Details of the Drug

General Information of Drug (ID: DM3L52Q)

Drug Name

Chlorcyclizine

Synonyms

1-(4-Chlorobenzhydryl)-4-methylpiperazine; Alergicide; Chlorcycline; Chlorcyclizine [INN:BAN]; Chlorcyclizinum; Chlorcyclizinum [INN-Latin]; Chlorocycline; Chlorocyclizine; Clorciclizina; Clorciclizina [DCIT]; Clorciclizinio [INN-Spanish]; Compound 47-282; Di-Paralene; Di-paralen; Diparalene; HSDB 3217; Histachlorazene; Histantin; Histantine; N-Methyl-N'-(4-chlorobenzhydryl)piperazine; NSC 25246; Perazyl; Piparalene; Trihistan; chlorcyclizine

Indication

Disease Entry	ICD 11	Status	REF
Hepatitis C virus infection	1E51.1	Phase 1	[1]

Therapeutic Class

Antihistamines

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

300.83

Topological Polar Surface Area (xlogp)

4.5

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Half-life: The concentration or amount of drug in body reduced by one-half in 12 hours [2]
Metabolism: The drug is metabolized via the liver [3]

Chemical Identifiers

Formula: C18H21ClN2
IUPAC Name: 1-[(4-chlorophenyl)-phenylmethyl]-4-methylpiperazine
Canonical SMILES: CN1CCN(CC1)C(C2=CC=CC=C2)C3=CC=C(C=C3)Cl
InChI: InChI=1S/C18H21ClN2/c1-20-11-13-21(14-12-20)18(15-5-3-2-4-6-15)16-7-9-17(19)10-8-16/h2-10,18H,11-14H2,1H3
InChIKey: WFNAKBGANONZEQ-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 2710
ChEBI ID: CHEBI:94402
CAS Number: 82-93-9
DrugBank ID: DB08936
VARIDT ID: DR01215

Molecular Interaction Atlas of This Drug

Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Multidrug resistance-associated protein 1 (ABCC1)	DTSYQGK	MRP1_HUMAN	Substrate	[4]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	ClinicalTrials.gov (NCT02118012) Evaluation of Safety, Tolerability, and Antiviral Activity of Chlorcyclizine HCl Alone or in Combination With Ribavirin in Patients With Chronic Hepatitis C
2	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
3	FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
4	Carrier mediated transport of chlorpheniramine and chlorcyclizine across bovine olfactory mucosa: implications on nose-to-brain transport. J Pharm Sci. 2005 Mar;94(3):613-24.
5	The role of bioreductive activation of doxorubicin in cytotoxic activity against leukaemia HL60-sensitive cell line and its multidrug-resistant sublines. Br J Cancer. 2005 Jul 11;93(1):89-97.
6	Transport of methotrexate (MTX) and folates by multidrug resistance protein (MRP) 3 and MRP1: effect of polyglutamylation on MTX transport. Cancer Res. 2001 Oct 1;61(19):7225-32.
7	Folate concentration dependent transport activity of the Multidrug Resistance Protein 1 (ABCC1). Biochem Pharmacol. 2004 Apr 15;67(8):1541-8.
8	Hammerhead ribozyme against gamma-glutamylcysteine synthetase sensitizes human colonic cancer cells to cisplatin by down-regulating both the glutathione synthesis and the expression of multidrug resistance proteins. Cancer Gene Ther. 2001 Oct;8(10):803-14.
9	Multidrug resistance-associated protein-1 functional activity in Calu-3 cells. J Pharmacol Exp Ther. 2001 Sep;298(3):1199-205.
10	Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
11	ATP-Dependent efflux of CPT-11 and SN-38 by the multidrug resistance protein (MRP) and its inhibition by PAK-104P. Mol Pharmacol. 1999 May;55(5):921-8.
12	Structural determinants of substrate specificity differences between human multidrug resistance protein (MRP) 1 (ABCC1) and MRP3 (ABCC3). Drug Metab Dispos. 2008 Dec;36(12):2571-81.
13	Evaluation of transport of common antiepileptic drugs by human multidrug resistance-associated proteins (MRP1, 2 and 5) that are overexpressed in pharmacoresistant epilepsy. Neuropharmacology. 2010 Jun;58(7):1019-32.
14	Vinblastine and sulfinpyrazone export by the multidrug resistance protein MRP2 is associated with glutathione export. Br J Cancer. 2000 Aug;83(3):375-83.