138-14-7

Basic information

• Product Name: DEFEROXAMINE MESYLATE
• Synonyms: deferoxaminebmesylate;deferoxaminemesilate;deferoxaminemethanesulfonate;desferal;desferalmesylate;desferalmethanesulfonate;desferrioxaminebmesylate;Deferoxamine Mesylate (300 mg)
• CAS NO: 138-14-7
• Molecular Formula: CH₃O₃S*C₂₅H₄₉N₆O₈
• Molecular Weight: 656.79
• EINECS: 205-314-3
• Product Categories: Pharmaceuticals;DESFERAL;Inhibitors;Aliphatics;Amines;Chelating Agents & Ligands;Intermediates & Fine Chemicals
• Mol File: 138-14-7.mol
• Article Data: 1

Chemical Properties

• Melting Point: 148-149°
• Boiling Point: 966.9 °C at 760 mmHg
• Flash Point: 538.5 °C
• Appearance: white to off-white/powder
• Vapor Pressure: 0mmHg at 25°C
• Storage Temp.: −20°C
• Solubility: H2O: 50 mg/mL
• CAS DataBase Reference: DEFEROXAMINE MESYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: DEFEROXAMINE MESYLATE(138-14-7)
• EPA Substance Registry System: DEFEROXAMINE MESYLATE(138-14-7)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 2
• RTECS: UG5310000
• Hazardous Substances Data: 138-14-7(Hazardous Substances Data)

Usage

Description

Deferoxamine is a bacterial siderophore that chelates iron. It is used to experimentally inhibit iron-dependent prolyl hydroxylases (EC50 = 17.8 μM), thus preventing the degradation of isoforms of hypoxia inducible factor during normoxia. Deferoxamine has applications in diseases that are characterized by high levels of circulating iron, such as thalassemia major.

Chemical Properties

DEFEROXAMINE MESYLATE is white or almost white powder.

Uses

Different sources of media describe the Uses of 138-14-7 differently. You can refer to the following data:
1. DEFEROXAMINE MESYLATE is an iron chelating agent used in therapy for patients with sickle cell diseases and iron overload. Studies suggest that it can exert potential antioxidant neuroprotective effects in stroke patients
2. chelating agent (Fe & Al)

Brand name

Desferal (Novartis).

Biochem/physiol Actions

An iron chelator used often in the studies of cell proliferation and apoptosis. Has been shown to have anti-proliferative effects on vascular smooth muscle cells in vitro and in vivo and to arrest cells in the G1 phase. Also reported to induce p53. Induces apoptosis in HL-60 cells by chelating iron. After 48 hrs treatment with 1μM deferoxamine, DNA fragmentation was apparent. Cells treated with 0.1 μM deferoxamine for as little as 24 hours were committed to apoptosis; by 48 hrs nuclear collapse was observed. In some studies it has been shown to have antioxidant properties and to protect cells against H2O2-induced damage.

Clinical Use

Chelating agent:Acute iron poisoningChronic iron or aluminium overload

Veterinary Drugs and Treatments

Deferoxamine is used for the treatment of either acute or chronic iron toxicity. It is being evaluated as an iron chelator for adjunctive treatment of acute cardiac ischemia and as a chelator for aluminum toxicity. Its efficacy in treating reperfusion injuries has been disappointing.

Drug interactions

Potentially hazardous interactions with other drugsAvoid prochlorperazine, levomepromazine and methotrimeprazine (prolonged unconsciousness).Do not administer with blood.

Metabolism

When given parenterally desferrioxamine forms chelates with iron and aluminium ions to form ferrioxamine and aluminoxamine, respectively. The chelates are excreted in the urine and faeces via the bile. Desferrioxamine is metabolised, mainly in the plasma. Four metabolites of desferrioxamine were isolated from urine of patients with iron overload. The following biotransformation reactions were found to occur with desferrioxamine: transamination and oxidation yielding an acid metabolite, beta-oxidation also yielding an acid metabolite, decarboxylation and N-hydroxylation yielding neutral metabolites.

