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(2R,3R,4S,5S,6R)-2-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;iron

PubChem CID
49800026
Structure
(2R,3R,4S,5S,6R)-2-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;iron_small.png
(2R,3R,4S,5S,6R)-2-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;iron_3D_Structure.png
Molecular Formula
Synonyms
  • Iron sucrose
  • SCHEMBL106974
  • (2R,3R,4S,5S,6R)-2-{[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol iron
Molecular Weight
398.14 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Parent Compound
Dates
  • Create:
    2010-12-22
  • Modify:
    2025-01-25
Description
Iron sucrose (sucroferric oxyhydroxide or iron saccharate) is used as a source of iron in patients with iron deficiency anemia with chronic kidney disease (CKD), including those who are undergoing dialysis (hemodialysis or peritoneal) and those who do not require dialysis. Due to less side effects than iron dextran, iron sucrose is more preferred in chronic kidney disease patients.
Iron Sucrose is a sterile aqueous complex of polynuclear iron (III)-hydroxide in sucrose for intravenous use. Following intravenous administration, iron sucrose is dissociated by the reticuloendothelial system into iron and sucrose; the sucrose component is eliminated mainly by urinary excretion. Iron sucrose can be administered with or without erythropoietin to raise hemoglobin levels and may be used in cases of oral iron therapy intolerance or ineffectiveness. Hypersensitivity reactions are less common with iron sucrose compared to other parenteral iron products, such as iron dextran.
A glucaric acid-iron conjugate that is used in the treatment of IRON-DEFICIENCY ANEMIA, including in patients with chronic kidney disease, when oral iron therapy is ineffective or impractical.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
(2R,3R,4S,5S,6R)-2-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;iron.png

1.2 3D Conformer

3D Conformer of Parent

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R,3R,4S,5S,6R)-2-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;iron
Computed by Lexichem TK 2.7.0 (PubChem release 2021.05.07)

2.1.2 InChI

InChI=1S/C12H22O11.Fe/c13-1-4-6(16)8(18)9(19)11(21-4)23-12(3-15)10(20)7(17)5(2-14)22-12;/h4-11,13-20H,1-3H2;/t4-,5-,6-,7-,8+,9-,10+,11-,12+;/m1./s1
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

2.1.3 InChIKey

HQXGNTOSLWOUDQ-AKSHDPDZSA-N
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

2.1.4 SMILES

C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@]2([C@H]([C@@H]([C@H](O2)CO)O)O)CO)O)O)O)O.[Fe]
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C12H22FeO11
Computed by PubChem 2.1 (PubChem release 2021.05.07)

2.3 Other Identifiers

2.3.1 CAS

8047-67-4

2.3.2 DrugBank ID

2.3.3 NCI Thesaurus Code

2.3.4 RXCUI

2.3.5 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • D-Glucaric acid, iron(2+) salt (1:1)
  • Ferri Saccharate
  • ferri-saccharate
  • ferric oxide, saccharated
  • ferric saccharate
  • Hippiron
  • iron oxide (saccharated)
  • Iron Saccharate
  • iron sucrose
  • iron(III)-hydroxide sucrose complex
  • iron-saccharate
  • Saccharated Ferric Oxide
  • Venofer

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
398.14 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Donor Count
Property Value
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Acceptor Count
Property Value
11
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Rotatable Bond Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Exact Mass
Property Value
398.051147 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
398.051147 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
190 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Heavy Atom Count
Property Value
24
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
395
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
9
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
2
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2019.01.04)

3.2 Chemical Classes

3.2.1 Drugs

3.2.1.1 Human Drugs
Breast Feeding; Lactation; Milk, Human; Ferric Compounds; Hematinics; Iron Compounds

5 Chemical Vendors

6 Drug and Medication Information

6.1 Drug Indication

Iron sucrose is elemental iron as an injection. It replenishes body iron stores in patients with iron deficiency.

