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Preussischblau

Preussischblau

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Also known as: Ferric ferrocyanide, Iron(iii) hexacyanoferrate(ii), Prussian blue insoluble, Iron(2+);iron(3+);octadecacyanide, Iron(iii) ferrocyanide; milori blue, Ferrocin

Molecular Formula

C₁₈Fe₇N₁₈

Molecular Weight

859.2 g/mol

InChI Key

DCYOBGZUOMKFPA-UHFFFAOYSA-N

Prussian blue is described as a deep blue pigment that is produced when the oxidation of ferrous ferrocyanide salts occurs. It contains ferric hexacyanoferrate(II) in a cubic lattice crystal structure. It is insoluble in water but also tends to form a colloid thus can exist in either colloidal or water-soluble form, and an insoluble form. It is orally administered for clinical purposes to be used as an antidote for certain kinds of heavy metal poisoning, such as thallium and radioactive isotopes of caesium. Prussian blue is included in the World Health Organization Model List of Essential Medicines as a specific antidote used in poisonings to provide symptomatic and supportive treatment. It was also administered in individuals exposed to 137-Cs+ during Goinia accident, one of the worst radioactive contamination incidents that occured in Brazil, 1983.

1 2D Structure

Preussischblau

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

iron(2+);iron(3+);octadecacyanide

2.1.2 InChI

InChI=1S/18CN.7Fe/c18*1-2;;;;;;;/q18*-1;3*+2;4*+3

2.1.3 InChI Key

DCYOBGZUOMKFPA-UHFFFAOYSA-N

2.1.4 Canonical SMILES

[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[Fe+2].[Fe+2].[Fe+2].[Fe+3].[Fe+3].[Fe+3].[Fe+3]

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Berlin Blue

2. Ferric Ferrocyanide

3. Ferrihexacyanoferrate

4. Ferrocin

5. Ferrotsin

2.2.2 Depositor-Supplied Synonyms

1. Ferric Ferrocyanide

2. Iron(iii) Hexacyanoferrate(ii)

3. Prussian Blue Insoluble

4. Iron(2+);iron(3+);octadecacyanide

5. Iron(iii) Ferrocyanide; Milori Blue

6. Ferrocin

7. Parisian Blue

8. Preussischblau

9. Turnbulls Blau

10. Berliner Blau

11. Mfcd00135663

12. Iron (iii) Ferrocyanide

13. Chebi:30069

14. Iron(3+) Hexacyanoferrate(4-)

15. Iron(iii) Hexacyanidoferrate(ii)

16. Iron(3+) Hexacyanidoferrate(4-)

17. Akos025310680

18. Db06783

19. Q421894

2.3 Create Date

2005-07-19

3 Chemical and Physical Properties

Molecular Formula	C₁₈Fe₇N₁₈
Molecular Weight	859.2 g/mol
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	36
Rotatable Bond Count	0
Exact Mass	859.59988 g/mol
Monoisotopic Mass	859.59988 g/mol
Topological Polar Surface Area	428 Å²
Heavy Atom Count	43
Formal Charge	0
Complexity	127
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	25

4 Drug and Medication Information

4.1 Drug Indication

Indicated for treatment of patients with known or suspected internal contamination with radioactive cesium and/or radioactive or non-radioactive thallium to increase their rates of elimination.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Prussian blue is an insoluble radioactive metals chelating agent and absorbent. It acts by ion-exchange, adsorption, and mechanical trapping within the crystal structure and has a very high affinity for radioactive and non-radioactive cesium and thallium. The antidote therapy greatly minimizes the extent of contamination and reduces the half life of radioactive isotopes which have relatively long physicall half life and uniform tissue distribution. Data suggest that in humans, Prussian blue can reduce cesiums half-life by approximately 43% and reduce total body burdens by significantly increasing the feces-to-urine excretion ratio.

5.2 MeSH Pharmacological Classification

Antidotes

Agents counteracting or neutralizing the action of POISONS. (See all compounds classified as Antidotes.)

Coloring Agents

Chemicals and substances that impart color including soluble dyes and insoluble pigments. They are used in INKS; PAINTS; and as INDICATORS AND REAGENTS. (See all compounds classified as Coloring Agents.)

5.3 ATC Code

V - Various

V03 - All other therapeutic products

V03A - All other therapeutic products

V03AB - Antidotes

V03AB31 - Prussian blue

5.4 Absorption, Distribution and Excretion

Absorption

It is poorly or not absorbed from the gastrointestinal tract walls after oral ingestion. Systemic absorption is assumed to be insignificant, with minimal release of cyanide from the complex. A small amount (approximately 2%) of the hexacyanoferrate ion was absorbed after oral ingestion of prussian blue but with no signs of decomposition. Prussian blue is not systemically bioavailable.

Route of Elimination

It predominantly depends on fecal excretion, and does not depend on renal elimination. Based on animal data, 99% of a single dose of 40 mg of labeled insoluble Prussian blue was excreted unchanged in feces.

Volume of Distribution

Histopathological examination of different organs showed no deposits of prussian blue after oral administration of insoluble prussian blue.

Clearance

The clearance from the body depends on the gastrointestinal tract transit time.

5.5 Metabolism/Metabolites

No evidence of decomposition after oral ingestion. Prussian blue does not undergo hepatic metabolism; use of the drug is not contraindicated in patients with hepatic impairment.

5.6 Mechanism of Action

Prussian blue binds cesium and thallium isotopes in the gastrointestinal tract after ingestion or excreted in the bile by the liver, therby reduces gastrointestinal reabsorption into the enterohepatic circulation. It serves as an ion exchanger for univalent cations and it preferentially binds to cesium or thallium as its affinity for cations increases as the ionic radius of the cation increases. Prussian blue exchanges potassium for cesium or thallium at the surface of the crystal in the intestinal lumen. The insoluble complex is excreted without being absorbed from the intestinal walls. Insoluble prussian blue decreases the half life of cesium by 33% and from 3.8 to 2.2 days for thallium. The rate of cesium and thallium elimination is proportional to the dose and duration of prussian blue.