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Details

Stereochemistry ACHIRAL
Molecular Formula C34H32N4O4.Cl.Fe
Molecular Weight 651.94
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HEMIN

SMILES

[Cl-].[Fe+3].CC1=C(CCC(O)=O)C2=CC3=NC(=CC4=C(C=C)C(C)=C([N-]4)C=C5N=C(C=C1[N-]2)C(C)=C5C=C)C(C)=C3CCC(O)=O

InChI

InChIKey=BTIJJDXEELBZFS-HXFTUNQESA-K
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-;;

HIDE SMILES / InChI

Molecular Formula C34H30N4O4
Molecular Weight 558.6264
Charge -2
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula Fe
Molecular Weight 55.845
Charge 3
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/17766326

Hemin (trade name Panhematin) is a protoporphyrin IX containing a ferric iron ion (heme B) with a chloride ligand, which is is indicated for the amelioration of recurrent attacks of acute intermittent porphyria temporally related to the menstrual cycle in susceptible women. Manifestations such as pain, hypertension, tachycardia, abnormal mental status and mild to progressive neurologic signs may be controlled in selected patients with this disorder. the therapy for the acute porphyrias is not curative. Heme acts to limit the hepatic and/or marrow synthesis of porphyrin. This action is likely due to the inhibition of δ-aminolevulinic acid synthetase, the enzyme which limits the rate of the porphyrin/heme biosynthetic pathway. The exact mechanism by which hematin produces symptomatic improvement in patients with acute episodes of the hepatic porphyrias has not been elucidated.

CNS Activity

Curator's Comment: hemin improves barrier function and neurological outcome in experimental models of traumatic and ischemic CNS injury

Originator

Curator's Comment: Protoporphyrin was first found to be an iron-free derivative of hemoglobin by Kämmerer in 1923

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Prolmon

Approved Use

Treatment of liver disorders
Primary
Panhematin

Approved Use

PANHEMATIN (hemin for injection) is indicated for the amelioration of recurrent attacks of acute intermittent porphyria temporally related to the menstrual cycle in susceptible women. Manifestations such as pain, hypertension, tachycardia, abnormal mental status and mild to progressive neurologic signs may be controlled in selected patients with this disorder. Similar findings have been reported in other patients with acute intermittent porphyria, porphyria variegata and hereditary coproporphyria. PANHEMATIN is not indicated in porphyria cutanea tarda.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
742 ng/mL
40 mg single, oral
dose: 40 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PROTOPORPHYRIN plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
9.6 μg × h/mL
40 mg single, oral
dose: 40 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PROTOPORPHYRIN plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4 h
40 mg single, oral
dose: 40 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PROTOPORPHYRIN plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

