TERAMEPROCOL

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(OC)=C(OC)C=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 2778
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 2778

Conditions

Condition	Modality	Highest Phase	Product
Leukemia 87 Sources: https://clinicaltrials.gov/ct2/show/NCT00664677	Primary	Phase I 428	Unknown Approved Use Unknown
Refractory solid tumor 1 Sources: https://clinicaltrials.gov/ct2/show/NCT00664586	Primary	Phase I 428	Unknown Approved Use Unknown
Glioma 21 Sources: https://clinicaltrials.gov/ct2/show/NCT00404248	Primary	Phase II 1132	Unknown Approved Use Unknown
Cervical intraepithelial neoplasia 1 Sources: https://clinicaltrials.gov/ct2/show/NCT00154089	Primary	Phase II 1132	Unknown Approved Use Unknown
Head and neck cancer 50 Sources: https://clinicaltrials.gov/ct2/show/NCT00057512	Primary	Phase I 428	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
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
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/

PubMed

Title	Date	PubMed
Antiviral activities of methylated nordihydroguaiaretic acids. 1. Synthesis, structure identification, and inhibition of tat-regulated HIV transactivation.	1998 Jul 30	9685238
Tetra-O-methyl nordihydroguaiaretic acid induces G2 arrest in mammalian cells and exhibits tumoricidal activity in vivo.	2001 Jul 15	11454698
Terameprocol, a novel site-specific transcription inhibitor with anticancer activity.	2008 Mar	18311658
New nordihydroguaiaretic acid derivatives as anti-HIV agents.	2008 Mar 15	18321703
Lignans with anti-HIV activity from Schisandra propinqua var. sinensis.	2009 Jun	19413342
Phase I study of terameprocol in patients with recurrent high-grade glioma.	2012 Apr	22323663

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 `Fri Dec 15 17:28:08 UTC 2023` Edited by `admin` on `Fri Dec 15 17:28:08 UTC 2023`
Record UNII	53YET703F2
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TERAMEPROCOL

Official 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

EM1421

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