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
CHEBI:31403
CAS Number
16699-20-0
UNII
3DI2E1X18L
DrugBank ID
DB00568
TTD ID
D0Q3YO
INTEDE ID
DR0329
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

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]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

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.