6.2 Drug Classes

Breast Feeding; Lactation; Milk, Human; Ferric Compounds; Hematinics; Iron Compounds

6.3 FDA National Drug Code Directory

6.4 Drug Labels

Drug and label
Active ingredient and drug

6.5 Clinical Trials

6.5.1 ClinicalTrials.gov

6.5.2 EU Clinical Trials Register

7 Pharmacology and Biochemistry

7.1 Pharmacodynamics

Significant increases in serum iron and serum ferritin and significant decreases in total iron binding capacity occurred four weeks from the initiation of iron sucrose treatment.

7.2 MeSH Pharmacological Classification

Hematinics
Agents which improve the quality of the blood, increasing the hemoglobin level and the number of erythrocytes. They are used in the treatment of anemias. (See all compounds classified as Hematinics.)

7.3 FDA Pharmacological Classification

Non-Proprietary Name
IRON SUCROSE
Pharmacological Classes
Phosphate Chelating Activity [MoA]; Iron [CS]; Phosphate Binder [EPC]; Parenteral Iron Replacement [EPC]

7.4 Absorption, Distribution and Excretion

Absorption
The intravensously administered iron sucrose injection would result rapidly in high serum iron levels. Maximum measured levels occured after 10 min of injection with an average of 30.00 mg/l.
Route of Elimination
Renal elimination of iron contributed very little to the total elimination (in average less than 5%). While, renal elimination of sucrose accounts for 68-75% of the administered dose after 4 and 24 hours respectively.
Volume of Distribution
Vd is 7.3 L
Clearance
Total body clearance is 20.5 ml/min.

7.5 Metabolism / Metabolites

Following IV administration, dissociated into iron and sucrose by the reticuloendothelial system.

7.6 Biological Half-Life

6 hours.

7.7 Mechanism of Action

Following intravenous administration, iron sucrose is dissociated into iron and sucrose and the iron is transported as a complex with transferrin to target cells including erythroid precursor cells. The iron is then incorporated into hemoglobin as the cells mature into red blood cells.

8 Toxicity

8.1 Toxicological Information

8.1.1 Effects During Pregnancy and Lactation

◉ Summary of Use during Lactation

Limited data indicate that breastmilk iron is not increased after intravenous infusion of iron sucrose. Amounts of iron ingested by the infant would be normal and are not expected to cause any adverse effects in breastfed infants. The oral form of the drug, called sucroferric oxyhydroxide and used as a phosphate binder, is not orally absorbed and it is unlikely to reach the breastmilk or adversely affect the breastfed infant. No special precautions are required. For additional information on iron use during breastfeeding, see the monograph on Iron Salts.

◉ Effects in Breastfed Infants

In a study of 104 women with postpartum anemia, 78 women received 300 mg of intravenous iron sucrose over 3 days. All women were breastfeeding and had amenorrhea. No adverse reactions were reported in their infants.

◉ Effects on Lactation and Breastmilk

Relevant published information was not found as of the revision date.

8.1.2 Protein Binding

It binds with transferrin.

9 Literature

9.1 Consolidated References

9.2 NLM Curated PubMed Citations

9.3 Chemical Co-Occurrences in Literature

9.4 Chemical-Gene Co-Occurrences in Literature

9.5 Chemical-Disease Co-Occurrences in Literature

10 Patents

10.1 Depositor-Supplied Patent Identifiers

11 Interactions and Pathways

11.1 Drug-Drug Interactions

11.2 Drug-Food Interactions

Take with food. Take with meals to maximize phosphate binding capacity and reduce phosphate absorption.

12 Classification

12.1 MeSH Tree

13 Information Sources

  1. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  2. DailyMed
  3. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  4. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  5. Drugs and Lactation Database (LactMed)
  6. EU Clinical Trials Register
  7. National Drug Code (NDC) Directory
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  8. NLM RxNorm Terminology
    LICENSE
    The RxNorm Terminology is created by the National Library of Medicine (NLM) and is in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from NLM. Credit to the U.S. National Library of Medicine as the source is appreciated but not required. The full RxNorm dataset requires a free license.
    https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html
  9. Wikipedia
  10. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  11. PubChem
CONTENTS