Details of the Drug

General Information of Drug (ID: DM7U5QJ)

Drug Name
Cinnarizine
Synonyms
Aplactan; Aplexal; Apotomin; Artate; Carecin; Cerebolan; Cinaperazine; Cinarizina; Cinarizine; Cinazyn; Cinnacet; Cinnageron; Cinnarizinum; Corathiem; Denapol; Dimitron; Dimitronal; Eglen; Folcodal; Giganten; Glanil; Hilactan; Ixertol; Katoseran; Labyrin; Lazeta; Libotasin; Marisan; Midronal; Mitronal; Olamin; Processine; Sedatromin; Senoger; Sepan; Siptazin; Spaderizine; Stugeron; Stutgeron; Stutgin; Toliman; Votegol; Zepamol; Cinnarizine Stugeron; C 5270; MD 516; R 1575; R 516; Cero-Aterin; Cinarizina [INN-Spanish]; Cinnarizinum [INN-Latin]; R-516; Stugeron (TN); Stunarone (TN); Cinnarizine (JAN/USAN/INN); Cinnarizine [USAN:INN:BAN:JAN]; N-Benzhydryl-N'-cinnamylpiperazine; 1-(Diphenylmethyl)-4-(3-phenyl-2-propenyl)piperazine; 1-(diphenylmethyl)-4-(3-phenyl-2-propenyl)-piperazine; 1-(diphenylmethyl)-4-[(2E)-3-phenylprop-2-en-1-yl]piperazine; 1-Benzhydryl-4-cinnamylpiperazin; 1-Cinnamyl-4-(diphenylmethyl)piperazine; 1-benzhydryl-4-[(E)-3-phenylprop-2-enyl]piperazine; 1-trans-Cinnamyl-4-diphenylmethylpiperazine
Indication
Disease Entry ICD 11 Status REF
Meniere disease AB31.0 Approved [1]
Nausea MD90 Approved [2]
Vertigo meniere disease AB31.0 Approved [3]
Therapeutic Class
Antiallergic Agents
Affected Organisms
Humans and other mammals
ATC Code
N07CA02: Cinnarizine
N07CA: Antivertigo preparations
N07C: ANTIVERTIGO PREPARATIONS
N07: OTHER NERVOUS SYSTEM DRUGS
N: NERVOUS SYSTEM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 368.5
Logarithm of the Partition Coefficient (xlogp) 5.8
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C26H28N2
IUPAC Name
1-benzhydryl-4-[(E)-3-phenylprop-2-enyl]piperazine
Canonical SMILES
C1CN(CCN1C/C=C/C2=CC=CC=C2)C(C3=CC=CC=C3)C4=CC=CC=C4
InChI
InChI=1S/C26H28N2/c1-4-11-23(12-5-1)13-10-18-27-19-21-28(22-20-27)26(24-14-6-2-7-15-24)25-16-8-3-9-17-25/h1-17,26H,18-22H2/b13-10+
InChIKey
DERZBLKQOCDDDZ-JLHYYAGUSA-N
Cross-matching ID
PubChem CID
1547484
ChEBI ID
CHEMBL43064
CAS Number
16699-20-0
UNII
3DI2E1X18L
DrugBank ID
DB00568
TTD ID
D0Q3YO
INTEDE ID
DR0329
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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 [4]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [5]
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Substrate [6]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [6]
Cytochrome P450 2A6 (CYP2A6) DEJVYAZ CP2A6_HUMAN Substrate [6]
Cytochrome P450 1A2 (CYP1A2) DEJGDUW CP1A2_HUMAN Substrate [7]
Cytochrome P450 2B6 (CYP2B6) DEPKLMQ CP2B6_HUMAN Substrate [6]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Bile salt export pump (ABCB11) OTRU7THO ABCBB_HUMAN Gene/Protein Processing [8]
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Molecular Expression Atlas of This Drug

The Studied Disease Meniere disease
ICD Disease Classification AB31.0
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
Cytochrome P450 2B6 (CYP2B6) DME CYP2B6 4.32E-01 4.39E-02 4.30E-01
Cytochrome P450 2A6 (CYP2A6) DME CYP2A6 8.99E-01 4.59E-03 2.19E-02
Cytochrome P450 1A2 (CYP1A2) DME CYP1A2 8.46E-01 -6.63E-03 -4.49E-02
Cytochrome P450 2D6 (CYP2D6) DME CYP2D6 8.70E-01 2.98E-02 1.22E-01
Cytochrome P450 2C9 (CYP2C9) DME CYP2C9 2.35E-01 2.78E-02 2.09E-01
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 1.76E-01 1.26E-01 8.27E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Association of cinnarizine and betahistine in prophylactic therapy for Mnire's disease with and without migraine. Acta Otorhinolaryngol Ital. 2014 Oct;34(5):349-53.
2 Cinnarizine: A Contemporary Review. Indian J Otolaryngol Head Neck Surg. 2019 Nov;71(Suppl 2):1060-1068.
3 Drug information of Cinnarizine, 2008. eduDrugs.
4 Central effects of cinnarizine: restricted use in aircrew. Aviat Space Environ Med. 2002 Jun;73(6):570-4.
5 Integrated analysis on the physicochemical properties of dihydropyridine calcium channel blockers in grapefruit juice interactions. Curr Pharm Biotechnol. 2012 Jul;13(9):1705-17.
6 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
7 Insights into the substrate specificity, inhibitors, regulation, and polymorphisms and the clinical impact of human cytochrome P450 1A2. AAPS J. 2009 Sep;11(3):481-94.
8 Interference with bile salt export pump function is a susceptibility factor for human liver injury in drug development. Toxicol Sci. 2010 Dec; 118(2):485-500.