Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C34H32N4O4.Fe.HO |
| Molecular Weight | 633.495 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[OH-].[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=C)=C5C)C(C)=C3CCC(O)=O
InChI
InChIKey=BMUDPLZKKRQECS-HXFTUNQESA-K
InChI=1S/C34H34N4O4.Fe.H2O/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);;1H2/q;+3;/p-3/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-;;
| Molecular Formula | HO |
| Molecular Weight | 17.0073 |
| Charge | -1 |
| 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 |
| Molecular Formula | C34H32N4O4 |
| Molecular Weight | 560.6423 |
| Charge | -2 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/17766326
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.
Originator
Sources: http://www.nejm.org/doi/full/10.1056/NEJM194501042320103#t=articlehttp://adisinsight.springer.com/drugs/800002495
Curator's Comment: Protoporphyrin was first found to be an iron-free derivative of hemoglobin by Kämmerer in 1923
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: Ultrasonically-induced cell damage |
|||
Target ID: CHEMBL243 |
200.0 µM [IC50] | ||
Target ID: CHEMBL2823 |
|||
Target ID: CHEMBL2977 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Prolmon Approved UseTreatment of liver disorders |
|||
| Primary | Panhematin Approved UsePANHEMATIN (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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
742 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9372622/ |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
9.6 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9372622/ |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9372622/ |
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 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Micro-scale photofluorometric determination of "free erythrocyte pophyrin" (protoporphyrin IX). | 1975 Oct |
|
| [Erythrocyte protoporphyrin IX in occupational exposure to asbestos]. | 1984 |
|
| Accumulation and drainage of hemin in the red cell membrane. | 1985 Dec 5 |
|
| [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 |
|
| [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 |
|
| Effects of hemin on erythropoiesis. | 1989 |
|
| The concentration of protoporphyrin IX in workers occupationally exposed to lead. | 1989 Apr-Jun |
|
| Interaction of hemin with erythrocyte membranes: alterations in the physical state of the major sialoglycoprotein. | 1989 Feb 13 |
|
| 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 |
|
| Cloning and expression of a cDNA for mu-class glutathione S-transferase from rabbit liver. | 1995 Apr 20 |
|
| 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 |
|
| 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 |
|
| Comparative effect of ALA derivatives on protoporphyrin IX production in human and rat skin organ cultures. | 1999 Jul |
|
| 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 |
|
| 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 |
|
| Astaxanthin protects against MPP(+)-induced oxidative stress in PC12 cells via the HO-1/NOX2 axis. | 2012 Dec 29 |
|
| A functional link between heme oxygenase-1 and tristetraprolin in the anti-inflammatory effects of nicotine. | 2013 Dec |
|
| The role of catechol-O-methyltransferase in catechol-enhanced erythroid differentiation of K562 cells. | 2013 Dec 15 |
|
| Structural requirements within protoporphyrin IX in the inhibition of heat shock protein 90. | 2013 Jun 25 |
|
| Small molecule activators of the Nrf2-HO-1 antioxidant axis modulate heme metabolism and inflammation in BV2 microglia cells. | 2013 Oct |
|
| Changes in DNA methylation of erythroid-specific genes in K562 cells exposed to phenol and hydroquinone. | 2013 Oct 4 |
|
| Heme oxygenase-1 alleviates vascular complications associated with metabolic syndrome: Effect on endothelial dependent relaxation and NO production. | 2014 Nov 5 |
|
| Transcriptional upregulation centra of HO-1 by EGB via the MAPKs/Nrf2 pathway in mouse C2C12 myoblasts. | 2015 Mar |
|
| Constitutive active/androstane receptor, peroxisome proliferator-activated receptor α, and cytotoxicity are involved in oxadiazon-induced liver tumor development in mice. | 2016 Feb |
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
0WP180G15G
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| Record Status |
Validated (UNII)
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| Record Version |
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Preferred Name | English | ||
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WHO-ATC |
B06AB01
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WHO-VATC |
QB06AB01
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15489-90-4
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4565
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