miltefosine (CHEBI:75283)

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ChEBI Name	miltefosine

ChEBI ID	CHEBI:75283

Definition	A phospholipid that is the hexadecyl monoester of phosphocholine.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	ChemicalBook:CB6370752, eMolecules:748094, Selleckchem:miltefosine-hexadecylphosphocholine

Download	Molfile XML SDF

Wikipedia	License
Miltefosine, sold under the trade name Impavido among others, is a medication mainly used to treat leishmaniasis and free-living amoeba infections such as Naegleria fowleri and Balamuthia mandrillaris. This includes the three forms of leishmaniasis: cutaneous, visceral and mucosal. It may be used with liposomal amphotericin B or paromomycin. It is taken by mouth. Common side effects include vomiting, abdominal pain, fever, headaches, and decreased kidney function. More severe side effects may include Stevens–Johnson syndrome or low blood platelets. Use during pregnancy appears to cause harm to the baby and use during breastfeeding is not recommended. How it works is not entirely clear. Miltefosine was first made in the early 1980s and studied as a treatment for cancer. A few years later it was found to be useful for leishmaniasis and was approved for this use in 2002 in India. It is on the World Health Organization's List of Essential Medicines.
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Formula

C21H46NO4P

Net Charge

Average Mass

407.56800

Monoisotopic Mass

407.31645

InChI

InChI=1S/C21H46NO4P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-20-25-27(23,24)26-21-19-22(2,3)4/h5-21H2,1-4H3

InChIKey

PQLXHQMOHUQAKB-UHFFFAOYSA-N

SMILES

CCCCCCCCCCCCCCCCOP([O-])(=O)OCC[N+](C)(C)C

Roles Classification
Biological Role(s):	anticoronaviral agent Any antiviral agent which inhibits the activity of coronaviruses. immunomodulator Biologically active substance whose activity affects or plays a role in the functioning of the immune system. apoptosis inducer Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms. protein kinase inhibitor An EC 2.7.* (P-containing group transferase) inhibitor that interferes with the action of protein kinases. antiprotozoal drug Any antimicrobial drug which is used to treat or prevent protozoal infections. antifungal agent An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.

Application(s):	immunomodulator Biologically active substance whose activity affects or plays a role in the functioning of the immune system. anti-inflammatory agent Any compound that has anti-inflammatory effects. antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. antiprotozoal drug Any antimicrobial drug which is used to treat or prevent protozoal infections.

ChEBI Ontology
Outgoing	miltefosine (CHEBI:75283) has role anti-inflammatory agent (CHEBI:67079) miltefosine (CHEBI:75283) has role anticoronaviral agent (CHEBI:149553) miltefosine (CHEBI:75283) has role antifungal agent (CHEBI:35718) miltefosine (CHEBI:75283) has role antineoplastic agent (CHEBI:35610) miltefosine (CHEBI:75283) has role antiprotozoal drug (CHEBI:35820) miltefosine (CHEBI:75283) has role apoptosis inducer (CHEBI:68495) miltefosine (CHEBI:75283) has role immunomodulator (CHEBI:50846) miltefosine (CHEBI:75283) has role protein kinase inhibitor (CHEBI:37699) miltefosine (CHEBI:75283) is a phosphocholines (CHEBI:36700) miltefosine (CHEBI:75283) is a phospholipid (CHEBI:16247)

Synonyms	Sources
Hexadecylphosphocholine	ChemIDplus
Hexadecylphosphorylcholine	ChemIDplus
monohexadecylphosphocholine	ChEBI
monohexadecylphosphorylcholine	ChEBI

Citations

Last Modified

23 April 2020