This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.


Generic Name
DrugBank Accession Number

Not Available

Small Molecule
Average: 47.057
Monoisotopic: 47.037113785
Chemical Formula
Not Available
External IDs
  • TRC102



Investigated for use/treatment in cancer/tumors (unspecified).

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Contraindications & Blackbox Warnings
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Not Available

Mechanism of action

Methoyxamine is investigated for use as an adjunct to alkylating agents, reverse resistance to chemotherapy, and enhancing radiation therapy.
Methoxyamine’s proposed mechanism of action is through blocking of the abasic sites (apurinic/apyrimidinic - AP sites) created by the cleavage of base excision repair (BER) glycoslyates. DNA alkylating agents cause cell death through excessive DNA damage by adduct formation. The human mechanism for DNA repair is very efficient and cancer therapeutics which use this mechanism are often ineffective due to resistance by efficient repair mechanisms such as base excision repair (BER). Alkylating agents such as tezmozolomide form methylated DNA adducts such as O6-methylguanine (O6mG), 7-methylguanine (N7mG) and 3-methyladenine (N3mA). O6mG is a cytotoxic and genotoxic adduct which is repaired by O6-methylguanine DNA-methyltransferase (MGMT). O6mG’s cytotoxicity is due to the mismatch repair mechanism (MMR), but cell induced defects in this repair pathway can lead to drug resistance. The N7mG (dominant lesions caused by methylating agents) and N3mA adducts are both repaired by the BER mechanism. Methoxyamine disrupts the BER pathway, increasing the amount of cytotoxic adducts, which results in cell death. Methoxyamine inhibits BER by stabilizing the AP sites created by cleavage of BER glysosylates, forming MX-AP lesions.

Methoxyamine may be an effective adjunct to iododeoxyuridine(IUdR) induced radiosensitization and radiation treatment. IUdR is a halogenated pyrimidine which is incorporated into cellular DNA instead of thymidine, which enhances radiotumor sensitivity. Methoxyamine is proposed to have a dual action in this treatment as it alters cell cycle kinetics as well as prevents repair of DNA by BER, allowing increased sensitivity of tumor cells to DNA damage by radiation therapy. The efficiency of cell cycle repair has been shown to be cell cycle dependent, with the G1 phase being second most sensitive to ionizing radiation (the mitotic, M, phase is the most sensitive). Methoxyamine increases the amount of protein 53 (P53) and protein Rb (pRB), senescence factors which cause the cell to remain in the G1 phase. Methoxyamine also creates a stringent checkpoint at the G1/S boundary as well as an insufficient checkpoint at the G2 stage, preventing cells from going into the S phase. The increased number of G1 cells makes methoxyamine treated tumors more susceptible to ionizing radiation.

The temozolomide and methoxyamine created lesion MX-AP not only disrupts the BER pathway but inhibits topoisomerase II alpha (topo II), an enzyme necessary for DNA replication, recombination and chromosome segregation. MX-AP sites block DNA replication and interfere with choromosome splitting. It is currently uncertain how what the interaction between topoisomerase II and methoxyamine causes cytotoxicity, but several mechanisms have been proposed, such as MX-AP sites binding to topo II, thus reducing their functionality by forming a toxic complex.

UDNANot AvailableHumans

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Not Available
Route of elimination

Not Available


Not Available


Not Available

Adverse Effects
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Not Available

Not Available
Pharmacogenomic Effects/ADRs
Not Available


Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available


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Product Ingredients
IngredientUNIICASInChI Key
Methoxyamine hydrochloride203546OLMF593-56-6XNXVOSBNFZWHBV-UHFFFAOYSA-N


Drug Categories
Chemical TaxonomyProvided by Classyfire
This compound belongs to the class of organic compounds known as organooxygen compounds. These are organic compounds containing a bond between a carbon atom and an oxygen atom.
Organic compounds
Super Class
Organic oxygen compounds
Organooxygen compounds
Sub Class
Not Available
Direct Parent
Organooxygen compounds
Alternative Parents
Organic nitrogen compounds / Hydrocarbon derivatives
Aliphatic acyclic compound / Hydrocarbon derivative / Organic nitrogen compound / Organooxygen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
a small molecule (CPD-7648)
Affected organisms
Not Available

