Pseudoephedrine
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Basic Info
| Common Name | Pseudoephedrine(F05457) |
| 2D Structure | |
| Description | An alpha- and beta-adrenergic agonist that may also enhance release of norepinephrine. It has been used in the treatment of several disorders including asthma, heart failure, rhinitis, and urinary incontinence, and for its central nervous system stimulatory effects in the treatment of narcolepsy and depression. It has become less extensively used with the advent of more selective agonists. [PubChem] |
| FRCD ID | F05457 |
| CAS Number | 90-82-4 |
| PubChem CID | 7028 |
| Formula | C10H15NO |
| IUPAC Name | (1S,2S)-2-(methylamino)-1-phenylpropan-1-ol |
| InChI Key | KWGRBVOPPLSCSI-WCBMZHEXSA-N |
| InChI | InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10+/m0/s1 |
| Canonical SMILES | CC(C(C1=CC=CC=C1)O)NC |
| Isomeric SMILES | C[C@@H]([C@H](C1=CC=CC=C1)O)NC |
| Wikipedia | Pseudoephedrine |
| Synonyms |
d-Isoephedrine
PSEUDOEPHEDRINE
(+)-Pseudoephedrine
Isoephedrine
d-Pseudoephedrine
Sudafed
trans-Ephedrine
Psi-ephedrin
Psi-ephedrine
d-psi-Ephedrine
|
| Classifies |
Illegal Additives
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Phenylpropanes |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Phenylpropanes |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Phenylpropane - Aralkylamine - 1,2-aminoalcohol - Secondary alcohol - Secondary aliphatic amine - Secondary amine - Alcohol - Organopnictogen compound - Organic oxygen compound - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Amine - Aromatic alcohol - Hydrocarbon derivative - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 165.236 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 3 |
| Complexity | 121 |
| Monoisotopic Mass | 165.115 |
| Exact Mass | 165.115 |
| XLogP | 0.9 |
| Formal Charge | 0 |
| Heavy Atom Count | 12 |
| Defined Atom Stereocenter Count | 2 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.5638 |
| Human Intestinal Absorption | HIA+ | 0.9645 |
| Caco-2 Permeability | Caco2+ | 0.8866 |
| P-glycoprotein Substrate | Non-substrate | 0.7182 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9795 |
| Non-inhibitor | 0.9840 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8965 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.5451 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8001 |
| CYP450 2D6 Substrate | Non-substrate | 0.7839 |
| CYP450 3A4 Substrate | Non-substrate | 0.7235 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.5595 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.7209 |
| CYP450 2D6 Inhibitor | Inhibitor | 0.5846 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.5737 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9431 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9070 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9329 |
| Non-inhibitor | 0.9277 | |
| AMES Toxicity | Non AMES toxic | 0.9517 |
| Carcinogens | Non-carcinogens | 0.7739 |
| Fish Toxicity | Low FHMT | 0.6240 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9074 |
| Honey Bee Toxicity | Low HBT | 0.5194 |
| Biodegradation | Not ready biodegradable | 0.7807 |
| Acute Oral Toxicity | III | 0.8940 |
| Carcinogenicity (Three-class) | Non-required | 0.7401 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.4821 | LogS |
| Caco-2 Permeability | 1.1338 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.3882 | LD50, mol/kg |
| Fish Toxicity | 3.0367 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.2968 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Capillary electrophoresis separation of phenethylamine enantiomers using aminoacid based ionic liquids. | J Pharm Biomed Anal | 2018 Jan 30 | 29059613 |
| In vitro, in vivo, and clinical studies of tedizolid to assess the potential for peripheral or central monoamine oxidase interactions. | Antimicrob Agents Chemother | 2013 Jul | 23612197 |
| Sinusitis (acute). | BMJ Clin Evid | 2008 Mar 10 | 19450327 |
| Bitterness suppression with zinc sulfate and na-cyclamate: a model of combinedperipheral and central neural approaches to flavor modification. | Pharm Res | 2005 Nov | 16132352 |
| Population pharmacokinetics and pharmacodynamics of garenoxacin in patients with community-acquired respiratory tract infections. | Antimicrob Agents Chemother | 2004 Dec | 15561855 |
| Clinical pharmacokinetics of linezolid, a novel oxazolidinone antibacterial. | Clin Pharmacokinet | 2003 | 14531724 |
| Liquid chromatography/tandem mass spectrometric bioanalysis using normal-phasecolumns with aqueous/organic mobile phases - a novel approach of eliminatingevaporation and reconstitution steps in 96-well SPE. | Rapid Commun Mass Spectrom | 2002 | 12362389 |
| Study on the chiral recognition of the enantiomers of ephedrine derivatives with neutral and sulfated heptakis(2,3-O-diacetyl)-beta-cyclodextrins using capillary electrophoresis, UV, nuclear magnetic resonance spectroscopy and massspectrometry. | J Chromatogr A | 2001 Apr 20 | 11358226 |
Targets
- General Function:
- Protein heterodimerization activity
- Specific Function:
- This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine(PE)-stimulated ERK signaling in cardiac myocytes.
- Gene Name:
- ADRA1A
- Uniprot ID:
- P35348
- Molecular Weight:
- 51486.005 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Protein homodimerization activity
- Specific Function:
- Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine.
