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
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-;;
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 |
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.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24952361
Curator's Comment: hemin improves barrier function and neurological outcome in experimental models of traumatic and ischemic CNS injury
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 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20189622 |
|||
Target ID: CHEMBL243 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1527792 |
200.0 µM [IC50] | ||
Target ID: CHEMBL2823 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26877238 |
|||
Target ID: CHEMBL2977 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26255181 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Prolmon Approved UseTreatment of liver disorders |
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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 |
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[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 |
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Micro-scale photofluorometric determination of "free erythrocyte pophyrin" (protoporphyrin IX). | 1975 Oct |
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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 |
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[Erythrocyte protoporphyrin IX in occupational exposure to asbestos]. | 1984 |
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[Protoporphyrin IX level in erythrocytes of persons with alcoholic liver cirrhosis]. | 1985 Jul 15 |
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Simultaneous quantification of erythrocyte zinc protoporphyrin and protoporphyrin IX by liquid chromatography. | 1986 Dec |
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Prevention of anthracycline-induced cytotoxicity in hemopoietic cells by hemin. | 1986 Jul |
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[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 |
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Evidence suggesting that the two forms of heme oxygenase are products of different genes. | 1988 Mar 5 |
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[Automated HPLC method for determining zinc protoporphyrin IX and protoporphyrin IX in erythrocytes of workers exposed to lead]. | 1988 Nov |
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The concentration of protoporphyrin IX in workers occupationally exposed to lead. | 1989 Apr-Jun |
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Anti-HIV activity of protoporphyrin. | 1989 Jun |
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Protoporphyrin IX photosensitization of corneal endothelium. | 1989 Oct |
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Specific inhibition of HIV-1 protease by boronated porphyrins. | 1992 Sep 4 |
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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 |
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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 |
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Effects of combinations of stem cell factor and hemin on erythropoiesis after azidothymidine treatment of immunosuppressed mice. | 1996 Aug |
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Expression of heme oxygenase isozyme mRNAs in the human brain and induction of heme oxygenase-1 by nitric oxide donors. | 1996 Aug |
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Pharmacokinetics of 5-aminolevulinic acid-induced protoporphyrin IX in skin and blood. | 1997 Oct |
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Development of refractoriness of induced human heme oxygenase-1 gene expression to reinduction by UVA irradiation and hemin. | 1997 Oct |
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Effect of lindane and heptachlor on delta-aminolaevulinate synthase and its regulation. | 1998 Nov |
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Involvement of the tyrosine phosphorylation pathway in induction of human heme oxygenase-1 by hemin, sodium arsenite, and cadmium chloride. | 1998 Sep |
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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 |
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Non-iron metalloporphyrins: potent antibacterial compounds that exploit haem/Hb uptake systems of pathogenic bacteria. | 1999 Jan |
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Comparative effect of ALA derivatives on protoporphyrin IX production in human and rat skin organ cultures. | 1999 Jul |
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A screening assay for antiviral compounds targeted to the HIV-1 gp41 core structure using a conformation-specific monoclonal antibody. | 1999 Jun |
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MAP kinase-independent induction of proto-oncogene c-fos mRNA by hemin in human cells. | 1999 Jun 24 |
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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 |
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Cell-type specific protoporphyrin IX metabolism in human bladder cancer in vitro. | 2000 Aug |
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The heme synthesis and degradation pathways: role in oxidant sensitivity. Heme oxygenase has both pro- and antioxidant properties. | 2000 Jan 15 |
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Accumulation of protoporphyrin-IX (PpIX) in leukemic cell lines following induction by 5-aminolevulinic acid (ALA). | 2000 Jul |
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The morphological changes in rat bladder after photodynamic therapy with 5-aminolaevulinic acid-induced protoporphyrin IX. | 2000 Jul |
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A key role for the mitochondrial benzodiazepine receptor in cellular photosensitisation with delta-aminolaevulinic acid. | 2000 Oct 13 |
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Oral aminolevulinic acid induces protoporphyrin IX fluorescence in psoriatic plaques and peripheral blood cells. | 2001 Aug |
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The influence of UV exposure on 5-aminolevulinic acid-induced protoporphyrin IX production in skin. | 2001 Dec |
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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 |
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Fluorescence microspectroscopy technique for the study of intracellular protoporphyrin IX dynamics. | 2003 Jun |
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A spectrophotometric micromethod for determining erythrocyte protoporphyrin-IX in whole blood or erythrocytes. | 2005 |
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Residues stabilizing the heme moiety of the nitric oxide sensor soluble guanylate cyclase. | 2005 Apr 18 |
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Metalloporphyrins inactivate caspase-3 and -8. | 2005 Aug |
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Correlation between macroscopic fluorescence and protoporphyrin IX content in psoriasis and actinic keratosis following application of aminolevulinic acid. | 2005 Oct |
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Novel lipid mediator aspirin-triggered lipoxin A4 induces heme oxygenase-1 in endothelial cells. | 2005 Sep |
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Accumulation of protoporphyrin-IX in rat Leydig cells following induction by 5-aminolevulinic acid and tramadol. | 2007 Dec |
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Regulation of heme synthesis and proteasomal activity by copper: possible implications for Wilson's disease. | 2009 |
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Reactive oxygen species-independent apoptosis in doxorubicin-treated H9c2 cardiomyocytes: role for heme oxygenase-1 down-modulation. | 2009 Jan 15 |
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Sulfasalazine induces haem oxygenase-1 via ROS-dependent Nrf2 signalling, leading to control of neointimal hyperplasia. | 2009 Jun 1 |
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Myrrh mediates haem oxygenase-1 expression to suppress the lipopolysaccharide-induced inflammatory response in RAW264.7 macrophages. | 2011 Sep |
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Structural requirements within protoporphyrin IX in the inhibition of heat shock protein 90. | 2013 Jun 25 |
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Key role of phosphodiesterase 4A (PDE4A) in autophagy triggered by yessotoxin. | 2015 Mar 2 |
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Constitutive active/androstane receptor, peroxisome proliferator-activated receptor α, and cytotoxicity are involved in oxadiazon-induced liver tumor development in mice. | 2016 Feb |
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26690352
5uM of protoporphyrin reduced HLA I Ab-dependent up-regulation of VCAM-1
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:42:10 UTC 2023
by
admin
on
Fri Dec 15 16:42:10 UTC 2023
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Record UNII |
743LRP9S7N
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Record Status |
Validated (UNII)
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Record Version |
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FDA ORPHAN DRUG |
683
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FDA ORPHAN DRUG |
77393
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743LRP9S7N
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5117
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DB03404
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240-140-1
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16009-13-5
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D006427
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SUB14075MIG
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743LRP9S7N
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HEMIN
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m5949
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5175
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100000077913
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50385
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122707
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DTXSID9037662
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