Details of the Drug

General Information of Drug (ID: DMZKYIV)

• Drug Name: Amsacrine
• Synonyms: Acridinylanisidide; Amecrin; Amekrin; Amsacrina; Amsacrinum; Amsidine; Amsidyl; Amsine; Lamasine; MAMSA; NAMSA; Acridinyl Anisidide; SN 21429; SN11841; AMSA P-D; Acridinyl anisidide (TN); Amsacrina [INN-Spanish]; Amsacrinum [INN-Latin]; Amsidyl (TN); Cain's Acridine; M-AMSA; Meta-AMSA; Meta-Amsacrine; SN-11841; Amsacrine (USAN/INN); Amsacrine [USAN:BAN:INN]; M-AMSA (TN); N-[4-(9-Acridinylamino)-3-methoxyphenyl]methanesulfonamide; N-(4-(9-Acridinylamino)-3-methoxyphenyl)methanesulfonamide; N-[4-(9-Acridinylamino)-3-methoxy-phenyl]methanesulfonamide; N-[4-(acridin-9-ylamino)-3-methoxyphenyl]methanesulfonamide; N-[4-(acridin-9-ylmethyl)-3-methoxyphenyl]methanesulfonamide; N-(4-(Acridin-9-ylamino)-3-methoxyphenyl)methanesulfonamide; N-[4-(Acridin-9-ylamino)-3-(methyloxy)phenyl]methanesulfonamide; N-[4-(acridin-9-ylamino)-3-(methyloxy)phenyl]methanesulfonamide; 4'-(9-Acridinylamino)-3'-methoxymethanesulfonanilide; 4'-(9-Acridinylamino)methanesulfon-m-anisidide; 4'-(9-Acridinylamino)methanesulfon-meta-anisidide; 4'-(9-Acridinylamino)methanesulphon-m-anisidide

Indication

Disease Entry	ICD 11	Status	REF
Acute lymphoblastic leukaemia	2A85	Approved	[1]

• Therapeutic Class: Anticancer Agents
• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 393.5
  Topological Polar Surface Area (xlogp); 4
  Rotatable Bond Count (rotbonds); 5
  Hydrogen Bond Donor Count (hbonddonor); 2
  Hydrogen Bond Acceptor Count (hbondacc); 6
• ADMET Property:
  Absorption: The drug is poorly absorbed [2]
  BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [3]
  Clearance: The drug present in the plasma can be removed from the body at the rate of 4.3 mL/min/kg [4]
  Elimination: 10% of drug is excreted from urine in the unchanged form [3]
  Half-life: The concentration or amount of drug in body reduced by one-half in 8 - 9 hours [4]
  Metabolism: The drug is metabolized via the hepatic [2]
  MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 10.05 micromolar/kg/day [5]
  Unbound Fraction: The unbound fraction of drug in plasma is 0.029% [4]
  Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 1.6 L/kg [4]
• Chemical Identifiers:
  Formula: C21H19N3O3S
  IUPAC Name: N-[4-(acridin-9-ylamino)-3-methoxyphenyl]methanesulfonamide
  Canonical SMILES: COC1=C(C=CC(=C1)NS(=O)(=O)C)NC2=C3C=CC=CC3=NC4=CC=CC=C42
  InChI: InChI=1S/C21H19N3O3S/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/h3-13,24H,1-2H3,(H,22,23)
  InChIKey: XCPGHVQEEXUHNC-UHFFFAOYSA-N
• Cross-matching ID:
  PubChem CID: 2179
  ChEBI ID: CHEBI:2687
  CAS Number: 51264-14-3
  DrugBank ID: DB00276
  TTD ID: D0G9YH
  VARIDT ID: DR00917
  INTEDE ID: DR0109

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
DNA topoisomerase II (TOP2)	TT0IHXV	TOP2A_HUMAN; TOP2B_HUMAN	Inhibitor	[6]

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 2D6 (CYP2D6) Main DME	DECB0K3	CP2D6_HUMAN	Substrate	[7]

References

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• [3] BDDCS applied to over 900 drugs
• [4] Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
• [5] Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
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• [20] Mitoxantrone, a topoisomerase II inhibitor, induces apoptosis of B-chronic lymphocytic leukaemia cells. Br J Haematol. 1998 Jan;100(1):142-6.
• [21] Inhibition of human topoisomerase IIalpha by fluoroquinolones and ultraviolet A irradiation. Toxicol Sci. 2002 Sep;69(1):16-22.
• [22] Antitumor properties of podophyllotoxin and related compounds. Curr Pharm Des. 2000 Dec;6(18):1811-39.
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