InChI:InChI=1/C25H48N6O8.2CH4O3S/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;2*1-5(2,3)4/h37-39H,2-20,26H2,1H3,(H,27,33)(H,28,34);2*1H3,(H,2,3,4)

Synthetic route

deferoxamine mesylate (138-14-7) + 89Zr(Ox)2 → C25H45N6O8(89)Zr

Conditions	Yield
With sodium carbonate In water at 24℃; for 0.25h; pH=7 - 7.5;	100%

succinic acid anhydride (108-30-5) + deferoxamine mesylate (138-14-7) → N-Succinyl-desferri-ferrioxyamin B (84211-47-2)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 42h; Inert atmosphere;	97%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 50℃; Solvent; Temperature; Inert atmosphere;
With pyridine at 20℃; Inert atmosphere;	0.232 g

2-benzyloxybenzoyl chloride (4349-62-6) + deferoxamine mesylate (138-14-7) → N,O',O'',O'''-Tetra(2-benzyloxy-benzoyl)desferri-ferrioxamin B (101536-58-7)

Conditions	Yield
With sodium hydrogencarbonate In diethyl ether; water for 1h;	93%

deferoxamine mesylate (138-14-7) + biotin N-Hydroxysuccinimide ester (35013-72-0) → DFOB-AdA (1150314-06-9)

Conditions	Yield
With sodium hydroxide In methanol at 40℃; for 4h; Product distribution / selectivity;	92%

1-(N-succinimidyloxycarbonyl)adamantane (28320-76-5) + deferoxamine mesylate (138-14-7) → DFOB-AdA (1150314-06-9)

Conditions	Yield
Stage #1: deferoxamine mesylate With sodium hydroxide In methanol Stage #2: 1-(N-succinimidyloxycarbonyl)adamantane In methanol at 55℃; for 4h; Product distribution / selectivity;	92%

1 ,4-phenylenediisothiocyanate (4044-65-9) + deferoxamine mesylate (138-14-7) → N-[5-({3-[5-(acetyl-hydroxy-amino)-pentylcarbamoyl]-propionyl}-hydroxy-amino)-pentyl]-N'-hydroxy-N'-{5-[3-(4-isothiocyanato-phenyl)-thioureido]-pentyl}-succinamide (1222468-90-7)

Conditions	Yield
With triethylamine In chloroform; water; isopropyl alcohol	85%

di-tert-butyl dicarbonate (24424-99-5) + deferoxamine mesylate (138-14-7) → 1-(tert-Butoxycarbonyl)-7,18,29-trihydroxy-8,11,19,22,30-pentaoxo-1,7,12,18,23,29-hexaazahentriacontane (106339-54-2)

Conditions	Yield
With triethylamine In 1,4-dioxane; water at 40℃; for 16h;	83%
With sodium carbonate In 1,4-dioxane; water

deferoxamine mesylate (138-14-7) + 3,4-diethoxy-3-cyclobuten-1,2-dione (5231-87-8) → C31H52N6O11

Conditions	Yield
Stage #1: deferoxamine mesylate With N-ethyl-N,N-diisopropylamine In ethanol at 50℃; for 1h; Stage #2: 3,4-diethoxy-3-cyclobuten-1,2-dione In ethanol at 50℃; for 0.5h;	83%
Stage #1: deferoxamine mesylate With N-ethyl-N,N-diisopropylamine In ethanol at 50℃; for 1h; Stage #2: 3,4-diethoxy-3-cyclobuten-1,2-dione In ethanol at 50℃; for 0.5h;	83%

C19H22N2O9 + deferoxamine mesylate (138-14-7) → C41H67N7O14

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide for 4h;	82%

3,5-dimethyl-1-adamantanecarboxylic acid (14670-94-1) + deferoxamine mesylate (138-14-7) → DFOB-AdAdMe (1149568-52-4)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	80%

deferoxamine mesylate (138-14-7) + (adamant-1-yl)-acetic acid (4942-47-6) → DFOB-AdAc (1149568-54-6)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	80%

aluminum(III) nitrate nonahydrate + deferoxamine mesylate (138-14-7) → (Al(III)desferrioxamin B complex)CH3SO3

Conditions	Yield
With potassium hydroxide In water addn. of desferal to fresh prepared Al(OH)3 gel in water (by hydrolysis of Al(NO3)3 with a pH 10 NH4+/NH3 buffer soln. or 0.5 m KOH soln.), stirring overnight; filtn. and solvent removal under vac., elem. anal., mixt. of 2 isomers;	78%

deferoxamine mesylate (138-14-7) + 2-tert-butoxycarbonylamino-3-(tritylsulfanyl)propionic acid 2,5-dioxopyrrolidin-1-yl ester (87242-61-3, 75179-29-2) → tert-butyl (12,23,34-trihydroxy-5,13,16,24,27,35-hexaoxo-1,1,1-triphenyl-2-thia-6,12,17,23,28,34-hexaazahexatriacontan-4-yl)carbamate

