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Details

Stereochemistry ACHIRAL
Molecular Formula C27H31N7O2
Molecular Weight 485.5807
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AZ-5104

SMILES

COC1=CC(N(C)CCN(C)C)=C(NC(=O)C=C)C=C1NC2=NC(=CC=N2)C3=CNC4=C3C=CC=C4

InChI

InChIKey=IQNVEOMHJHBNHC-UHFFFAOYSA-N
InChI=1S/C27H31N7O2/c1-6-26(35)30-22-15-23(25(36-5)16-24(22)34(4)14-13-33(2)3)32-27-28-12-11-21(31-27)19-17-29-20-10-8-7-9-18(19)20/h6-12,15-17,29H,1,13-14H2,2-5H3,(H,30,35)(H,28,31,32)

HIDE SMILES / InChI
Molecular Formula C27H31N7O2
Molecular Weight 485.5807
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

AZ5104 is a demethylated metabolite of Osimertinib. AZ5104 potently and irreversibly inhibits both wild-type and mutant (exon 19 and L858R) EGFR and demonstrates good anti-cancer effect in both cell-based and in vivo experiments. Although AZ5104 was tested on preclinical models of lung cancer, it is used only in the prodrug form.

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Epidermal growth factor receptor
49
Target ID: P00533|||Q9GZX1
Gene ID: 1956.0
Gene Symbol: EGFR
Target Organism: Homo sapiens (Human)
Inhibitor
8504
 25.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Irreversible Inhibition of EGFR: Modeling the Combined Pharmacokinetic-Pharmacodynamic Relationship of Osimertinib and Its Active Metabolite AZ5104.
2016-10
Patents

Patents

US2015119379
1
US8946235
1

Sample Use Guides

In Vivo Use Guide
In preclinical sudy AZ5104 was given orally at a dose 5 mg/kg/day.
Route of Administration: Oral
In Vitro Use Guide
H1781 cells, which contain a VC insertion at G776 in exon 20 of HER2, were treated with AZ5104 (0-10 uM) for 5 days to test the effect of the drug on cells growth.
Substance Class Chemical
Created
by admin
on Wed Apr 02 00:27:05 GMT 2025
Edited
by admin
on Wed Apr 02 00:27:05 GMT 2025
Record UNII
2DWZ6SE1E1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AZ5104
Preferred Name English
AZ-5104
Code English
N-(2-((2-(DIMETHYLAMINO)ETHYL)METHYLAMINO)-5-((4-(1H-INDOL-3-YL)-2-PYRIMIDINYL)AMINO)-4-METHOXYPHENYL)-2-PROPENAMIDE
Systematic Name English
OSIMERTINIB METABOLITE M6
Common Name English
2-PROPENAMIDE, N-(2-((2-(DIMETHYLAMINO)ETHYL)METHYLAMINO)-5-((4-(1H-INDOL-3-YL)-2-PYRIMIDINYL)AMINO)-4-METHOXYPHENYL)-
Systematic Name English
Code System Code Type Description
CAS
1421373-98-9
Created by admin on Wed Apr 02 00:27:05 GMT 2025 , Edited by admin on Wed Apr 02 00:27:05 GMT 2025
PRIMARY
PUBCHEM
71496460
Created by admin on Wed Apr 02 00:27:05 GMT 2025 , Edited by admin on Wed Apr 02 00:27:05 GMT 2025
PRIMARY
FDA UNII
2DWZ6SE1E1
Created by admin on Wed Apr 02 00:27:05 GMT 2025 , Edited by admin on Wed Apr 02 00:27:05 GMT 2025
PRIMARY
Related Record Type Details
Structure of OSIMERTINIB
PARENT -> METABOLITE ACTIVE
FECAL; URINE
Structure of OSIMERTINIB
PARENT -> METABOLITE ACTIVE
Accounts for about 10% of the systematic exposure. AZ5104 showed greater potency than osimertinib against exon 19 deletion and T790?M mutants (˜8-fold) and wild-type (˜15-fold) EGFR
PLASMA
Structure of Asandeutertinib
PARENT -> METABOLITE ACTIVE
The AUC and Cmax of osimertinib increased sharply after deuteration. Systemic exposure of AZ5104 was remarkably reduced.
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC
NIH
NCATS
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