Identification

Name
Miltefosine
Accession Number
DB09031
Type
Small Molecule
Groups
Approved, Investigational
Description

Miltefosine is a broad spectrum antimicrobial, anti-leishmanial, phospholipid drug that was originally developed in the 1980s as an anti-cancer agent. It is currently the only recognized oral agent used to treat visceral, cutaneous, and mucosal forms of leishmaniasis, a neglected tropical disease. It can be administered topically or orally and is only indicated in patients aged 12 years or older. The CDC has also recommended it as a first line treatment for free-living amebae (FLA) infections such as primary amebic meningoencephalitis and granulomatous amebic encephalitis.

Structure
Thumb
Synonyms
  • HDPC
  • hexadecyl 2-(trimethylazaniumyl)ethyl phosphate
  • Hexadecylphosphocholine
  • Hexadecylphosphorylcholine
  • Miltefosin
  • Miltefosina
  • Miltéfosine
  • Miltefosine
  • Monohexadecylphosphocholine
  • Monohexadecylphosphorylcholine
External IDs
D-18506
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ImpavidoCapsule50 mg/1OralPaladin Therapeutics Inc.2014-09-19Not applicableUs
ImpavidoCapsule50 mg/1OralProfounda, Inc.2015-10-29Not applicableUs
International/Other Brands
Miltex (Baxter)
Categories
UNII
53EY29W7EC
CAS number
58066-85-6
Weight
Average: 407.576
Monoisotopic: 407.316445963
Chemical Formula
C21H46NO4P
InChI Key
PQLXHQMOHUQAKB-UHFFFAOYSA-N
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
IUPAC Name
hexadecyl 2-(trimethylazaniumyl)ethyl phosphate
SMILES
CCCCCCCCCCCCCCCCOP([O-])(=O)OCC[N+](C)(C)C

Pharmacology

Indication

For the treatment of mucosal (caused by Leishmania braziliensis), cutaneous (caused by L. braziliensis, L. guyanensis, and L. panamensis), and visceral leishmaniasis (caused by L. donovani). In comparing Leishmania drug susceptibility, it has been found that L. donovani is the most susceptible to miltefosine while L. major is the least susceptible. Off-label use includes treatment of free-living amebae (FLA) infections (unlabeled use; CDC, 2013).

Structured Indications
Pharmacodynamics

Little is known about the clinical pharmacodynamics of miltefosine and other antileishmanial drugs.

Mechanism of action

Miltefosine has demonstrated activity against Leishmania parasites and neoplastic cells primarily due to its effects on apoptosis and disturbance of lipid-dependent cell signalling pathways. Several potential antileishmanial mechanisms of action have been proposed, however no mechanism has been identified definitely. Within the mitochondria, miltefosine inhibits cytochrome-c oxidase leading to mitochondrial dysfunction and apoptosis-like cell death. Antineoplastic mechanisms of action are related to antileishmanial targets and include inhibition of phosphatidylcholine biosynthesis and inhibition of Akt (also known as protein kinase B), which is a crucial protein within the PI3K/Akt/mTOR intracellular signalling pathway involved in regulating the cell cycle. Animal studies also suggest it may be effective against Trypanosome cruzi (the organism responsible for Chagas' disease), metronidazole-resistant strains of Trichonomas vaginalis, and it may have broad-spectrum anti-fungal activity.

TargetActionsOrganism
UMultidrug resistance protein 1Not AvailableHuman
Absorption

After oral administration, miltefosine is slowly absorbed from the gastrointestinal tract with an absolute bioavailability of 82% in rats and 94% in dogs. Absolute bioavailability has not been assessed in humans, however GI absorption rate in a two-compartment model is estimated to be 0.416 hr-1.

Volume of distribution

Radioactivity studies have found that miltefosine has a wide distribution with high levels in the kidney, intestinal mucosa, liver, and spleen.

Protein binding

Plasma protein binding ranges from 96% to 98%. Miltefosine binds to both serum albumin (97% bound) and low-density lipoprotein (3% bound).

