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			{{Short description\|Class of compounds; (chloro)porphyrinato iron(III) complexes}}
	{{for\|the given name\|Hemin (given name)}}
			{{About\|\|the given name\|Hemin (given name)\|the Buddhist monk\|Haemin (monk)}}
	{{drugbox
			{{Use dmy dates\|date=August 2024}}
	\| verifiedrevid = 390283117
			{{cs1 config \|name-list-style=vanc \|display-authors=6}}
	\| IUPAC_name = chloroiron(III)
			{{Infobox drug
	\| image = Hemin.svg
			\| Verifiedfields = changed
	\| image2 = Hemin edit1.jpg
			\| Watchedfields = changed
	\| CASNo_Ref = {{cascite\|correct\|CAS}}
			\| verifiedrevid = 396492199
			\| image = Hemin.svg
			\| image2 = Hemin edit1.jpg

			<!--Clinical data-->
			\| tradename =
			\| Drugs.com = {{drugs.com\|CDI\|hemin}}
			\| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
			\| routes_of_administration = ]

			\| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
			\| legal_CA = Rx-only
			\| legal_CA_comment = /{{nbsp}}Schedule D<ref>{{cite web \| url=https://hpr-rps.hres.ca/reg-content/regulatory-decision-summary-detail.php?lang=en&linkID=RDS00395 \| title=Regulatory Decision Summary for Panhematin \| date=23 October 2014 }}</ref>
			\| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
			\| legal_US = Rx-only
			\| legal_status =

			<!--Pharmacokinetic data-->
			\| bioavailability =
			\| protein_bound =
			\| metabolism =
			\| elimination_half-life =
			\| excretion =

			<!--Identifiers-->
			\| CAS_number_Ref = {{cascite\|correct\|??}}
			\| CAS_number = 16009-13-5
			\| ATC_prefix = B06
			\| ATC_suffix = AB01
			\| PubChem = 5318002
			\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
			\| DrugBank =
			\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 21160444		\| ChemSpiderID = 21160444
			\| ChEBI = 50385
	\| UNII_Ref = {{fdacite\|correct\|FDA}}		\| UNII_Ref = {{fdacite\|correct\|FDA}}
	\| UNII = 743LRP9S7N		\| UNII = 743LRP9S7N
			\| ChEMBL_Ref = {{ebicite\|changed\|EBI}}
	\| InChI = 1/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-,32-16u;;/rC34H32ClFeN4O4/c1-7-21-17(3)26-14-31-22(8-2)19(5)29-13-25-18(4)23(9-11-33(41)42)28(38-25)16-32-24(10-12-34(43)44)20(6)30(15-27(21)37-26)40(32)36(35)39(29)31/h7-8,13-16H,1-2,9-12H2,3-6H3,(H,41,42)(H,43,44)/b25-13-,26-14-,27-15-,28-16-,29-13-,30-15-,31-14-,32-16u
			\| ChEMBL = 1628226
	\| InChIKey = BTIJJDXEELBZFS-GASBFGGMBO

			<!--Chemical data-->
			\| IUPAC_name = Chloroiron(III)
			\| C=34 \| H=32 \| Cl=1 \| Fe=1 \| N=4 \| O=4
			\| smiles = OC(=O)CCC=5C1=C\C6=N\C(=C/c3n2(Cl)N1C(=C\C4=N\C(=C/c2c(C=C)c3C)C(/C)=C4/C=C)/C=5C)C(\C)=C6\CCC(O)=O
			\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChI = 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?;;		\| StdInChI = 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?;;
			\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChIKey = BTIJJDXEELBZFS-UKFHATERSA-K		\| StdInChIKey = BTIJJDXEELBZFS-UKFHATERSA-K
	\| CAS_number = 16009-13-5
	\| ATC_prefix = B06
	\| ATC_suffix = AB01
	\| PubChem = 5318002
	\| DrugBank =
	\| C=34\|H=32\|Cl=1\|Fe=1\|N=4\|O=4
	\| molecular_weight = 651.94 g/mol
	\| smiles = OC(=O)CCC=5C1=C\C6=N\C(=C/c3n2(Cl)N1C(=C\C4=N\C(=C/c2c(C=C)c3C)C(/C)=C4/C=C)/C=5C)C(\C)=C6\CCC(O)=O
	\| bioavailability =
	\| protein_bound =
	\| metabolism =
	\| elimination_half-life =
	\| excretion =
	\| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
	\| pregnancy_US = C
	\| pregnancy_category=
	\| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
	\| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
	\| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
	\| legal_US = Rx-only
	\| legal_status =
	\| routes_of_administration = ]
	}}		}}
	'''Hemin''' (trade name '''Panhematin''') is an ]-containing ].<ref>{{DorlandsDict\|four/000048040\|hemin}}</ref> More specifically, it is ] containing a ] iron ion (]) with a ] ligand.


