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].Cc1c(CCC(O)=O)c2cc3[n-]c(cc4nc(cc5[n-]c(cc1n2)c(C=C)c5C)c(C=C)c4C)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 | 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 | 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 | C34H30N4O4 |
| Molecular Weight | 558.6264 |
| 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 |
|---|---|---|
| Constitutive active/androstane receptor, peroxisome proliferator-activated receptor α, and cytotoxicity are involved in oxadiazon-induced liver tumor development in mice. | 2016-02 |
|
| Structural requirements within protoporphyrin IX in the inhibition of heat shock protein 90. | 2013-06-25 |
|
| Myrrh mediates haem oxygenase-1 expression to suppress the lipopolysaccharide-induced inflammatory response in RAW264.7 macrophages. | 2011-09 |
|
| Sulfasalazine induces haem oxygenase-1 via ROS-dependent Nrf2 signalling, leading to control of neointimal hyperplasia. | 2009-06-01 |
|
| Reactive oxygen species-independent apoptosis in doxorubicin-treated H9c2 cardiomyocytes: role for heme oxygenase-1 down-modulation. | 2009-01-15 |
|
| Regulation of heme synthesis and proteasomal activity by copper: possible implications for Wilson's disease. | 2009 |
|
| Accumulation of protoporphyrin-IX in rat Leydig cells following induction by 5-aminolevulinic acid and tramadol. | 2007-12 |
|
| Correlation between macroscopic fluorescence and protoporphyrin IX content in psoriasis and actinic keratosis following application of aminolevulinic acid. | 2005-10 |
|
| Novel lipid mediator aspirin-triggered lipoxin A4 induces heme oxygenase-1 in endothelial cells. | 2005-09 |
|
| Metalloporphyrins inactivate caspase-3 and -8. | 2005-08 |
|
| Residues stabilizing the heme moiety of the nitric oxide sensor soluble guanylate cyclase. | 2005-04-18 |
|
| A spectrophotometric micromethod for determining erythrocyte protoporphyrin-IX in whole blood or erythrocytes. | 2005 |
|
| Fluorescence microspectroscopy technique for the study of intracellular protoporphyrin IX dynamics. | 2003-06 |
|
| Quantitative model calculation of the time-dependent protoporphyrin IX concentration in normal human epidermis after delivery of ALA by passive topical application or lontophoresis. | 2002-04 |
|
| The influence of UV exposure on 5-aminolevulinic acid-induced protoporphyrin IX production in skin. | 2001-12 |
|
| Oral aminolevulinic acid induces protoporphyrin IX fluorescence in psoriatic plaques and peripheral blood cells. | 2001-08 |
|
| A key role for the mitochondrial benzodiazepine receptor in cellular photosensitisation with delta-aminolaevulinic acid. | 2000-10-13 |
|
| Cell-type specific protoporphyrin IX metabolism in human bladder cancer in vitro. | 2000-08 |
|
| Accumulation of protoporphyrin-IX (PpIX) in leukemic cell lines following induction by 5-aminolevulinic acid (ALA). | 2000-07 |
|
| The morphological changes in rat bladder after photodynamic therapy with 5-aminolaevulinic acid-induced protoporphyrin IX. | 2000-07 |
|
| 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. | 2000-04-03 |
|
| The heme synthesis and degradation pathways: role in oxidant sensitivity. Heme oxygenase has both pro- and antioxidant properties. | 2000-01-15 |
|
| Comparative effect of ALA derivatives on protoporphyrin IX production in human and rat skin organ cultures. | 1999-07 |
|
| MAP kinase-independent induction of proto-oncogene c-fos mRNA by hemin in human cells. | 1999-06-24 |
|
| A screening assay for antiviral compounds targeted to the HIV-1 gp41 core structure using a conformation-specific monoclonal antibody. | 1999-06 |
|
| Endoscopic fluorescence detection of dysplasia in patients with Barrett's esophagus, ulcerative colitis, or adenomatous polyps after 5-aminolevulinic acid-induced protoporphyrin IX sensitization. | 1999-01 |
|
| Non-iron metalloporphyrins: potent antibacterial compounds that exploit haem/Hb uptake systems of pathogenic bacteria. | 1999-01 |
|
| Effect of lindane and heptachlor on delta-aminolaevulinate synthase and its regulation. | 1998-11 |
|
| Involvement of the tyrosine phosphorylation pathway in induction of human heme oxygenase-1 by hemin, sodium arsenite, and cadmium chloride. | 1998-09 |
|
| Pharmacokinetics of 5-aminolevulinic acid-induced protoporphyrin IX in skin and blood. | 1997-10 |
|
| Development of refractoriness of induced human heme oxygenase-1 gene expression to reinduction by UVA irradiation and hemin. | 1997-10 |
|
| Effects of combinations of stem cell factor and hemin on erythropoiesis after azidothymidine treatment of immunosuppressed mice. | 1996-08 |
|
| Expression of heme oxygenase isozyme mRNAs in the human brain and induction of heme oxygenase-1 by nitric oxide donors. | 1996-08 |
|
| Cloning and expression of a cDNA for mu-class glutathione S-transferase from rabbit liver. | 1995-04-20 |
|
| 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. | 1994-08-15 |
|
| 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. | 1994-04-15 |
|
| Specific inhibition of HIV-1 protease by boronated porphyrins. | 1992-09-04 |
|
| Protoporphyrin IX photosensitization of corneal endothelium. | 1989-10 |
|
| Anti-HIV activity of protoporphyrin. | 1989-06 |
|
| The concentration of protoporphyrin IX in workers occupationally exposed to lead. | 1989-04-01 |
|
| [Automated HPLC method for determining zinc protoporphyrin IX and protoporphyrin IX in erythrocytes of workers exposed to lead]. | 1988-11 |
|
| Simultaneous quantification of erythrocyte zinc protoporphyrin and protoporphyrin IX by liquid chromatography. | 1986-12 |
|
| [Plasma indicators of iron metabolism in persons occupationally exposed to organic solvents with normal and increased levels of protoporphyrin IX in erythrocytes]. | 1986-07-07 |
|
| Prevention of anthracycline-induced cytotoxicity in hemopoietic cells by hemin. | 1986-07 |
|
| Accumulation and drainage of hemin in the red cell membrane. | 1985-12-05 |
|
| [Protoporphyrin IX level in erythrocytes of persons with alcoholic liver cirrhosis]. | 1985-07-15 |
|
| [Erythrocyte protoporphyrin IX in occupational exposure to asbestos]. | 1984 |
|
| 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. | 1983-09 |
|
| Micro-scale photofluorometric determination of "free erythrocyte pophyrin" (protoporphyrin IX). | 1975-10 |
|
| [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]. | 1968-06-04 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:34:56 GMT 2025
by
admin
on
Mon Mar 31 18:34:56 GMT 2025
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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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| Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
683
Created by
admin on Mon Mar 31 18:34:56 GMT 2025 , Edited by admin on Mon Mar 31 18:34:56 GMT 2025
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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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ACTIVE MOIETY |
