Details of the Drug

General Information of Drug (ID: DMMZPWT)

Drug Name

Levocabastine

Synonyms

Levocabastin; Levocabastina; Levocabastinum; Livostin; Levocabastina [Spanish]; Levocabastinum [Latin]; Levocabastine (INN); Levocabastine [INN:BAN]; Livostin (TN); (3S,4R)-1-[4-cyano-4-(4-fluorophenyl)cyclohexyl]-3-methyl-4-phenylpiperidine-4-carboxylic acid; 1-(4-cyano-4-(4-fluorophenyl)cyclohexyl)-3-methyl-4-phenyl-4-piperidinecarboxylic acid

Indication

Disease Entry	ICD 11	Status	REF
Allergic conjunctivitis	9A60.02	Approved	[1]

Therapeutic Class

Antiallergic Agents

Affected Organisms

Humans and other mammals

ATC Code

R01AC02: Levocabastine

R01AC: Antiallergic agents, excl. corticosteroids

R01A: DECONGESTANTS AND OTHER NASAL PREPARATIONS FOR TOPICAL USE

R01: NASAL PREPARATIONS

R: RESPIRATORY SYSTEM

S01GX02: Levocabastine

S01GX: Other antiallergics

S01G: DECONGESTANTS AND ANTIALLERGICS

S01: OPHTHALMOLOGICALS

S: SENSORY ORGANS

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

420.5

Logarithm of the Partition Coefficient (xlogp)

2.5

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 4: low solubility and low permeability [2]
Bioavailability: 99% of drug becomes completely available to its intended biological destination(s) [3]
Clearance: The drug present in the plasma can be removed from the body at the rate of 0.43 mL/min/kg [4]
Elimination: 70% of drug is excreted from urine in the unchanged form [2]
Half-life: The concentration or amount of drug in body reduced by one-half in 36 hours [4]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.0679 micromolar/kg/day [5]
Unbound Fraction: The unbound fraction of drug in plasma is 0.453% [4]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 1.17 L/kg [4]

Chemical Identifiers

Formula: C26H29FN2O2
IUPAC Name: (3S,4R)-1-[4-cyano-4-(4-fluorophenyl)cyclohexyl]-3-methyl-4-phenylpiperidine-4-carboxylic acid
Canonical SMILES: C[C@@H]1CN(CC[C@@]1(C2=CC=CC=C2)C(=O)O)C3CCC(CC3)(C#N)C4=CC=C(C=C4)F
InChI: InChI=1S/C26H29FN2O2/c1-19-17-29(16-15-26(19,24(30)31)21-5-3-2-4-6-21)23-11-13-25(18-28,14-12-23)20-7-9-22(27)10-8-20/h2-10,19,23H,11-17H2,1H3,(H,30,31)/t19-,23?,25?,26-/m1/s1
InChIKey: ZCGOMHNNNFPNMX-YHYDXASRSA-N

Cross-matching ID

PubChem CID: 54385
ChEBI ID: CHEMBL92584
CAS Number: 79449-98-2
UNII: H68BP06S81
DrugBank ID: DB01106
TTD ID: D08SEI

Drug-Molecule Activity Atlas (DMA)^NEW

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Drug Pharmacogenomic Perturbation (DPP)^NEW

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Drug ADMET Endpoint Profile (DAE)^NEW

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Histamine H1 receptor (H1R)	TTTIBOJ	HRH1_HUMAN	Antagonist	[6]

Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Allergic conjunctivitis

ICD Disease Classification

9A60.02

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Histamine H1 receptor (H1R)	DTT	HRH1	6.74E-01	0.13	0.43

Molecular Expression Atlas (MEA)

MEA Detail

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References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 1586).
2	BDDCS applied to over 900 drugs
3	Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
4	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
6	Contribution of alpha4beta1 integrin to the antiallergic effect of levocabastine. Biochem Pharmacol. 2008 Sep 15;76(6):751-62.