Metabolism

Miltefosine is metabolized mainly by phospholipase D, releasing choline, choline-containing metabolites, and hexadecanol, which are likely to enter the intermediary metabolism. The metabolites produced by this reaction are all endogenous and are likely used for bio-synthesis of acetylcholine, cell membranes, and long-chain fatty acids.

Route of elimination

Miltefosine is almost completely eliminated by degradation via phospholipase D. Drug keeps accumulating until the end of treatment due to the extremely slow elimination, as seen by the long elimination half lives.

Half life

The primary elimination half life is 7.05 days (range: 5.45-9.10 days) and the terminal half-life is 30.9 days (range: 30.8-31.2 days).

Clearance

Plasma clearance is very low and the terminal elimination half life was found to be 84 and 159 hours in rats and dogs respectively.

Toxicity

Preclinical reproductive toxicity studies in animals showed fetal death and teratogenicity at doses lower than the recommended human dose. Use of miltefosine during pregnancy is therefore strictly contraindicated, and contraceptive use is mandatory for females of child-bearing age during therapy and for 5 months afterwards. Preclinical studies additionally showed impaired female and male fertility in animals. Stevens-Johnson syndrome has been reported, therefore therapy should be discontinued if an exfoliative or bullous rash occurs during treatment.

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcemetacinThe therapeutic efficacy of Acemetacin can be decreased when used in combination with Miltefosine.Approved, Experimental, Investigational
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Miltefosine.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Miltefosine.Experimental
AgmatineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Agmatine.Experimental, Investigational
AmiodaroneThe therapeutic efficacy of Miltefosine can be increased when used in combination with Amiodarone.Approved, Investigational
AmlodipineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Amlodipine.Approved
Amphotericin BThe therapeutic efficacy of Amphotericin B can be decreased when used in combination with Miltefosine.Approved, Investigational
AmrinoneThe therapeutic efficacy of Miltefosine can be increased when used in combination with Amrinone.Approved
AncestimThe risk or severity of cytotoxicity can be increased when Ancestim is combined with Miltefosine.Approved, Investigational, Withdrawn
AzelnidipineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Azelnidipine.Approved, Investigational
AzimilideThe therapeutic efficacy of Miltefosine can be increased when used in combination with Azimilide.Investigational
BarnidipineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Barnidipine.Approved
BencyclaneThe therapeutic efficacy of Miltefosine can be increased when used in combination with Bencyclane.Experimental
BenidipineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Benidipine.Approved, Investigational
BepridilThe therapeutic efficacy of Miltefosine can be increased when used in combination with Bepridil.Approved, Withdrawn
BevacizumabBevacizumab may increase the cardiotoxic activities of Miltefosine.Approved, Investigational
BuspironeThe metabolism of Buspirone can be decreased when combined with Miltefosine.Approved, Investigational
BusulfanThe serum concentration of Busulfan can be increased when it is combined with Miltefosine.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Miltefosine.Approved
Calcium carbimideThe risk or severity of adverse effects can be increased when Calcium carbimide is combined with Miltefosine.Approved, Withdrawn
CarboxyamidotriazoleThe therapeutic efficacy of Miltefosine can be increased when used in combination with Carboxyamidotriazole.Investigational
CaroverineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Caroverine.Experimental
CilnidipineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Cilnidipine.Approved, Investigational
CinnarizineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Cinnarizine.Approved, Investigational
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Miltefosine.Approved, Investigational, Withdrawn
ClevidipineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Clevidipine.Approved, Investigational
CyclandelateThe therapeutic efficacy of Miltefosine can be increased when used in combination with Cyclandelate.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Miltefosine.Approved, Investigational
CyclosporineThe metabolism of Cyclosporine can be decreased when combined with Miltefosine.Approved, Investigational, Vet Approved
CymarinCymarin may decrease the cardiotoxic activities of Miltefosine.Experimental
DarodipineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Darodipine.Experimental
DeslanosideDeslanoside may decrease the cardiotoxic activities of Miltefosine.Approved
DidanosineDidanosine can cause a decrease in the absorption of Miltefosine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Miltefosine.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Miltefosine.Approved
Digoxin Immune Fab (Ovine)Digoxin Immune Fab (Ovine) may decrease the cardiotoxic activities of Miltefosine.Approved
DiltiazemThe therapeutic efficacy of Miltefosine can be increased when used in combination with Diltiazem.Approved, Investigational
DocetaxelThe metabolism of Docetaxel can be decreased when combined with Miltefosine.Approved, Investigational
DofetilideThe serum concentration of Dofetilide can be increased when it is combined with Miltefosine.Approved, Investigational
DotarizineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Dotarizine.Investigational
EfonidipineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Efonidipine.Approved, Investigational
EperisoneThe therapeutic efficacy of Miltefosine can be increased when used in combination with Eperisone.Approved, Investigational
EthosuximideThe therapeutic efficacy of Miltefosine can be increased when used in combination with Ethosuximide.Approved
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Miltefosine.Approved
FelodipineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Felodipine.Approved, Investigational
FendilineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Fendiline.Withdrawn
FlunarizineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Flunarizine.Approved
FluspirileneThe therapeutic efficacy of Miltefosine can be increased when used in combination with Fluspirilene.Approved, Investigational
FosphenytoinThe serum concentration of Miltefosine can be decreased when it is combined with Fosphenytoin.Approved, Investigational
