NAV

Protoporphyrin

Identification

Generic Name
Protoporphyrin
DrugBank Accession Number
DB02285
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 562.6582
Monoisotopic: 562.258005596
Chemical Formula
C34H34N4O4
Synonyms
  • Protoporphyrin IX

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UFerritin light chainNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
PathwayCategory
Porphyrin MetabolismMetabolic
Acute Intermittent PorphyriaDisease
Porphyria Variegata (PV)Disease
Hereditary Coproporphyria (HCP)Disease
Congenital Erythropoietic Porphyria (CEP) or Gunther DiseaseDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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interactions in your software
PadeliporfinProtoporphyrin may increase the photosensitizing activities of Padeliporfin.
Porfimer sodiumProtoporphyrin may increase the photosensitizing activities of Porfimer sodium.
TretinoinThe risk or severity of adverse effects can be increased when Tretinoin is combined with Protoporphyrin.
VerteporfinProtoporphyrin may increase the photosensitizing activities of Verteporfin.
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Food Interactions
Not Available

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
C2K325S808
CAS number
553-12-8
InChI Key
KSFOVUSSGSKXFI-UJJXFSCMSA-N
InChI
InChI=1S/C34H34N4O4/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/h7-8,13-16,35,38H,1-2,9-12H2,3-6H3,(H,39,40)(H,41,42)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-
IUPAC Name
3-[20-(2-carboxyethyl)-9,14-diethenyl-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid
SMILES
CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(C=C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C=C)=C4C)/C(C)=C3CCC(O)=O

References

Synthesis Reference

Elaine A. Best, Charles Lee Hershberger, Christopher Carl Frye, "Methods of reducing the levels of protoporphyrin IX in recombinant hemoglobin preparations." U.S. Patent US6136565, issued April, 1998.

US6136565
General References
Not Available
Human Metabolome Database
HMDB0000241
KEGG Compound
C02191
PubChem Compound
4971
PubChem Substance
46506247
ChemSpider
10469486
BindingDB
50004784
ChEBI
15430
ChEMBL
CHEMBL1325592
Therapeutic Targets Database
DNC001154
PDBe Ligand
PP9
Wikipedia
Protoporphyrin_IX

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubility169 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
Predicted Properties
PropertyValueSource
Water Solubility0.0217 mg/mLALOGPS
logP4.4ALOGPS
logP6.58ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)3.79ChemAxon
pKa (Strongest Basic)5.09ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area131.96 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity163.81 m3·mol-1ChemAxon
Polarizability66.03 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.622
Blood Brain Barrier+0.6268
Caco-2 permeable-0.7138
P-glycoprotein substrateSubstrate0.6404
P-glycoprotein inhibitor INon-inhibitor0.705
P-glycoprotein inhibitor IINon-inhibitor0.8478
Renal organic cation transporterNon-inhibitor0.8067
CYP450 2C9 substrateNon-substrate0.8106
CYP450 2D6 substrateNon-substrate0.8237
CYP450 3A4 substrateSubstrate0.5341
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorInhibitor0.8949
CYP450 2D6 inhibitorNon-inhibitor0.7052
CYP450 2C19 inhibitorNon-inhibitor0.8749
CYP450 3A4 inhibitorNon-inhibitor0.8733
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8535
Ames testNon AMES toxic0.7111
CarcinogenicityNon-carcinogens0.9123
BiodegradationNot ready biodegradable0.9479
Rat acute toxicity2.5655 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9808
hERG inhibition (predictor II)Non-inhibitor0.9459
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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Details1. Ferritin light chain
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Iron ion binding
Specific Function
Stores iron in a soluble, non-toxic, readily available form. Important for iron homeostasis. Iron is taken up in the ferrous form and deposited as ferric hydroxides after oxidation. Also plays a ro...
Gene Name
FTL
Uniprot ID
P02792
Uniprot Name
Ferritin light chain
Molecular Weight
20019.49 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at June 13, 2005 13:24 / Updated at July 02, 2020 13:14