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=CC=C(NCCNCCO)C2=C1C(=O)C3=C(C=CC=C3)C2=O

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 8297

PubMed

Title	Date	PubMed
Metabolite fingerprinting in transgenic Nicotiana tabacum altered by the Escherichia coli glutamate dehydrogenase gene.	2005 Jun 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 `Fri Dec 15 16:02:25 GMT 2023` Edited by `admin` on `Fri Dec 15 16:02:25 GMT 2023`
Record UNII	PNT6041ST1
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

AMETANTRONE

Official Name

English

ametantrone [INN]

Common Name

English

NSC-196473

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C253