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Details

Stereochemistry ACHIRAL
Molecular Formula CH5NO
Molecular Weight 47.0565
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Methoxyamine

SMILES

CON

InChI

InChIKey=GMPKIPWJBDOURN-UHFFFAOYSA-N
InChI=1S/CH5NO/c1-3-2/h2H2,1H3

HIDE SMILES / InChI

Description
Curator's Comment: The description was created based on several sources, including https://clinicaltrials.gov/ct2/show/NCT01851369 | https://www.ncbi.nlm.nih.gov/pubmed/29108368 | https://clinicaltrials.gov/ct2/show/NCT02395692 | https://www.ncbi.nlm.nih.gov/pubmed/28670521

Methoxyamine (TRC102) is an orally bioavailable small molecule with potential adjuvant activity, that may potentiate the antitumor activity of alkylating agents. Methoxyamine covalently binds to apurinic/apyrimidinic (AP) DNA damage sites and inhibits base excision repair (BER) that causes topoisomerase II-dependent irreversible strand breaks and apoptosis. Methoxyamine is currently being studied in multiple Phase 1 and Phase 2 clinical trials sponsored by the National Cancer Institute or Case Comprehensive Cancer Center.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
64.3 ng/mL
30 mg/m² single, oral
dose: 30 mg/m²
route of administration: Oral
experiment type: SINGLE
co-administered:
METHOXYAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
19.7 ng/mL
15 mg/m² single, oral
dose: 15 mg/m²
route of administration: Oral
experiment type: SINGLE
co-administered:
METHOXYAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
126 ng/mL
30 mg/m² 1 times / day multiple, oral
dose: 30 mg/m²
route of administration: Oral
experiment type: MULTIPLE
co-administered:
METHOXYAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
68.1 ng/mL
15 mg/m² 1 times / day multiple, oral
dose: 15 mg/m²
route of administration: Oral
experiment type: MULTIPLE
co-administered:
METHOXYAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
327 ng/mL
60 mg/m² 1 times / day multiple, oral
dose: 60 mg/m²
route of administration: Oral
experiment type: MULTIPLE
co-administered:
METHOXYAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
152 ng/mL
100 mg/m² single, oral
dose: 100 mg/m²
route of administration: Oral
experiment type: SINGLE
co-administered:
METHOXYAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
119 ng/mL
60 mg/m² single, oral
dose: 60 mg/m²
route of administration: Oral
experiment type: SINGLE
co-administered:
METHOXYAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
247 ng/mL
100 mg/m² 1 times / day multiple, oral
dose: 100 mg/m²
route of administration: Oral
experiment type: MULTIPLE
co-administered:
METHOXYAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1041 ng × h/mL
30 mg/m² single, oral
dose: 30 mg/m²
route of administration: Oral
experiment type: SINGLE
co-administered:
METHOXYAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
287 ng × h/mL
15 mg/m² single, oral
dose: 15 mg/m²
route of administration: Oral
experiment type: SINGLE
co-administered:
METHOXYAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1960 ng × h/mL
30 mg/m² 1 times / day multiple, oral
dose: 30 mg/m²
route of administration: Oral
experiment type: MULTIPLE
co-administered:
METHOXYAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1136 ng × h/mL
15 mg/m² 1 times / day multiple, oral
dose: 15 mg/m²
route of administration: Oral
experiment type: MULTIPLE
co-administered:
METHOXYAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
5812 ng × h/mL
60 mg/m² 1 times / day multiple, oral
dose: 60 mg/m²
route of administration: Oral
experiment type: MULTIPLE
co-administered:
METHOXYAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2312 ng × h/mL
100 mg/m² single, oral
dose: 100 mg/m²
route of administration: Oral
experiment type: SINGLE
co-administered:
METHOXYAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1991 ng × h/mL
60 mg/m² single, oral
dose: 60 mg/m²
route of administration: Oral
experiment type: SINGLE
co-administered:
METHOXYAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
3105 ng × h/mL
100 mg/m² 1 times / day multiple, oral
dose: 100 mg/m²
route of administration: Oral
experiment type: MULTIPLE
co-administered:
METHOXYAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
21.8 h
30 mg/m² single, oral
dose: 30 mg/m²
route of administration: Oral
experiment type: SINGLE
co-administered:
METHOXYAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
37.3 h
15 mg/m² single, oral
dose: 15 mg/m²
route of administration: Oral
experiment type: SINGLE
co-administered:
METHOXYAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
30.9 h
30 mg/m² 1 times / day multiple, oral
dose: 30 mg/m²
route of administration: Oral
experiment type: MULTIPLE
co-administered:
METHOXYAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
41.5 h
15 mg/m² 1 times / day multiple, oral
dose: 15 mg/m²
route of administration: Oral
experiment type: MULTIPLE
co-administered:
METHOXYAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
26.9 h
60 mg/m² 1 times / day multiple, oral
dose: 60 mg/m²
route of administration: Oral
experiment type: MULTIPLE
co-administered:
METHOXYAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
26.8 h
100 mg/m² single, oral
dose: 100 mg/m²
route of administration: Oral
experiment type: SINGLE
co-administered:
METHOXYAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
21.9 h
60 mg/m² single, oral
dose: 60 mg/m²
route of administration: Oral
experiment type: SINGLE
co-administered:
METHOXYAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
25 h
100 mg/m² 1 times / day multiple, oral
dose: 100 mg/m²
route of administration: Oral
experiment type: MULTIPLE
co-administered:
METHOXYAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
100 mg/m2 1 times / day multiple, oral
Highest studied dose
Dose: 100 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg/m2, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
DLT: Anemia...
Disc. AE: Anemia...
Dose limiting toxicities:
Anemia (grade 3, 50%)
AEs leading to
discontinuation/dose reduction:
Anemia (grade 2-3, 66.7%)
Sources:
60 mg/m2 1 times / day multiple, oral
MTD
Dose: 60 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg/m2, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
DLT: Anemia...
Dose limiting toxicities:
Anemia (grade 4, 9%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Anemia grade 2-3, 66.7%
Disc. AE
100 mg/m2 1 times / day multiple, oral
Highest studied dose
Dose: 100 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg/m2, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Anemia grade 3, 50%
DLT
100 mg/m2 1 times / day multiple, oral
Highest studied dose
Dose: 100 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg/m2, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Anemia grade 4, 9%
DLT, Disc. AE
60 mg/m2 1 times / day multiple, oral
MTD
Dose: 60 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg/m2, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
A rapid microwave-assisted derivatization of bacterial metabolome samples for gas chromatography/mass spectrometry analysis.
2010-06-15
Water deficit alters differentially metabolic pathways affecting important flavor and quality traits in grape berries of Cabernet Sauvignon and Chardonnay.
2009-05-08
Flame acceleration and the development of detonation in fuel-oxygen mixtures at elevated temperatures and pressures.
2009-04-30
O(6)-methylguanine-DNA methyltransferase depletion and DNA damage in patients with melanoma treated with temozolomide alone or with lomeguatrib.
2009-04-21
Coordination of DNA mismatch repair and base excision repair processing of chemotherapy and radiation damage for targeting resistant cancers.
2009-03-15
Novel metabolites of amodiaquine formed by CYP1A1 and CYP1B1: structure elucidation using electrochemistry, mass spectrometry, and NMR.
2009-03
Metabolite profiling studies in Saccharomyces cerevisiae: an assisting tool to prioritize host targets for antiviral drug screening.
2009-01-30
Improper excess light energy dissipation in Arabidopsis results in a metabolic reprogramming.
2009-01-26
Influence of high dietary sodium intake on the functional subtypes of alpha-adrenoceptors in the renal cortical vasculature of Wistar-Kyoto rats.
2009-01
Metabolomics of the interaction between PPAR-alpha and age in the PPAR-alpha-null mouse.
2009
Characterization of leaf apoplastic peroxidases and metabolites in Vigna unguiculata in response to toxic manganese supply and silicon.
2009
Oxidized phospholipids as potential molecular targets for antimicrobial peptides.
2008-10
The mismatch repair-mediated cell cycle checkpoint response to fluorodeoxyuridine.
2008-09-01
Importance of tyrosine residues of Bacillus stearothermophilus serine hydroxymethyltransferase in cofactor binding and L-allo-Thr cleavage.
