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Record Information
Version2.0
Creation Date2014-08-30 21:04:24 UTC
Update Date2014-12-24 20:26:52 UTC
Accession NumberT3D4560
Identification
Common NamePromethazine
ClassSmall Molecule
DescriptionA phenothiazine derivative with histamine H1-blocking, antimuscarinic, and sedative properties. It is used as an antiallergic, in pruritus, for motion sickness and sedation, and also in animals. [PubChem]
Compound Type
  • Amine
  • Anti-Allergic Agent
  • Antipruritic
  • Drug
  • Ether
  • Histamine H1 Antagonist
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
(2-dimethylamino-2-methyl)ethyl-N-dibenzoparathiazine
10-(2-Dimethylaminopropyl)phenothiazine
10-[2-(dimethylamino)Propyl]phenothiazine
Avomine
Fargan
Farganesse
Lergigan
N,N,alpha-Trimethyl-10H-phenothiazine-10-ethanamine
N,N,α-trimethyl-10H-phenothiazine-10-ethanamine
N-(2'-dimethylamino-2'-Methyl)ethylphenothiazine
PHENADOZ
Phenergan
Proazamine
Prometazina
Promethazinum
Promethegan
Prothiazine
Receptozine
Romergan
Sominex
Chemical FormulaC17H20N2S
Average Molecular Mass284.419 g/mol
Monoisotopic Mass284.135 g/mol
CAS Registry Number60-87-7
IUPAC Namedimethyl[1-(10H-phenothiazin-10-yl)propan-2-yl]amine
Traditional Namepromethazine
SMILESCC(CN1C2=CC=CC=C2SC2=CC=CC=C12)N(C)C
InChI IdentifierInChI=1/C17H20N2S/c1-13(18(2)3)12-19-14-8-4-6-10-16(14)20-17-11-7-5-9-15(17)19/h4-11,13H,12H2,1-3H3
InChI KeyInChIKey=PWWVAXIEGOYWEE-UHFFFAOYNA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazines
Sub ClassPhenothiazines
Direct ParentPhenothiazines
Alternative Parents
Substituents
  • Phenothiazine
  • Alkyldiarylamine
  • Diarylthioether
  • Aryl thioether
  • Tertiary aliphatic/aromatic amine
  • Para-thiazine
  • Benzenoid
  • Tertiary amine
  • Tertiary aliphatic amine
  • Thioether
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point60 °C
Boiling Point190-192 °C at 3.00E+00 mm Hg
Solubility15.6 mg/L (at 24 °C)
LogP4.81
Predicted Properties
PropertyValueSource
Water Solubility0.024 g/LALOGPS
logP4.52ALOGPS
logP4.29ChemAxon
logS-4.1ALOGPS
pKa (Strongest Basic)9.05ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area6.48 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity88.5 m³·mol⁻¹ChemAxon
Polarizability32.38 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-000i-0090000000-f1fe9756bed13819bbb4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-9000000000-abbdf5514dccef4821b2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-9100000000-9bef9a6b83d662fc7e2cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0079-8290000000-fe5d6b4e9f62b7270798JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-000i-0090000000-f1fe9756bed13819bbb4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-9000000000-abbdf5514dccef4821b2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-9100000000-9bef9a6b83d662fc7e2cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0079-8290000000-fe5d6b4e9f62b7270798JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0229-9150000000-19753aa755aa19143e9bJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000j-0690000000-0b4dfbac9712d2e36046JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-9220000000-9d761be1437f10dcc94bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000i-9120000000-53ae2d83de014d922ec7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0002-0920000000-c051699dc72e950f2e98JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0002-0910000000-e92aacd8ca86df8a0e18JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0002-0910000000-0ce89af1c9b2c4633edaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0002-0950000000-70d959c63d9e713a865aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-842e411dfa4c9fad1f7fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2090000000-76a910470a52a47a6757JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000f-8090000000-d597b4b7604e8276f449JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dr-9110000000-cbed4a551fc77cf0e5b9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-e24a248a31f0e31f1ec5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-009t-0940000000-afb556a81c40edffb9a1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-3910000000-3daef27d94a5cac7d4a7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9070000000-e74135a63711b2ca001fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9020000000-25ad7e0e10410cbe88c3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000j-9610000000-32a1e6113f4291e6a186JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-a26692bb509bb9fc8701JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-0590000000-3a84419d780b185fa21aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ot-0940000000-7c01990eb3e291008595JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-00di-9210000000-7167670dff3395a6ade2JSpectraViewer | MoNA
Toxicity Profile
Route of ExposureOn average, 88% of a promethazine dose is absorbed after oral administration; however, the absolute bioavailability is only 25% because of first-pass clearance.
