Details of the Drug

General Information of Drug (ID: DMGC287)

Drug Name
Heme
Synonyms
heme; protoheme; Haem; ferroprotoporphyrin; UNII-42VZT0U6YR; Iron protoporphyrin ix; Protohaem; Ferroheme; Reduced hematin; Ferrous protoheme; Iron protoporphyrin; Ferrous protoheme IX; Ferroprotoporphyrin IX; 14875-96-8; 42VZT0U6YR; Iron(II) protoporphyrin IX; Protoheme IX (VAN); Ferroheme (VAN); Heme (VAN); 85758-EP2305825A1; 85758-EP2305243A1; 85758-EP2270505A1; 85758-EP2270016A1; 3-[18-(2-carboxyethyl)-7,12-bis(ethenyl)-3,8,13,17-tetramethylporphyrin-21,23-diid-2-yl]propanoic acid; iron(2+); NSC 16669; NSC 267100; AC1L9FPJ; Hemin
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
ATC Code
B06AB01: Heme
B06AB: Heme products
B06A: OTHER HEMATOLOGICAL AGENTS
B06: OTHER HEMATOLOGICAL AGENTS
B: BLOOD AND BLOOD FORMING ORGANS
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski):
1		 Molecular Weight 616.5
Logarithm of the Partition Coefficient Not Available
Rotatable Bond Count 8
Hydrogen Bond Donor Count 2
Hydrogen Bond Acceptor Count 8
Chemical Identifiers
Formula
C34H32FeN4O4
IUPAC Name
3-[18-(2-carboxyethyl)-8,13-bis(ethenyl)-3,7,12,17-tetramethylporphyrin-21,24-diid-2-yl]propanoic acid;iron(2+)
Canonical SMILES
CC1=C(C2=CC3=C(C(=C([N-]3)C=C4C(=C(C(=N4)C=C5C(=C(C(=N5)C=C1[N-]2)C)C=C)C)C=C)C)CCC(=O)O)CCC(=O)O.[Fe+2]
InChI
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
InChIKey
KABFMIBPWCXCRK-UHFFFAOYSA-L
Cross-matching ID
PubChem CID
26945
CAS Number
14875-96-8
UNII
743LRP9S7N
DrugBank ID
DB03404
TTD ID
D0UU1I
VARIDT ID
DR00298
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Albendazole monooxygenase (CYP3A4) TTXV4FI CP3A4_HUMAN Inhibitor [2]
Arachidonate 5-lipoxygenase (5-LOX) TT2J34L LOX5_HUMAN Inhibitor [2]
Bacterial Flavohemoglobin (Bact hmp) TTNAW8S HMP_ECOLI Inhibitor [2]
Bacterial Fumarate reductase flavoprotein (Bact frdA) TTHDSE2 FRDA_HELPY Inhibitor [2]
Cystathionine beta-synthase (CBS) TTVZJ7G CBS_HUMAN Inhibitor [2]
Heme oxygenase 1 (HMOX1) TTI6V2A HMOX1_HUMAN Inhibitor [2]
Hemoglobin (HB) TTQO71U HBA_HUMAN Inhibitor [2]
Mycobacterium Cytochrome p450 121 (MycB cyp121) TTBK0PU CP121_MYCBO Inhibitor [2]
Nitric-oxide synthase brain (NOS1) TTZUFI5 NOS1_HUMAN Inhibitor [2]
Nitric-oxide synthase endothelial (NOS3) TTCM4B3 NOS3_HUMAN Inhibitor [2]
Nitric-oxide synthase inducible (NOS2) TTF10I9 NOS2_HUMAN Inhibitor [2]
Prostaglandin G/H synthase 1 (COX-1) TT8NGED PGH1_HUMAN Inhibitor [2]
Prostaglandin G/H synthase 2 (COX-2) TTVKILB PGH2_HUMAN Inhibitor [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
5-aminolevulinate synthase, non-specific, mitochondrial (ALAS1) OTQY6ZSF HEM1_HUMAN Gene/Protein Processing [3]
Albumin (ALB) OTVMM513 ALBU_HUMAN Protein Interaction/Cellular Processes [4]
Amyloid-beta precursor protein (APP) OTKFD7R4 A4_HUMAN Drug Response [5]
C-C motif chemokine 3 (CCL3) OTW2H3ND CCL3_HUMAN Protein Interaction/Cellular Processes [6]
Microprocessor complex subunit DGCR8 (DGCR8) OT62LXE4 DGCR8_HUMAN Drug Response [7]
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Gene/Protein Processing [8]
Mitogen-activated protein kinase 3 (MAPK3) OTCYKGKO MK03_HUMAN Gene/Protein Processing [8]
Nuclear factor NF-kappa-B p105 subunit (NFKB1) OTNRRD8I NFKB1_HUMAN Protein Interaction/Cellular Processes [6]
Oxygen-dependent coproporphyrinogen-III oxidase, mitochondrial (CPOX) OTIAY121 HEM6_HUMAN Biotransformations [9]
Protein AMBP (AMBP) OTLU8GU8 AMBP_HUMAN Gene/Protein Processing [10]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Discovery agent
ICD Disease Classification N.A.
