Page last updated: 2024-11-04

porphobilinogen

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Cross-References

ID SourceID
PubMed CID1021
CHEMBL ID1235151
CHEBI ID17381
SCHEMBL ID188532
MeSH IDM0017331

Synonyms (36)

Synonym
5-(aminomethyl)-4-(carboxymethyl)-pyrrole-3-propionic acid
CHEMBL1235151 ,
CHEBI:17381 ,
3-[5-(aminomethyl)-4-(carboxymethyl)-1h-pyrrol-3-yl]propanoic acid
1h-pyrrole-3-propanoic acid, 5-(aminomethyl)-4-(carboxymethyl)-
5-(aminomethyl)-4-(carboxymethyl)-1h-pyrrole-3-propionic acid
2-aminomethylpyrrol-3-acetic acid 4-propionic acid
1h-pyrrole-3-propanoic acid, 5-(aminomethyl)-4-(carboxymethyl)- (9ci)
5-(aminomethyl)-4-(carboxymethyl)-1h-pyrrole-3-propanoic acid
pyrrole-3-propionic acid, 5-(aminomethyl)-4-(carboxymethyl)-
pyrrole-3-propionic acid, 5-(aminomethyl)-4-(carboxymethyl)- (6ci,8ci)
PORPHOBILINOGEN ,
C00931
487-90-1
porphobilinogen, powder
DB02272
49E0A216-4AD4-42E3-B491-2A6371927562
74khc72qxk ,
unii-74khc72qxk
einecs 207-666-3
FT-0673977
AKOS015894423
3-(5-(aminomethyl)-4-(carboxymethyl)-1h-pyrrol-3-yl)propanoic acid
porphobilinogen [mi]
SCHEMBL188532
DTXSID4060070
QSHWIQZFGQKFMA-UHFFFAOYSA-N
5-(aminomethyl)-4-(carboxymethyl)-pyrrole-3-propionate
CS-W014211
HY-W013495
Q421178
3-(5-aminomethyl-4-carboxymethyl-1h-pyrrol-3-yl)-propionic acid
F85627
3-[5-(aminomethyl)-4-(carboxymethyl)-1h-pyrrol-3-yl]propanoic acid hydrate
3-(5-(aminomethyl)-4-(carboxymethyl)-1h-pyrrol-3-yl)propanoicacid
bdbm50596183

Research Excerpts

Effects

ExcerptReferenceRelevance
"Porphobilinogen deaminase has been purified and crystallized from an overproducing recombinant strain of Escherichia coli harbouring a hemC-containing plasmid which has permitted the purification of milligram quantities of the enzyme. "( Purification, crystallization and properties of porphobilinogen deaminase from a recombinant strain of Escherichia coli K12.
Jordan, PM; Thomas, SD; Warren, MJ, 1988
)
1.97

Toxicity

ExcerptReferenceRelevance
" Only ALA (10 microM) and glutamic acid (1 mM) were toxic towards neurons in culture, as measured by cell survival after 5 days' exposure."( [Mechanism of delta-aminolevulinic acid neurotoxicity].
Lamm, MC; McCarthy, BW; Neethling, AC; Percy, VA; Taljaard, JJ; Truter, L, 1981
)
0.26
"No serious adverse events were observed."( Safety, pharmacokinetics and pharmocodynamics of recombinant human porphobilinogen deaminase in healthy subjects and asymptomatic carriers of the acute intermittent porphyria gene who have increased porphyrin precursor excretion.
Andersson, DE; Harper, P; Rejkjaer, L; Sardh, E, 2007
)
0.58
"The recombinant human porphobilinogen deaminase enzyme preparation was found to be safe to administer and effective for removal of the accumulated metabolite porphobilinogen from plasma and urine."( Safety, pharmacokinetics and pharmocodynamics of recombinant human porphobilinogen deaminase in healthy subjects and asymptomatic carriers of the acute intermittent porphyria gene who have increased porphyrin precursor excretion.
Andersson, DE; Harper, P; Rejkjaer, L; Sardh, E, 2007
)
0.89

Pharmacokinetics

The pharmacokinetic profile of recombinant human porphobilinogen deaminase showed dose proportionality, and the elimination half-life was about 2. The pharmacodynamic effect of the enzyme was studied through changes in plasma porphMobilinogen concentrations.

