Ametantrone

HCID 2134

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Basic information

CAS: 64862-96-0
Standard SMILES: O=C1c2ccccc2C(=O)c2c(NCCNCCO)ccc(NCCNCCO)c21
InChIKey: FFGSXKJJVBXWCY-UHFFFAOYSA-N
Molecular formula: C22H28N4O4
Average molar mass: 412.5 g/mol
Monoisotopic mass: 412.21105539

Overview

Ametantrone is a small molecule drug. Ametantrone has a monoisotopic molecular weight of 412.21 Da.

Names & identifiers

Preferred name: Ametantrone
IUPAC: 1,4-bis[2-(2-hydroxyethylamino)ethylamino]anthracene-9,10-dione
English name: Ametantrone
Molecular formula: C22H28N4O4
Molecular weight: 412.48

Names & synonyms

Ametantrone64862-96-0AmetantronaNSC-196473AmetantronumNSC 1964731,4-bis[2-(2-hydroxyethylamino)ethylamino]anthracene-9,10-dionePNT6041ST1NSC196473DTXSID602151531,4-Bis((2-((2-hydroxyethyl)amino)ethyl)amino)-9,10-anthracenedione1,4-bis(2-(2-hydroxyethylamino)ethylamino)anthracene-9,10-dione

Show more names

HAQCS-1411NSC 290813NSC-287513Ametantrone, >=98%ametantrone diacetate.1,4-BIS(2-(2-HYDROXYETHYLAMINO)ETHYLAMINO)ANTHRACENE-9,10-DIOL

RefChem:111904DTXCID601376441,4-bis((2-((2-Hydroxyethyl)amino)ethyl)amino)9,10-anthracenedione9, 10-Anthracenedione, 1, 4-bis((2-((2-hydroxyethyl)amino)ethyl)amino)-Ametantrone [INN]1,4-Bis((2-((2-hydroxyethyl)amino)ethyl)amino)anthracene-9,10-dioneAmetantrone(NSC 196473)Anthracenedione deriv.

Database identifiers

CAS: 64862-96-0
PubChem CID: 2134
DTXSID: DTXSID60215153
ChEMBL: CHEMBL49442
UNII: PNT6041ST1
Nikkaji: J67.628D、J710.750A

Properties

Computed structural properties

XLogP: 1.7
Topological polar surface area: 123 Å²
Hydrogen bond donors: 6
Hydrogen bond acceptors: 8
Rotatable bonds: 12
Heavy atoms: 30
Formal charge: 0
Complexity: 513

Physicochemical properties

Melting point: 156 · 156-158 °C
Boiling point: 531.92 °C · 531.92°C (rough estimate)
Density: 1.2344 · 1.2344 (rough estimate)
refractive index: 1.65 · 1.6500 (estimate)
storage temp.: -20 °C · Store at -20°C
solubility: DMSO: soluble
form: A crystalline solid
pka: 14.47 · 14.47±0.10(Predicted)
FDA UNII: 6041 ST1 · PNT6041ST1
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335
Precautionary statements: 261 · P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

Signal word: Warning
Symbol(GHS): GHS07
Hazard statements: H302-H315-H319-H335
Precautionary statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

Substances that inhibit or prevent the proliferation of NEOPLASMS.

Agents that are capable of inserting themselves between the successive bases in DNA, thus kinking, uncoiling or otherwise deforming it and therefore preventing its proper functioning. They are used in the study of DNA.

Applications · 2 items

DescriptionAmetantrone is an inhibitor of topoisomerase II. It induces double-strand breaks in SV40 DNA in the presence, but not absence, of topoisomerase II and induces single-strand breaks in DNA in NCI H187 cells. It also induces interstrand DNA cross-links in HeLa S3 cells at a minimum concentration of 4.1 μM. Ametantrone is cytotoxic to NCI H187 and HL-60 cells (IC50s = 112 and 0.44 μM, respectively). It inhibits tumor growth in a Ridgway osteogenic sarcoma mouse model when administered at a dose of 5 mg/kg, however, it increases tumor growth in mouse models of mammary adenocarcinoma and colon adenocarcinoma 11a.

UsesAmetantrone (NSC 196473) is an antitumor agent that intercalates into DNA and induces topoisomerase II (TOP2)-mediated DNA break[1].

Suppliers38 total

武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]

湖北瑞玛标物科技有限公司15787879035 15787875101 · [email protected]

欧利希（湖北）医药科技有限公司17316404525 17316404525 · [email protected]

United Life Science020-82099279 18988968278 · [email protected]

AdooQ BioScience, LLC+1 (866) 930-6790 · [email protected]

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Compound notes

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