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70-51-9

Basic Information
CAS No.: 70-51-9
Name: Deferoxamine
Article Data: 10
Molecular Structure:
Molecular Structure of 70-51-9 (Deferoxamine)
Formula: C25H48 N6 O8
Molecular Weight: 560.692
Synonyms: Butanediamide,N'-[5-[[4-[[5-(acetylhydroxyamino)pentyl]amino]-1,4-dioxobutyl]hydroxyamino]pentyl]-N-(5-aminopentyl)-N-hydroxy-(9CI); Propionohydroxamic acid,N-[5-[3-[(5-aminopentyl)hydroxycarbamoyl]propionamido]pentyl]-3-[[5-(N-hydroxyacetamido)pentyl]carbamoyl]-(8CI); 3,9,14,20,25-Pentaazatriacontane-2,10,13,21,24-pentone,30-amino-3,14,25-trihydroxy-; 30-Amino-3,14,25-trihydroxy-3,9,14,20,25pentaazatriacontane-2,10,13,21,24-pentaone; Deferoxamin; Deferoxamine;Deferoxamine B; Deferriferrioxamine B; Deferrioxamine; Deferrioxamine B;Desferan; Desferex; Desferin; Desferioxamine B; Desferrin; Desferrioxamine;Desferrioxamine B;N-[5-[3-[(5-Aminopentyl)hydroxycarbamoyl]propionamido]pentyl]-3-[[5-(N-hydroxyacetamido)pentyl]carbamoyl]propionohydroxamicacid; NSC 527604
EINECS: 200-738-5
Density: 1.212g/cm3
Melting Point: 139°C
Boiling Point: 627.9°C (rough estimate)
Safety: Poison by intravenous route. Moderately toxic by ingestion, intraperitoneal and subcutaneous routes. Human systemic effects: changes in hearing acuity, eye hemorrhage, optic nerve neuropathy, thrombocytopenia, visual field changes. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
PSA: 205.84000
LogP: 2.40420
Synthetic route

C46H64N8O8

70-51-9

deferoxamine

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen; acetic acid In methanol at 25℃; under 760.051 Torr; for 0.333333h;50%
402913-84-2

1-Carbobenzoxyamino-6,17-dihydroxy-7,10,18,21-tetraoxy-27-(N-acetyl-hydroxyamino)-6,11,17,22-tetraaza-hepteikosan

70-51-9

deferoxamine

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; palladium on activated charcoal In methanol
112139-65-8

N'-<5-<<4-<<5-pentyl>amino>-1,4-dioxobutyl>(phenylmethoxy)amino>pentyl>-N-(4-cyanobutyl)-N-(phenylmethoxy)butanediamide

70-51-9

deferoxamine

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; palladium on activated charcoal In methanol
129245-21-2

N-(5-aminopentyl)-N-(tert-butoxycarbonyl)-O-benzylhydroxylamine

70-51-9

deferoxamine

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 99 percent / diphenyl phosphorazidate, triethylamine / dimethylformamide / 17 h / 0 - 20 °C
2: 87 percent / trifluoroacetic acid (TFA) / CH2Cl2 / 0.75 h / 0 - 20 °C
3: 96 percent / pyridine
4: 95 percent / diphenyl phosphorazidate, triethylamine / dimethylformamide / 17 h / 0 - 20 °C
5: 100 percent / trifluoroacetic acid (TFA) / CH2Cl2
6: 91 percent / pyridine / 12 h
7: H2, HCl / 10percent Pd/C / methanol
View Scheme
129245-24-5

5,16-bis(benzyloxy)-20-cyano-4,12,15-trioxo-5,11,16-triazaeicosanoic acid

70-51-9

deferoxamine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 95 percent / diphenyl phosphorazidate, triethylamine / dimethylformamide / 17 h / 0 - 20 °C
2: 100 percent / trifluoroacetic acid (TFA) / CH2Cl2
3: 91 percent / pyridine / 12 h
4: H2, HCl / 10percent Pd/C / methanol
View Scheme
130946-41-7

27--6,17-bis(benzyloxy)-7,10,18,21-tetraoxo-6,11,17,22-tetraazaheptacosanenitrile

70-51-9

deferoxamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / pyridine / 12 h
2: H2, HCl / 10percent Pd/C / methanol
View Scheme
130946-40-6

27--6,17-bis(benzyloxy)-7,10,18,21-tetraoxo-6,11,17,22-tetraazaheptacosanenitrile

70-51-9

deferoxamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 100 percent / trifluoroacetic acid (TFA) / CH2Cl2
2: 91 percent / pyridine / 12 h
3: H2, HCl / 10percent Pd/C / methanol
View Scheme
112139-60-3