GabapentinThe therapeutic efficacy of Miltefosine can be increased when used in combination with Gabapentin.Approved, Investigational
GallopamilThe therapeutic efficacy of Miltefosine can be increased when used in combination with Gallopamil.Investigational
GitoformateGitoformate may decrease the cardiotoxic activities of Miltefosine.Experimental
IsradipineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Isradipine.Approved, Investigational
LacidipineMiltefosine may increase the hypotensive activities of Lacidipine.Approved, Investigational
LamotrigineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Lamotrigine.Approved, Investigational
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Miltefosine.Experimental
LercanidipineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Lercanidipine.Approved, Investigational
LevetiracetamThe therapeutic efficacy of Miltefosine can be increased when used in combination with Levetiracetam.Approved, Investigational
LidoflazineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Lidoflazine.Experimental
LoperamideThe therapeutic efficacy of Miltefosine can be increased when used in combination with Loperamide.Approved
LorpiprazoleThe therapeutic efficacy of Miltefosine can be increased when used in combination with Lorpiprazole.Approved
LosartanThe metabolism of Losartan can be decreased when combined with Miltefosine.Approved
Magnesium SulfateThe therapeutic efficacy of Miltefosine can be increased when used in combination with Magnesium Sulfate.Approved, Investigational, Vet Approved
ManidipineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Manidipine.Approved, Investigational
MethsuximideThe therapeutic efficacy of Miltefosine can be increased when used in combination with Methsuximide.Approved
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Miltefosine.Experimental
MibefradilThe therapeutic efficacy of Miltefosine can be increased when used in combination with Mibefradil.Investigational, Withdrawn
NaftopidilThe therapeutic efficacy of Miltefosine can be increased when used in combination with Naftopidil.Investigational
NicardipineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Nicardipine.Approved, Investigational
NifedipineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Nifedipine.Approved
NiguldipineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Niguldipine.Experimental
NiludipineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Niludipine.Experimental
NilvadipineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Nilvadipine.Approved, Investigational
NimesulideThe therapeutic efficacy of Miltefosine can be increased when used in combination with Nimesulide.Approved, Investigational, Withdrawn
NimodipineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Nimodipine.Approved, Investigational
NisoldipineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Nisoldipine.Approved
NitrendipineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Nitrendipine.Approved, Investigational
OleandrinOleandrin may decrease the cardiotoxic activities of Miltefosine.Experimental, Investigational
OtiloniumThe therapeutic efficacy of Miltefosine can be increased when used in combination with Otilonium.Experimental, Investigational
OuabainOuabain may decrease the cardiotoxic activities of Miltefosine.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Miltefosine.Approved, Vet Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of Miltefosine.Experimental
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Miltefosine.Approved, Vet Approved
PinaveriumThe therapeutic efficacy of Miltefosine can be increased when used in combination with Pinaverium.Approved
PrenylamineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Prenylamine.Withdrawn
ProgesteroneThe absorption of Progesterone can be decreased when combined with Miltefosine.Approved, Vet Approved
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Miltefosine.Experimental
QuinidineThe serum concentration of Quinidine can be increased when it is combined with Miltefosine.Approved, Investigational
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Miltefosine.Approved, Investigational
RifabutinThe serum concentration of Rifabutin can be increased when it is combined with Miltefosine.Approved, Investigational
RifampicinThe serum concentration of Rifampicin can be increased when it is combined with Miltefosine.Approved
RifapentineThe serum concentration of Rifapentine can be increased when it is combined with Miltefosine.Approved, Investigational
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Miltefosine.Approved, Investigational
SeletracetamThe therapeutic efficacy of Miltefosine can be increased when used in combination with Seletracetam.Investigational
SolifenacinThe metabolism of Solifenacin can be decreased when combined with Miltefosine.Approved
SucralfateSucralfate can cause a decrease in the absorption of Miltefosine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
SunitinibThe metabolism of Sunitinib can be decreased when combined with Miltefosine.Approved, Investigational
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Miltefosine.Approved, Investigational
TerodilineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Terodiline.Experimental
TetrahydropalmatineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Tetrahydropalmatine.Investigational
Tolfenamic AcidThe therapeutic efficacy of Miltefosine can be increased when used in combination with Tolfenamic Acid.Approved, Investigational
TranilastThe therapeutic efficacy of Miltefosine can be increased when used in combination with Tranilast.Approved, Investigational
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Miltefosine.Approved, Investigational
TrimebutineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Trimebutine.Approved
TrimethadioneThe therapeutic efficacy of Miltefosine can be increased when used in combination with Trimethadione.Approved
VerapamilThe therapeutic efficacy of Miltefosine can be increased when used in combination with Verapamil.Approved
VinpocetineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Vinpocetine.Investigational
WIN 55212-2The therapeutic efficacy of Miltefosine can be increased when used in combination with WIN 55212-2.Experimental
XylometazolineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Xylometazoline.Approved, Investigational
ZiconotideThe therapeutic efficacy of Miltefosine can be increased when used in combination with Ziconotide.Approved
ZolpidemThe serum concentration of Zolpidem can be increased when it is combined with Miltefosine.Approved
ZonisamideThe therapeutic efficacy of Miltefosine can be increased when used in combination with Zonisamide.Approved, Investigational
Food Interactions
Not Available

