NP-MRD: Showing NP-Card for Cetirizine (NP0334568)

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Record Information

Version

2.0

Created at

2024-09-10 18:56:32 UTC

Updated at

2024-09-10 18:56:32 UTC

NP-MRD ID

NP0334568

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cetirizine

Description

Cetirizine, also known as cetiderm or reactine, 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. Cetirizine is a very strong basic compound (based on its pKa). In humans, cetirizine is involved in cetirizine h1-antihistamine action. Cetirizine is a potentially toxic compound. Cetirizine was first documented in 1987 (PMID: 2885355). Cetirizine crosses the blood–brain barrier only slightly, and for this reason, it produces minimal sedation compared to many other antihistamines (PMID: 15237765) (PMID: 10898119) (PMID: 15286093) (PMID: 1346737) (PMID: 2887304) (PMID: 10435475).

Structure

MOL SDF PDB SMILES InChI

341
  Mrv0541 02231214362D          

 27 29  0  0  1  0            999 V2000
    1.6500   -4.1746    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.0130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    3.6631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    3.6631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.6995    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.0495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -3.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -2.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -3.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -4.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -4.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -3.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.2506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 24  1  0  0  0  0
  2 15  1  0  0  0  0
  2 26  1  0  0  0  0
  3 27  1  0  0  0  0
  4 27  2  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  5 11  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  6 12  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  2  0  0  0  0
 13 17  1  0  0  0  0
 14 18  2  0  0  0  0
 14 19  1  0  0  0  0
 16 20  1  0  0  0  0
 17 21  2  0  0  0  0
 18 22  1  0  0  0  0
 19 23  2  0  0  0  0
 20 24  2  0  0  0  0
 21 24  1  0  0  0  0
 22 25  2  0  0  0  0
 23 25  1  0  0  0  0
 26 27  1  0  0  0  0
M  END

341
  Mrv0541 02231214362D          

 27 29  0  0  1  0            999 V2000
    1.6500   -4.1746    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.0130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    3.6631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    3.6631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.6995    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.0495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -3.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -2.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -3.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -4.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -4.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -3.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.2506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 24  1  0  0  0  0
  2 15  1  0  0  0  0
  2 26  1  0  0  0  0
  3 27  1  0  0  0  0
  4 27  2  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  5 11  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  6 12  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  2  0  0  0  0
 13 17  1  0  0  0  0
 14 18  2  0  0  0  0
 14 19  1  0  0  0  0
 16 20  1  0  0  0  0
 17 21  2  0  0  0  0
 18 22  1  0  0  0  0
 19 23  2  0  0  0  0
 20 24  2  0  0  0  0
 21 24  1  0  0  0  0
 22 25  2  0  0  0  0
 23 25  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334568

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)COCCN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H25ClN2O3/c22-19-8-6-18(7-9-19)21(17-4-2-1-3-5-17)24-12-10-23(11-13-24)14-15-27-16-20(25)26/h1-9,21H,10-16H2,(H,25,26)

> <INCHI_KEY>
ZKLPARSLTMPFCP-UHFFFAOYSA-N

> <FORMULA>
C21H25ClN2O3

> <MOLECULAR_WEIGHT>
388.888

> <EXACT_MASS>
388.155370383

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
41.878150049336554

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2-{4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethoxy)acetic acid