N-(4-Cyanobutyl)-N-(benzyloxy)succinamic Acid

70-51-9

deferoxamine

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 99 percent / diphenyl phosphorazidate, triethylamine / dimethylformamide / 17 h / 0 - 20 °C
2: 87 percent / trifluoroacetic acid (TFA) / CH2Cl2 / 0.75 h / 0 - 20 °C
3: 96 percent / pyridine
4: 95 percent / diphenyl phosphorazidate, triethylamine / dimethylformamide / 17 h / 0 - 20 °C
5: 100 percent / trifluoroacetic acid (TFA) / CH2Cl2
6: 91 percent / pyridine / 12 h
7: H2, HCl / 10percent Pd/C / methanol
View Scheme
129245-23-4

N-(4-cyanobutyl)-3-<<5-<(benzyloxy)amino>pentyl>carbamoyl>-O-benzylpropionohydroxamic acid

70-51-9

deferoxamine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 96 percent / pyridine
2: 95 percent / diphenyl phosphorazidate, triethylamine / dimethylformamide / 17 h / 0 - 20 °C
3: 100 percent / trifluoroacetic acid (TFA) / CH2Cl2
4: 91 percent / pyridine / 12 h
5: H2, HCl / 10percent Pd/C / methanol
View Scheme
129245-22-3

N-(4-cyanobutyl)-3-<<5-<(benzyloxy)-tert-butoxy-carbonylamino>pentyl>carbamoyl>-O-benzylpropionohydroxamic acid

70-51-9

deferoxamine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 87 percent / trifluoroacetic acid (TFA) / CH2Cl2 / 0.75 h / 0 - 20 °C
2: 96 percent / pyridine
3: 95 percent / diphenyl phosphorazidate, triethylamine / dimethylformamide / 17 h / 0 - 20 °C
4: 100 percent / trifluoroacetic acid (TFA) / CH2Cl2
5: 91 percent / pyridine / 12 h
6: H2, HCl / 10percent Pd/C / methanol
View Scheme
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Chemistry

Molecular Formula: C25H48N6O8
Molar mass: 560.684 g/mol
EINECS: 200-738-5
Density: 1.212 g/cm3
Index of Refraction: 1.537
Structure of Deferoxamine (CAS NO.70-51-9):
               

Uses

  Deferoxamine (CAS NO.70-51-9) is used to treat acute iron poisoning, especially in small children and is also frequently used to treat hemochromatosis, a disease of iron accumulation that can be either genetic or acquired. Another, it has also been used in the treatment of a patient with aceruloplasminemia.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo multiple routes 440mg/kg/6D-I (440mg/kg) SENSE ORGANS AND SPECIAL SENSES: "RETINAL CHANGES (PIGMENTARY DEPOSITIONS, RETINITIS, OTHER): EYE" Archives of Disease in Childhood. Vol. 63, Pg. 250, 1988.
child TDLo subcutaneous 12gm/kg/17W-I (12000mg/kg) SENSE ORGANS AND SPECIAL SENSES: OPTIC NERVE NEUROPATHY: EYE
SENSE ORGANS AND SPECIAL SENSES: CHANGE IN ACUITY: EAR
New England Journal of Medicine. Vol. 314, Pg. 869, 1986.
human TDLo subcutaneous 37gm/kg/2Y-I (37000mg/kg) SENSE ORGANS AND SPECIAL SENSES: OPTIC NERVE NEUROPATHY: EYE New England Journal of Medicine. Vol. 314, Pg. 869, 1986.
man TDLo intravenous 86mg/kg/1H-C (86mg/kg) BLOOD: THROMBOCYTOPENIA American Journal of Kidney Diseases. Vol. 6, Pg. 254, 1985.
mouse LD50 intraperitoneal 1680mg/kg (1680mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 4, Pg. 99, 1970.
mouse LD50 intravenous 250mg/kg (250mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA United States Patent Document. Vol. #4863964,
mouse LD50 oral 1340mg/kg (1340mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 17, Pg. 748, 1967.
mouse LD50 subcutaneous 1450mg/kg (1450mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 6, Pg. 119, 1975.
rat LD50 intravenous 329mg/kg (329mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
rat LD50 subcutaneous 12240mg/kg (12240mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 6, Pg. 119, 1975.
women TDLo intravenous 40mg/kg (40mg/kg) SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE
SENSE ORGANS AND SPECIAL SENSES: HEMORRHAGE: EYE
Nephron. Vol. 46, Pg. 211, 1987.
 

Safety Profile

Poison by intravenous route. Moderately toxic by ingestion, intraperitoneal and subcutaneous routes. Human systemic effects: changes in hearing acuity, eye hemorrhage, optic nerve neuropathy, thrombocytopenia, visual field changes. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Specification

 Deferoxamine ,its cas register number is 70-51-9. It also can be called Desferrioxamine B ; Desferoxamine B ; DFO-B ; DFOA ; DFB or Desferal . It acts by binding free iron in the bloodstream and enhancing its elimination in the urine. Deferoxamine (CAS NO.70-51-9) may modulate expression and release of inflammatory mediators by specific cell types. A recent study shows that it speeds healing of nerve damage. Its administration after acute intoxication may color the urine a pinkish red, a phenomenon termed "vin rose urine".