FERROHEME

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C34H32N4O4.Fe
Molecular Weight	616.487
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Fe++].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=KABFMIBPWCXCRK-RGGAHWMASA-L

InChI=1S/C34H34N4O4.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);/q;+2/p-2/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-;

HIDE SMILES / InChI

Molecular Formula	Fe
Molecular Weight	55.845
Charge	2
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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21371326
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/9057849

Ferroheme is formed when iron is inserted into protoporphyrin IX. The active center of hemoglobin and myoglobin consists of iron Ferroheme complex bound through a single, “proximal”, axial histidine (His) to the protein It is an iron containing cofactor that is involved with a wide range of cellular functions including oxygen transport. The antimalarial activity of a number of artemisinin derivatives, both newly synthesized and currently used as drugs, against Plasmodium falciparum in culture shows a correlation with their affinity of binding with Ferroheme.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Additive effect of erythropoietin and heme on murine hematopoietic recovery after azidothymidine treatment.	1993 Dec 15	8260696
Long-term bone marrow stromal and hemopoietic toxicity to AZT: protective role of heme and IL-1.	1993 Feb	7678812
Identification of a second region upstream of the mouse heme oxygenase-1 gene that functions as a basal level and inducer-dependent transcription enhancer.	1995 May 19	7538129
The heme-responsive element of the mouse heme oxygenase-1 gene is an extended AP-1 binding site that resembles the recognition sequences for MAF and NF-E2 transcription factors.	1996 Apr 25	8630002
Inhibition of human immunodeficiency virus-1 reverse transcriptase by heme and synthetic heme analogs.	1996 Jan	8834064
Mechanism of induction of heme oxygenase by metalloporphyrins in primary chick embryo liver cells: evidence against a stress-mediated response.	1997 Apr	9089626
Regulation of expression of the human heme oxygenase-1 gene in transfected chick embryo liver cell cultures.	1997 Jun 26	9224953
Non-iron metalloporphyrins: potent antibacterial compounds that exploit haem/Hb uptake systems of pathogenic bacteria.	1999 Jan	10027961
Mechanism of heme oxygenase-1 gene activation by cadmium in MCF-7 mammary epithelial cells. Role of p38 kinase and Nrf2 transcription factor.	2000 Sep 8	10874044
Cadmium induces nuclear export of Bach1, a transcriptional repressor of heme oxygenase-1 gene.	2003 Dec 5	14504288
The heme-heme oxygenase system: a molecular switch in wound healing.	2003 Jul 15	12649161
An internal enhancer regulates heme- and cadmium-mediated induction of human heme oxygenase-1.	2003 Sep	12783778
The role of endogenous heme synthesis and degradation domain cysteines in cellular iron-dependent degradation of IRP2.	2003 Sep-Oct	12972033
Identification of key elements that are responsible for heme-mediated induction of the avian heme oxygenase-1 gene.	2004 Aug 12	15297142
Heme oxygenase-1 inhibits angiotensin II-induced cardiac hypertrophy in vitro and in vivo.	2004 Jul 20	15226216
Enhancement of heme-induced membrane damage by the anti-malarial clotrimazole: the role of colloid-osmotic forces.	2004 Mar	14993803
Upstream stimulatory factors, USF1 and USF2, bind to the human haem oxygenase-1 proximal promoter in vivo and regulate its transcription.	2004 Oct 15	15242350
Identification of a human heme exporter that is essential for erythropoiesis.	2004 Sep 17	15369674
Allosteric modulation of anti-HIV drug and ferric heme binding to human serum albumin.	2005 Dec	16336266
Differential gene expression in rat colon by dietary heme and calcium.	2005 Jan	15539406
Dynamic cytoplasmic anchoring of the transcription factor Bach1 by intracellular hyaluronic acid binding protein IHABP.	2005 Mar	15809329