2008-09
[Effects of manumycin combined with methoxyamine on apoptosis in myeloid leukemia U937 cells].
2008-08
Chrysomelidial in the opisthonotal glands of the oribatid mite, Oribotritia berlesei.
2008-08
Carmustine-resistant cancer cells are sensitized to temozolomide as a result of enhanced mismatch repair during the development of carmustine resistance.
2008-07
Ion trap MS/MS of intact testosterone and epitestosterone conjugates--adducts, fragile ions and the advantages of derivatisation.
2008-07
Excision repair is required for genotoxin-induced mutagenesis in mammalian cells.
2008-05
High quality metabolomic data for Chlamydomonas reinhardtii.
2008-04-28
Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling.
2008-04-10
Mutants of GABA transaminase (POP2) suppress the severe phenotype of succinic semialdehyde dehydrogenase (ssadh) mutants in Arabidopsis.
2008
Biocatalytic enantioselective synthesis of N-substituted aspartic acids by aspartate ammonia lyase.
2008
Transcriptomic and metabolite analyses of Cabernet Sauvignon grape berry development.
2007-11-22
Unbiased characterization of genotype-dependent metabolic regulations by metabolomic approach in Arabidopsis thaliana.
2007-11-21
Pharmacokinetic study of three cardiovascular drugs by high-performance liquid chromatography using pre-column derivatization with 9,10-anthraquinone-2-sulfonyl chloride.
2007-10-15
Well-defined polymers with activated ester and protected aldehyde side chains for bio-functionalization.
2007-10-08
Rapid quantification of urinary oxycodone and oxymorphone using fast gas chromatography-mass spectrometry.
2007-10
A screen for suppressors of gross chromosomal rearrangements identifies a conserved role for PLP in preventing DNA lesions.
2007-08
GC-MS analysis of multiply derivatized opioids in urine.
2007-08
Hexose-6-phosphate dehydrogenase modulates 11beta-hydroxysteroid dehydrogenase type 1-dependent metabolism of 7-keto- and 7beta-hydroxy-neurosteroids.
2007-06-27
Anaphylactic shock associated with cefuroxime axetil: structure-activity relationships.
2007-06
Genotoxicity of 2-(3-chlorobenzyloxy)-6-(piperazinyl)pyrazine, a novel 5-hydroxytryptamine2c receptor agonist for the treatment of obesity: role of metabolic activation.
2007-06
Analysis of synthetic 19-norsteroids trenbolone, tetrahydrogestrinone and gestrinone by gas chromatography-mass spectrometry.
2007-05-25
Enantioselective oxidation of O-methyl-N-hydroxylamines using monoamine oxidase N as catalyst.
2007-04-21
The DNA base excision repair protein Ape1/Ref-1 as a therapeutic and chemopreventive target.
2007-04-03
Combined treatment with temozolomide and methoxyamine: blocking apurininc/pyrimidinic site repair coupled with targeting topoisomerase IIalpha.
2007-03-01
Ape1 regulates hematopoietic differentiation of embryonic stem cells through its redox functional domain.
2007-03-01
Role for DNA polymerase beta in response to ionizing radiation.
2007-02-04
Manipulation of base excision repair to sensitize ovarian cancer cells to alkylating agent temozolomide.
2007-01-01
A re-investigation of the path of carbon in photosynthesis utilizing GC/MS methodology. Unequivocal verification of the participation of octulose phosphates in the pathway.
2006-11
DNA polymerase-beta is expressed early in neurons of Alzheimer's disease brain and is loaded into DNA replication forks in neurons challenged with beta-amyloid.
2006-10-25
A stronger DNA damage-induced G2 checkpoint due to over-activated CHK1 in the absence of PARP-1.
2006-10
Base excision repair of both uracil and oxidatively damaged bases contribute to thymidine deprivation-induced radiosensitization.
2006-08-01
On systems and control approaches to therapeutic gain.
2006-04-25
Methoxyamine potentiates iododeoxyuridine-induced radiosensitization by altering cell cycle kinetics and enhancing senescence.
2006-04
CASPT2 study of the decomposition of nitrosomethane and its tautomerization reactions in the ground and low-lying excited states.
2006-02-03
Role of DNA polymerase theta in tolerance of endogenous and exogenous DNA damage in mouse B cells.
2006-02
Characterization of the aldehyde reactive probe reaction with AP-sites in DNA: influence of AP-lyase on adduct stability.
2006
Aliphatic amidase from Rhodococcus rhodochrous M8 is related to the nitrilase/cyanide hydratase family.
2005-11
Patents

