HEMIN

US Approved Rx (1983)

First approved in 1983

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

Structure Search

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-;;

HIDE SMILES / InChI

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26255181http://www.rxlist.com/panhematin-drug.htm
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Ultrasonically-induced cell damage 4 Target ID: Ultrasonically-induced cell damage Sources: https://www.ncbi.nlm.nih.gov/pubmed/20189622	Activator 1447
Human immunodeficiency virus type 1 protease 36 Target ID: CHEMBL243 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1527792	Inhibitor 8504	200.0 µM [IC50]
Heme oxygenase 1 15 Target ID: CHEMBL2823 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26877238	Activator 1447
Cyclooxygenase-2 201 Target ID: CHEMBL2977 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26255181	Activator 1447

Conditions

Condition	Modality	Highest Phase	Product
Diabetic neuropathy 23 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26730587	Primary	Basic research	Unknown Approved Use Unknown
Parkinson's disease 232 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26385576	Primary	Basic research	Unknown Approved Use Unknown
Type 1 diabetes mellitus 18 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26252059	Primary	Basic research	Unknown Approved Use Unknown
Liver diseases 15 Sources: http://211.103.242.133:8080/ziyuan/CDDPdf/med/base/%E8%8D%AF%E5%93%81hu/%E6%B6%88%E5%8C%96%E7%B3%BB%E7%BB%9F%E8%8D%AF%E7%89%A9/1013.pdf http://jglobal.jst.go.jp/public/20090422/200902091490310298	Primary	Approved 8583	Prolmon Approved Use Treatment of liver disorders
Acute intermittent porphyria 7 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=d84808a8-d039-6293-6e0d-782327f0a5c0	Primary	Approved 8583	Panhematin Approved Use PANHEMATIN (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.

C_max

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

T_1/2

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

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	BCRP 697

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
BCRP 697	substrate 4014 Sources: https://www.tandfonline.com/doi/pdf/10.4161/cbt.4.2.1440\|https://pubmed.ncbi.nlm.nih.gov/28118809/	major

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:15430	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:15430
eMolecules	18593072	https://www.emolecules.com/cgi-bin/more?vid=18593072
eMolecules	531182	https://www.emolecules.com/cgi-bin/more?vid=531182
MolPort	MolPort-003-665-944	https://www.molport.com/shop/molecule-link/MolPort-003-665-944

PubMed

Title	Date	PubMed
Micro-scale photofluorometric determination of "free erythrocyte pophyrin" (protoporphyrin IX).	1975 Oct	1164799
Effect of hemin and Protoporphyrin IX on the protein-synthesizing activity of human granulocytes, lymphocytes and platelets.	1979	108889
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	6628580
Prevention of anthracycline-induced cytotoxicity in hemopoietic cells by hemin.	1986 Jul	3708575
Interaction of hemin with erythrocyte membranes: alterations in the physical state of the major sialoglycoprotein.	1989 Feb 13	2537104
Specific inhibition of HIV-1 protease by boronated porphyrins.	1992 Sep 4	1527792
Development of refractoriness of induced human heme oxygenase-1 gene expression to reinduction by UVA irradiation and hemin.	1997 Oct	9337616
Involvement of the tyrosine phosphorylation pathway in induction of human heme oxygenase-1 by hemin, sodium arsenite, and cadmium chloride.	1998 Sep	9722676
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	9869731
Comparative effect of ALA derivatives on protoporphyrin IX production in human and rat skin organ cultures.	1999 Jul	10408393
Suppression of heme oxygenase-1 mRNA expression by interferon-gamma in human glioblastoma cells.	1999 Jun	10349844
Nrf2, a Cap'n'Collar transcription factor, regulates induction of the heme oxygenase-1 gene.	1999 Sep 10	10473555
The morphological changes in rat bladder after photodynamic therapy with 5-aminolaevulinic acid-induced protoporphyrin IX.	2000 Jul	10886096
Evidence for a functional link between the heme oxygenase-carbon monoxide pathway and corticotropin-releasing hormone release from primary cultures of human trophoblast cells.	2001 Jan	11232018
Regulation of the 75-kDa subunit of mitochondrial complex I by iron.	2001 Jul 20	11313346
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	12003134
Overexpression of transglutaminase 2 accelerates the erythroid differentiation of human chronic myelogenous leukemia K562 cell line through PI3K/Akt signaling pathway.	2004 Nov 19	15556610
Metalloporphyrins inactivate caspase-3 and -8.	2005 Aug	16051694
Distinct protective mechanisms of HO-1 and HO-2 against hydroperoxide-induced cytotoxicity.	2005 Jan 1	15589375
Apigenin decreases hemin-mediated heme oxygenase-1 induction.	2005 Sep 15	16109301
The novel antioxidant 3-O-caffeoyl-1-methylquinic acid induces Nrf2-dependent phase II detoxifying genes and alters intracellular glutathione redox.	2006 Apr 15	16631525
Increased intracavernosal pressure response in hypertensive rats after chronic hemin treatment.	2006 Jul	16839318
JWA, a novel signaling molecule, involved in the induction of differentiation of human myeloid leukemia cells.	2006 Mar 10	16430862
Regulation of heme synthesis and proteasomal activity by copper: possible implications for Wilson's disease.	2009	19888908
Upregulating the heme oxygenase system suppresses left ventricular hypertrophy in adult spontaneously hypertensive rats for 3 months.	2009 Sep	19700139
Up-regulating the heme oxygenase system with hemin improves insulin sensitivity and glucose metabolism in adult spontaneously hypertensive rats.	2010 Feb	20016031
Arsenite suppression of involucrin transcription through AP1 promoter sites in cultured human keratinocytes.	2010 Mar 15	20006635
Arsenite down-regulates cytochrome P450 1A1 at the transcriptional and posttranslational levels in human HepG2 cells.	2010 May 15	20188822
DMF inhibits PDGF-BB induced airway smooth muscle cell proliferation through induction of heme-oxygenase-1.	2010 Oct 20	20961405
Pro-healing potential of hemin: an inducer of heme oxygenase-1.	2010 Oct 25	20638379
Changes in DNA methylation of erythroid-specific genes in K562 cells exposed to phenol and hydroquinone.	2013 Oct 4	23973255

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

5uM of protoporphyrin reduced HLA I Ab-dependent up-regulation of VCAM-1

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:34:56 GMT 2025` Edited by `admin` on `Mon Mar 31 18:34:56 GMT 2025`
Record UNII	743LRP9S7N
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-122707

Preferred Name

English

HEMIN

Common Name

English

Hemin [WHO-DD]

Common Name

English

HEMIN [MI]

Common Name

English

FERRIPROTOPORPHYRIN CHLORIDE

Common Name

English

HEMIN [JAN]

Common Name

English

FERRATE(2-), CHLORO(7,12-DIETHENYL-3,8,13,17-TETRAMETHYL-21H,23H-PORPHINE-2,18-DIPROPANOATO(4-)-N21,N22,N23,N24)-, DIHYDROGEN

Common Name

English

HEMIN [VANDF]

Common Name

English

CHLOROHEMIN

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

683