Showing Compound Loratadine (FDB023577)

Record Information

Version

1.0

Creation date

2011-09-21 00:31:52 UTC

Update date

2015-10-09 22:33:18 UTC

Primary ID

FDB023577

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Loratadine

Description

desloratadine is available off the shelf in Canada); Loratadine is a tricyclic antihistamine, which has a selective and peripheral H1-antagonist action. It has a long-lasting effect and does not normally cause drowsiness because it does not readily enter the central nervous system; An antiviral that is used in the prophylactic or symptomatic treatment of influenza A. It is also used as an antiparkinsonian agent, to treat extrapyramidal reactions, and for postherpetic neuralgia. The mechanisms of its effects in movement disorders are not well understood but probably reflect an increase in synthesis and release of dopamine, with perhaps some inhibition of dopamine uptake; Loratadine is a drug used to treat allergies. It is marketed by Schering-Plough under several trade names such as Claritin, Clarityn or Claratyne depending on the market, by Lek as Lomilan and by Wyeth as Alavert. It is also available as a generic; Loratadine is a drug used to treat allergies. It is marketed by Schering-Plough under several trade names such as Claritin, Clarityn or Claratyne depending on the market, by Lek as Lomilan and by Wyeth as Alavert. It is also available as a generic. Its active metabolite, desloratadine, is also on the market, though loratadine itself is the only drug of its class available over the counter (at least in the U.S. as of 2005. Loratadine is available off the shelf in the UK [HMDB]

CAS Number

79794-75-5

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
4-(8-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-1-piperidinecarboxylic acid ethyl ester	ChEBI
Aerotina	ChEBI
Alarin	ChEBI
Alavert	ChEBI
Alerpriv	ChEBI
Allerclear	ChEBI
Civeran	ChEBI
Claratyne	ChEBI
Claritin	ChEBI
Loracert	ChEBI
Loradamed	ChEBI
Loradex	ChEBI
Lorastine	ChEBI
Loratadina	ChEBI
Loratadinum	ChEBI
Loratyne	ChEBI
Wal-itin	ChEBI
4-(8-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-1-piperidinecarboxylate ethyl ester	Generator
4-(8-Chloro-5,6-dihydro-11H-benzo(5,6)cyclohepta(1,2-b)pyridin-11-ylidene)-1-piperidinecarboxylic acid ethyl ester	MeSH
Clarium	MeSH
Amantadine	HMDB
Anhissen	HMDB
Bonalerg	HMDB
Claritine	HMDB
Clarityn	HMDB
Clarityne	HMDB
Cronopen	HMDB
Flonidan	HMDB
Fristamin	HMDB
Histaloran	HMDB
Klaritin	HMDB
Lertamine	HMDB
Lisino	HMDB
Loranox	HMDB
Loratidine	HMDB
Loratadine wyeth brand	MeSH, HMDB
Wyeth brand OF loratadine	MeSH, HMDB
Loratadine	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	4.8	ALOGPS
logP	4.55	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	4.33	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	42.43 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	116.98 m³·mol⁻¹	ChemAxon
Polarizability	41.68 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C22H23ClN2O2

IUPAC name

ethyl 4-{13-chloro-4-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene}piperidine-1-carboxylate

InChI Identifier

InChI=1S/C22H23ClN2O2/c1-2-27-22(26)25-12-9-15(10-13-25)20-19-8-7-18(23)14-17(19)6-5-16-4-3-11-24-21(16)20/h3-4,7-8,11,14H,2,5-6,9-10,12-13H2,1H3

InChI Key

JCCNYMKQOSZNPW-UHFFFAOYSA-N

Isomeric SMILES

CCOC(=O)N1CCC(CC1)=C1C2=C(CCC3=C1N=CC=C3)C=C(Cl)C=C2

Average Molecular Weight

382.883

Monoisotopic Molecular Weight

382.144805697

Classification

Description

Belongs to the class of organic compounds known as benzocycloheptapyridines. These are aromatic compounds containing a benzene ring and a pyridine ring fused to a seven membered carbocycle.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzocycloheptapyridines

Sub Class

Not Available

Direct Parent

Benzocycloheptapyridines

Alternative Parents

Substituents

Benzocycloheptapyridine
Piperidinecarboxylic acid
Aryl chloride
Aryl halide
Piperidine
Pyridine
Benzenoid
Heteroaromatic compound
Carbamic acid ester
Carbonic acid derivative
Azacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect:

Health condition:

Gastrointestinal disorders:

Dry mouth

Eye disorders:

Blurred vision

Nervous system disorders:

Headache

Renal and urinary disorders:

Urinary retention

Ingestion

Biological location:

Organ and components:

Subcellular:

Biofluid and excreta:

Blood

Role

Industrial application:

Drug

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Loratadine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-6059000000-3d596b5ab5499c4089ca	Spectrum
Predicted GC-MS	Loratadine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-001r-0039000000-928ed9c6b46ba83ebe20	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-001r-1279000000-1c522c39e53b6bbfb9aa	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-001r-0039000000-928ed9c6b46ba83ebe20	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-067r-1292000000-3869907bd01f927b6f22	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-067i-0090000000-9bcbcadeda0bf07da702	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-0frx-0090000000-2f8b7b5acca254e4cb20	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-067i-0090000000-b247e61957d933538341	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0009000000-dce8adc02434b224d589	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0009000000-7d2b8c3f5f87f99fcf7a	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0api-0090000000-8419cf3b0c888e52c95b	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-067r-0093000000-956a3618f6003ae45808	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-067i-0090000000-b62a29b4d6252b26f2bf	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-001r-0009000000-d32917132c3359e65572	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0019-0019000000-1acbfc6c05c2d600a966	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-001i-0009000000-4558440f48e82bf6eefb	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0019-0009000000-ea1b61e9df959d6680c2	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-067i-0090000000-cf7d75b43a3c2c0f0d1e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-066r-0090000000-c5d1377bb7159732d4db	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-015i-0092000000-9bb7dcefe2f2f4f14bfd	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0009000000-41dd9857a0206fa0f4e8	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06ri-1029000000-0c5a179194107a35af3e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-015c-2091000000-fb50d1834a9a1d8d6c90	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001r-1009000000-78af7865fc3439c125c5	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-2009000000-df88de530c8ff41c69f4	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0adl-7069000000-a5804bf835988dc83d2a	2016-08-03	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		Spectrum