Sample Use Guides

Twenty-eight patients were treated with TRC102 at 15, 30, 60 or 100 mg/m2/d. The MTD was exceeded at 100 mg/m2/d due to grade 3 anemia in 50 % of patients.
Route of Administration: Oral
The human colorectal cancer cell line, HT29 were used for activity evaluation. HT29 cells were cultured at a density of 2×104 per well in multiwell plates (24 wells/plate, SPL). After 24 hours, we treated the cells with different concentrations of 5-FU (5-Fluorouracil) (0, 1, 5, 10, 50, 100 µM) or Mx (Methoxyamine) (0, 1, 6, 30, 60, 120 mM). After 24 hours, cell viability was determined by the trypan blue dye exclusion assay.
Name Type Language
Methoxyamine
MI   WHO-DD  
Systematic Name English
O-METHYLHYDROXYLAMINE
HSDB  
Preferred Name English
HYDROXYLAMINE, O-METHYL-
Systematic Name English
Methoxyamine [WHO-DD]
Common Name English
O-METHYLHYDROXYLAMINE [HSDB]
Common Name English
METHOXYAMINE [MI]
Common Name English
HYDROXYLAMINE METHYL ETHER
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C274
Created by admin on Mon Mar 31 18:31:23 GMT 2025 , Edited by admin on Mon Mar 31 18:31:23 GMT 2025
Code System Code Type Description
NCI_THESAURUS
C78084
Created by admin on Mon Mar 31 18:31:23 GMT 2025 , Edited by admin on Mon Mar 31 18:31:23 GMT 2025
PRIMARY
PUBCHEM
4113
Created by admin on Mon Mar 31 18:31:23 GMT 2025 , Edited by admin on Mon Mar 31 18:31:23 GMT 2025
PRIMARY
EPA CompTox
DTXSID8043862
Created by admin on Mon Mar 31 18:31:23 GMT 2025 , Edited by admin on Mon Mar 31 18:31:23 GMT 2025
PRIMARY
WIKIPEDIA
Methoxyamine
Created by admin on Mon Mar 31 18:31:23 GMT 2025 , Edited by admin on Mon Mar 31 18:31:23 GMT 2025
PRIMARY
FDA UNII
9TZH4WY30J
Created by admin on Mon Mar 31 18:31:23 GMT 2025 , Edited by admin on Mon Mar 31 18:31:23 GMT 2025
PRIMARY
DRUG BANK
DB06328
Created by admin on Mon Mar 31 18:31:23 GMT 2025 , Edited by admin on Mon Mar 31 18:31:23 GMT 2025
PRIMARY
MERCK INDEX
m7330
Created by admin on Mon Mar 31 18:31:23 GMT 2025 , Edited by admin on Mon Mar 31 18:31:23 GMT 2025
PRIMARY Merck Index
CAS
67-62-9
Created by admin on Mon Mar 31 18:31:23 GMT 2025 , Edited by admin on Mon Mar 31 18:31:23 GMT 2025
PRIMARY
SMS_ID
100000176656
Created by admin on Mon Mar 31 18:31:23 GMT 2025 , Edited by admin on Mon Mar 31 18:31:23 GMT 2025
PRIMARY
MESH
C005214
Created by admin on Mon Mar 31 18:31:23 GMT 2025 , Edited by admin on Mon Mar 31 18:31:23 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-660-1
Created by admin on Mon Mar 31 18:31:23 GMT 2025 , Edited by admin on Mon Mar 31 18:31:23 GMT 2025
PRIMARY
HSDB
2883
Created by admin on Mon Mar 31 18:31:23 GMT 2025 , Edited by admin on Mon Mar 31 18:31:23 GMT 2025
PRIMARY