Chemical Identifiers

CAS number
InChI Key


General References
  1. Yan L, Bulgar A, Miao Y, Mahajan V, Donze JR, Gerson SL, Liu L: Combined treatment with temozolomide and methoxyamine: blocking apurininc/pyrimidinic site repair coupled with targeting topoisomerase IIalpha. Clin Cancer Res. 2007 Mar 1;13(5):1532-9. [Article]
  2. Yan T, Seo Y, Schupp JE, Zeng X, Desai AB, Kinsella TJ: Methoxyamine potentiates iododeoxyuridine-induced radiosensitization by altering cell cycle kinetics and enhancing senescence. Mol Cancer Ther. 2006 Apr;5(4):893-902. [Article]
  3. Liu L, Gerson SL: Therapeutic impact of methoxyamine: blocking repair of abasic sites in the base excision repair pathway. Curr Opin Investig Drugs. 2004 Jun;5(6):623-7. [Article]

Clinical Trials

Clinical Trials
2RecruitingTreatmentAdenocarcinoma of the Lung / Lung Large Cell Carcinoma / Non-squamous Non-small-cell Lung Cancer (NSQ NSCLC) / Stage III Lung Cancer AJCC v81
2TerminatedTreatmentAdult Glioblastoma1
1CompletedTreatmentAdult Nasal Type Extranodal NK/T-Cell Lymphoma / Anaplastic Large Cell Lymphoma / Angioimmunoblastic T-cell Lymphoma (AITL) / B-Cell Non-Hodgkin Lymphoma (NHL) of the Skin / B-cell Small Lymphocytic Lymphoma Recurrent / Extranodal marginal zone B-cell lymphoma (MALT type) / Hepato-splenic T-cell Lymphoma / Intraocular Lymphoma / Nodal marginal zone B-cell lymphomas / Peripheral T-Cell Lymphoma (PTCL) / Recurrent Adult Burkitt Lymphoma / Recurrent Adult Diffuse Large Cell Lymphoma / Recurrent Adult Diffuse Mixed Cell Lymphoma / Recurrent Adult Diffuse Small Cleaved Cell Lymphoma / Recurrent Adult Grade III Lymphomatoid Granulomatosis / Recurrent Adult Hodgkin's Lymphoma / Recurrent Adult Immunoblastic Large Cell Lymphoma / Recurrent Adult Lymphoblastic Lymphoma / Recurrent Adult T-Cell Leukemia/Lymphoma / Recurrent Cutaneous T-Cell Non-Hodgkin Lymphoma / Recurrent Grade 1 Follicular Lymphoma / Recurrent Grade 2 Follicular Lymphoma / Recurrent Grade 3 Follicular Lymphoma / Recurrent Mantle Cell Lymphoma / Recurrent Marginal Zone Lymphoma / Recurrent Mycosis Fungoides and Sezary Syndrome / Refractory Chronic Lymphocytic Leukemia (CLL) / Refractory Multiple Myeloma / Relapsing Chronic Myelogenous Leukemia / Small Intestine Lymphoma / Splenic Marginal Zone Lymphoma / Stage III Chronic Lymphocytic Leukemia / Testicular Lymphoma / Waldenström's Macroglobulinemia (WM)1
1CompletedTreatmentLocally Advanced Lung Non-Squamous Non-Small Cell Carcinoma / Stage III Lung Adenocarcinoma AJCC v7 / Stage III Lung Large Cell Carcinoma AJCC v7 / Stage III Non-Small Cell Lung Cancer AJCC v7 / Stage IIIA Lung Adenocarcinoma AJCC v7 / Stage IIIA Lung Large Cell Carcinoma AJCC v7 / Stage IIIA Non-Small Cell Lung Cancer AJCC v7 / Stage IIIB Lung Adenocarcinoma AJCC v7 / Stage IIIB Lung Large Cell Carcinoma AJCC v7 / Stage IIIB Non-Small Cell Lung Cancer AJCC v7 / Stage IV Lung Adenocarcinoma AJCC v7 / Stage IV Lung Large Cell Carcinoma AJCC v7 / Stage IV Non-Small Cell Lung Cancer AJCC v71


Not Available
Not Available
Dosage Forms
Not Available
Not Available
Not Available


Experimental Properties
Not Available
Predicted Properties
Water Solubility600.0 mg/mLALOGPS
pKa (Strongest Basic)4.32Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area35.25 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity12.33 m3·mol-1Chemaxon
Polarizability4.7 Å3Chemaxon
Number of Rings0Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available


Mass Spec (NIST)
Not Available
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0002-9000000000-9145bf1ed99362d118cc
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-9000000000-a073cad6e8629f599f73
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-9000000000-a96f2b5b258fa6941fff
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-9000000000-73b71642646b44867317
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-9000000000-9cf2215e8f4daee08f0c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001j-9000000000-72377960e33d464ffb98
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-9000000000-c8cf8ad87feb5ad856eb
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
DeepCCS 1.0 (2019)
DeepCCS 1.0 (2019)
DeepCCS 1.0 (2019)


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Pharmacological action
DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.

Drug created at March 19, 2008 16:24 / Updated at June 12, 2020 16:52