PubMed

PubMed

TitleDatePubMed
[Thin layer chromatographic separation of porphyrins, hemin and lipids on Silica Gel H plates for the determination of the erythrocyte porphyrins as their methyl esters].
1968 Jun 4
Micro-scale photofluorometric determination of "free erythrocyte pophyrin" (protoporphyrin IX).
1975 Oct
The selective enhancing influence of hemin and products of human erythrocytes on colony formation by human multipotential (CFUGEMM) and erythroid (BFUE) progenitor cells in vitro.
1983 Sep
[Erythrocyte protoporphyrin IX in occupational exposure to asbestos].
1984
[Protoporphyrin IX level in erythrocytes of persons with alcoholic liver cirrhosis].
1985 Jul 15
Simultaneous quantification of erythrocyte zinc protoporphyrin and protoporphyrin IX by liquid chromatography.
1986 Dec
Prevention of anthracycline-induced cytotoxicity in hemopoietic cells by hemin.
1986 Jul
[Plasma indicators of iron metabolism in persons occupationally exposed to organic solvents with normal and increased levels of protoporphyrin IX in erythrocytes].
1986 Jul 7
Evidence suggesting that the two forms of heme oxygenase are products of different genes.
1988 Mar 5
[Automated HPLC method for determining zinc protoporphyrin IX and protoporphyrin IX in erythrocytes of workers exposed to lead].
1988 Nov
The concentration of protoporphyrin IX in workers occupationally exposed to lead.
1989 Apr-Jun
Anti-HIV activity of protoporphyrin.
1989 Jun
Protoporphyrin IX photosensitization of corneal endothelium.
1989 Oct
Specific inhibition of HIV-1 protease by boronated porphyrins.
1992 Sep 4
Three-dimensional structure-activity analysis of a series of porphyrin derivatives with anti-HIV-1 activity targeted to the V3 loop of the gp120 envelope glycoprotein of the human immunodeficiency virus type 1.
1994 Apr 15
Iron protoporphyrin IX (hemin) but not tin or zinc protoporphyrin IX can stimulate gene expression in K562 cells from enhancer elements containing binding sites for NF-E2.
1994 Aug 15
Effects of combinations of stem cell factor and hemin on erythropoiesis after azidothymidine treatment of immunosuppressed mice.
1996 Aug
Expression of heme oxygenase isozyme mRNAs in the human brain and induction of heme oxygenase-1 by nitric oxide donors.
1996 Aug
Pharmacokinetics of 5-aminolevulinic acid-induced protoporphyrin IX in skin and blood.
1997 Oct
Development of refractoriness of induced human heme oxygenase-1 gene expression to reinduction by UVA irradiation and hemin.
1997 Oct
Effect of lindane and heptachlor on delta-aminolaevulinate synthase and its regulation.
1998 Nov
Involvement of the tyrosine phosphorylation pathway in induction of human heme oxygenase-1 by hemin, sodium arsenite, and cadmium chloride.
1998 Sep
Endoscopic fluorescence detection of dysplasia in patients with Barrett's esophagus, ulcerative colitis, or adenomatous polyps after 5-aminolevulinic acid-induced protoporphyrin IX sensitization.
1999 Jan
Non-iron metalloporphyrins: potent antibacterial compounds that exploit haem/Hb uptake systems of pathogenic bacteria.
1999 Jan
Comparative effect of ALA derivatives on protoporphyrin IX production in human and rat skin organ cultures.
1999 Jul
A screening assay for antiviral compounds targeted to the HIV-1 gp41 core structure using a conformation-specific monoclonal antibody.
1999 Jun
MAP kinase-independent induction of proto-oncogene c-fos mRNA by hemin in human cells.
1999 Jun 24
A vehicle for photodynamic therapy of skin cancer: influence of dimethylsulphoxide on 5-aminolevulinic acid in vitro cutaneous permeation and in vivo protoporphyrin IX accumulation determined by confocal microscopy.
2000 Apr 3
Cell-type specific protoporphyrin IX metabolism in human bladder cancer in vitro.
2000 Aug
The heme synthesis and degradation pathways: role in oxidant sensitivity. Heme oxygenase has both pro- and antioxidant properties.
2000 Jan 15
Accumulation of protoporphyrin-IX (PpIX) in leukemic cell lines following induction by 5-aminolevulinic acid (ALA).
2000 Jul
The morphological changes in rat bladder after photodynamic therapy with 5-aminolaevulinic acid-induced protoporphyrin IX.
2000 Jul
A key role for the mitochondrial benzodiazepine receptor in cellular photosensitisation with delta-aminolaevulinic acid.
2000 Oct 13
Oral aminolevulinic acid induces protoporphyrin IX fluorescence in psoriatic plaques and peripheral blood cells.
2001 Aug
The influence of UV exposure on 5-aminolevulinic acid-induced protoporphyrin IX production in skin.
2001 Dec
Quantitative model calculation of the time-dependent protoporphyrin IX concentration in normal human epidermis after delivery of ALA by passive topical application or lontophoresis.
2002 Apr