Up-regulation of heme oxygenase provides vascular protection in an animal model of diabetes through its antioxidant and antiapoptotic effects.	2006 Dec	16959961
Identification of heme as the ligand for the orphan nuclear receptors REV-ERBalpha and REV-ERBbeta.	2007 Dec	18037887
Rev-erbalpha, a heme sensor that coordinates metabolic and circadian pathways.	2007 Dec 14	18006707
Heme induces endothelial tissue factor expression: potential role in hemostatic activation in patients with hemolytic anemia.	2008 Dec	18983524
Heme oxygenase-1 induction depletes heme and attenuates pulmonary artery relaxation and guanylate cyclase activation by nitric oxide.	2008 Mar	18178725
Regulation of heme synthesis and proteasomal activity by copper: possible implications for Wilson's disease.	2009	19888908
15-Deoxy-Delta12,14-prostaglandin J2 upregulates the expression of heme oxygenase-1 and subsequently matrix metalloproteinase-1 in human breast cancer cells: possible roles of iron and ROS.	2009 Apr	19136476
Preparation of a biologically active apo-cytochrome b5 via heterologous expression in Escherichia coli.	2009 Aug	19358889
Protein assay for heme oxygenase-1 (HO-1) induced by chemicals in HepG2 cells.	2009 Dec	19952508
Role for copper in the cellular and regulatory effects of heme-hemopexin.	2009 Jun	19039664
Comparative analysis of gene expression changes mediated by individual constituents of hemozoin.	2009 Mar 16	19191707
Pro-healing potential of hemin: an inducer of heme oxygenase-1.	2010 Oct 25	20638379
Lon peptidase 1 (LONP1)-dependent breakdown of mitochondrial 5-aminolevulinic acid synthase protein by heme in human liver cells.	2011 Jul 29	21659532
DiGeorge critical region 8 (DGCR8) is a double-cysteine-ligated heme protein.	2011 May 13	21454614
Concomitant induction of heme oxygenase-1 attenuates the cytotoxicity of arsenic species from lumbricus extract in human liver HepG2 cells.	2012 Apr	22492492
Enhancement of nitrite on heme-induced oxidative reactions: A potential toxicological implication.	2012 Feb	22056765
Heme and heme biosynthesis intermediates induce heme oxygenase-1 and cytochrome P450 2A5, enzymes with putative sequential roles in heme and bilirubin metabolism: different requirement for transcription factor nuclear factor erythroid- derived 2-like 2.	2012 Nov	22859313
Structure of REV-ERBβ ligand-binding domain bound to a porphyrin antagonist.	2014 Jul 18	24872411
Nitration of Y10 in Aβ1-40: is it a compensatory reaction against oxidative/nitrative stress and Aβ aggregation?	2015 Mar 16	25387246
Key roles for tyrosine 10 in aβ-heme complexes and its relevance to oxidative stress.	2015 Mar 16	25211009

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

The matrix fraction of rat liver mitochondria has a high binding capacity for protoheme IX with an almost linear increase in binding up to at least 28 nmol heme/mg protein. Since free heme could not be detected until the heme to protein ratio exceeded 14 nmol heme/mg protein, it is suggested that there is a substantial high-affinity binding of heme to matrix components, probably those of high molecular weight and low electrophoretic mobility.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 20:17:31 GMT 2025` Edited by `admin` on `Mon Mar 31 20:17:31 GMT 2025`
Record UNII	42VZT0U6YR
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FERROHEME

Common Name

English

HEME	Locators: MI Sources:

Preferred Name

English

PROTOHEME

Common Name

English

NSC-267100

Code

English

NORMOSANG

Brand Name

English

GLOBIFER

Brand Name

English

REDUCED HEMATIN

Common Name

English

PROTOHEME IX

Common Name

English

HUMAN HEMIN

Common Name

English

HEME IRON

Common Name

English

HEME [MI]

Common Name

English

FERROPROTOPORPHYRIN

Common Name

English

HEME B

Common Name

English

Classification Tree Code System Code

EU-Orphan Drug

EU/3/13/1149