loperamide
CHEBI:6532
·resolve ·ANTIVIRAL
·EXACT
SEEDED
A synthetic piperidine derivative, effective against diarrhoea resulting from gastroenteritis or inflammatory bowel disease. — ChEBI
Machine-generated and unreviewed. Identity, structure and
cross-references come straight from ChEBI's and CARD's own data; no curator has
signed off on this record yet.
Classification
Strictly broader compounds or drug classes this molecule belongs to.
Chemical structure
Computed structure properties
| Molecular formula | C29H33ClN2O2 |
|---|
| Charge | 0 |
|---|
| Average mass | 477.048 Da |
|---|
| Monoisotopic mass | 476.22306 Da |
|---|
| Source | ChEBI |
|---|
| InChIKey | RDOIQAHITMMDAJ-UHFFFAOYSA-N |
|---|
SMILES
CN(C)C(=O)C(CCN1CCC(O)(c2ccc(Cl)cc2)CC1)(c1ccccc1)c1ccccc1
InChI
InChI=1S/C29H33ClN2O2/c1-31(2)27(33)29(24-9-5-3-6-10-24,25-11-7-4-8-12-25)19-22-32-20-17-28(34,18-21-32)23-13-15-26(30)16-14-23/h3-16,34H,17-22H2,1-2H3
Also called
- loperamida (INN)— chebi
- loperamidum (INN)— chebi
- 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide (EXACT_SYNONYM)— chebi
- Loperamide (EXACT_SYNONYM)— chebi
- lopéramide (EXACT_SYNONYM)— chebi
Cross-references
Equivalent identifiers for this same structure in other resources.
Activity roles
Every antimicrobial role a source asserts for this compound — the
unreduced evidence behind its antimicrobial_class.
Source concepts
Every upstream concept that resolved to this record. The merge is
the product: this is what shows ChEBI and CARD are describing the same structure.
Upstream concepts merged into this record
| Source | Native ID | Label | Minted CURIE | Version |
|---|
| CHEBI |
CHEBI:6532 |
loperamide |
antibioticmech:chebi-fa39440487 |
2026-08-30 |
Molecular targets
The molecular entity or process this compound acts on. Each target
carries evidence — this is a mechanistic claim, not a classification.
Orf1a protein VIRAL_PROTEIN MEASURED_TARGET_ASSOCIATION
BindingDB quantitative measurement in the named target organism; source assay descriptions and identifiers are retained per measurement. Evidence status: PRIMARY_EVIDENCE. Source: BINDINGDB 2026-09 (retrieved 2026-08-31).
Middle East respiratory syndrome-related coronavirus NCBITaxon:1335626
Quantitative measurements
| Type | Reported value | Assay | BindingDB IDs | Reference |
|---|
| EC50 |
4800 nM |
No assay is provided
This is a review article. |
RSID 868957
assay 8918_1
monomer 50017698 |
PMID:32852058 |
| EC50 |
4800 nM |
No assay is provided
This is a review article. |
RSID 868981
assay 8918_1
monomer 50017698 |
PMID:32852058 |
Organism-specific examples
| Protein | Gene | Organism | Entry |
|---|
Orf1a protein UniProtKB:A0A1L2E0X0 |
— |
Middle East respiratory syndrome-related coronavirus |
UNREVIEWED |
- PMID:32852058 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)
Replicase polyprotein 1ab VIRAL_PROTEIN MEASURED_TARGET_ASSOCIATION
BindingDB quantitative measurement in the named target organism; source assay descriptions and identifiers are retained per measurement. Evidence status: PRIMARY_EVIDENCE. Source: BINDINGDB 2026-09 (retrieved 2026-08-31).