- Gene Name:
- ADRB2
- Uniprot ID:
- P07550
- Molecular Weight:
- 46458.32 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Monoamine transmembrane transporter activity
- Specific Function:
- Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
- Gene Name:
- SLC6A3
- Uniprot ID:
- Q01959
- Molecular Weight:
- 68494.255 Da
References
- Wee S, Ordway GA, Woolverton WL: Reinforcing effect of pseudoephedrine isomers and the mechanism of action. Eur J Pharmacol. 2004 Jun 16;493(1-3):117-25. [15189772 ]
- General Function:
- Norepinephrine:sodium symporter activity
- Specific Function:
- Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
- Gene Name:
- SLC6A2
- Uniprot ID:
- P23975
- Molecular Weight:
- 69331.42 Da
References
- Wee S, Ordway GA, Woolverton WL: Reinforcing effect of pseudoephedrine isomers and the mechanism of action. Eur J Pharmacol. 2004 Jun 16;493(1-3):117-25. [15189772 ]
- General Function:
- Receptor signaling protein activity
- Specific Function:
- Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity. Mediates Ras activation through G(s)-alpha- and cAMP-mediated signaling.
- Gene Name:
- ADRB1
- Uniprot ID:
- P08588
- Molecular Weight:
- 51322.1 Da
References
- Vansal SS, Feller DR: Direct effects of ephedrine isomers on human beta-adrenergic receptor subtypes. Biochem Pharmacol. 1999 Sep 1;58(5):807-10. [10449190 ]
- General Function:
- Kinase activator activity
- Specific Function:
- Produced by T-cells in response to antigenic or mitogenic stimulation, this protein is required for T-cell proliferation and other activities crucial to regulation of the immune response. Can stimulate B-cells, monocytes, lymphokine-activated killer cells, natural killer cells, and glioma cells.
- Gene Name:
- IL2
- Uniprot ID:
- P60568
- Molecular Weight:
- 17627.52 Da
References
- Fiebich BL, Collado JA, Stratz C, Valina C, Hochholzer W, Munoz E, Bellido LM: Pseudoephedrine inhibits T-cell activation by targeting NF-kappaB, NFAT and AP-1 signaling pathways. Immunopharmacol Immunotoxicol. 2012 Feb;34(1):98-106. doi: 10.3109/08923973.2011.582118. Epub 2011 Jun 2. [21631396 ]
- General Function:
- Transcriptional activator activity, rna polymerase ii distal enhancer sequence-specific binding
- Specific Function:
- Plays a role in the inducible expression of cytokine genes in T-cells, especially in the induction of the IL-2 or IL-4 gene transcription. Also controls gene expression in embryonic cardiac cells. Could regulate not only the activation and proliferation but also the differentiation and programmed death of T-lymphocytes as well as lymphoid and non-lymphoid cells.
- Gene Name:
- NFATC1
- Uniprot ID:
- O95644
- Molecular Weight:
- 101241.73 Da
References
- Fiebich BL, Collado JA, Stratz C, Valina C, Hochholzer W, Munoz E, Bellido LM: Pseudoephedrine inhibits T-cell activation by targeting NF-kappaB, NFAT and AP-1 signaling pathways. Immunopharmacol Immunotoxicol. 2012 Feb;34(1):98-106. doi: 10.3109/08923973.2011.582118. Epub 2011 Jun 2. [21631396 ]
- General Function:
- Serotonin:sodium symporter activity
- Specific Function:
- Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin and recycles it in a sodium-dependent manner.
- Gene Name:
- SLC6A4
- Uniprot ID:
- P31645
- Molecular Weight:
- 70324.165 Da
References
- Wee S, Ordway GA, Woolverton WL: Reinforcing effect of pseudoephedrine isomers and the mechanism of action. Eur J Pharmacol. 2004 Jun 16;493(1-3):117-25. [15189772 ]
References
- Fiebich BL, Collado JA, Stratz C, Valina C, Hochholzer W, Munoz E, Bellido LM: Pseudoephedrine inhibits T-cell activation by targeting NF-kappaB, NFAT and AP-1 signaling pathways. Immunopharmacol Immunotoxicol. 2012 Feb;34(1):98-106. doi: 10.3109/08923973.2011.582118. Epub 2011 Jun 2. [21631396 ]
- General Function:
- Thioesterase binding
- Specific Function:
- Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol.
- Gene Name:
- ADRA2A
- Uniprot ID:
- P08913
- Molecular Weight:
- 48956.275 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Tumor necrosis factor receptor binding
- Specific Function:
- Cytokine that binds to TNFRSF1A/TNFR1 and TNFRSF1B/TNFBR. It is mainly secreted by macrophages and can induce cell death of certain tumor cell lines. It is potent pyrogen causing fever by direct action or by stimulation of interleukin-1 secretion and is implicated in the induction of cachexia, Under certain conditions it can stimulate cell proliferation and induce cell differentiation. Impairs regulatory T-cells (Treg) function in individuals with rheumatoid arthritis via FOXP3 dephosphorylation. Upregulates the expression of protein phosphatase 1 (PP1), which dephosphorylates the key 'Ser-418' residue of FOXP3, thereby inactivating FOXP3 and rendering Treg cells functionally defective (PubMed:23396208). Key mediator of cell death in the anticancer action of BCG-stimulated neutrophils in combination with DIABLO/SMAC mimetic in the RT4v6 bladder cancer cell line (PubMed:22517918).The TNF intracellular domain (ICD) form induces IL12 production in dendritic cells.
- Gene Name:
- TNF
- Uniprot ID:
- P01375
- Molecular Weight:
- 25644.15 Da
References
- Fiebich BL, Collado JA, Stratz C, Valina C, Hochholzer W, Munoz E, Bellido LM: Pseudoephedrine inhibits T-cell activation by targeting NF-kappaB, NFAT and AP-1 signaling pathways. Immunopharmacol Immunotoxicol. 2012 Feb;34(1):98-106. doi: 10.3109/08923973.2011.582118. Epub 2011 Jun 2. [21631396 ]