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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL125
CHEMBL125
Compound Name MILTEFOSINE
ChEMBL Synonyms D-18506 | Miltex | Miltefosine | IMPAVIDO | HDPC
Max Phase 4 (Approved)
Trade Names Miltex | IMPAVIDO | Miltefosine
Molecular Formula C21H46NO4P

Additional synonyms for CHEMBL125 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CCCCCCCCCCCCCCCCOP(=O)([O-])OCC[N+](C)(C)C
Standard InChI InChI=1S/C21H46NO4P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18- ...
Download InChI
Standard InChI Key PQLXHQMOHUQAKB-UHFFFAOYSA-N

Sources

  • MMV Pathogen Box
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL125

Molecule Features

CHEMBL125 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:N First In Class:Y Chirality:Racemic Mixture Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:N Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Unknown Not Available FDA PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
LeishmaniasisD007896EFO:0005044Leishmaniasis3ClinicalTrials
Leishmaniasis, CutaneousD016773EFO:0005046cutaneous Leishmaniasis4ClinicalTrials
DailyMed
Leishmaniasis, VisceralD007898EFO:0005045visceral Leishmaniasis4ClinicalTrials
DailyMed
Leishmaniasis, MucocutaneousD007897EFO:0007379mucocutaneous Leishmaniasis4ClinicalTrials
DailyMed
NeoplasmsD009369EFO:0000616neoplasm4ATC
UrticariaD014581EFO:0005531urticaria2ClinicalTrials

Clinical Data

ClinicalTrials.gov MILTEFOSINE
The Cochrane Collaboration MILTEFOSINE

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL125. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL3250 Lysophosphatidic acid receptor Edg-7 Homo sapiens 1.000
CHEMBL3724 Lysophosphatidic acid receptor Edg-4 Homo sapiens 1.000
CHEMBL2955 Sphingosine 1-phosphate receptor Edg-5 Homo sapiens 1.000
CHEMBL4769 Geranylgeranyl pyrophosphate synthetase Homo sapiens 1.000
CHEMBL3230 Sphingosine 1-phosphate receptor Edg-6 Homo sapiens 1.000
CHEMBL3816 Cytosolic phospholipase A2 Homo sapiens 0.999
CHEMBL1782 Farnesyl diphosphate synthase Homo sapiens 0.999
CHEMBL5831 Farnesyl diphosphate synthase Toxoplasma gondii 0.999
CHEMBL283 Matrix metalloproteinase 3 Homo sapiens 0.998
CHEMBL3762 Voltage-gated L-type calcium channel alpha-1C subunit Rattus norvegicus 0.992
CHEMBL253 Cannabinoid CB2 receptor Homo sapiens 0.981
CHEMBL276 Muscarinic acetylcholine receptor M1 Rattus norvegicus 0.952
CHEMBL2274 Sphingosine 1-phosphate receptor Edg-8 Homo sapiens 0.945
CHEMBL2001 Purinergic receptor P2Y12 Homo sapiens 0.883
CHEMBL2265 Acyl coenzyme A:cholesterol acyltransferase Homo sapiens 0.870
CHEMBL3455 Anandamide amidohydrolase Mus musculus 0.869
CHEMBL2623 Acyl coenzyme A:cholesterol acyltransferase Oryctolagus cuniculus 0.858
CHEMBL3911 Leukotriene B4 receptor 1 Homo sapiens 0.847
CHEMBL3474 Phospholipase A2 group IIA Homo sapiens 0.828
CHEMBL321 Matrix metalloproteinase 9 Homo sapiens 0.791



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL4769 Geranylgeranyl pyrophosphate synthetase Homo sapiens 1.000
CHEMBL3724 Lysophosphatidic acid receptor Edg-4 Homo sapiens 1.000
CHEMBL3250 Lysophosphatidic acid receptor Edg-7 Homo sapiens 1.000
CHEMBL2955 Sphingosine 1-phosphate receptor Edg-5 Homo sapiens 1.000
CHEMBL4958 Dynamin-1 Homo sapiens 1.000
CHEMBL5982 ADAM9 Homo sapiens 1.000
CHEMBL1782 Farnesyl diphosphate synthase Homo sapiens 0.999
CHEMBL3230 Sphingosine 1-phosphate receptor Edg-6 Homo sapiens 0.999
CHEMBL5831 Farnesyl diphosphate synthase Toxoplasma gondii 0.998
CHEMBL3383 Carboxylesterase Sus scrofa 0.997
CHEMBL283 Matrix metalloproteinase 3 Homo sapiens 0.997
CHEMBL3693 Farnesyl pyrophosphate synthase Leishmania donovani 0.995
CHEMBL3762 Voltage-gated L-type calcium channel alpha-1C subunit Rattus norvegicus 0.995
CHEMBL3816 Cytosolic phospholipase A2 Homo sapiens 0.991
CHEMBL3474 Phospholipase A2 group IIA Homo sapiens 0.991
CHEMBL2304401 Cytosolic phospholipase A2 Bos taurus 0.991
CHEMBL1860 Thyroid hormone receptor alpha Homo sapiens 0.989
CHEMBL253 Cannabinoid CB2 receptor Homo sapiens 0.983
CHEMBL6135 Neuraminidase Influenza A virus 0.971
CHEMBL2623 Acyl coenzyme A:cholesterol acyltransferase Oryctolagus cuniculus 0.892

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
407.6 407.3164 5.68 20 58.59 ACID


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
4 0 1 5 0 1


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
1.28 - 3.41 4.01 0 27 0.15

Structural Alerts

There are 14 structural alerts for CHEMBL125. To view alerts please click here.

Compound Cross References

ATC L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L01 - ANTINEOPLASTIC AGENTS
L01X - OTHER ANTINEOPLASTIC AGENTS
L01XX - Other antineoplastic agents
L01XX09 - miltefosine

ChemSpider ChemSpider:PQLXHQMOHUQAKB-UHFFFAOYSA-N
DailyMed miltefosine
PubChem SID: 144205019 SID: 170465622 SID: 26749044 SID: 484338
Wikipedia Miltefosine

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL125



ACToR 58066-85-6
BindingDB 50034220
Brenda 145945 8615 113620 49554 113621 31494 145032
ChEBI 75283
ChemicalBook CB6370752
DrugBank DB09031
DrugCentral 1810
eMolecules 748094
EPA CompTox Dashboard DTXSID7045942
FDA SRS 53EY29W7EC
MolPort MolPort-003-665-519
PubChem 3599
PubChem: Drugs of the Future 12014266
PubChem: Thomson Pharma 14781695
Selleck miltefosine-hexadecylphosphocholine
SureChEMBL SCHEMBL26215

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/PQLXHQMOHUQAKB-UHFFFAOYSA-N spacer
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