Deferoxamine (mesylate)

Modify Date: 2024-01-01 17:25:28

Deferoxamine (mesylate) Structure
Deferoxamine (mesylate) structure
Common Name Deferoxamine (mesylate)
CAS Number 138-14-7 Molecular Weight 752.895
Density N/A Boiling Point 966.9ºC at 760 mmHg
Molecular Formula C26H52N6O11S Melting Point 148-149°
MSDS Chinese USA Flash Point 538.5ºC

 Use of Deferoxamine (mesylate)


Deferoxamine mesylate is an iron chelator that binds free iron in a stable complex, preventing it from engaging in chemical reactions.

 Names

Name desferrioxamine B mesylate
Synonym More Synonyms

 Deferoxamine (mesylate) Biological Activity

Description Deferoxamine mesylate is an iron chelator that binds free iron in a stable complex, preventing it from engaging in chemical reactions.
Related Catalog
In Vitro Deferoxamine treatment significantly increases HIF-1α binding under all culture conditions, including hypoxic and high-glucose. The mechanism of deferoxamine is through improving HIF-1α biological function through scavenging oxygen free radicals[1]. Deferoxamine (5 μM) has significant effect on the tumor-associated stromal cells cellular multiplication, and cells die at day 7 after exposure to 50 μM and 100 μM deferoxamine. Deferoxamine (5 μM-100 μM) inhibits the proliferation of BMMSCs, and induces apoptosis of MSCs in a dose-dependent manner. Deferoxamine influences the expression of adhesion proteins on MSCs[3]. Deferoxamine (30, 60, 120 μM) shows lower expression of HIF-1α in a concentration dependent way in AdMSCs[4].
In Vivo Deferoxamine (100 mg/kg, i.p.) lowers the mortality rate of subarachnoid hemorrhage (SAH) rat. Deferoxamine (100 mg/kg, i.p.) attenuates Evan’s blue extravasation in cortex, ameliorates the tight junction detachment and preserves the integrity of the base membrane examined in electron microscope at day 3 after SAH. Deferoxamine attenuates degradation of BBB proteins after SAH and significantly reduces ferritin expression at day 3 in the cortex, and improves neurologic behavior and cognitive deficits after experimental[1]. Ten µL of 1 mM deferoxamine-treated wounds display significantly accelerated healing from day 7 onward and heal significantly faster than control-treated wounds in diabetic mice. Deferoxamine-treated wounds and dimethyloxalylglycine-treated wounds heal significantly faster than control-treated wounds in aged mice[2]. In deferoxamine (10 mg/mL)-treated TG mice, there is a decrease in both soluble and insoluble Aβ40 and Aβ42. Both pGSK3β and β-catenin are significantly increased by approximately 50% in the deferoxamine-treated mice[5].
Cell Assay Harvested murine tumor and bone marrow-derived MSCs are exposed to varying doses of deferoxamine. Cell viability is assessed by trypan blue exclusion assay. The viable cells are more than 98% before enrolled for experiments. A total of 1.5×105 TAMSCs/well or 3×105 BMMSCs/well are seeded in 6-well plates. Then MSCs are exposed to 5, 10, 25, 50, and 100 μM deferoxamine on the following day. After 7 days, the number of TAMSCs is counted. To assess the cytotoxicity of deferoxamine to primary bone marrow MSCs, 2×106 bone marrow cells/well are seeded in 24-well plates. After 9 days, the number of survival cells is counted. To assess the cell cycle, TAMSCs are stained with propidium iodide, and cell cycle distribution is analyzed by flow cytometry.
Animal Admin Mice are divided into three treatment groups of 17 each: (1) TG mice given IN Deferoxamine (TG-DFO), (2) TG mice given IN phosphate buffered saline (TG-PBS), and (3) WT mice given IN PBS (WT-PBS). At 30 weeks of age, mice are acclimated to handling and then treated intranasally every monday, wednesday, and friday, starting at 36 weeks of age. Mice are dosed for 18 weeks, until behavior tests at 54 weeks. Dosing continues during the 4 weeks of behavior to measure both chronic and acute effects. After behavior mice are dosed a final time, and 24 h later euthanized and tissues collected for biochemical analyses. These include soluble and insoluble amyloid as measured by ELISA and IHC, quantification of proteins with Western blot and oxidative markers.
References

[1]. Li Y, et al. Effects of deferoxamine on blood-brain barrier disruption after subarachnoid hemorrhage. PLoS One. 2017 Mar 1;12(3):e0172784