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 18h;	77%

C15H18ClNO5 + deferoxamine mesylate (138-14-7) → C40H65N7O13

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃;	74%

2-(4-methylphenoxy)acetic acid (940-64-7) + deferoxamine mesylate (138-14-7) → DFOB-MPOAc (1149568-53-5)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	73%

2-(1-imidazolyl)acetic acid hydrochloride + deferoxamine mesylate (138-14-7) → C30H52N8O9

Conditions	Yield
Stage #1: 2-(1-imidazolyl)acetic acid hydrochloride; deferoxamine mesylate With benzotriazol-1-ol; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 45℃; for 1h; Inert atmosphere; Stage #2: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 8h;	72%

1-octyl-3-(carboxymethyl)-imidazolium bromide (1309877-54-0) + deferoxamine mesylate (138-14-7) → C38H69N8O9(1+)*CH3O3S(1-)

Conditions	Yield
Stage #1: 1-octyl-3-(carboxymethyl)-imidazolium bromide; deferoxamine mesylate With benzotriazol-1-ol; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 50℃; for 1h; Inert atmosphere; Stage #2: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	71%

hydrated ferric ammonium sulfate + deferoxamine mesylate (138-14-7) → ferrioxamine B perchlorate pentahydrate (82265-74-5)

Conditions

Yield

With perchloric acid; sodium hydrogencarbonate In water ligand was dissolved in H2O, Fe-salt was added with stirring for 30 min, solid NaHCO3 was added, stirred for 1 h, filtered, passed through anion-exchange column (HClO4), washed, solvent was removed under reduced pressure, dissolved in MeOH, filtered; poured with excess of EtOAc with stirring, collected by centrifugation,redissolved in MeOH, filtered, EtOAc was added, collected, supernatant was decanted, solvent was slowly removed under midl vac. in vac. desiccator at 90°C for 2 d; elem. anal;

70%

1-Adamantanecarboxylic acid (828-51-3) + deferoxamine mesylate (138-14-7) → DFOB-AdA (1150314-06-9)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	70%

deferoxamine mesylate (138-14-7) + 1-carboxymethyl-3-hydroxy-2-methylpyridin-4-one (60603-99-8) → DFOB-L1D (1149568-64-8)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	70%

6-dibenzocyclooctynamidehexanoic acid + deferoxamine mesylate (138-14-7) → C46H65N7O10

Conditions	Yield
Stage #1: 6-dibenzocyclooctynamidehexanoic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: deferoxamine mesylate With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	69%

deferoxamine mesylate (138-14-7) + trolox (56305-04-5, 53188-07-1) → N1-hydroxy-N-(5-(4-(hydroxy(1-(6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxamido)-1λ5,5λ3-pentyl)amino)-4-oxobutanamido)pentyl)-N4-(5-(N-hydroxyacetamido)pentyl)succinamide

Conditions	Yield
Stage #1: trolox With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 1h; Inert atmosphere; Stage #2: deferoxamine mesylate In N,N-dimethyl-formamide for 16h; Inert atmosphere;	68.8%

deferoxamine mesylate (138-14-7) + biotin N-Hydroxysuccinimide ester (35013-72-0) → biotin-DFOB (148942-68-1)

Conditions	Yield
Stage #1: deferoxamine mesylate With sodium hydroxide In methanol Stage #2: biotin N-Hydroxysuccinimide ester In methanol at 55℃; for 4h;	68%
With sodium hydroxide In methanol at 60℃; Inert atmosphere;	55%

1-carboxymethyl-3-methyl-3H-imidazolium bromide (671793-14-9) + deferoxamine mesylate (138-14-7) → C31H55N8O9(1+)*CH3O3S(1-)

Conditions	Yield
Stage #1: 1-carboxymethyl-3-methyl-3H-imidazolium bromide; deferoxamine mesylate With benzotriazol-1-ol; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 50℃; for 1h; Inert atmosphere; Stage #2: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	68%

C29H45N3O13 + deferoxamine mesylate (138-14-7) → C54H91N9O20

Conditions	Yield
Stage #1: C29H45N3O13 With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide for 0.166667h; Stage #2: deferoxamine mesylate In dimethyl sulfoxide for 3h;	68%