Fluorescence microspectroscopy technique for the study of intracellular protoporphyrin IX dynamics.
2003 Jun
A spectrophotometric micromethod for determining erythrocyte protoporphyrin-IX in whole blood or erythrocytes.
2005
Residues stabilizing the heme moiety of the nitric oxide sensor soluble guanylate cyclase.
2005 Apr 18
Metalloporphyrins inactivate caspase-3 and -8.
2005 Aug
Correlation between macroscopic fluorescence and protoporphyrin IX content in psoriasis and actinic keratosis following application of aminolevulinic acid.
2005 Oct
Novel lipid mediator aspirin-triggered lipoxin A4 induces heme oxygenase-1 in endothelial cells.
2005 Sep
Accumulation of protoporphyrin-IX in rat Leydig cells following induction by 5-aminolevulinic acid and tramadol.
2007 Dec
Regulation of heme synthesis and proteasomal activity by copper: possible implications for Wilson's disease.
2009
Reactive oxygen species-independent apoptosis in doxorubicin-treated H9c2 cardiomyocytes: role for heme oxygenase-1 down-modulation.
2009 Jan 15
Sulfasalazine induces haem oxygenase-1 via ROS-dependent Nrf2 signalling, leading to control of neointimal hyperplasia.
2009 Jun 1
Myrrh mediates haem oxygenase-1 expression to suppress the lipopolysaccharide-induced inflammatory response in RAW264.7 macrophages.
2011 Sep
Structural requirements within protoporphyrin IX in the inhibition of heat shock protein 90.
2013 Jun 25
Key role of phosphodiesterase 4A (PDE4A) in autophagy triggered by yessotoxin.
2015 Mar 2
Constitutive active/androstane receptor, peroxisome proliferator-activated receptor α, and cytotoxicity are involved in oxadiazon-induced liver tumor development in mice.
2016 Feb
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
5uM of protoporphyrin reduced HLA I Ab-dependent up-regulation of VCAM-1
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:42:10 UTC 2023
Edited
by admin
on Fri Dec 15 16:42:10 UTC 2023
Record UNII
743LRP9S7N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HEMIN
MI   VANDF   WHO-DD  
Common Name English
Hemin [WHO-DD]
Common Name English
HEMIN [MI]
Common Name English
FERRIPROTOPORPHYRIN CHLORIDE
Common Name English
NSC-122707
Code English
HEMIN [JAN]
Common Name English
FERRATE(2-), CHLORO(7,12-DIETHENYL-3,8,13,17-TETRAMETHYL-21H,23H-PORPHINE-2,18-DIPROPANOATO(4-)-N21,N22,N23,N24)-, DIHYDROGEN
Common Name English
HEMIN [VANDF]
Common Name English
CHLOROHEMIN
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 683
Created by admin on Fri Dec 15 16:42:10 UTC 2023 , Edited by admin on Fri Dec 15 16:42:10 UTC 2023
FDA ORPHAN DRUG 77393
Created by admin on Fri Dec 15 16:42:10 UTC 2023 , Edited by admin on Fri Dec 15 16:42:10 UTC 2023
Code System Code Type Description
DAILYMED
743LRP9S7N
Created by admin on Fri Dec 15 16:42:10 UTC 2023 , Edited by admin on Fri Dec 15 16:42:10 UTC 2023
PRIMARY
DRUG CENTRAL
5117
Created by admin on Fri Dec 15 16:42:10 UTC 2023 , Edited by admin on Fri Dec 15 16:42:10 UTC 2023
PRIMARY
DRUG BANK
DB03404
Created by admin on Fri Dec 15 16:42:10 UTC 2023 , Edited by admin on Fri Dec 15 16:42:10 UTC 2023
PRIMARY
ECHA (EC/EINECS)
240-140-1
Created by admin on Fri Dec 15 16:42:10 UTC 2023 , Edited by admin on Fri Dec 15 16:42:10 UTC 2023
PRIMARY
CAS
16009-13-5
Created by admin on Fri Dec 15 16:42:10 UTC 2023 , Edited by admin on Fri Dec 15 16:42:10 UTC 2023
PRIMARY
MESH
D006427
Created by admin on Fri Dec 15 16:42:10 UTC 2023 , Edited by admin on Fri Dec 15 16:42:10 UTC 2023
PRIMARY
EVMPD
SUB14075MIG
Created by admin on Fri Dec 15 16:42:10 UTC 2023 , Edited by admin on Fri Dec 15 16:42:10 UTC 2023
PRIMARY
FDA UNII
743LRP9S7N
Created by admin on Fri Dec 15 16:42:10 UTC 2023 , Edited by admin on Fri Dec 15 16:42:10 UTC 2023
PRIMARY
WIKIPEDIA
HEMIN
Created by admin on Fri Dec 15 16:42:10 UTC 2023 , Edited by admin on Fri Dec 15 16:42:10 UTC 2023
PRIMARY
MERCK INDEX
m5949
Created by admin on Fri Dec 15 16:42:10 UTC 2023 , Edited by admin on Fri Dec 15 16:42:10 UTC 2023
PRIMARY Merck Index
RXCUI
5175
Created by admin on Fri Dec 15 16:42:10 UTC 2023 , Edited by admin on Fri Dec 15 16:42:10 UTC 2023
PRIMARY RxNorm
SMS_ID
100000077913
Created by admin on Fri Dec 15 16:42:10 UTC 2023 , Edited by admin on Fri Dec 15 16:42:10 UTC 2023
PRIMARY
CHEBI
50385
Created by admin on Fri Dec 15 16:42:10 UTC 2023 , Edited by admin on Fri Dec 15 16:42:10 UTC 2023
PRIMARY
NSC
122707
Created by admin on Fri Dec 15 16:42:10 UTC 2023 , Edited by admin on Fri Dec 15 16:42:10 UTC 2023
PRIMARY
EPA CompTox
DTXSID9037662
Created by admin on Fri Dec 15 16:42:10 UTC 2023 , Edited by admin on Fri Dec 15 16:42:10 UTC 2023
PRIMARY
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PARENT -> SALT/SOLVATE
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ACTIVE MOIETY