DEFEROXAMINE MESYLATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C25H48N6O8.CH4O3S
Molecular Weight	656.79
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CS(O)(=O)=O.CC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCN

InChI

InChIKey=IDDIJAWJANBQLJ-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C25H48N6O8
Molecular Weight	560.684
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	CH4O3S
Molecular Weight	96.106
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

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.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Iron 18	Chelating Agent 142

Conditions

Condition	Modality	Targets	Highest Phase	Product
Acute iron intoxication 5	Palliative		Approved 8,429	DESFERAL
Chronic iron overload 5	Palliative		Approved 8,429	DESFERAL

C_max

Value	Dose	Analyte	Population
6.1 μM	10 mg/kg single, intravenous	DEFEROXAMINE plasma	Homo sapiens
2.5 μM	10 mg/kg single, intravenous	DEFEROXAMINE plasma	Homo sapiens
12.9 μM	100 mg/kg 1 times / day other, intravenous	DEFEROXAMINE plasma	Homo sapiens
2.7 μM	100 mg/kg 1 times / day other, intravenous	DEFEROXAMINE plasma	Homo sapiens
7.4 μM	10 mg/kg 1 times / day other, intravenous	DEFEROXAMINE plasma	Homo sapiens
15.7 μM	10 mg/kg single, intramuscular	DEFEROXAMINE plasma	Homo sapiens
7 μM	10 mg/kg single, intramuscular	DEFEROXAMINE plasma	Homo sapiens
10.1 μM	40 mg/kg single, subcutaneous	DEFEROXAMINE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
354 μM × h	10 mg/kg 1 times / day other, intravenous		DEFEROXAMINE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
3.05 h	10 mg/kg 1 times / day other, intravenous		DEFEROXAMINE plasma	Homo sapiens
7.59 h	40 mg/kg single, subcutaneous		DEFEROXAMINE plasma	Homo sapiens

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1,587	inhibitor 1,767	inhibitor 1,852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1,524 CYP2C19 1,478 OATP1B1 788 OATP1B3 706

Drug as perpetrator

Show entries

Target	Modality	Activity
CYP1A2 1,692	inhibitor 3,277	no [Activation >10 uM]
CYP2C19 1,553	inhibitor 3,277	no [Activation >10 uM]
CYP2C9 1,819	inhibitor 3,277	no [Activation >10 uM]
CYP2D6 1,891	inhibitor 3,277	no [Activation >10 uM]
CYP3A4 1,925	inhibitor 3,277	no [Activation >10 uM]

Showing 1 to 5 of 7 entries

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Sourcing

Sourcing

Show entries

Vendor/Aggregator	ID	URL
001 Chemical	DY567909	https://www.001chemical.com/chem/70-51-9
AK Scientific, Inc. (AKSCI)	0917AC	http://www.aksci.com/item_detail.php?cat=0917AC
Alfa Chemistry	70-51-9	https://www.alfa-chemistry.com/deferoxamine-cas-70-51-9-item-293386.htm
Ambeed	A698741	https://www.ambeed.com/products/70-51-9.html
Angel Pharmatech	AG105071	http://www.angelpharmatech.com/70-51-9.html

Showing 1 to 5 of 23 entries

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PubMed

Show entries

Title	Date	PubMed
Inhibition of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD)-stimulated Cyp1a1 promoter activity by hypoxic agents.	2000 Jun 15	10799651
Neurons and astrocytes express EPO mRNA: oxygen-sensing mechanisms that involve the redox-state of the brain.	2000 May	10756076
Persistence of delayed adrenarche in boys with thalassemia.	2001 Apr	11327374
mRNA localization by a 145-nucleotide region of the c-fos 3'--untranslated region. Links to translation but not stability.	2001 Apr 27	11139568
Klebsiella pneumoniae meningitis in thalassemia major patients.	2001 Apr-May	11293293

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Patents

Sample Use Guides

In Vivo Use Guide

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

Unknown