IMEXON

Investigational

Details

Stereochemistry	RACEMIC
Molecular Formula	C4H5N3O
Molecular Weight	111.102
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC(=O)N2CC12

InChI

InChIKey=BIXBBIPTYBJTRY-UHFFFAOYSA-N

InChI=1S/C4H5N3O/c5-3-2-1-7(2)4(8)6-3/h2H,1H2,(H2,5,6,8)

HIDE SMILES / InChI

Molecular Formula	C4H5N3O
Molecular Weight	111.102
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.drugbank.ca/drugs/DB05003
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/20571355 | https://www.ncbi.nlm.nih.gov/pubmed/25016003 | https://www.ncbi.nlm.nih.gov/pubmed/25078786 | https://www.ncbi.nlm.nih.gov/pubmed/22275514 | https://www.ncbi.nlm.nih.gov/pubmed/22998528

Imexon (INN, trade name Amplimexon) is a substance that is being studied in the treatment of some types of cancer, including pancreatic, lung, breast, prostate, melanoma, and multiple myeloma. Imexon is a thiol-binding small molecule which induces mitochondrial oxidation, a loss of membrane potential and cytochrome C, leading to apoptosis.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
response to oxidative stress 20 Target ID: GO:0006979 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25078786	Activator 1447

Conditions

Condition	Modality	Highest Phase	Product
B-cell non-Hodgkin lymphoma 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25016003	Primary	Phase II 1147	Unknown Approved Use Unknown
Multiple myeloma 159 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20571355	Primary	Phase II 1147	Unknown Approved Use Unknown
Malignant melanoma 22 Sources: https://clinicaltrials.gov/ct2/show/NCT00327600	Primary	Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
62 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/20564083	1000 mg/m² 1 times / day other, intravenous dose: 1000 mg/m² route of administration: Intravenous experiment type: OTHER co-administered: DACARBAZINE	DACARBAZINE	IMEXON plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
38.5 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/20564083	1000 mg/m² 1 times / day other, intravenous dose: 1000 mg/m² route of administration: Intravenous experiment type: OTHER co-administered: DACARBAZINE	DACARBAZINE	IMEXON plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
82.1 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/20564083	1000 mg/m² 1 times / day other, intravenous dose: 1000 mg/m² route of administration: Intravenous experiment type: OTHER co-administered: DACARBAZINE	DACARBAZINE	IMEXON plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
55.3 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/20564083	1000 mg/m² 1 times / day other, intravenous dose: 1000 mg/m² route of administration: Intravenous experiment type: OTHER co-administered: DACARBAZINE	DACARBAZINE	IMEXON plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
1 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/20564083	1000 mg/m² 1 times / day other, intravenous dose: 1000 mg/m² route of administration: Intravenous experiment type: OTHER co-administered: DACARBAZINE	DACARBAZINE	IMEXON plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
0.99 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/20564083	1000 mg/m² 1 times / day other, intravenous dose: 1000 mg/m² route of administration: Intravenous experiment type: OTHER co-administered: DACARBAZINE	DACARBAZINE	IMEXON plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
1700 mg/m2 1 times / day multiple, intravenous Highest studied dose Dose: 1700 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 1700 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/19499186	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/19499186	DLT: Non-cardiac chest pain... Dose limiting toxicities: Non-cardiac chest pain (grade 3, 66.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/19499186
1300 mg/m2 1 times / day multiple, intravenous MTD Dose: 1300 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 1300 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/19499186	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/19499186	Sources: https://pubmed.ncbi.nlm.nih.gov/19499186
875 mg/m2 1 times / day multiple, intravenous MTD Dose: 875 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 875 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17470869	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17470869	Other AEs: Thrombocytopenia... Other AEs: Thrombocytopenia (grade 3, 11.1%) Sources: https://pubmed.ncbi.nlm.nih.gov/17470869
1000 mg/m2 1 times / day multiple, intravenous Studied dose Dose: 1000 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 1000 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17470869	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17470869	DLT: Abdominal pain, Fatigue... Other AEs: Anemia, Thrombocytopenia... Dose limiting toxicities: Abdominal pain (grade 3, 50%) Fatigue (grade 3, 50%) Neutropenia (grade 4, 50%) Other AEs: Anemia (grade 3, 50%) Thrombocytopenia (grade 4, 50%) Sources: https://pubmed.ncbi.nlm.nih.gov/17470869
1500 mg/m2 1 times / day multiple, intravenous Studied dose Dose: 1500 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 1500 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/19499186	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/19499186	DLT: Non-cardiac chest pain, Diarrhea... Dose limiting toxicities: Non-cardiac chest pain (grade 3, 40%) Diarrhea (grade 3, 40%) Sources: https://pubmed.ncbi.nlm.nih.gov/19499186