ExcerptReferenceRelevance
" The pharmacodynamic effect of the enzyme was studied through changes in plasma porphobilinogen concentrations."( Safety, pharmacokinetics and pharmocodynamics of recombinant human porphobilinogen deaminase in healthy subjects and asymptomatic carriers of the acute intermittent porphyria gene who have increased porphyrin precursor excretion.
Andersson, DE; Harper, P; Rejkjaer, L; Sardh, E, 2007
)
0.8
" This phase I study evaluated the safety, pharmacokinetic, and pharmacodynamic profile of subcutaneously (SC) administered givosiran in patients with acute intermittent porphyria, the most common AHP type."( Pharmacokinetics and Pharmacodynamics of the Small Interfering Ribonucleic Acid, Givosiran, in Patients With Acute Hepatic Porphyria.
Agarwal, S; Clausen, VA; Goel, V; Habtemariam, BA; Kim, JB; Robbie, GJ; Simon, AR, 2020
)
0.56

Bioavailability

ExcerptReferenceRelevance
" However, typical Bodipys are highly lipophilic, which often results in nonfluorescent aggregates in aqueous solution and also severely limits their bioavailability to cells and tissues."( Carbon-Dipyrromethenes: Bright Cationic Fluorescent Dyes and Potential Application in Revealing Cellular Trafficking of Mitochondrial Glutathione Conjugates.
Guo, W; Liu, J; Liu, M; Sun, YQ; Zhang, H, 2020
)
0.56
" In AIP mice, preventive treatment with an experimental fusion protein of insulin and apolipoprotein A-I improved the disease by promoting fat mobilization in adipose tissue, increasing the metabolite bioavailability for the TCA cycle and inducing mitochondrial biogenesis in the liver."( Understanding Carbohydrate Metabolism and Insulin Resistance in Acute Intermittent Porphyria.
Córdoba, KM; Ena, J; Enríquez de Salamanca, R; Fontanellas, A; Jericó, D; Morales-Conejo, M; Solares, I, 2022
)
0.72

Dosage Studied

ExcerptRelevanceReference
" After treatment with Resochin in an erroneously high dosage (1."( [Accident in treatment of porphyria cutanea tarda by chloroquine (Resochin) (author's transl)].
Eichenauer, MG; Goerz, G; Krieg, T, 1976
)
0.26
" Adjustments in dosage or route of administration were sometimes needed."( A gonadotropin releasing hormone analogue prevents cyclical attacks of porphyria.
Anderson, KE; Bardin, CW; Kappas, A; Spitz, IM, 1990
)
0.28
" For groups 2 and 6, atracurium was administered at a dosage of 4 mg/kg of body weight, followed by a continuous infusion of 15 mg/kg/h."( Porphyrinogenic effects of atracurium, vecuronium, and pancuronium in a primed rat model.
Bach, A; Böhrer, H; Bolsen, K; Goerz, G; Kohl, B; Martin, E; Schmidt, H, 1994
)
0.29
" Finally, a theoretical hemin effect was implemented to illustrate the applicability of the model to dosage optimization in drug therapies."( Computational disease model of phenobarbital-induced acute attacks in an acute intermittent porphyria mouse model.
Fontanellas, A; Jericó, D; Parra-Guillén, ZP; Sampedro, A; Serrano-Mendioroz, I; Trocóniz, IF; Vera-Yunca, D, 2019
)
0.51
" Greater and more sustained reductions in ALA and PBG were achieved with once monthly dosing compared with once quarterly dosing."( Pharmacokinetics and Pharmacodynamics of the Small Interfering Ribonucleic Acid, Givosiran, in Patients With Acute Hepatic Porphyria.
Agarwal, S; Clausen, VA; Goel, V; Habtemariam, BA; Kim, JB; Robbie, GJ; Simon, AR, 2020
)
0.56
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Escherichia coli metaboliteAny bacterial metabolite produced during a metabolic reaction in Escherichia coli.
mouse metaboliteAny mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

ClassDescription
pyrrolesAn azole that includes only one N atom and no other heteroatom as a part of the aromatic skeleton.
dicarboxylic acidAny carboxylic acid containing two carboxy groups.
aralkylamino compoundAn organic amino compound in which an aminoalkyl group is linked to an arene.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (10)

PathwayProteinsCompounds
Porphyrin Metabolism1636
Acute Intermittent Porphyria1636
Porphyria Variegata (PV)1636
Congenital Erythropoietic Porphyria (CEP) or Gunther Disease1636
Hereditary Coproporphyria (HCP)1636
Porphyrin_metabolism ( Porphyrin metabolism )716
Hemesynthesis defects and porphyrias018
Biochemical pathways: part I0466
Tyrosine metabolism and related disorders724
Heme biosynthesis012

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Macrophage migration inhibitory factorHomo sapiens (human)IC50 (µMol)400.00000.03803.09109.8000AID1877334
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (35)