Mechanism of ToxicityLike other H1-antagonists, promethazine competes with free histamine for binding at H1-receptor sites in the GI tract, uterus, large blood vessels, and bronchial muscle. The relief of nausea appears to be related to central anticholinergic actions and may implicate activity on the medullary chemoreceptor trigger zone.
MetabolismHepatic Route of Elimination: Promethazine hydrochloride is metabolized in the liver, with the sulfoxides of promethazine and N-desmethylpromethazine being the predominant metabolites appearing in the urine. Half Life: 16-19 hours
Toxicity ValuesIV, Mouse: LD50=55mg/kg
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the treatment of allergic disorders, and nausea/vomiting.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSymptoms of overdose include mild depression of the central nervous system and cardiovascular system to profound hypotension, respiratory depression, unconsciousness, and sudden death. Other reported reactions include hyperreflexia, hypertonia, ataxia, athetosis, and extensor-plantar reflexes (Babinski reflex).
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB01069
HMDB IDNot Available
PubChem Compound ID4927
ChEMBL IDCHEMBL643
ChemSpider ID4758
KEGG IDC07404
UniProt IDNot Available
OMIM ID
ChEBI ID8461
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkPromethazine
References
Synthesis Reference

DrugSyn.org

MSDST3D4560.pdf
General References
  1. Peters RJ Jr, Kelder SH, Markham CM, Yacoubian GS Jr, Peters LA, Ellis A: Beliefs and social norms about codeine and promethazine hydrochloride cough syrup (CPHCS) onset and perceived addiction among urban Houstonian adolescents: an addiction trend in the city of lean. J Drug Educ. 2003;33(4):415-25. [15237866 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Histamine receptor activity
Specific Function:
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system.
Gene Name:
HRH1
Uniprot ID:
P35367
Molecular Weight:
55783.61 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
  2. Suzuki A, Yasui-Furukori N, Mihara K, Kondo T, Furukori H, Inoue Y, Kaneko S, Otani K: Histamine H1-receptor antagonists, promethazine and homochlorcyclizine, increase the steady-state plasma concentrations of haloperidol and reduced haloperidol. Ther Drug Monit. 2003 Apr;25(2):192-6. [12657913 ]
  3. Smith BN, Armstrong WE: Histamine enhances the depolarizing afterpotential of immunohistochemically identified vasopressin neurons in the rat supraoptic nucleus via H1-receptor activation. Neuroscience. 1993 Apr;53(3):855-64. [8098142 ]
  4. Miller RA, Tu AT: Factors in snake venoms that increase capillary permeability. J Pharm Pharmacol. 1989 Nov;41(11):792-4. [2576052 ]
  5. Claro E, Arbones L, Garcia A, Picatoste F: Phosphoinositide hydrolysis mediated by histamine H1-receptors in rat brain cortex. Eur J Pharmacol. 1986 Apr 16;123(2):187-96. [3011460 ]
  6. Ikeda H, Kubo N, Nakamura A, Harada N, Minamino M, Yamashita T: Histamine-induced calcium released from cultured human mucosal microvascular endothelial cells from nasal inferior turbinate. Acta Otolaryngol. 1997 Nov;117(6):864-70. [9442829 ]
  7. Paton DM, Webster DR: Clinical pharmacokinetics of H1-receptor antagonists (the antihistamines). Clin Pharmacokinet. 1985 Nov-Dec;10(6):477-97. [2866055 ]
  8. Dick W, Lorenz W, Heintz D, Sitter H, Doenicke A: [Histamine release during induction of combination anesthesia using nalbuphine or fentanyl. Modulation of the reaction by premedication with promethazine/pethidine]. Anaesthesist. 1992;41(5):239-47. [1377455 ]
General Function:
Virus receptor activity
Specific Function:
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling activates phospholipase C and a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and promotes the release of Ca(2+) ions from intracellular stores. Affects neural activity, perception, cognition and mood. Plays a role in the regulation of behavior, including responses to anxiogenic situations and psychoactive substances. Plays a role in intestinal smooth muscle contraction, and may play a role in arterial vasoconstriction.(Microbial infection) Acts as a receptor for human JC polyomavirus/JCPyV.
