Amsacrine (gluconate)

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Description

Amsacrine gluconate is an inhibitor of topoisomerase II, and acts as an antineoplastic agent which can intercalates into the DNA of tumor cells.

CAS Number

80277-07-2

Product Name Alternative

M-AMSA (gluconate) ; Acridinyl anisidide (gluconate)

UNSPSC

12352005

Target

Autophagy; Topoisomerase

Type

Reference compound

Related Pathways

Autophagy; Cell Cycle/DNA Damage

Field of Research

Cancer

Assay Protocol

https://www.medchemexpress.com/amsacrine-gluconate.html

Smiles

OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.COC(C=C(C=C1)NS(C)(=O)=O)=C1NC2=C(C=CC=C3)C3=NC4=C2C=CC=C4

Molecular Formula

C27H31N3O10S

Molecular Weight

589.61

References & Citations

[1]Thomas D, et al. Inhibition of cardiac HERG currents by the DNA topoisomerase II inhibitor amsacrine: mode of action. Br J Pharmacol. 2004 Jun;142 (3) :485-94.|[2]Attia SM. Molecular cytogenetic evaluation of the mechanism of genotoxic potential of amsacrine and nocodazole in mouse bone marrow cells. J Appl Toxicol. 2013 Jun;33 (6) :426-33.|[3]Kao-Shan CS, et al. Cytogenetic effects of amsacrine on human lymphocytes in vivo and in vitro. Cancer Treat Rep. 1984 Jul-Aug;68 (7-8) :989-97.|[4]Lee YC, et al. Amsacrine-induced apoptosis of human leukemia U937 cells is mediated by the inhibition of AKT- and ERK-induced stabilization of MCL1. Apoptosis. 2016 Oct 19

Shipping Conditions

Room temperature

Scientific Category

Reference compound1

Clinical Information

Phase 3

Chemical Information

Amsacrine gluconate

CAS Number	80277-07-2
PubChem CID	22824017
IUPAC Name	N-[4-(acridin-9-ylamino)-3-methoxyphenyl]methanesulfonamide;(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid
Molecular Formula	C27H31N3O10S
Molecular Weight	589.6
Topological Polar Surface Area	227
Hydrogen Bond Donor Count	8
Hydrogen Bond Acceptor Count	13
Rotatable Bond Count	10
Heavy Atom Count	41
Formal Charge	0
Complexity	771

SMILES

COC1=C(C=CC(=C1)NS(=O)(=O)C)NC2=C3C=CC=CC3=NC4=CC=CC=C42.C([C@H]([C@H]([C@@H]([C@H](C(=O)O)O)O)O)O)O

InChI

InChI=1S/C21H19N3O3S.C6H12O7/c1-27-20-13-14(24-28(2,25)26)11-12-19(20)23-21-15-7-3-5-9-17(15)22-18-10-6-4-8-16(18)21;7-1-2(8)3(9)4(10)5(11)6(12)13/h3-13,24H,1-2H3,(H,22,23);2-5,7-11H,1H2,(H,12,13)/t;2-,3-,4+,5-/m.1/s1

InChIKey

XXNAQBNJPZNRSZ-IFWQJVLJSA-N

Chemical Structure

2D Structure

CAS: 80277-07-2

CID: 22824017

Formula: C27H31N3O10S

MW: 589.6

Interactive 3D Structure

Loading 3D structure...

View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	589.6
Hydrogen Bond Donor Count	8
Hydrogen Bond Acceptor Count	13
Rotatable Bond Count	10
Exact Mass	589.17301537
Monoisotopic Mass	589.17301537
Topological Polar Surface Area	227 Å²
Heavy Atom Count	41
Formal Charge	0
Complexity	771
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	2
Compound Is Canonicalized	Yes

Related Products

Catalog	Name
HY-13551-01	Amsacrine
HY-13551A-01	Amsacrine (hydrochloride)
HY-13551R-01	Amsacrine (Standard)
HY-13551AR-01	Amsacrine (hydrochloride) (Standard)
HY-N0052C	Sanguinarine (gluconate)
HY-125654C	Olanexidine (gluconate)
HY-B1092A-01	Gluconate (sodium)
HY-W698249-01	Ferrous gluconate
HY-B1092-01	Gluconate (Calcium)
HY-W145486	Calcium gluconate

Alternative Products

Catalog	Name
T68673-01	Amsacrine gluconate
T1206-01	Amsacrine

Amsacrine (gluconate)

Chemical Information

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