Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C25H48N6O8 |
| Molecular Weight | 560.684 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCN
InChI
InChIKey=UBQYURCVBFRUQT-UHFFFAOYSA-N
InChI=1S/C25H48N6O8/c1-21(32)29(37)18-9-3-6-16-27-22(33)12-14-25(36)31(39)20-10-4-7-17-28-23(34)11-13-24(35)30(38)19-8-2-5-15-26/h37-39H,2-20,26H2,1H3,(H,27,33)(H,28,34)
| Molecular Formula | C25H48N6O8 |
| Molecular Weight | 560.684 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Deferoxamine (brand name Desferal) an iron chelator, is a drug for the treatment of acute iron intoxication and of chronic iron overload due to transfusion-dependent anemias. Deferoxamine chelates iron by forming a stable complex that prevents the iron entering into further chemical reactions. However, drug may cause hypersensitivity reactions, systemic allergic reactions, and cardiovascular, hematologic and neurological adverse reactions. Serious adverse reactions include significant hypotension and marked body weight loss. Principally plasma enzymes metabolize deferoxamine, but the pathways have not yet been defined. The chelate is readily soluble in water and passes easily through the kidney, giving the urine a characteristic reddish color. Some is also excreted in the feces via the bile.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2363058 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Palliative | DESFERAL Approved UseDeferoxamine Mesylate for Injection, USP is indicated for the treatment of acute iron intoxication and of chronic iron overload due to transfusion-dependent anemias. Acute Iron Intoxication Deferoxamine mesylate is an adjunct to, and not a substitute for, standard measures used in treating acute iron intoxication, which may include the following: induction of emesis with syrup of ipecac; gastric lavage; suction and maintenance of a clear airway; control of shock with intravenous fluids, blood, oxygen, and vasopressors; and correction of acidosis. Chronic Iron Overload Deferoxamine mesylate can promote iron excretion in patients with secondary iron overload from multiple transfusions (as may occur in the treatment of some chronic anemias, including thalassemia). Long-term therapy with deferoxamine mesylate slows accumulation of hepatic iron and retards or eliminates progression of hepatic fibrosis. Iron mobilization with deferoxamine mesylate is relatively poor in patients under the age of 3 years with relatively little iron overload. The drug should ordinarily not be given to such patients unless significant iron mobilization (e.g., 1 mg or more of iron per day) can be demonstrated. Deferoxamine mesylate is not indicated for the treatment of primary hemochromatosis, since phlebotomy is the method of choice for removing excess iron in this disorder. Launch Date1968 |
|||
| Palliative | DESFERAL Approved UseDeferoxamine Mesylate for Injection, USP is indicated for the treatment of acute iron intoxication and of chronic iron overload due to transfusion-dependent anemias. Acute Iron Intoxication Deferoxamine mesylate is an adjunct to, and not a substitute for, standard measures used in treating acute iron intoxication, which may include the following: induction of emesis with syrup of ipecac; gastric lavage; suction and maintenance of a clear airway; control of shock with intravenous fluids, blood, oxygen, and vasopressors; and correction of acidosis. Chronic Iron Overload Deferoxamine mesylate can promote iron excretion in patients with secondary iron overload from multiple transfusions (as may occur in the treatment of some chronic anemias, including thalassemia). Long-term therapy with deferoxamine mesylate slows accumulation of hepatic iron and retards or eliminates progression of hepatic fibrosis. Iron mobilization with deferoxamine mesylate is relatively poor in patients under the age of 3 years with relatively little iron overload. The drug should ordinarily not be given to such patients unless significant iron mobilization (e.g., 1 mg or more of iron per day) can be demonstrated. Deferoxamine mesylate is not indicated for the treatment of primary hemochromatosis, since phlebotomy is the method of choice for removing excess iron in this disorder. Launch Date1968 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
6.1 μM |
10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
DEFEROXAMINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
2.5 μM |
10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
DEFEROXAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
12.9 μM |
100 mg/kg 1 times / day other, intravenous dose: 100 mg/kg route of administration: Intravenous experiment type: OTHER co-administered: |
DEFEROXAMINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
2.7 μM |
100 mg/kg 1 times / day other, intravenous dose: 100 mg/kg route of administration: Intravenous experiment type: OTHER co-administered: |
DEFEROXAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
7.4 μM |
10 mg/kg 1 times / day other, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: OTHER co-administered: |
DEFEROXAMINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
15.7 μM |
10 mg/kg single, intramuscular dose: 10 mg/kg route of administration: Intramuscular experiment type: SINGLE co-administered: |
DEFEROXAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
7 μM |
10 mg/kg single, intramuscular dose: 10 mg/kg route of administration: Intramuscular experiment type: SINGLE co-administered: |
DEFEROXAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
10.1 μM |
40 mg/kg single, subcutaneous dose: 40 mg/kg route of administration: Subcutaneous experiment type: SINGLE co-administered: |
DEFEROXAMINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
354 μM × h |
10 mg/kg 1 times / day other, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: OTHER co-administered: |
DEFEROXAMINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3.05 h |
10 mg/kg 1 times / day other, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: OTHER co-administered: |
DEFEROXAMINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
7.59 h |
40 mg/kg single, subcutaneous dose: 40 mg/kg route of administration: Subcutaneous experiment type: SINGLE co-administered: |
DEFEROXAMINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no [Activation >10 uM] | ||||
| no [Activation >10 uM] | ||||
| no [Activation >10 uM] | ||||
| no [Activation >10 uM] | ||||
| no [Activation >10 uM] | ||||
| yes | ||||
| yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Regulation of the 75-kDa subunit of mitochondrial complex I by iron. | 2001-07-20 |
|
| Hypoxia induces the activation of the phosphatidylinositol 3-kinase/Akt cell survival pathway in PC12 cells: protective role in apoptosis. | 2001-06-22 |
|
| Vanadium-induced nuclear factor of activated T cells activation through hydrogen peroxide. | 2001-06-22 |
|
| Up-regulation of apoptosis inhibitory protein IAP-2 by hypoxia. Hif-1-independent mechanisms. | 2001-06-01 |
|
| Induction of oxidative stress by humic acid through increasing intracellular iron: a possible mechanism leading to atherothrombotic vascular disorder in blackfoot disease. | 2001-05-18 |
|
| Comparison of IY81149 with omeprazole in rat reflux oesophagitis. | 2001-05-15 |
|
| Hypoxia induces lytic replication of Kaposi sarcoma-associated herpesvirus. | 2001-05-15 |
|
| Cellular titration of apoptosis with steady state concentrations of H(2)O(2): submicromolar levels of H(2)O(2) induce apoptosis through Fenton chemistry independent of the cellular thiol state. | 2001-05-01 |
|
| DNA breakage induced by 1,2,4-benzenetriol: relative contributions of oxygen-derived active species and transition metal ions. | 2001-05-01 |
|
| Regulatory interactions between iron and nitric oxide metabolism for immune defense against Plasmodium falciparum infection. | 2001-05-01 |
|
| Evaluation of a new selective medium for methicillin-resistant Staphyloccocus aureus. | 2001-05 |
|
| Asbestos causes apoptosis in alveolar epithelial cells: role of iron-induced free radicals. | 2001-05 |
|
| The controversial role of deferiprone in the treatment of thalassemia. | 2001-05 |
|
| Tc-99m MDP and Ga-67 citrate scintigraphic findings in sarcoidosis with osseous involvement. | 2001-05 |
|
| A case of malignant lymphoma with testis involvement detected by Ga-67 scan. | 2001-05 |
|
| Primary breast lymphoma detected with Tc-99m tetrofosmin scintigraphy. | 2001-05 |
|
| HIFalpha targeted for VHL-mediated destruction by proline hydroxylation: implications for O2 sensing. | 2001-04-20 |
|
| Targeting of HIF-alpha to the von Hippel-Lindau ubiquitylation complex by O2-regulated prolyl hydroxylation. | 2001-04-20 |
|
| Inhibitory effect of YC-1 on the hypoxic induction of erythropoietin and vascular endothelial growth factor in Hep3B cells. | 2001-04-15 |
|
| Klebsiella pneumoniae meningitis in thalassemia major patients. | 2001-04-11 |
