AMETANTRONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H28N4O4
Molecular Weight	412.4821
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OCCNCCNC1=C2C(=O)C3=CC=CC=C3C(=O)C2=C(NCCNCCO)C=C1

InChI

InChIKey=FFGSXKJJVBXWCY-UHFFFAOYSA-N

InChI=1S/C22H28N4O4/c27-13-11-23-7-9-25-17-5-6-18(26-10-8-24-12-14-28)20-19(17)21(29)15-3-1-2-4-16(15)22(20)30/h1-6,23-28H,7-14H2

HIDE SMILES / InChI

Molecular Formula	C22H28N4O4
Molecular Weight	412.4821
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20458714 | https://www.ncbi.nlm.nih.gov/pubmed/3798363 | https://www.ncbi.nlm.nih.gov/pubmed/10755405 | https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&ns=NCI_Thesaurus&code=C1342 | https://www.ncbi.nlm.nih.gov/pubmed/7199472

Ametantrone (AM) is a synthetic 9,10-anthracenedione bearing two (hydroxyethylamino)ethylamino residues at positions 1 and 4; along with other anthraquinones and anthracyclines, it shares a polycyclic intercalating moiety and charged side chains that stabilize DNA binding. Ametantrone is anticancer drug candidate targeting DNA. Ametantrone is a topoisomerase II inhibitor of the anthrapyrazole family. Ametantrone induces interstrand DNA cross-links in HeLa S3 cells. These cross-links were observed only in cellular system suggesting that metabolism of the drugs is a necessary step leading to DNA cross-linking. Ametantrone appeared to be very well tolerated and easy to handle. A dose-schedule of 135 mg/m2 q 2–3 weeks was recommended for phase II studies in solid tumors.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA topoisomerase II 66 Target ID: CHEMBL2094255 Sources: https://medkoo.com/products/8985 \| (1996) Current Medicinal Chemistry, v.3, page 444, retrieved from: https://books.google.ru/books?id=1UVqJKdasNIC	Inhibitor 8504

PubMed

Title	Date	PubMed
Metabolite fingerprinting in transgenic Nicotiana tabacum altered by the Escherichia coli glutamate dehydrogenase gene.	2005-06-30	16046826

Patents

Sample Use Guides

In Vivo Use Guide

Sixteen patients received 33 courses of drug as a single iv dose given every 3 weeks. Escalations proceeded from 120 to 180 mg/m2. A dose of 140-160 mg/m2 is recommended as the starting dose for phase II trials in patients who have received prior chemotherapy or radiotherapy.

Route of Administration: Intravenous

In Vitro Use Guide

84 of 228 tumors plated for the ametantrone study were evaluable for drug-sensitivity assays. The overall in vitro response rates (defined as a less than or equal to 50% survival of tumor colony-forming units) for ametantrone were 13%, 21%, and 26% at 0.1, 1, and 10 ug/ml, respectively.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:17:05 GMT 2025` Edited by `admin` on `Mon Mar 31 18:17:05 GMT 2025`
Record UNII	PNT6041ST1
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-196473

Preferred Name

English

AMETANTRONE

Official Name

English

ametantrone [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C253