> <ALOGPS_LOGP>
2.98

> <JCHEM_LOGP>
0.8598093028281057

> <ALOGPS_LOGS>
-3.77

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.596630966769094

> <JCHEM_PKA_STRONGEST_BASIC>
7.789172195841928

> <JCHEM_POLAR_SURFACE_AREA>
53.010000000000005

> <JCHEM_REFRACTIVITY>
106.86650000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.58e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cetirizine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 341                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       3.080  -7.793   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       9.748   3.758   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      12.416   6.838   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.748   6.838   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       8.415  -3.172   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       8.415  -0.092   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       9.748  -2.402   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081  -2.402   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.748  -0.862   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.081  -0.862   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415  -4.713   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.415   1.448   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.081  -5.483   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.748  -5.483   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.748   2.218   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.081  -7.023   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.748  -4.713   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.082  -4.713   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.748  -7.023   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.748  -7.793   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.414  -5.483   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.416  -5.483   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.082  -7.793   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.414  -7.023   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.416  -7.023   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.082   4.528   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.082   6.068   0.000  0.00  0.00           C+0
CONECT    1   24                                                            
CONECT    2   15   26                                                       
CONECT    3   27                                                            
CONECT    4   27                                                            
CONECT    5    7    8   11                                                  
CONECT    6    9   10   12                                                  
CONECT    7    5    9                                                       
CONECT    8    5   10                                                       
CONECT    9    6    7                                                       
CONECT   10    6    8                                                       
CONECT   11    5   13   14                                                  
CONECT   12    6   15                                                       
CONECT   13   11   16   17                                                  
CONECT   14   11   18   19                                                  
CONECT   15    2   12                                                       
CONECT   16   13   20                                                       
CONECT   17   13   21                                                       
CONECT   18   14   22                                                       
CONECT   19   14   23                                                       
CONECT   20   16   24                                                       
CONECT   21   17   24                                                       
CONECT   22   18   25                                                       
CONECT   23   19   25                                                       
CONECT   24    1   20   21                                                  
CONECT   25   22   23                                                       
CONECT   26    2   27                                                       
CONECT   27    3    4   26                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Value	Source
Cetirizin	ChEBI
Cetirizina	ChEBI
Cetirizinum	ChEBI
Cetiderm	Kegg
Benaday	HMDB
Cetirizine hydrochloride	HMDB
Humex	HMDB
Reactine	HMDB
Virlix	HMDB
Zirtek	HMDB
Zyrlex	HMDB
Zyrtec	HMDB
Alpharma brand OF cetirizine dihydrochloride	HMDB
Ceti-puren	HMDB
CetiLich	HMDB
Cetirigamma	HMDB
Cetirizin al	HMDB
Dihydrochloride, cetirizine	HMDB
Glaxo wellcome brand OF cetirizine dihydrochloride	HMDB
TAD brand OF cetirizine dihydrochloride	HMDB
UCB brand OF cetirizine dihydrochloride	HMDB
Voltric	HMDB
CT-Arzneimittel brand OF cetirizine dihydrochloride	HMDB
Azupharma brand OF cetirizine dihydrochloride	HMDB
Basics brand OF cetirizine dihydrochloride	HMDB
Cetalerg	HMDB
Dermapharm brand OF cetirizine dihydrochloride	HMDB
Krewel brand OF cetirizine dihydrochloride	HMDB
Lacer brand OF cetirizine dihydrochloride	HMDB
Menarini brand OF cetirizine dihydrochloride	HMDB
Pfizer brand OF cetirizine dihydrochloride	HMDB
Pfizer consumer healthcare brand OF cetirizine dihydrochloride	HMDB
UCB pharma brand OF cetirizine dihydrochloride	HMDB
AWD.pharma brand OF cetirizine dihydrochloride	HMDB
Aliud brand OF cetirizine dihydrochloride	HMDB
Ceti tad	HMDB
Cetidura	HMDB
Cetirizin azu	HMDB
Cetirizine dihydrochloride	HMDB
Cetirlan	HMDB
Lichtenstein brand OF cetirizine dihydrochloride	HMDB
Rodleben brand OF cetirizine	HMDB
United drug brand OF cetirizine dihydrochloride	HMDB
Wolff brand OF cetirizine dihydrochloride	HMDB
(2-(4-((4-Chlorophenyl)phenylmethyl)-1-piperazinyl)ethoxy)acetic acid	HMDB
Alerlisin	HMDB
Ceterifug	HMDB
Cetil von CT	HMDB
Cetirizin basics	HMDB
Merck dura brand OF cetirizine dihydrochloride	HMDB
Sanofi synthelabo brand OF cetirizine dihydrochloride	HMDB
Wörwag brand OF cetirizine dihydrochloride	HMDB
Zetir	HMDB

Chemical Formula

C₂₁H₂₅ClN₂O₃

Average Mass

388.8880 Da

Monoisotopic Mass

388.15537 Da

IUPAC Name

2-(2-{4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethoxy)acetic acid

Traditional Name

cetirizine

CAS Registry Number

Not Available

SMILES

OC(=O)COCCN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C1

InChI Identifier

InChI=1S/C21H25ClN2O3/c22-19-8-6-18(7-9-19)21(17-4-2-1-3-5-17)24-12-10-23(11-13-24)14-15-27-16-20(25)26/h1-9,21H,10-16H2,(H,25,26)

InChI Key

ZKLPARSLTMPFCP-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Chlorobenzene
Halobenzene
N-alkylpiperazine
Aralkylamine
Aryl halide
1,4-diazinane
Aryl chloride
Piperazine
Amino acid
Amino acid or derivatives
Tertiary amine
Tertiary aliphatic amine
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Monocarboxylic acid or derivatives
Azacycle
Ether
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Organohalogen compound
Amine
Organochloride
Organonitrogen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:3561 )
ether (CHEBI:3561 )
monochlorobenzenes (CHEBI:3561 )
piperazines (CHEBI:3561 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.98	ALOGPS
logP	0.86	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	3.6	ChemAxon
pKa (Strongest Basic)	7.79	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	53.01 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	106.87 m³·mol⁻¹	ChemAxon
Polarizability	41.88 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0005032

DrugBank ID

DB00341

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023599

KNApSAcK ID

Not Available

Chemspider ID

2577

KEGG Compound ID

C07778

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cetirizine

METLIN ID

1641

PubChem Compound

2678

PDB ID

Not Available

ChEBI ID

3561

Good Scents ID

Not Available

References

General References

Purohit A, Melac M, Pauli G, Frossard N: Comparative activity of cetirizine and desloratadine on histamine-induced wheal-and-flare responses during 24 hours. Ann Allergy Asthma Immunol. 2004 Jun;92(6):635-40. [PubMed:15237765 ]
Ramboer I, Bumtbacea R, Lazarescu D, Radu JR: Cetirizine and loratadine: a comparison using the ED50 in skin reactions. J Int Med Res. 2000 Mar-Apr;28(2):69-77. [PubMed:10898119 ]
Tashiro M, Sakurada Y, Iwabuchi K, Mochizuki H, Kato M, Aoki M, Funaki Y, Itoh M, Iwata R, Wong DF, Yanai K: Central effects of fexofenadine and cetirizine: measurement of psychomotor performance, subjective sleepiness, and brain histamine H1-receptor occupancy using 11C-doxepin positron emission tomography. J Clin Pharmacol. 2004 Aug;44(8):890-900. doi: 10.1177/0091270004267590. [PubMed:15286093 ]
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Showing NP-Card for Cetirizine (NP0334568)

MOL for NP0334568 (Cetirizine)

3D MOL for NP0334568 (Cetirizine)

3D SDF for NP0334568 (Cetirizine)

3D-SDF for NP0334568 (Cetirizine)

PDB for NP0334568 (Cetirizine)

3D PDB for NP0334568 (Cetirizine)

SMILES for NP0334568 (Cetirizine)

INCHI for NP0334568 (Cetirizine)

Structure for NP0334568 (Cetirizine)

3D Structure for NP0334568 (Cetirizine)