			'''Hemin''' ('''haemin'''; ferric chloride heme) is an ]-containing ] with chlorine that can be formed from a ] group, such as ] found in the ] of human blood.
	It is used in the management of ] attacks, particularly in ].

			==Chemistry==
	It is sometimes distinguished from '''Hematin''' which has a ] ligand in place of the chloride. However, the terms are sometimes equated.<ref>{{DorlandsDict\|four/000047749\|hematin}}</ref>
			Hemin is ] containing a ] iron (Fe<sup>3+</sup>) ion with a ] ] ligand.

			Chemically, hemin differs from the related heme-compound ] chiefly in that the coordinating ion is a chloride ion in hemin, whereas the coordinating ion is a ] ion in hematin.<ref>{{cite journal \| vauthors = Grenoble DC, Drickamer HG \| title = The effect of pressure on the oxidation state of iron. 3. Hemin and hematin \| journal = Proceedings of the National Academy of Sciences of the United States of America \| volume = 61 \| issue = 4 \| pages = 1177–82 \| date = December 1968 \| pmid = 5249803 \| pmc = 225235 \| doi = 10.1073/pnas.61.4.1177 \| bibcode = 1968PNAS...61.1177G \| url = http://www.pnas.org/content/61/4/1177.full.pdf \| doi-access = free }}</ref> The iron ion in haem is ferrous (Fe<sup>2+</sup>), whereas it is ferric (Fe<sup>3+</sup>) in both hemin and hematin.
	Hematin is considered the "X factor" required for the growth of '']''.<ref name="isbn0-8385-8529-9">{{cite book \|author=Sherris, John C.; Ryan, Kenneth J.; Ray, C. L. \|title=Sherris medical microbiology: an introduction to infectious diseases \|publisher=McGraw-Hill \|location=New York \|year=2004 \|pages=395 \|isbn=0-8385-8529-9 \|oclc= \|doi= \|accessdate=}}</ref>

			Hemin is endogenously produced in the human body, for example during the turnover of old ]s. It can form inappropriately as a result of ] or vascular injury. Several proteins in human blood bind to hemin, such as ] and ].
	==References==
	{{reflist}}

			==Pharmacological use==
	==External links==
			A lyophilised form of hemin is used as a pharmacological agent in certain cases for the treatment of ] attacks, particularly in ]. Administration of hemin can reduce heme deficits in such patients, thereby suppressing the activity of ] (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 with ] prior to administration by a medical professional, to reduce the risk of ] 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<ref>{{Cite web\|url=http://www.porphyriafoundation.com/content/panhematin-acute-porphyria\|title=Panhematin for Acute Porphyria\|website=American Porphyria Foundation\|access-date=30 September 2017\|archive-date=12 March 2018\|archive-url=https://web.archive.org/web/20180312084311/http://www.porphyriafoundation.com/content/panhematin-acute-porphyria\|url-status=dead}}</ref> and Normosang.<ref>{{Cite web\|url=https://www.medicines.org.uk/emc/medicine/20795\|title=Normosang \|website=Electronic Medicines Compendium (eMC)}}</ref>
	* from the American Porphyria Foundation, including emergency delivery information
	*
	*{{MeshName\|Hemin}}

