TRIHEXYPHENIDYL HYDROCHLORIDE

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Search structure


Trade Names	ARTANE TREMIN TRIHEXYPHENIDYL HYDROCHLORIDE
Synonyms	Agitane Aparkane Artane Bentex Benzhexol Benzhexol hydrochloride Broflex Cyclodol Cyclodolum NSC-757357 Parcopane Romparkin Sedrina Tremin Trihexyphenidyl HCl Trihexyphenidyl hcl Trihexyphenidyl hydrochloride Trihexyphenidyli hydrochloridum Triphedinon
Status
Molecule Category	Salt-form
UNII	AO61G82577
EPA CompTox	DTXSID8045802
Parent Compound:	TRIHEXYPHENIDYL


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	QDWJJTJNXAKQKD-UHFFFAOYSA-N
Smiles	Cl.OC(CCN1CCCCC1)(c1ccccc1)C1CCCCC1
InChI	InChI=1S/C20H31NO.ClH/c22-20(18-10-4-1-5-11-18,19-12-6-2-7-13-19)14-17-21-15-8-3-9-16-21;/h1,4-5,10-11,19,22H,2-3,6-9,12-17H2;1H

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C20H32ClNO
Molecular Weight	337.94
AlogP	4.33
Hydrogen Bond Acceptor	2.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	5.0
Polar Surface Area	23.47
Molecular species	BASE
Aromatic Rings	1.0
Heavy Atoms	22.0

Metabolites Network

visNetwork

Bioactivity

Mechanism of Action	Action	Reference
Muscarinic acetylcholine receptor M1 antagonist	ANTAGONIST	ISBN PubMed PubMed Wikipedia


Protein: Muscarinic acetylcholine receptor M1 Description: Muscarinic acetylcholine receptor M1 Organism : Homo sapiens P11229 ENSG00000168539

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Acetylcholine receptor	-	1	-	-	-
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides	-	-	-	-	74

Assay Description	Organism	Bioactivity	Reference
Evaluated for its binding affinity at human muscarinic receptor m2 by displacement of [3H]NMS binding using membranes from transfected chinese hamster ovarian cell	None	18.6 nM
Evaluated for its binding affinity at human muscarinic receptor m1 by displacement of [3H]NMS binding using membranes in transfected chinese hamster ovarian cell	None	1.3 nM
Evaluated for its binding affinity at human muscarinic receptor m3 by the displacement of [3H]NMS binding using membranes from transfected chinese hamster ovarian cell	None	26.3 nM
Evaluated for its binding affinity at human muscarinic receptor m4 by the displacement of [3H]NMS binding using membranes from transfected chinese hamster ovarian cell	None	6.7 nM
Evaluated for its binding affinity at human muscarinic receptor m5 by the displacement of [3H]NMS binding using membranes from transfected chinese hamster ovarian cell	None	10.3 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	83.05 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	73.95 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600)	Staphylococcus aureus subsp. aureus	17.03 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600)	Escherichia coli	7.07 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600)	Klebsiella pneumoniae	14.55 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600)	Pseudomonas aeruginosa	14.72 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600	Acinetobacter baumannii	37.84 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630	Candida albicans	4.22 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570)	Cryptococcus neoformans	-0.68 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	-3.19 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	6.361 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.13 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.13 %

Cross References

Resources	Reference
ChEBI	9721
ChEMBL	CHEMBL1092
FDA SRS	AO61G82577
Guide to Pharmacology	7315
KEGG	C07171
PubChem	66007
SureChEMBL	SCHEMBL42410
ZINC	ZINC00968274

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).