|
| Hypercalcemia and human nature. | 2001-04 |
|
| Persistence of delayed adrenarche in boys with thalassemia. | 2001-04 |
|
| Yersinia enterocolitica as a cause of intra-abdominal abscess: the role of iron. | 2001-04 |
|
| Relationship of fiber surface iron and active oxygen species to expression of procollagen, PDGF-A, and TGF-beta(1) in tracheal explants exposed to amosite asbestos. | 2001-04 |
|
| A new molecular role for iron in regulation of cell cycling and differentiation of HL-60 human leukemia cells: iron is required for transcription of p21(WAF1/CIP1) in cells induced by phorbol myristate acetate. | 2001-04 |
|
| Temporary treatment with sirolimus and low-trough cyclosporine prevents acute islet allograft rejection, and combination with starch-conjugated deferoxamine promotes islet engraftment in the preclinical pig model. | 2001-03-27 |
|
| Heme oxygenase-1 inhibits atherosclerotic lesion formation in ldl-receptor knockout mice. | 2001-03-16 |
|
| Atherosclerosis: defeat of the defense? | 2001-03-16 |
|
| Enterobactin: the characteristic catecholate siderophore of Enterobacteriaceae is produced by Streptomyces species.(1). | 2001-03-15 |
|
| Cytosolic xanthine oxidoreductase mediated bioactivation of ethanol to acetaldehyde and free radicals in rat breast tissue. Its potential role in alcohol-promoted mammary cancer. | 2001-03-07 |
|
| Possible role of hydroxyl radicals in the oxidation of dichloroacetonitrile by Fenton-like reaction. | 2001-03 |
|
| Classification of Ralstonia pickettii biovar 3/'thomasii' strains (Pickett 1994) and of new isolates related to nosocomial recurrent meningitis as Ralstonia mannitolytica sp. nov. | 2001-03 |
|
| Pharmacosurveillance and quality of care of thalassaemic patients. A large scale epidemiological survey. | 2001-03 |
|
| Rapid recovery with oral zinc sulphate in deferoxamine-induced presumed optic neuropathy and hearing loss. | 2001-03 |
|
| Hemoproteins affect H(2)O(2) removal from rat tissues. | 2001-03 |
|
| Role of the epithelium in opposing H(2)O(2)-induced modulation of acetylcholine-induced contractions in rabbit intrapulmonary bronchiole. | 2001-03 |
|
| Influence of iron restriction on Chlamydia pneumoniae and C. trachomatis. | 2001-03 |
|
| Mitochondrial involvement in cocaine-treated rat hepatocytes: effect of N-acetylcysteine and deferoxamine. | 2001-03 |
|
| IL-4 gene expression up-regulated by mercury in rat mast cells: a role of oxidant stress in IL-4 transcription. | 2001-03 |
|
| Iron-induced changes in nitric oxide and superoxide radical generation in rat liver after lindane or thyroid hormone treatment. | 2001-02-28 |
|
| Cytochrome b(5) plays a key role in human microsomal chromium(VI) reduction. | 2001-02-28 |
|
| Desferrioxamine, an iron chelator, upregulates cyclooxygenase-2 expression and prostaglandin production in a human macrophage cell line. | 2001-02-26 |
|
| Cellular sites of H2O2-induced damage and their protection by nitroxides. | 2001-02-16 |
|
| Inhibition of N-myc expression and induction of apoptosis by iron chelation in human neuroblastoma cells. | 2001-02-01 |
|
| Lucigenin chemiluminescence in human seminal plasma. | 2001-02 |
|
| Interaction between iron(II) and hydroxamic acids: oxidation of iron(II) to iron(III) by desferrioxamine B under anaerobic conditions. | 2001-01-15 |
|
| Effects of hyperoxia and iron on iron regulatory protein-1 activity and the ferritin synthesis in mouse peritoneal macrophages. | 2001-01-12 |
|
| The role of oxygen-derived free radicals in augmented relaxations to levcromakalim in the aorta from hypertensive rats. | 2001-01 |
|
| Oxidative insult in sheep red blood cells induced by T-butyl hydroperoxide: the roles of glutathione and glutathione peroxidase. | 2001-01 |
|
| Electron paramagnetic resonance detection of free radicals in UV-irradiated human and mouse skin. | 2001 |
Sample Use Guides
Acute Iron Intoxication:
Intramuscular Administration: This route is preferred and should be used for ALL PATIENTS NOT IN SHOCK: A dose of 1000 mg should be administered initially. This may be followed by 500 mg every 4 hours
for two doses. Depending upon the clinical response, subsequent doses of 500 mg may be administered every 4-12 hours. The total amount administered should not exceed 6000 mg in 24 hours