AEs

AE	Significance	Dose	Population
Non-cardiac chest pain	grade 3, 66.7% DLT	1700 mg/m2 1 times / day multiple, intravenous Highest studied dose Dose: 1700 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 1700 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/19499186	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/19499186
Thrombocytopenia	grade 3, 11.1%	875 mg/m2 1 times / day multiple, intravenous MTD Dose: 875 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 875 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17470869	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17470869
Anemia	grade 3, 50%	1000 mg/m2 1 times / day multiple, intravenous Studied dose Dose: 1000 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 1000 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17470869	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17470869
Abdominal pain	grade 3, 50% DLT	1000 mg/m2 1 times / day multiple, intravenous Studied dose Dose: 1000 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 1000 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17470869	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17470869
Fatigue	grade 3, 50% DLT	1000 mg/m2 1 times / day multiple, intravenous Studied dose Dose: 1000 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 1000 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17470869	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17470869
Thrombocytopenia	grade 4, 50%	1000 mg/m2 1 times / day multiple, intravenous Studied dose Dose: 1000 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 1000 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17470869	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17470869
Neutropenia	grade 4, 50% DLT	1000 mg/m2 1 times / day multiple, intravenous Studied dose Dose: 1000 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 1000 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17470869	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17470869
Diarrhea	grade 3, 40% DLT	1500 mg/m2 1 times / day multiple, intravenous Studied dose Dose: 1500 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 1500 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/19499186	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/19499186
Non-cardiac chest pain	grade 3, 40% DLT	1500 mg/m2 1 times / day multiple, intravenous Studied dose Dose: 1500 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 1500 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/19499186	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/19499186

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B3-044023	http://www.3bsc.com/index/pro_info.php?id=76215
AA Blocks	AA00EIOJ	https://www.aablocks.com/goods/Goods/detail?id=AA00EIOJ
Achemtek	0102-013901	http://www.achemtek.com/59643-91-3
AHH Chemical co.,ltd	MT-42491	http://www.ahhchemical.com/product/MT-42491.html
Ambinter	Amb22295837	http://www.ambinter.com/reference/22295837
Ambinter	Amb22352757	http://www.ambinter.com/reference/22352757
ChemMol	49424589	http://www.chemmol.com/chemmol/49424589.html
ChemMol	99111522	http://www.chemmol.com/chemmol/99111522.html
DC Chemicals	DC20669	http://www.dcchemicals.com/product_show-DC20669.html
eNovation Chemicals	D672873	https://www.enovationchem.com/ProductDetails.asp?ProductID=D672873
iChemical	EBD13413	http://www.ichemical.com/chemicals/cas-59643-91-3
Lab Network	LN01345925	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01345925
MuseChem	I007277	https://www.musechem.com/product/I007277.html
OChem	19865	http://www.ocheminc.com/index.php?act=psearch&pid=643I913
Parchem	29138	http://www.parchem.com/chemical-supplier-distributor/Imexon-019138.aspx

PubMed

Title	Date	PubMed
Chemistry and pharmacology of imexon and related cyanoaziridines.	2012	22998528
Redox-directed cancer therapeutics: molecular mechanisms and opportunities.	2009-12	19496700
The antitumor agent imexon activates antioxidant gene expression: evidence for an oxidative stress response.	2007-06-01	17545547
Oxidative stress and apoptosis: a new treatment paradigm in cancer.	2006-01-01	16146732
Imexon-induced apoptosis in multiple myeloma tumor cells is caspase-8 dependent.	2004-02-15	14977852
Induction of oxidative stress and apoptosis in myeloma cells by the aziridine-containing agent imexon.	2000-09-15	10930529
Antiproliferative and antitumor activity of the 2-cyanoaziridine compound imexon on tumor cell lines and fresh tumor cells in vitro.	1992-08-19	1640482
Antiviral efficacy of Imexon in the Rauscher murine retrovirus AIDS model.	1990	1693633

Patents

Sample Use Guides

In Vivo Use Guide

Imexon was administered at 1000 mg/m2 IV over 60 minutes daily for the first 5 days of each 21-day treatment cycle. Treatment continued until disease progression or unacceptable toxicity

Route of Administration: Intravenous

In Vitro Use Guide

Colony-forming assays were conducted on MiaPaca-2 cells transfected with eIF2B5 or nontargeting siRNA (Dharmacon ON-TARGET plus SmartPool siRNA), followed by exposure to imexon for an additional 72 hours. Imexon was removed and cells were then plated in MethoCult (StemCell Technologies, Inc.) following the manufacturer's instructions and incubated for 7 to 10 days, and colony formation (>50 cells) was monitored by manual colony counting using a scoring grid.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:31:11 GMT 2025` Edited by `admin` on `Mon Mar 31 18:31:11 GMT 2025`
Record UNII	8F63U28T2V
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-313425

Preferred Name

English

IMEXON

Official Name

English

IMEXON [USAN]

Common Name

English

imexon [INN]

Common Name

English

Imexon [WHO-DD]

Common Name

English

IMEXON [MART.]

Common Name

English

(5RS)-4-Amino-1,3-diazabicyclo[3.1.0]hex-3-en-2-one

Systematic Name

English

1,3-DIAZABICYCLO(3.1.0)HEX-3-EN-2-ONE, 4-AMINO-

Systematic Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

142501