Gene Name:
HTR2A
Uniprot ID:
P28223
Molecular Weight:
52602.58 Da
References
  1. Bileviciute I, Stenfors C, Theodorsson E, Lundeberg T: Unilateral injection of calcitonin gene-related peptide (CGRP) induces bilateral oedema formation and release of CGRP-like immunoreactivity in the rat hindpaw. Br J Pharmacol. 1998 Nov;125(6):1304-12. [9863661 ]
  2. Kelley BM, Porter JH: The role of muscarinic cholinergic receptors in the discriminative stimulus properties of clozapine in rats. Pharmacol Biochem Behav. 1997 Aug;57(4):707-19. [9258998 ]
  3. Hoenicke EM, Vanecek SA, Woods JH: The discriminative stimulus effects of clozapine in pigeons: involvement of 5-hydroxytryptamine1C and 5-hydroxytryptamine2 receptors. J Pharmacol Exp Ther. 1992 Oct;263(1):276-84. [1403790 ]
  4. Martinez F, Coleman JW: A comparison of the effects of chlorpromazine and more selective histamine and 5-hydroxytryptamine antagonists on human IgG synthesis in vitro. Int J Immunopharmacol. 1990;12(2):185-91. [2329012 ]
  5. Fiorella D, Rabin RA, Winter JC: The role of the 5-HT2A and 5-HT2C receptors in the stimulus effects of hallucinogenic drugs. I: Antagonist correlation analysis. Psychopharmacology (Berl). 1995 Oct;121(3):347-56. [8584617 ]
General Function:
Titin binding
Specific Function:
Calmodulin mediates the control of a large number of enzymes, ion channels, aquaporins and other proteins by Ca(2+). Among the enzymes to be stimulated by the calmodulin-Ca(2+) complex are a number of protein kinases and phosphatases. Together with CCP110 and centrin, is involved in a genetic pathway that regulates the centrosome cycle and progression through cytokinesis.
Gene Name:
CALM1
Uniprot ID:
P0DP23
Molecular Weight:
16837.47 Da
References
  1. Cohen ME, Sharp GW, Donowitz M: Suggestion of a role for calmodulin and phosphorylation in regulation of rabbit ileal electrolyte transport: effects of promethazine. Am J Physiol. 1986 Nov;251(5 Pt 1):G710-7. [3022601 ]
  2. Scott JA, Khaw BA, Fallon JT, Locke E, Rabito CA, Peto CA, Homcy CJ: The effect of phenothiazines upon maintenance of membrane integrity in the cultured myocardial cell. J Mol Cell Cardiol. 1986 Dec;18(12):1243-54. [3820316 ]
  3. Lohr KM, Feix JB, Kurth C: Chlorpromazine inhibits neutrophil chemotaxis beyond the chemotactic receptor-ligand interaction. J Infect Dis. 1984 Nov;150(5):643-52. [6092486 ]
  4. DiPaola M, Keith CH, Feldman D, Tycko B, Maxfield FR: Loss of alpha 2-macroglobulin and epidermal growth factor surface binding induced by phenothiazines and naphthalene sulfonamides. J Cell Physiol. 1984 Feb;118(2):193-202. [6319437 ]
  5. Luchowski EM, Yousif F, Triggle DJ, Maurer SC, Sarmiento JG, Janis RA: Effects of metal cations and calmodulin antagonists on [3H] nitrendipine binding in smooth and cardiac muscle. J Pharmacol Exp Ther. 1984 Sep;230(3):607-13. [6433001 ]
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  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. [17016423 ]
General Function:
Potassium channel regulator activity
Specific Function:
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name:
DRD2
Uniprot ID:
P14416
Molecular Weight:
50618.91 Da
References
  1. Golembiewski JA, O'Brien D: A systematic approach to the management of postoperative nausea and vomiting. J Perianesth Nurs. 2002 Dec;17(6):364-76. [12476402 ]
General Function:
Histamine receptor activity
Specific Function:
The H2 subclass of histamine receptors mediates gastric acid secretion. Also appears to regulate gastrointestinal motility and intestinal secretion. Possible role in regulating cell growth and differentiation. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase and, through a separate G protein-dependent mechanism, the phosphoinositide/protein kinase (PKC) signaling pathway (By similarity).