			==History of isolation==
			Hemin was first crystallized out of blood in 1853, by ]. Teichmann discovered that blood pigments can form microscopic crystals. Thus, crystals of hemin are occasionally referred to as 'Teichmann crystals'. ] synthesized hemin, for which he was awarded the Nobel Prize in Chemistry in 1930.<ref>{{Cite web\|url=https://www.nobelprize.org/nobel_prizes/chemistry/laureates/1930/fischer-lecture.pdf \| first = Hans \| last = Fischer \| name-list-style = vanc \|work = Nobel Lecture \| title = On hemin and the relationships between hemin and chlorophyll \| publisher = Nobel Prize Foundation}}</ref> Fischer's procedure involves treating defibrinated blood with a solution of sodium chloride in acetic acid.<ref>{{cite journal\|title=Hemin \| first = Hans \| last = Fischer \| name-list-style = vanc \|journal=Org. Synth.\|year= 1941\|volume=21\|page=53\|doi=10.15227/orgsyn.021.0053}}</ref>

			==Forensics==
			Hemin can be produced from hemoglobin by the so-called '''Teichmann 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 of '']''.<ref name="isbn0-8385-8529-9">{{cite book\|title=Sherris medical microbiology: an introduction to infectious diseases\| vauthors = Sherris JC, Ryan KJ, Ray CL \|publisher=McGraw-Hill\|year=2004\|isbn=0-8385-8529-9\|location=New York\|pages=395}}</ref>

			== References ==
			{{reflist}}

			== External links ==
			* {{MeSH name\|Hemin}}

			{{Portal bar \| Medicine}}
	{{blood-drug-stub}}
			{{Authority control}}
	{{biochem-stub}}

	]		]
			]
	]
	]
	]
	]
	]
	]

Latest revision as of 03:21, 14 August 2024

Class of compounds; (chloro)porphyrinato iron(III) complexes For the given name, see Hemin (given name). For the Buddhist monk, see Haemin (monk).

Pharmaceutical compound

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 Chloroiron(III)
CAS Number	16009-13-5
PubChem CID	5318002
ChemSpider	21160444
UNII	743LRP9S7N
ChEBI	CHEBI:50385
ChEMBL	ChEMBL1628226
Chemical and physical data
Formula	C₃₄H₃₂ClFeN₄O₄
Molar mass	651.95 g·mol
3D model (JSmol)	Interactive image
SMILES OC(=O)CCC=5C1=C\C6=N\C(=C/c3n2(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
(what is this?) (verify)

Hemin (haemin; ferric chloride heme) is an iron-containing porphyrin with chlorine that can be formed from a heme group, such as heme B found in the hemoglobin of human blood.

Chemistry

Hemin is protoporphyrin IX containing a ferric iron (Fe) ion with a coordinating chloride ligand.

Chemically, hemin differs from the related heme-compound hematin chiefly in that the coordinating ion is a chloride ion in hemin, whereas the coordinating ion is a hydroxide ion in hematin. The iron ion in haem is ferrous (Fe), whereas it is ferric (Fe) in both hemin and hematin.

Hemin is endogenously produced in the human body, for example during the turnover of old red blood cells. It can form inappropriately as a result of hemolysis or vascular injury. Several proteins in human blood bind to hemin, such as hemopexin and serum albumin.

Pharmacological use

A lyophilised form of hemin is used as a pharmacological agent in certain cases for the treatment of porphyria attacks, particularly in acute intermittent porphyria. Administration of hemin can reduce heme deficits in such patients, thereby suppressing the activity of delta-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 with human albumin prior to administration by a medical professional, to reduce the risk of phlebitis 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 and Normosang.

History of isolation

Hemin was first crystallized out of blood in 1853, by Ludwik 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. Fischer's procedure involves treating defibrinated blood with a solution of sodium chloride in acetic acid.

Forensics

Hemin can be produced from hemoglobin by the so-called Teichmann 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 of Haemophilus influenzae.

References

"Regulatory Decision Summary for Panhematin". 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. PMC 225235. PMID 5249803.
"Panhematin for Acute Porphyria". American Porphyria Foundation. Archived from the original on 12 March 2018. Retrieved 30 September 2017.
"Normosang". Electronic Medicines Compendium (eMC).
Fischer H. "On hemin and the relationships between hemin and chlorophyll" (PDF). Nobel Lecture. Nobel Prize Foundation.{{cite web}}: CS1 maint: overridden setting (link)
Fischer H (1941). "Hemin". Org. Synth. 21: 53. doi:10.15227/orgsyn.021.0053.{{cite journal}}: CS1 maint: overridden setting (link)
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

Hemin at the U.S. National Library of Medicine Medical Subject Headings (MeSH)

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