Human coronavirus 229E NCBITaxon:11137
Quantitative measurements
| Type | Reported value | Assay | BindingDB IDs | Reference |
|---|
| EC50 |
4000 nM |
No assay is provided
This is a review article. |
RSID 868959
assay 8918_1
monomer 50017698 |
PMID:32852058 |
Organism-specific examples
| Protein | Gene | Organism | Entry |
|---|
Replicase polyprotein 1ab UniProtKB:P0C6X1 |
— |
Human coronavirus 229E |
REVIEWED |
- PMID:32852058 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)
Replicase polyprotein 1ab VIRAL_PROTEIN MEASURED_TARGET_ASSOCIATION
BindingDB quantitative measurement in the named target organism; source assay descriptions and identifiers are retained per measurement. Evidence status: PRIMARY_EVIDENCE. Source: BINDINGDB 2026-09 (retrieved 2026-08-31).
Severe acute respiratory syndrome coronavirus 2 NCBITaxon:2697049
Quantitative measurements
| Type | Reported value | Assay | BindingDB IDs | Reference |
|---|
| IC50 |
9270 nM |
DRC analysis by immunofluorescence
Ten-point DRCs were generated for each drug. Vero cells were seeded at 1.2 × 104 cells per well in DMEM, supplemented with 2% FBS and 1× antibiotic-antimycotic solution (Gibco), in black, 384-well μClear plates (Greiner Bio-One) 24 h prior to the experiment. Ten-point DRCs were generated, with compound concentrations ranging from 0.1 to 50 μM. For the viral infections, plates were transferred into the BSL3 containment facility and SARS-CoV-2 was added at a multiplicity of infection (MOI) of 0.0125. The cells were fixed at 24 hours postinfection (hpi) with 4% PFA and analyzed by immunofluorescence. The acquired images were analyzed using in-house software to quantify cell numbers and infection ratios, and antiviral activity was normalized to positive (mock) and negative (0.5% DMSO) controls in each assay plate. DRCs were fitted by sigmoidal dose-response models, with the following equation: Y = bottom + (top − bottom)/[1 + (IC50/X)Hillslope], using XLfit 4 software or Prism7. IC50 values were calculated from the normalized activity data set-fitted curves. All IC50 and 50% cytotoxic concentration (CC50) values were measured in duplicate, and the quality of each assay was controlled by Z -factor and the coefficient of variation in percent (%CV). |
RSID 874403
assay 8945_1
monomer 50017698 |
PMID:32366720 |
Organism-specific examples
| Protein | Gene | Organism | Entry |
|---|
Replicase polyprotein 1ab UniProtKB:P0DTD1 |
— |
Severe acute respiratory syndrome coronavirus 2 |
REVIEWED |
- PMID:32366720 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)
Replicase polyprotein 1ab VIRAL_PROTEIN MEASURED_TARGET_ASSOCIATION
BindingDB quantitative measurement in the named target organism; source assay descriptions and identifiers are retained per measurement. Evidence status: PRIMARY_EVIDENCE. Source: BINDINGDB 2026-09 (retrieved 2026-08-31).
Severe acute respiratory syndrome coronavirus NCBITaxon:2901879
Quantitative measurements
| Type | Reported value | Assay | BindingDB IDs | Reference |
|---|
| EC50 |
5900 nM |
No assay is provided
This is a review article. |
RSID 868958
assay 8918_1
monomer 50017698 |
PMID:32852058 |
| EC50 |
5900 nM |
No assay is provided
This is a review article. |
RSID 868982
assay 8918_1
monomer 50017698 |
PMID:32852058 |
Organism-specific examples
| Protein | Gene | Organism | Entry |
|---|
Replicase polyprotein 1ab UniProtKB:P0C6X7 |
— |
Severe acute respiratory syndrome coronavirus |
REVIEWED |
- PMID:32852058 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)
Curation history
-
SEEDED_FROM_SOURCES
2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
-
RESEEDED_FROM_SOURCES
2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
-
RESEEDED_FROM_SOURCES
2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
-
RESEEDED_FROM_SOURCES
2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
Provenance
Seeded by scripts/seed_from_sources.py from the committed
inventories in data/raw/.
View the record.