CHLORPHENIRAMINE

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Search structure


Synonyms	Antagonate Chlor-Trimeton Chlorphenamine Chlorpheniramine Isoclor Kloromin Phenetron Teldrin
Status
Molecule Category	UNKNOWN
UNII	3U6IO1965U
EPA CompTox	DTXSID0022804


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

Structure


InChI Key	SOYKEARSMXGVTM-UHFFFAOYSA-N
Smiles	CN(C)CCC(c1ccc(Cl)cc1)c1ccccn1
InChI	InChI=1S/C16H19ClN2/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13/h3-9,11,15H,10,12H2,1-2H3

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C16H19ClN2
Molecular Weight	274.8
AlogP	3.82
Hydrogen Bond Acceptor	2.0
Hydrogen Bond Donor	0.0
Number of Rotational Bond	5.0
Polar Surface Area	16.13
Molecular species	BASE
Aromatic Rings	2.0
Heavy Atoms	19.0

Assay Description	Organism	Bioactivity	Reference
Dissociation constant (KD) of the compound	None	3.7 nM
pA2 value is determined compared to standard H1-antagonists	None	3.981 nM
Inhibition of [3H]mepyramine binding to the Histamine H1 receptor in guinea pig cortex	Cavia porcellus	8.8 nM
Binding affinity against Histamine H1 receptor using receptor binding assay in rat brain membranes	None	5.5 nM
Binding affinity to histamine H1 receptor in rat brain membranes was evaluated using [3H]-pyrilamine as radioligand	None	5.5 nM
Ability to displace [3H]pyrilamine from histamine H1 receptor in male Sprague-Dawley rat brain membranes	None	2.0 nM
Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on voltage dependent sodium channels in a vesicular preparation from guinea pig cerebral cortex at 10 uM	Cavia porcellus	49.7 %
Displacement of [3H]pyrilamine from human histamine receptor subtype 1 expressed in CHO cells	Homo sapiens	66.0 nM
Binding affinity to histamine H1 receptor	None	7.0 nM
Inhibition of histamine H1 receptor in guinea pig ileum assessed as inhibition of histamine-induced muscle spasms at 2 x 10 '-3 mg/ml after 5 mins (Rvb = 0.31 %)	Cavia porcellus	41.31 %
Displacement of [3H]Pyrilamine from histamine H1 receptor (unknown origin)	Homo sapiens	4.467 nM		Displacement of [3H]Pyrilamine from histamine H1 receptor (unknown origin)	Homo sapiens	0.92 nM
Antiallergic activity in rat RBL2H3 cells assessed as inhibition of C48/80-induced mast cell degranulation preincubated with compound for 30 mins and then treated with C48/80 for 1 hr by neutral red dye based method	Rattus norvegicus	31.8 nM
Antiallergic activity in rat RBL2H3 cells assessed as inhibition of C48/80-induced histamine release preincubated with compound for 30 mins followed by C48/80 stimulation for 1 hr	Rattus norvegicus	53.6 nM
Antiallergic activity in IgE/Ag-stimulated rat RBL2H3 cells assessed as inhibition of HSA-induced beta-hexosaminidase release preincubated with compound for 30 mins and then stimulated with HSA for 15 mins followed by incubation with P-nitrophenyl-N-acetyl-beta-D-glucosaminide for 2 hrs	Rattus norvegicus	121.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	27.49 %
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	-0.05 %		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	-0.05 %

Related Entries

Cross References

Resources	Reference
ChEBI	52010
ChEMBL	CHEMBL505
DrugBank	DB01114
DrugCentral	616
FDA SRS	3U6IO1965U
Human Metabolome Database	HMDB0001944
Guide to Pharmacology	6976
KEGG	C06905
PharmGKB	PA448960
PubChem	2725
SureChEMBL	SCHEMBL4219

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).