Gene Name:
HRH2
Uniprot ID:
P25021
Molecular Weight:
40097.65 Da
References
  1. Dick W, Lorenz W, Heintz D, Sitter H, Doenicke A: [Histamine release during induction of combination anesthesia using nalbuphine or fentanyl. Modulation of the reaction by premedication with promethazine/pethidine]. Anaesthesist. 1992;41(5):239-47. [1377455 ]
General Function:
Histamine receptor activity
Specific Function:
The H4 subclass of histamine receptors could mediate the histamine signals in peripheral tissues. Displays a significant level of constitutive activity (spontaneous activity in the absence of agonist).
Gene Name:
HRH4
Uniprot ID:
Q9H3N8
Molecular Weight:
44495.375 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory0.1502 uMNot AvailableBindingDB 50017696
References
  1. Nguyen T, Shapiro DA, George SR, Setola V, Lee DK, Cheng R, Rauser L, Lee SP, Lynch KR, Roth BL, O'Dowd BF: Discovery of a novel member of the histamine receptor family. Mol Pharmacol. 2001 Mar;59(3):427-33. [11179435 ]
General Function:
Phosphatidylinositol phospholipase c activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM1
Uniprot ID:
P11229
Molecular Weight:
51420.375 Da
References
  1. Golembiewski JA, O'Brien D: A systematic approach to the management of postoperative nausea and vomiting. J Perianesth Nurs. 2002 Dec;17(6):364-76. [12476402 ]
General Function:
G-protein coupled acetylcholine receptor activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition. Signaling promotes phospholipase C activity, leading to the release of inositol trisphosphate (IP3); this then triggers calcium ion release into the cytosol.
Gene Name:
CHRM2
Uniprot ID:
P08172
Molecular Weight:
51714.605 Da
References
  1. Golembiewski JA, O'Brien D: A systematic approach to the management of postoperative nausea and vomiting. J Perianesth Nurs. 2002 Dec;17(6):364-76. [12476402 ]
General Function:
Receptor activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM3
Uniprot ID:
P20309
Molecular Weight:
66127.445 Da
References
  1. Golembiewski JA, O'Brien D: A systematic approach to the management of postoperative nausea and vomiting. J Perianesth Nurs. 2002 Dec;17(6):364-76. [12476402 ]
General Function:
Guanyl-nucleotide exchange factor activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is inhibition of adenylate cyclase.
Gene Name:
CHRM4
Uniprot ID:
P08173
Molecular Weight:
53048.65 Da
References
  1. Golembiewski JA, O'Brien D: A systematic approach to the management of postoperative nausea and vomiting. J Perianesth Nurs. 2002 Dec;17(6):364-76. [12476402 ]
General Function:
Phosphatidylinositol phospholipase c activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM5
Uniprot ID:
P08912
Molecular Weight:
60073.205 Da
References
  1. Golembiewski JA, O'Brien D: A systematic approach to the management of postoperative nausea and vomiting. J Perianesth Nurs. 2002 Dec;17(6):364-76. [12476402 ]
General Function:
Secondary active organic cation transmembrane transporter activity
Specific Function:
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin-dependent kinase II and LCK tyrosine kinase.
Gene Name:
SLC22A1
Uniprot ID:
O15245
Molecular Weight:
61153.345 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
IC5035.1 uMNot AvailableBindingDB 50017696
References
  1. Ahlin G, Karlsson J, Pedersen JM, Gustavsson L, Larsson R, Matsson P, Norinder U, Bergstrom CA, Artursson P: Structural requirements for drug inhibition of the liver specific human organic cation transport protein 1. J Med Chem. 2008 Oct 9;51(19):5932-42. doi: 10.1021/jm8003152. Epub 2008 Sep 13. [18788725 ]