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	C34H32N4O4
Molecular Weight	560.6423
Charge	-2
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	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 2578

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
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
Mechanism of induction of heme oxygenase by metalloporphyrins in primary chick embryo liver cells: evidence against a stress-mediated response.	1997 Apr	9089626
The reactions of neuroglobin with CO: evidence for two forms of the ferrous protein.	2006 Aug	16684569
Mitochondria in hematopoiesis and hematological diseases.	2006 Aug 7	16892088
Up-regulation of heme oxygenase provides vascular protection in an animal model of diabetes through its antioxidant and antiapoptotic effects.	2006 Dec	16959961
Amyloid-beta peptide binds with heme to form a peroxidase: relationship to the cytopathologies of Alzheimer's disease.	2006 Feb 28	16492752
Carbon monoxide contributes to hypotension-induced cerebrovascular vasodilation in piglets.	2006 Nov	16751286
Identification of a mammalian mitochondrial porphyrin transporter.	2006 Oct 5	17006453
Functional characterization of human proton-coupled folate transporter/heme carrier protein 1 heterologously expressed in mammalian cells as a folate transporter.	2007 Aug	17475902
Rev-erbalpha, a heme sensor that coordinates metabolic and circadian pathways.	2007 Dec 14	18006707
Motexafin gadolinium-induced cell death correlates with heme oxygenase-1 expression and inhibition of P450 reductase-dependent activities.	2007 Jan	17018578
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
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
The Fowler syndrome-associated protein FLVCR2 is an importer of heme.	2010 Nov	20823265
Up-regulation of A1M/α1-microglobulin in skin by heme and reactive oxygen species gives protection from oxidative damage.	2011	22096585
Structure of REV-ERBβ ligand-binding domain bound to a porphyrin antagonist.	2014 Jul 18	24872411
Increased HO-1 levels ameliorate fatty liver development through a reduction of heme and recruitment of FGF21.	2014 Mar	23839791
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 `Fri Dec 15 21:17:07 GMT 2023` Edited by `admin` on `Fri Dec 15 21:17:07 GMT 2023`
Record UNII	42VZT0U6YR
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

FERROHEME

Common 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	Locators: MI Sources:

Common Name

English

HEME B

Common Name

English

Classification Tree Code System Code

EU-Orphan Drug

EU/3/13/1149