Processvia Protein(s)Taxonomy
prostaglandin biosynthetic processMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of cytokine productionMacrophage migration inhibitory factorHomo sapiens (human)
negative regulation of mature B cell apoptotic processMacrophage migration inhibitory factorHomo sapiens (human)
inflammatory responseMacrophage migration inhibitory factorHomo sapiens (human)
cell surface receptor signaling pathwayMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of cell population proliferationMacrophage migration inhibitory factorHomo sapiens (human)
negative regulation of gene expressionMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of protein kinase A signalingMacrophage migration inhibitory factorHomo sapiens (human)
negative regulation of macrophage chemotaxisMacrophage migration inhibitory factorHomo sapiens (human)
carboxylic acid metabolic processMacrophage migration inhibitory factorHomo sapiens (human)
DNA damage response, signal transduction by p53 class mediatorMacrophage migration inhibitory factorHomo sapiens (human)
negative regulation of cell migrationMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of B cell proliferationMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of lipopolysaccharide-mediated signaling pathwayMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of tumor necrosis factor productionMacrophage migration inhibitory factorHomo sapiens (human)
negative regulation of myeloid cell apoptotic processMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of peptidyl-serine phosphorylationMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of phosphorylationMacrophage migration inhibitory factorHomo sapiens (human)
regulation of macrophage activationMacrophage migration inhibitory factorHomo sapiens (human)
negative regulation of apoptotic processMacrophage migration inhibitory factorHomo sapiens (human)
negative regulation of DNA damage response, signal transduction by p53 class mediatorMacrophage migration inhibitory factorHomo sapiens (human)
innate immune responseMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of fibroblast proliferationMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of peptidyl-tyrosine phosphorylationMacrophage migration inhibitory factorHomo sapiens (human)
positive chemotaxisMacrophage migration inhibitory factorHomo sapiens (human)
negative regulation of protein metabolic processMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of prostaglandin secretion involved in immune responseMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of myeloid leukocyte cytokine production involved in immune responseMacrophage migration inhibitory factorHomo sapiens (human)
protein homotrimerizationMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of ERK1 and ERK2 cascadeMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of arachidonic acid secretionMacrophage migration inhibitory factorHomo sapiens (human)
cellular senescenceMacrophage migration inhibitory factorHomo sapiens (human)
negative regulation of intrinsic apoptotic signaling pathway in response to DNA damage by p53 class mediatorMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of chemokine (C-X-C motif) ligand 2 productionMacrophage migration inhibitory factorHomo sapiens (human)
negative regulation of cellular senescenceMacrophage migration inhibitory factorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
protease bindingMacrophage migration inhibitory factorHomo sapiens (human)
dopachrome isomerase activityMacrophage migration inhibitory factorHomo sapiens (human)
cytokine activityMacrophage migration inhibitory factorHomo sapiens (human)
cytokine receptor bindingMacrophage migration inhibitory factorHomo sapiens (human)
protein bindingMacrophage migration inhibitory factorHomo sapiens (human)
chemoattractant activityMacrophage migration inhibitory factorHomo sapiens (human)
identical protein bindingMacrophage migration inhibitory factorHomo sapiens (human)
phenylpyruvate tautomerase activityMacrophage migration inhibitory factorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (11)

Processvia Protein(s)Taxonomy
extracellular regionMacrophage migration inhibitory factorHomo sapiens (human)
extracellular spaceMacrophage migration inhibitory factorHomo sapiens (human)
nucleoplasmMacrophage migration inhibitory factorHomo sapiens (human)
cytoplasmMacrophage migration inhibitory factorHomo sapiens (human)
cytosolMacrophage migration inhibitory factorHomo sapiens (human)
plasma membraneMacrophage migration inhibitory factorHomo sapiens (human)
cell surfaceMacrophage migration inhibitory factorHomo sapiens (human)
vesicleMacrophage migration inhibitory factorHomo sapiens (human)
secretory granule lumenMacrophage migration inhibitory factorHomo sapiens (human)
extracellular exosomeMacrophage migration inhibitory factorHomo sapiens (human)
ficolin-1-rich granule lumenMacrophage migration inhibitory factorHomo sapiens (human)
extracellular spaceMacrophage migration inhibitory factorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (1)

Assay IDTitleYearJournalArticle
AID1877334Inhibition of MIF tautomerase (unknown origin) using 4-HPP as substrate preincubated for 1 hr followed by substrate addition2022Bioorganic & medicinal chemistry letters, 01-01, Volume: 55Repurposing old drugs as novel inhibitors of human MIF from structural and functional analysis.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (917)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990482 (52.56)18.7374
1990's93 (10.14)18.2507
2000's98 (10.69)29.6817
2010's176 (19.19)24.3611
2020's68 (7.42)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 53.86

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index53.86 (24.57)
Research Supply Index6.87 (2.92)
Research Growth Index4.61 (4.65)
Search Engine Demand Index90.42 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (53.86)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials11 (1.16%)5.53%
Reviews58 (6.09%)6.00%
Case Studies130 (13.66%)4.05%
Observational3 (0.32%)0.25%
Other750 (78.78%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]