Intravenous Administration: THIS ROUTE SHOULD BE USED ONLY FOR PATIENTS IN A STATE OF CARDIOVASCULAR COLLAPSE AND THEN ONLY BY SLOW INFUSION. THE RATE OF INFUSION SHOULD NOT EXCEED 15 MG/KG/HR FOR THE FIRST 1000 MG ADMINISTERED. SUBSEQUENT IV DOSING, IF NEEDED, MUST BE AT A SLOWER RATE, NOT TO EXCEED 125 MG/HR: An initial dose of 1000 mg should be administered at a rate NOT TO EXCEED 15 mg/kg/hr. This may be followed by 500 mg over 4 hours for two doses. Depending upon the clinical response, subsequent doses of 500 mg may be administered over 4-12 hours. The total amount administered should not exceed 6000 mg in 24 hours.
CHRONIC IRON OVERLOAD:
SUBCUTANEOUS ADMINISTRATION: A daily dose of 1000-2000 mg (20-40 mg/kg/day) should be administered over 8-24 hours, utilizing a
small portable pump capable of providing continuous mini-infusion. The duration of infusion must be individualized. In some patients, as much iron will be excreted after a short infusion of 8-12 hours as with the same dose given over 24 hours.
Intravenous Administration: The standard recommended method of Desferal administration is via slow subcutaneous infusion over 8 – 12 hours. In patients with intravenous access, the daily dose of Desferal can be administered intravenously. The standard dose is 20 – 40 mg/kg/day for children and 40–50 mg/kg/day over 8 – 12 hours in adults for 5 – 7 days per week. In children, average doses should not exceed 40 mg/kg/day until growth has ceased. In adults, average doses should not exceed 60 mg/kg/day. The intravenous infusion rate should not exceed 15 mg/kg/hour.
Intramuscular Administration: A daily dose of 500-1000 mg may be administered intramuscularly. The total daily dose should not exceed 1000 mg.
Route of Administration:
Other
In Vitro Use Guide
Curator's Comment: It was investigated the effect of deferoxamine on mesenchymal stromal cells (MSCs). Ex vivo cultured stem cells derived from tumor and bone marrow compartment were exposed to Deferoxamine (DFO). It was revealed, that DFO had growth-arresting and apoptosis-inducing effect on tumor-associated MSCs (TAMSCs) and bone marrow MSCs (BMMSCs). DFO also influenced the expression pattern of adhesion molecule VCAM-1 on both TAMSCs and BMMSCs.
Unknown
| Substance Class |
Chemical
Created
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| Record UNII |
J06Y7MXW4D
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Validated (UNII)
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WHO-VATC |
QV03AC01
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FDA ORPHAN DRUG |
52290
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FDA ORPHAN DRUG |
633618
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NDF-RT |
N0000175522
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LIVERTOX |
NBK547998
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WHO-ATC |
V03AC01
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NDF-RT |
N0000000144
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WHO-ESSENTIAL MEDICINES LIST |
10.3
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NCI_THESAURUS |
C62357
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WHO-ESSENTIAL MEDICINES LIST |
4.2
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2973
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1682
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100000083476
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3311
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DTXSID7022887
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DEFEROXAMINE
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70-51-9
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C416
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D003676
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SUB06942MIG
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m4133
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J06Y7MXW4D
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J06Y7MXW4D
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DB00746
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200-738-5
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3131
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792
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CHEMBL556
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527604
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4356
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Deferoxamine
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SOLVATE->ANHYDROUS |
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ACTIVE MOIETY |