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Prostaglandin G/H synthase 2 (COX-2) DTT PTGS2 7.93E-04 -0.29 -0.34
Prostaglandin G/H synthase 1 (COX-1) DTT PTGS1 3.97E-03 0.16 0.43
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Heme (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Inotersen DMJ93CT Moderate Increased risk of bleeding by the combination of Heme and Inotersen. Amyloidosis [5D00] [11]
Trastuzumab Emtansine DMU1LXS Moderate Increased risk of bleeding by the combination of Heme and Trastuzumab Emtansine. Breast cancer [2C60-2C6Y] [11]
Regorafenib DMHSY1I Moderate Increased risk of bleeding by the combination of Heme and Regorafenib. Colorectal cancer [2B91] [11]
Intedanib DMSTA36 Moderate Increased risk of bleeding by the combination of Heme and Intedanib. Colorectal cancer [2B91] [11]
Ardeparin DMYRX8B Moderate Increased risk of bleeding by the combination of Heme and Ardeparin. Coronary thrombosis [BA43] [11]
Rivaroxaban DMQMBZ1 Moderate Increased risk of bleeding by the combination of Heme and Rivaroxaban. Deep vein thrombosis [BD71] [11]
Tazemetostat DMWP1BH Moderate Increased risk of bleeding by the combination of Heme and Tazemetostat. Follicular lymphoma [2A80] [11]
Avapritinib DMK2GZX Moderate Increased risk of bleeding by the combination of Heme and Avapritinib. Gastrointestinal stromal tumour [2B5B] [11]
Acalabrutinib DM7GCVW Moderate Increased risk of bleeding by the combination of Heme and Acalabrutinib. Mature B-cell lymphoma [2A85] [11]
Ibrutinib DMHZCPO Moderate Increased risk of bleeding by the combination of Heme and Ibrutinib. Mature B-cell lymphoma [2A85] [11]
Ponatinib DMYGJQO Moderate Increased risk of bleeding by the combination of Heme and Ponatinib. Mature B-cell lymphoma [2A85] [11]
Panobinostat DM58WKG Moderate Increased risk of bleeding by the combination of Heme and Panobinostat. Multiple myeloma [2A83] [11]
Fedratinib DM4ZBK6 Moderate Increased risk of bleeding by the combination of Heme and Fedratinib. Myeloproliferative neoplasm [2A20] [11]
Ruxolitinib DM7Q98D Moderate Increased risk of bleeding by the combination of Heme and Ruxolitinib. Myeloproliferative neoplasm [2A20] [11]
Prasugrel DM7MT6E Moderate Increased risk of bleeding by the combination of Heme and Prasugrel. Myocardial infarction [BA41-BA43] [11]
Vorapaxar DMA16BR Moderate Increased risk of bleeding by the combination of Heme and Vorapaxar. Myocardial infarction [BA41-BA43] [11]
Caplacizumab DMPUKA7 Moderate Increased risk of bleeding by the combination of Heme and Caplacizumab. Thrombocytopenia [3B64] [11]
Apixaban DM89JLN Moderate Increased risk of bleeding by the combination of Heme and Apixaban. Thrombosis [DB61-GB90] [11]
Cangrelor DM8JRH0 Moderate Increased risk of bleeding by the combination of Heme and Cangrelor. Thrombosis [DB61-GB90] [11]
Brilinta DMBR01X Moderate Increased risk of bleeding by the combination of Heme and Brilinta. Thrombosis [DB61-GB90] [11]
Cabozantinib DMIYDT4 Moderate Increased risk of bleeding by the combination of Heme and Cabozantinib. Thyroid cancer [2D10] [11]
Betrixaban DM2C4RF Moderate Increased risk of bleeding by the combination of Heme and Betrixaban. Venous thromboembolism [BD72] [11]
⏷ Show the Full List of 22 DDI Information of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4349).
2 The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42.
3 Lon peptidase 1 (LONP1)-dependent breakdown of mitochondrial 5-aminolevulinic acid synthase protein by heme in human liver cells. J Biol Chem. 2011 Jul 29;286(30):26424-30. doi: 10.1074/jbc.M110.215772. Epub 2011 Jun 9.
4 Allosteric modulation of anti-HIV drug and ferric heme binding to human serum albumin. FEBS J. 2005 Dec;272(24):6287-96. doi: 10.1111/j.1742-4658.2005.05015.x.
5 Key roles for tyrosine 10 in a-heme complexes and its relevance to oxidative stress. Chem Res Toxicol. 2015 Mar 16;28(3):365-72. doi: 10.1021/tx5003035. Epub 2014 Sep 24.
6 Role of 15-hydroxyeicosatetraenoic acid in hemozoin-induced lysozyme release from human adherent monocytes. Biofactors. 2013 May-Jun;39(3):304-14. doi: 10.1002/biof.1071. Epub 2013 Jan 28.
7 DiGeorge critical region 8 (DGCR8) is a double-cysteine-ligated heme protein. J Biol Chem. 2011 May 13;286(19):16716-25. doi: 10.1074/jbc.M110.180844. Epub 2011 Mar 21.
8 Cytotoxic effects of metal protoporphyrins in glioblastoma cells: roles of albumin, reactive oxygen species, and heme oxygenase-1. Toxicol Lett. 2008 Mar 15;177(2):97-107. doi: 10.1016/j.toxlet.2008.01.004. Epub 2008 Jan 15.
9 Expression of coproporphyrinogen oxidase and synthesis of hemoglobin in human erythroleukemia K562 cells. Eur J Biochem. 2001 Mar;268(6):1705-11.
10 Up-regulation of A1M/1-microglobulin in skin by heme and reactive oxygen species gives protection from oxidative damage. PLoS One. 2011;6(11):e27505. doi: 10.1371/journal.pone.0027505. Epub 2011 Nov 11.
11 Product Information. Panhematin (hemin). Recordati Rare Diseases Inc, Lebanon, NJ.