LACIDIPINE

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Search structure


Synonyms	3,3'-iminobispropylamine 3,3'-iminodipropylamine 4-azaheptamethylenediamine Caldine Dipropylamine, 3,3'-diamino- Dipropylenetriamine GR 43659X GR-43659X Lacidipine Molap Motens NSC-7773
Status
Molecule Category	Free-form
ATC	C08CA09
UNII	260080034N
EPA CompTox	DTXSID1046429


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

Structure


InChI Key	GKQPCPXONLDCMU-CCEZHUSRSA-N
Smiles	CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1c1ccccc1/C=C/C(=O)OC(C)(C)C
InChI	InChI=1S/C26H33NO6/c1-8-31-24(29)21-16(3)27-17(4)22(25(30)32-9-2)23(21)19-13-11-10-12-18(19)14-15-20(28)33-26(5,6)7/h10-15,23,27H,8-9H2,1-7H3/b15-14+

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C26H33NO6
Molecular Weight	455.55
AlogP	4.4
Hydrogen Bond Acceptor	7.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	7.0
Polar Surface Area	90.93
Molecular species	NEUTRAL
Aromatic Rings	1.0
Heavy Atoms	33.0

Assay Description	Organism	Bioactivity	Reference
Antileishmanial activity against Leishmania donovani MHOH/IN/1983/AD83 promastigotes assessed as viability after 2 hrs by MTT assay	Leishmania donovani	2.5 ug.mL-1
Antileishmanial activity against Leishmania donovani MHOH/IN/1983/AD83 promastigotes assessed as growth inhibition after 3 days by MTT assay	Leishmania donovani	1.45 ug.mL-1
Antileishmanial activity against Leishmania donovani MHOH/IN/1983/AD83 amastigotes infected in BALB/c mouse peritoneal macrophage treated 6 hrs after infection measured after 48 hrs using Giemsa staining relative to control	Leishmania donovani	2.8 ug.mL-1
DRUGMATRIX: Calcium Channel Type L, Benzothiazepine radioligand binding (ligand: [3H] Diltiazem)	Rattus norvegicus	5.449 nM		DRUGMATRIX: Calcium Channel Type L, Benzothiazepine radioligand binding (ligand: [3H] Diltiazem)	Rattus norvegicus	4.843 nM
DRUGMATRIX: Calcium Channel Type L, Dihydropyridine radioligand binding (ligand: [3H] Nitrendipine)	Rattus norvegicus	0.4 nM		DRUGMATRIX: Calcium Channel Type L, Dihydropyridine radioligand binding (ligand: [3H] Nitrendipine)	Rattus norvegicus	0.257 nM
DRUGMATRIX: CYP450, 3A4 enzyme inhibition (substrate: 7-Benzyloxy-4-(trifluoromethyl)-coumarin)	None	900.0 nM
Inhibition of mouse Ido2 transfected in HEK293T cells using L-tryptophan as substrate assessed as kynurenine formation at 20 uM after 45 mins by spectrophotometric analysis relative to control	Mus musculus	55.0 %
Inhibition of IDO1 (unknown origin) at highest soluble concentration using L-tryptophan substrate incubated for 60 mins by HPLC	Homo sapiens	0.0 %
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	-1.68 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	18.02 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	4.861 %
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	6.34 %		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	0.03 %		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	6.34 %		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	0.03 %

Related Entries

Cross References

Resources	Reference
ChEBI	135737
ChEMBL	CHEMBL460291
DrugBank	DB09236
DrugCentral	1532
FDA SRS	260080034N
PubChem	5311217
SureChEMBL	SCHEMBL49277
ZINC	ZINC000100015470

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).