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Methoxyamine | CAS No: 67-62-9 | GMP-certified suppliers
A medication that is investigated as an adjunct in cancer treatment to enhance the efficacy of chemotherapy and radiation by targeting DNA repair mechanisms.
Therapeutic categories
Amines
Generic name
Methoxyamine
Molecule type
small molecule
CAS number
67-62-9
DrugBank ID
DB06328
Approval status
Investigational drug
Primary indications
- Investigated for use/treatment in cancer/tumors (unspecified)
Product Snapshot
- Methoxyamine is an oral small molecule formulation
- It is primarily investigated for oncological applications in cancer and tumor treatment
- The compound remains in the investigational stage without approved status in major regulatory markets
Clinical Overview
Methoxyamine (CAS 67-62-9) is an investigational organic compound classified as an organooxygen amine. It is under study primarily for its potential application in oncology as an adjunct in cancer treatment protocols, particularly in combination with alkylating chemotherapeutic agents and radiation therapy.
The pharmacological interest in methoxyamine centers on its ability to interfere with cellular DNA repair mechanisms, specifically the base excision repair (BER) pathway. Chemotherapeutic alkylating agents induce cytotoxicity through the formation of DNA adducts, including methylated bases such as O6-methylguanine, 7-methylguanine, and 3-methyladenine. While some lesions are repaired by O6-methylguanine DNA-methyltransferase, others like 7-methylguanine and 3-methyladenine are corrected by BER. Methoxyamine acts by binding to apurinic/apyrimidinic (AP) sites, which are intermediates in BER, stabilizing them and thus forming MX-AP complexes. This inhibits the BER process, leading to accumulation of cytotoxic DNA lesions and enhanced tumor cell death.
In addition to its role in chemotherapy, methoxyamine has been explored for its radiosensitizing properties, especially in combination with iododeoxyuridine (IUdR), a thymidine analog incorporated into DNA that increases tumor sensitivity to ionizing radiation. Methoxyamine modulates cell cycle checkpoints by increasing levels of tumor suppressor proteins such as p53 and retinoblastoma protein (pRb), causing tumor cells to accumulate in the G1 phase. This shift enhances susceptibility to radiation, as cells in G1 are more radiation-sensitive. Furthermore, the MX-AP lesions inhibit topoisomerase II alpha activity, which is critical for DNA replication and chromosome segregation, thereby contributing to the compound’s cytotoxic effects.
No marketed products currently list methoxyamine as an approved active pharmaceutical ingredient; its use is confined to clinical research settings. Safety and toxicity profiles remain under evaluation, with attention focused on potential off-target effects related to DNA repair inhibition in normal tissues.
When sourcing methoxyamine for investigational use, attention should be given to the compound’s purity, stability, and compliance with regulatory standards applicable to APIs intended for clinical trials. Reliable suppliers with validated manufacturing processes and appropriate documentation are critical to ensure reproducibility and safety in research applications.
The pharmacological interest in methoxyamine centers on its ability to interfere with cellular DNA repair mechanisms, specifically the base excision repair (BER) pathway. Chemotherapeutic alkylating agents induce cytotoxicity through the formation of DNA adducts, including methylated bases such as O6-methylguanine, 7-methylguanine, and 3-methyladenine. While some lesions are repaired by O6-methylguanine DNA-methyltransferase, others like 7-methylguanine and 3-methyladenine are corrected by BER. Methoxyamine acts by binding to apurinic/apyrimidinic (AP) sites, which are intermediates in BER, stabilizing them and thus forming MX-AP complexes. This inhibits the BER process, leading to accumulation of cytotoxic DNA lesions and enhanced tumor cell death.
In addition to its role in chemotherapy, methoxyamine has been explored for its radiosensitizing properties, especially in combination with iododeoxyuridine (IUdR), a thymidine analog incorporated into DNA that increases tumor sensitivity to ionizing radiation. Methoxyamine modulates cell cycle checkpoints by increasing levels of tumor suppressor proteins such as p53 and retinoblastoma protein (pRb), causing tumor cells to accumulate in the G1 phase. This shift enhances susceptibility to radiation, as cells in G1 are more radiation-sensitive. Furthermore, the MX-AP lesions inhibit topoisomerase II alpha activity, which is critical for DNA replication and chromosome segregation, thereby contributing to the compound’s cytotoxic effects.
No marketed products currently list methoxyamine as an approved active pharmaceutical ingredient; its use is confined to clinical research settings. Safety and toxicity profiles remain under evaluation, with attention focused on potential off-target effects related to DNA repair inhibition in normal tissues.
When sourcing methoxyamine for investigational use, attention should be given to the compound’s purity, stability, and compliance with regulatory standards applicable to APIs intended for clinical trials. Reliable suppliers with validated manufacturing processes and appropriate documentation are critical to ensure reproducibility and safety in research applications.
Identification & chemistry
| Generic name | Methoxyamine |
|---|---|
| Molecule type | Small molecule |
| CAS | 67-62-9 |
| UNII | 9TZH4WY30J |
| DrugBank ID | DB06328 |
Pharmacology
| Summary | Methoxyamine is an investigational agent that targets DNA repair mechanisms to enhance the cytotoxic effects of alkylating chemotherapy and radiation therapy. It inhibits the base excision repair (BER) pathway by stabilizing abasic (AP) sites, resulting in accumulation of cytotoxic DNA lesions that lead to cell death. Additionally, methoxyamine disrupts cell cycle progression and interferes with topoisomerase II alpha function, further sensitizing tumor cells to DNA damage. |
|---|---|
| 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. |
Targets
| Target | Organism | Actions |
|---|---|---|
| DNA | Humans |
Formulation & handling
- Methoxyamine is a small molecule compound primarily suited for oral formulation due to its solid state and favorable water solubility.
- The molecule exhibits moderate hydrophilicity with a logP of -0.36, indicating good aqueous solubility which may facilitate formulation in aqueous media.
- No peptide or biologic nature present, simplifying stability considerations without special handling for biological degradation.
Regulatory status
Methoxyamine is a type of Anticancer drugs
Anticancer drugs belong to the pharmaceutical API (Active Pharmaceutical Ingredient) category designed specifically to combat cancer cells. These powerful medications play a crucial role in cancer treatment and are developed to target and destroy cancerous cells, preventing their growth and spread.
Anticancer drugs are classified based on their mode of action and can include various types such as chemotherapy drugs, targeted therapy drugs, immunotherapy drugs, and hormonal therapy drugs. Chemotherapy drugs work by interfering with the cell division process, thereby inhibiting the growth of cancer cells. Targeted therapy drugs, on the other hand, are designed to attack specific molecules or genes involved in cancer growth, minimizing damage to healthy cells. Immunotherapy drugs stimulate the body's immune system to recognize and destroy cancer cells. Hormonal therapy drugs are used in cancers that are hormone-dependent, such as breast or prostate cancer, to block the hormones that fuel cancer cell growth.
These APIs are typically synthesized through complex chemical processes in state-of-the-art manufacturing facilities. Stringent quality control measures ensure the purity, potency, and safety of these drugs. Anticancer APIs undergo rigorous testing and adhere to stringent regulatory guidelines before being approved for clinical use.
Due to their critical role in cancer treatment, anticancer drugs are in high demand worldwide. Researchers and pharmaceutical companies continually strive to develop new and more effective APIs in this category to enhance treatment outcomes and minimize side effects. The ongoing advancements in the field of anticancer drug development offer hope for improved cancer therapies and better patient outcomes.
