Product Name

Amifostine

Name: Amifostine - LGM Pharma
SKU: 20537-88-6

CAS Number

20537-88-6

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Product Name:

Amifostine

CAS Number:

20537-88-6

Indication:

For reduction in the cumulative renal toxicity in patients with ovarian cancer (using cisplatin) and moderate to severe xerostomia in patients undergoing post-operative radiation treatment for head and neck cancer.

Mode of Action:

The thiol metabolite is responsible for most of the cytoprotective and radioprotective properties of amifostine. It is readily taken up by cells where it binds to and detoxifies reactive metabolites of platinum and alkylating agents as well as scavenges free radicals. Other possible effects include inhibition of apoptosis, alteration of gene expression and modification of enzyme activity.

Pharmacodynamics:

Amifostine is an organic thiophosphate cytoprotective agent indicated to reduce the cumulative renal toxicity associated with repeated administration of cisplatin in patients with advanced ovarian cancer or non-small cell lung cancer and also to reduce the incidence of moderate to severe xerostomia in patients undergoing post-operative radiation treatment for head and neck cancer. Amifostine is a prodrug that is dephosphorylated by alkaline phosphatase in tissues to a pharmacologically active free thiol metabolite, believed to be responsible for the reduction of the cumulative renal toxicity of cisplatin and for the reduction of the toxic effects of radiation on normal oral tissues. Healthy cells are preferentially protected because amifostine and metabolites are present in healthy cells at 100-fold greater concentrations than in tumour cells.

Metabolism:

Amifostine is rapidly dephosphorylated by alkaline phosphatase in tissues primarily to the active free thiol metabolite and, subsequently, to a less active disulfide metabolite.

Toxicity:

Rat LD₅₀: 826 mg/kg

IUPAC:

({2-[(3-aminopropyl)amino]ethyl}sulfanyl)phosphonic acid

ATC:

V03AF05

PubChem:

2141

DrugBank:

DB01143 (APRD00021)

Formula:

C₂₃H₃₆N₆O₅S

Molecular Mass:

214.223

Synonyms:

Amifostine Ethiofos Aminopropylaminoethyl Thiophosphate Apaetp Ethiofos Gammaphos SAPEP WR-1065

SMILES:

NCCCNCCSP(O)(O)=O

AHFS Code:

32:00.0

InChi:

JKOQGQFVAUAYPM-UHFFFAOYSA-N

General Reference:

Santini V, Giles FJ: The potential of amifostine: from cytoprotectant to therapeutic agent. Haematologica. 1999 Nov;84(11):1035-42. Pubmed

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Amifostine

20537-88-6

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