1-butyl-3-(carboxymethyl)-imidazolium bromide (1309877-52-8) + deferoxamine mesylate (138-14-7) → C34H61N8O9(1+)*CH3O3S(1-)

Conditions	Yield
Stage #1: 1-butyl-3-(carboxymethyl)-imidazolium bromide; deferoxamine mesylate With benzotriazol-1-ol; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 50℃; for 1h; Inert atmosphere; Stage #2: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	66%

deferoxamine mesylate (138-14-7) + deferasirox (201530-41-8) → DFOB-LDX (1149568-62-6)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	65%

deferoxamine mesylate (138-14-7) → C25H46N8O8

Conditions	Yield
Stage #1: deferoxamine mesylate With potassium carbonate In methanol at 20℃; for 0.5h; Stage #2: With copper(ll) sulfate pentahydrate; 3-azidosulfonyl-3H-imidazole-1-ium hydrogen sulfate In methanol; water at 20℃; for 4.5h;	65%

2-[({[(1S,2E,6S)-6-{[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}-6-methylcyclooct-2-en-1-yl]oxy}carbonyl)(methyl)amino]acetic acid + deferoxamine mesylate (138-14-7) → C43H70N8O15

Conditions	Yield
Stage #1: 2-[({[(1S,2E,6S)-6-{[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}-6-methylcyclooct-2-en-1-yl]oxy}carbonyl)(methyl)amino]acetic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide for 0.166667h; Stage #2: deferoxamine mesylate In dimethyl sulfoxide for 3h;	64%

deferoxamine mesylate (138-14-7) + (R)-trolox (53101-49-8) → (R)-N1-hydroxy-N1-(5-(4-(hydroxy(1-(6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxamido)-1λ5,5λ3-pentyl)amino)-4-oxobutanamido)pentyl)-N-(5-(N-hydroxyacetamido)pentyl)succinamide

Conditions	Yield
Stage #1: (R)-trolox With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide for 1h; Inert atmosphere; Stage #2: deferoxamine mesylate In N,N-dimethyl-formamide for 16h; Inert atmosphere;	62%

Downstream Products

• 1149568-53-5 DFOB-MPOAc 
• 1149568-62-6 DFOB-LDX 
• 156188-04-4 aluminoxamine 
• 84211-47-2 N-Succinyl-desferri-ferrioxyamin B 
• 1222468-90-7 N-[5-({3-[5-(acetyl-hydroxy-amino)-pentylcarbamoyl]-propionyl}-hydroxy-amino)-pentyl]-N'-hydroxy-N'-{5-[3-(4-isothiocyanato-phenyl)-thioureido]-pentyl}-succinamide 
• 14836-73-8 deferoxamine iron(III) complex 
• 122356-72-3 C₂₅H₄₅GaN₆O₈ 
• 94-93-9 N,N'-ethylenebis(salicylideneimine) 
• 929-24-8 N-(5-aminopentyl)hydroxylamine 
• 110-15-6 succinic acid 

Related news

DEFEROXAMINE MESYLATE (cas 138-14-7) enhances virulence of community-associated methicillin resistant Staphylococcus aureus09/29/2019

Staphylococcus aureus is a leading cause of bacterial infections. Strains of community-associated methicillin-resistant S. aureus (CA-MRSA), such as USA300, display enhanced virulence and fitness. Patients suffering from iron overload diseases often undergo iron chelation therapy with deferoxami...detailed

The Effects of DEFEROXAMINE MESYLATE (cas 138-14-7) on Iron Elimination after Blood Transfusion in Neonatal Foals10/01/2019

Background: Hepatic failure is one of the more common complications in foals requiring blood transfusion to treat neonatal isoerythrolysis. Iron intoxication is likely the cause of hepatic injury. Objectives: To determine the effects of deferoxamine on iron elimination in normal foals. Animals...detailed

Relevant articles and documents

Multistage process for the preparation of highly pure deferoxamine mesylate salt

The present invention provides a purification process whereby deferoxamine B produced by a microorganism and in mixture with other polyhydroxamates produced by the microorganism may be converted into its mesylate salt substantially free of the other polyhydroxamates and substantially free of chloride ion. The process includes adsorption and desorption of the deferoxamine B on an adsorption resin, direct precipitation of the deferoxamine free base out of the eluent from the adsorption resin, contacting of the deferoxamine B free base with methanesulfonic acid and isolation of the deferoxamine B mesylate salt by precipitation. This process minimizes decomposition of deferoxamine B.