[2]. Duscher D, et al. Comparison of the Hydroxylase Inhibitor Dimethyloxalylglycine and the Iron Chelator Deferoxamine in Diabetic and Aged Wound Healing. Plast Reconstr Surg. 2017 Mar;139(3):695e-706e

[3]. Wang G, et al. In vitro assessment of deferoxamine on mesenchymal stromal cells from tumor and bone marrow. Environ Toxicol Pharmacol. 2017 Jan;49:58-64

[4]. Wahl EA, et al. VEGF released by deferoxamine preconditioned mesenchymal stem cells seeded on collagen-GAG substrates enhances neovascularization. Sci Rep. 2016 Nov 10;6:36879

[5]. Fine JM, et al. Intranasal deferoxamine engages multiple pathways to decrease memory loss in the APP/PS1 model of amyloid accumulation. Neurosci Lett. 2015 Jan 1;584:362-7

 Chemical & Physical Properties

Boiling Point 966.9ºC at 760 mmHg
Melting Point 148-149°
Molecular Formula C26H52N6O11S
Molecular Weight 752.895
Flash Point 538.5ºC
Exact Mass 752.329590
PSA 268.59000
LogP 2.98900
Vapour Pressure 0mmHg at 25°C
Storage condition −20°C
Water Solubility H2O: 50 mg/mL

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UG5310000
CHEMICAL NAME :
Propionohydroxamic acid, N-(5-(3-((5-aminopentyl)hydroxycarbamoyl)propionamido )pentyl)- 3-((5-(N-hydroxyacetamido)pentyl)carbamoyl)-, monomethanesulfonate (salt)
CAS REGISTRY NUMBER :
138-14-7
LAST UPDATED :
199504
DATA ITEMS CITED :
12
MOLECULAR FORMULA :
C25-H48-N6-O8.C-H4-O3-S
MOLECULAR WEIGHT :
656.90
WISWESSER LINE NOTATION :
Z5NQV2VM5NQV2VM5NQV1 &WSQ1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
150 mg/kg/4D-I
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea Gastrointestinal - nausea or vomiting
REFERENCE :
BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 291,448,1985
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
143 mg/kg/4D-I
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - visual field changes Gastrointestinal - hypermotility, diarrhea Gastrointestinal - nausea or vomiting
REFERENCE :
BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 291,448,1985
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Parenteral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
16 gm/kg/34W-I
TOXIC EFFECTS :
Cardiac - pericarditis Gastrointestinal - ulceration or bleeding from small intestine Blood - other changes
REFERENCE :
AJKDDP American Journal of Kidney Diseases. (Grune & Stratton, Inc., Journal Subscription Dept., POB 6280, Duluth, MN 55806) V.1- 1981- Volume(issue)/page/year: 10,71,1987
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
900 mg/kg/30W-I
TOXIC EFFECTS :
Brain and Coverings - other degenerative changes Cardiac - cardiomyopathy including infarction Lungs, Thorax, or Respiration - acute pulmonary edema
REFERENCE :
AJMEAZ American Journal of Medicine. (Technical Pub., 875 Third Ave., New York, NY 10022) V.1- 1946- Volume(issue)/page/year: 87,468,1989
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
17300 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,496,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
5500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,496,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
330 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,496,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
15200 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,496,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1240 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 7,1181,1973
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1280 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 7,1181,1973
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
273 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,496,1982 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5340 No. of Facilities: 19 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 679 (estimated) No. of Female Employees: 350 (estimated)

 Safety Information

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Safety Phrases 22-24/25
RIDADR NONH for all modes of transport
WGK Germany 2
RTECS UG5310000

 Precursor & DownStream

Precursor  0

DownStream  2

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 Synonyms

Desferal methanesulfonate
DEFEROXAMINE MESYLATE
Deferoxamine Methanesulfonate
N'-{5-[Acetyl(hydroxy)amino]pentyl}-N-[5-({4-[(5-aminopentyl)(hydroxy)amino]-4-oxobutanoyl}amino)pentyl]-N-hydroxysuccinamide methanesulfonate (1:2)
Deferoxamine mesylate salt
DESFERAL MESYLATE
EINECS 205-314-3
Butanediamide, N-[5-(acetylhydroxyamino)pentyl]-N-[5-[[4-[(5-aminopentyl)hydroxyamino]-1,4-dioxobutyl]amino]pentyl]-N-hydroxy-, methanesulfonate (1:2) (salt)
MFCD00058605
DFOM,Deferoxamine methanesulfonate salt,Desferrioxamine mesylate salt
Deferoxamine (mesylate)
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