Details of the Drug

General Information of Drug (ID: DMK7CYX)

Drug Name

Vadimezan

Synonyms

DMXAA; AS-1404; ASA-404; R-1564; 5,6-MeXAA; 5,6-dimethylxanthenone-4-acetic acid

Indication

Disease Entry	ICD 11	Status	REF
Solid tumour/cancer	2A00-2F9Z	Phase 2	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

282.29

Logarithm of the Partition Coefficient (xlogp)

3.2

Rotatable Bond Count (rotbonds)

2

Hydrogen Bond Donor Count (hbonddonor)

1

Hydrogen Bond Acceptor Count (hbondacc)

4

Chemical Identifiers

Formula: C17H14O4
IUPAC Name: 2-(5,6-dimethyl-9-oxoxanthen-4-yl)acetic acid
Canonical SMILES: CC1=C(C2=C(C=C1)C(=O)C3=CC=CC(=C3O2)CC(=O)O)C
InChI: InChI=1S/C17H14O4/c1-9-6-7-13-15(20)12-5-3-4-11(8-14(18)19)17(12)21-16(13)10(9)2/h3-7H,8H2,1-2H3,(H,18,19)
InChIKey: XGOYIMQSIKSOBS-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 123964
ChEBI ID: CHEBI:75934
CAS Number: 117570-53-3
UNII: 0829J8133H
DrugBank ID: DB06235
TTD ID: D08UOY
INTEDE ID: DR1664

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Nuclear factor NF-kappa-B (NFKB)	TTSXVID	NFKB1_HUMAN ; NFKB2_HUMAN ; TF65_HUMAN ; RELB_HUMAN ; REL_HUMAN	Modulator	[2]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 1A2 (CYP1A2)	DEJGDUW	CP1A2_HUMAN	Substrate	[3]
UDP-glucuronosyltransferase 2B7 (UGT2B7)	DEB3CV1	UD2B7_HUMAN	Substrate	[3]
UDP-glucuronosyltransferase 1A9 (UGT1A9)	DE85D2P	UD19_HUMAN	Substrate	[4]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
ATP-binding cassette sub-family C member 2 (ABCC2)	OTJSIGV5	MRP2_HUMAN	Regulation of Drug Effects	[5]
Cytochrome P450 1A2 (CYP1A2)	OTLLBX48	CP1A2_HUMAN	Biotransformations	[6]
Multidrug resistance-associated protein 1 (ABCC1)	OTGUN89S	MRP1_HUMAN	Regulation of Drug Effects	[5]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Solid tumour/cancer

ICD Disease Classification

2A00-2F9Z

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Cytochrome P450 1A2 (CYP1A2)	DME	CYP1A2	9.96E-01	-7.53E-02	-5.68E-01

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

References

1	ClinicalTrials.gov (NCT01057342) Paclitaxel, Carboplatin, and Dimethylxanthenone Acetic Acid in Treating Patients With Extensive-Stage Small Cell Lung Cancer. U.S. National Institutes of Health.
2	Auckland Cancer Society Research Centre report
3	Preclinical factors affecting the interindividual variability in the clearance of the investigational anti-cancer drug 5,6-dimethylxanthenone-4-acetic acid. Biochem Pharmacol. 2003 Jun 1;65(11):1853-65.
4	Predicting pharmacokinetics and drug interactions in patients from in vitro and in vivo models: the experience with 5,6-dimethylxanthenone-4-acetic acid (DMXAA), an anti-cancer drug eliminated mainly by conjugation. Drug Metab Rev. 2002 Nov;34(4):751-90.
5	Transport of the investigational anti-cancer drug 5,6-dimethylxanthenone-4-acetic acid and its acyl glucuronide by human intestinal Caco-2 cells. Eur J Pharm Sci. 2005 Apr;24(5):513-24. doi: 10.1016/j.ejps.2005.01.006.
6	Inhibition of human CYP1A2 oxidation of 5,6-dimethyl-xanthenone-4-acetic acid by acridines: a molecular modelling study. Clin Exp Pharmacol Physiol. 2005 Aug;32(8):633-9.