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Hemin

From Wikipedia, the free encyclopedia
Class of compounds; (chloro)porphyrinato iron(III) complexes
For the given name, seeHemin (given name). For the Buddhist monk, seeHaemin (monk).

Pharmaceutical compound
Hemin
Clinical data
AHFS/Drugs.comConsumer Drug Information
Routes of
administration
Intravenous infusion
ATC code
Legal status
Legal status
Identifiers
  • Chloro[3,7,12,17-tetramethyl-8,13-divinylporphyrin-2,18-dipropanoato(2−)]iron(III)
CAS Number
PubChemCID
ChemSpider
UNII
ChEBI
ChEMBL
Chemical and physical data
FormulaC34H32ClFeN4O4
Molar mass651.95 g·mol−1
3D model (JSmol)
  • OC(=O)CCC=5C1=C\C6=N\C(=C/c3n2[Fe](Cl)N1C(=C\C4=N\C(=C/c2c(C=C)c3C)C(/C)=C4/C=C)/C=5C)C(\C)=C6\CCC(O)=O
  • InChI=1S/C34H34N4O4.ClH.Fe/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25;;/h7-8,13-16H,1-2,9-12H2,3-6H3,(H4,35,36,37,38,39,40,41,42);1H;/q;;+3/p-3/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16?;; checkY
  • Key:BTIJJDXEELBZFS-UKFHATERSA-K checkY
 ☒NcheckY (what is this?)  (verify)

Hemin (haemin; ferric chloride heme) is aniron-containingporphyrin with chlorine that can be formed from aheme group, such asheme B found in thehemoglobin of human blood.

Chemistry

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Hemin isprotoporphyrin IX containing aferric iron (Fe3+) ion with acoordinatingchloride ligand.

Chemically, hemin differs from the related heme-compoundhematin chiefly in that the coordinating ion is a chloride ion in hemin, whereas the coordinating ion is ahydroxide ion in hematin.[2] The iron ion in haem is ferrous (Fe2+), whereas it is ferric (Fe3+) in both hemin and hematin.

Hemin is endogenously produced in the human body, for example during the turnover of oldred blood cells. It can form inappropriately as a result ofhemolysis or vascular injury. Several proteins in human blood bind to hemin, such ashemopexin andserum albumin.

Pharmacological use

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A lyophilised form of hemin is used as a pharmacological agent in certain cases for the treatment ofporphyria attacks, particularly inacute intermittent porphyria. Administration of hemin can reduce heme deficits in such patients, thereby suppressing the activity ofdelta-amino-levulinic acid synthase (a key enzyme in the synthesis of the porphyrins) by biochemical feedback, which in turn reduces the production of porphyrins and of the toxic precursors of heme. In such pharmacological contexts, hemin is typically formulated withhuman albumin prior to administration by a medical professional, to reduce the risk ofphlebitis and to stabilize the compound, which is potentially reactive if allowed to circulate in free-form. Such pharmacological forms of hemin are sold under a range of trade names including the trademarks Panhematin[3] and Normosang.[4]

History of isolation

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Hemin was first crystallized out of blood in 1853, byLudwik Karol Teichmann. Teichmann discovered that blood pigments can form microscopic crystals. Thus, crystals of hemin are occasionally referred to as 'Teichmann crystals'.Hans Fischer synthesized hemin, for which he was awarded the Nobel Prize in Chemistry in 1930.[5] Fischer's procedure involves treating defibrinated blood with a solution of sodium chloride in acetic acid.[6]

Forensics

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Hemin can be produced from hemoglobin by the so-calledTeichmann test, when hemoglobin is heated with glacial acetic acid (saturated with saline). This can be used to detect blood traces.

Other

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Hemin is considered the "X factor" required for the growth ofHaemophilus influenzae.[7]

References

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  1. ^"Regulatory Decision Summary for Panhematin". 23 October 2014.
  2. ^Grenoble DC, Drickamer HG (December 1968)."The effect of pressure on the oxidation state of iron. 3. Hemin and hematin"(PDF).Proceedings of the National Academy of Sciences of the United States of America.61 (4):1177–82.Bibcode:1968PNAS...61.1177G.doi:10.1073/pnas.61.4.1177.PMC 225235.PMID 5249803.
  3. ^"Panhematin for Acute Porphyria".American Porphyria Foundation. Archived fromthe original on 12 March 2018. Retrieved30 September 2017.
  4. ^"Normosang".Electronic Medicines Compendium (eMC).
  5. ^Fischer H."On hemin and the relationships between hemin and chlorophyll"(PDF).Nobel Lecture. Nobel Prize Foundation.{{cite web}}: CS1 maint: overridden setting (link)
  6. ^Fischer H (1941). "Hemin".Org. Synth.21: 53.doi:10.15227/orgsyn.021.0053.{{cite journal}}: CS1 maint: overridden setting (link)
  7. ^Sherris JC, Ryan KJ, Ray CL (2004).Sherris medical microbiology: an introduction to infectious diseases. New York: McGraw-Hill. p. 395.ISBN 0-8385-8529-9.

External links

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