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Details

Stereochemistry ACHIRAL
Molecular Formula C32H37NO4
Molecular Weight 499.6417
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CAREBASTINE

SMILES

CC(C)(c1ccc(cc1)C(=O)CCCN2CCC(CC2)OC(c3ccccc3)c4ccccc4)C(=O)O

InChI

InChIKey=XGHOVGYJHWQGCC-UHFFFAOYSA-N
InChI=1S/C32H37NO4/c1-32(2,31(35)36)27-17-15-24(16-18-27)29(34)14-9-21-33-22-19-28(20-23-33)37-30(25-10-5-3-6-11-25)26-12-7-4-8-13-26/h3-8,10-13,15-18,28,30H,9,14,19-23H2,1-2H3,(H,35,36)

HIDE SMILES / InChI

Molecular Formula C32H37NO4
Molecular Weight 499.6417
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Carabestine is the active first-pass metabolite of Ebastine and acts as a histamine H1 receptor antagonist which has been investigated as a potential allergy medication. Ebastine is marketed under a number of brand names.

Originator

Curator's Comment:: Carebastine was first mentioned by Vincent, Liminana, Meredith and Reid from Stobhill General Hospital, Glasgow https://www.ncbi.nlm.nih.gov/pubmed/2905150

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P35367
Gene ID: 3269.0
Gene Symbol: HRH1
Target Organism: Homo sapiens (Human)
9.7 nM [Ki]
Conditions
PubMed

PubMed

TitleDatePubMed
The pharmacokinetics, antihistamine and concentration-effect relationship of ebastine in healthy subjects.
1988 Nov
Blood-brain barrier transport of H1-antagonist ebastine and its metabolite carebastine.
2000
Genetic deficiency of carnitine/organic cation transporter 2 (slc22a5) is associated with altered tissue distribution of its substrate pyrilamine in mice.
2009 Dec
Inverse agonistic activity of antihistamines and suppression of histamine H1 receptor gene expression.
2012
Patents

Sample Use Guides

In Phase III clinical trials patients were treated with a nasal spray containing Carebastine in a concentration of 2.5 mg/mL, and as an eye drop containing Carebastine at a concentration of 25 mg/mL.
Route of Administration: Other
In a dose–response study: CHO-H1R cells were incubated with Carebastine (1 nM – 1 μM) for 1 h. Effectiveness was assessed by measuring the accumulation of inositol phosphates.
Substance Class Chemical
Created
by admin
on Sat Jun 26 00:14:02 UTC 2021
Edited
by admin
on Sat Jun 26 00:14:02 UTC 2021
Record UNII
75DLN707DO
Record Status Validated (UNII)
Record Version
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Name Type Language
CAREBASTINE
INN  
INN  
Official Name English
CAREBASTINE [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Sat Jun 26 00:14:02 UTC 2021 , Edited by admin on Sat Jun 26 00:14:02 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL67654
Created by admin on Sat Jun 26 00:14:02 UTC 2021 , Edited by admin on Sat Jun 26 00:14:02 UTC 2021
PRIMARY
MESH
C058251
Created by admin on Sat Jun 26 00:14:02 UTC 2021 , Edited by admin on Sat Jun 26 00:14:02 UTC 2021
PRIMARY
CAS
90729-42-3
Created by admin on Sat Jun 26 00:14:02 UTC 2021 , Edited by admin on Sat Jun 26 00:14:02 UTC 2021
PRIMARY
NCI_THESAURUS
C77432
Created by admin on Sat Jun 26 00:14:02 UTC 2021 , Edited by admin on Sat Jun 26 00:14:02 UTC 2021
PRIMARY
FDA UNII
75DLN707DO
Created by admin on Sat Jun 26 00:14:02 UTC 2021 , Edited by admin on Sat Jun 26 00:14:02 UTC 2021
PRIMARY
PUBCHEM
65820
Created by admin on Sat Jun 26 00:14:02 UTC 2021 , Edited by admin on Sat Jun 26 00:14:02 UTC 2021
PRIMARY
EPA CompTox
90729-42-3
Created by admin on Sat Jun 26 00:14:02 UTC 2021 , Edited by admin on Sat Jun 26 00:14:02 UTC 2021
PRIMARY
EVMPD
SUB06623MIG
Created by admin on Sat Jun 26 00:14:02 UTC 2021 , Edited by admin on Sat Jun 26 00:14:02 UTC 2021
PRIMARY
INN
5634
Created by admin on Sat Jun 26 00:14:02 UTC 2021 , Edited by admin on Sat Jun 26 00:14:02 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> METABOLITE
Produced as oxidation product with mediator.
Related Record Type Details
ACTIVE MOIETY