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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2021-09-14 15:46:38 UTC
HMDB IDHMDB0014428
Secondary Accession Numbers
  • HMDB14428
Metabolite Identification
Common NameClemastine
DescriptionClemastine is only found in individuals that have used or taken this drug. It is an ethanolamine-derivative, first generation histamine H1 antagonist used in hay fever, rhinitis, allergic skin conditions, and pruritus. It causes drowsiness. [PubChem]Clemastine is a selective histamine H1 antagonist and binds to the histamine H1 receptor. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine.
Structure
Data?1582753178
Synonyms
ValueSource
(+)-(2R)-2-(2-(((R)-p-Chloro-alpha-methyl-alpha-phenylbenzyl)oxy)ethyl)-1-methylpyrrolidineChEBI
(+)-(2R)-2-[2-[[(R)-p-Chloro-alpha-methyl-alpha-phenylbenzyl]oxy]ethyl]-1-methylpyrrolidineChEBI
ClemastinaChEBI
ClemastinumChEBI
(+)-(2R)-2-(2-(((R)-p-Chloro-a-methyl-a-phenylbenzyl)oxy)ethyl)-1-methylpyrrolidineGenerator
(+)-(2R)-2-(2-(((R)-p-Chloro-α-methyl-α-phenylbenzyl)oxy)ethyl)-1-methylpyrrolidineGenerator
(+)-(2R)-2-[2-[[(R)-p-Chloro-a-methyl-a-phenylbenzyl]oxy]ethyl]-1-methylpyrrolidineGenerator
(+)-(2R)-2-[2-[[(R)-p-Chloro-α-methyl-α-phenylbenzyl]oxy]ethyl]-1-methylpyrrolidineGenerator
Clemastine fumarateHMDB
TavistHMDB
TavegylHMDB
2-(2-(1-(4-Chlorophenyl)-1-phenylethoxy)ethyl)-1-methylpyrrolidineHMDB
MeclastineHMDB
MecloprodinHMDB
Chemical FormulaC21H26ClNO
Average Molecular Weight343.89
Monoisotopic Molecular Weight343.170292166
IUPAC Name(2R)-2-{2-[(1R)-1-(4-chlorophenyl)-1-phenylethoxy]ethyl}-1-methylpyrrolidine
Traditional Nameclemastine
CAS Registry Number15686-51-8
SMILES
CN1CCC[C@@H]1CCO[C@](C)(C1=CC=CC=C1)C1=CC=C(Cl)C=C1
InChI Identifier
InChI=1S/C21H26ClNO/c1-21(17-7-4-3-5-8-17,18-10-12-19(22)13-11-18)24-16-14-20-9-6-15-23(20)2/h3-5,7-8,10-13,20H,6,9,14-16H2,1-2H3/t20-,21-/m1/s1
InChI KeyYNNUSGIPVFPVBX-NHCUHLMSSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Benzylether
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Dialkyl ether
  • Azacycle
  • Ether
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point178 °C (hydrogen fumarate formulation)Not Available
Boiling PointNot AvailableNot Available
Water Solubility0.0004 g/LNot Available
LogP5.2Not Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0004 g/LALOGPS
logP5.29ALOGPS
logP4.92ChemAxon
logS-5.9ALOGPS
pKa (Strongest Basic)9.55ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.47 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity101.65 m³·mol⁻¹ChemAxon
Polarizability39.06 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0159-9381000000-2be9b3484b69dbb1ec632017-09-01View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0219000000-53f17c8ceacb47bd50782016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-9654000000-256b7783ad5643c033a02016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0159-9230000000-a33cd510091ea6d3b4a22016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0049000000-3acb1542ee1bb658496b2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001l-1396000000-5c34f94642de71cce41b2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0159-4970000000-3e174d2a679bb5d9d1a82016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0292000000-dabaff00449bbd64c5d22021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0490000000-03484546c277f858fe092021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-017r-1940000000-1f12fcabbb87d6d6bb382021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0069000000-e82fab8cc80ce105c0c82021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uy3-2921000000-3f8372d3f78db3aa22f32021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02ti-3970000000-54df7e5483a5445882562021-09-08View Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00283 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00283 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00283
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID25129
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkClemastine
METLIN IDNot Available
PubChem Compound26987
PDB IDNot Available
ChEBI ID3738
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hayashi H, Okajima M, Yamada K: Atrial T (Ta) loop in dogs with or without atrial injury. Am Heart J. 1976 May;91(5):607-17. [PubMed:1266718 ]
  2. Schran HF, Petryk L, Chang CT, O'Connor R, Gelbert MB: The pharmacokinetics and bioavailability of clemastine and phenylpropanolamine in single-component and combination formulations. J Clin Pharmacol. 1996 Oct;36(10):911-22. [PubMed:8930778 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
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:
55783.6
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Taniguchi K, Urakami M, Takanaka K: [Effects of antiallergic agents on polymorphonuclear leukocytes. The inhibition of arachidonic acid release and superoxide production]. Nihon Yakurigaku Zasshi. 1987 Aug;90(2):97-103. [PubMed:2890562 ]
  3. Hallberg T, Dohlsten M, Baldetorp B: Demonstration of histamine receptors on human platelets by flow cytometry. Scand J Haematol. 1984 Feb;32(2):113-8. [PubMed:6701456 ]
  4. Dorsch W, Hintschich C, Neuhauser J, Weber J: Sequential histamine inhalations cause increased bronchial histamine reactivity in guinea pigs: role of platelets, thromboxanes and prostacyclin. Naunyn Schmiedebergs Arch Pharmacol. 1984 Sep;327(2):148-55. [PubMed:6387510 ]
  5. Taniguchi K, Masuda Y, Takanaka K: Inhibitory effects of histamine H1 receptor blocking drugs on metabolic activations of neutrophils. J Pharmacobiodyn. 1991 Feb;14(2):87-93. [PubMed:1678430 ]
  6. Oishi R, Shishido S, Yamori M, Saeki K: Comparison of the effects of eleven histamine H1-receptor antagonists on monoamine turnover in the mouse brain. Naunyn Schmiedebergs Arch Pharmacol. 1994 Feb;349(2):140-4. [PubMed:7513381 ]
  7. Thomas RH, Browne PD, Kirby JD: The influence of ranitidine, alone and in combination with clemastine, on histamine-mediated cutaneous weal and flare reactions in human skin. Br J Clin Pharmacol. 1985 Oct;20(4):377-82. [PubMed:4074605 ]
  8. Thomson NC, Kerr JW: Effect of inhaled H1 and H2 receptor antagonist in normal and asthmatic subjects. Thorax. 1980 Jun;35(6):428-34. [PubMed:6449094 ]
  9. Hayashi H, Okajima M, Yamada K: Atrial T (Ta) loop in dogs with or without atrial injury. Am Heart J. 1976 May;91(5):607-17. [PubMed:1266718 ]
  10. Schran HF, Petryk L, Chang CT, O'Connor R, Gelbert MB: The pharmacokinetics and bioavailability of clemastine and phenylpropanolamine in single-component and combination formulations. J Clin Pharmacol. 1996 Oct;36(10):911-22. [PubMed:8930778 ]