368832

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

Approved Use

Approved Use

Approved Use

T1/2

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: https://clinicaltrials.gov/ct2/show/NCT00664677 | https://www.drugbank.ca/drugs/DB12226 | https://www.ncbi.nlm.nih.gov/pubmed/15329416 | http://adisinsight.springer.com/drugs/800020885 | https://www.ncbi.nlm.nih.gov/pubmed/1368832

T_1/2