Hemin

Hemin
Clinical data
AHFS/Drugs.com	Consumer Drug Information
Routes of; administration	Intravenous infusion
ATC code	B06AB01(WHO);
Legal status
Legal status	CA:℞-only/Schedule D; US:℞-only;
Identifiers
	IUPAC name Chloro[3,7,12,17-tetramethyl-8,13-divinylporphyrin-2,18-dipropanoato(2−)]iron(III);
CAS Number	16009-13-5;
PubChemCID	5318002;
ChemSpider	21160444;
UNII	743LRP9S7N;
ChEBI	CHEBI:50385;
ChEMBL	ChEMBL1628226;
Chemical and physical data
Formula	C34H32ClFeN4O4
Molar mass	651.95g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 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?;;; Key:BTIJJDXEELBZFS-UKFHATERSA-K;
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Hemin(haemin;ferric chloride heme) is aniron-containingporphyrinwith chlorine that can be formed from ahemegroup, such asheme Bfound in thehemoglobinof human blood.

Chemistry

Hemin isprotoporphyrin IXcontaining aferriciron (Fe³⁺) ion with acoordinating chlorideligand.

Chemically, hemin differs from the related heme-compoundhematinchiefly in that the coordinating ion is a chloride ion in hemin, whereas the coordinating ion is ahydroxideion 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 ofhemolysisor vascular injury. Several proteins in human blood bind to hemin, such ashemopexinandserum albumin.

Pharmacological use

A lyophilised form of hemin is used as a pharmacological agent in certain cases for the treatment ofporphyriaattacks, 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 albuminprior to administration by a medical professional, to reduce the risk ofphlebitisand 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

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 Fischersynthesized 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

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

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

References

^"Search Page - Drug and Health Product Register".23 October 2014.
^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.PMC225235.PMID 5249803.
^"Panhematin for Acute Porphyria".American Porphyria Foundation.Archived fromthe originalon 2018-03-12.Retrieved2017-09-30.
^"Normosang".Electronic Medicines Compendium (eMC).
^Fischer H."On hemin and the relationships between hemin and chlorophyll"(PDF).Nobel Lecture.Nobel Prize Foundation.
^Fischer H (1941). "Hemin".Org. Synth.21:53.doi:10.15227/orgsyn.021.0053.
^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

Informationfrom the American Porphyria Foundation, including emergency delivery information
Hemin at RxList
Heminat the U.S. National Library of MedicineMedical Subject Headings(MeSH)

[1] "Search Page - Drug and Health Product Register".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.PMC225235.PMID 5249803.

[3] "Panhematin for Acute Porphyria".American Porphyria Foundation.Archived fromthe originalon 2018-03-12.Retrieved2017-09-30.

[4] "Normosang".Electronic Medicines Compendium (eMC).

[5] Fischer H."On hemin and the relationships between hemin and chlorophyll"(PDF).Nobel Lecture.Nobel Prize Foundation.

[6] Fischer H (1941). "Hemin".Org. Synth.21:53.doi:10.15227/orgsyn.021.0053.

[isbn0-8385-8529-9-7] 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.

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