References

Synthesis Reference

Eibl H, Engel J: Synthesis of hexadecylphosphocholine (miltefosine). Prog Exp Tumor Res. 1992;34:1-5. Pubmed

General References
  1. Monge-Maillo B, Lopez-Velez R: Miltefosine for visceral and cutaneous leishmaniasis: drug characteristics and evidence-based treatment recommendations. Clin Infect Dis. 2015 May 1;60(9):1398-404. doi: 10.1093/cid/civ004. Epub 2015 Jan 18. [PubMed:25601455]
  2. Dorlo TP, van Thiel PP, Huitema AD, Keizer RJ, de Vries HJ, Beijnen JH, de Vries PJ: Pharmacokinetics of miltefosine in Old World cutaneous leishmaniasis patients. Antimicrob Agents Chemother. 2008 Aug;52(8):2855-60. doi: 10.1128/AAC.00014-08. Epub 2008 Jun 2. [PubMed:18519729]
  3. Dorlo TP, Balasegaram M, Beijnen JH, de Vries PJ: Miltefosine: a review of its pharmacology and therapeutic efficacy in the treatment of leishmaniasis. J Antimicrob Chemother. 2012 Nov;67(11):2576-97. doi: 10.1093/jac/dks275. Epub 2012 Jul 24. [PubMed:22833634]
  4. Sindermann H, Engel J: Development of miltefosine as an oral treatment for leishmaniasis. Trans R Soc Trop Med Hyg. 2006 Dec;100 Suppl 1:S17-20. Epub 2006 May 26. [PubMed:16730362]
  5. Saraiva VB, Gibaldi D, Previato JO, Mendonca-Previato L, Bozza MT, Freire-De-Lima CG, Heise N: Proinflammatory and cytotoxic effects of hexadecylphosphocholine (miltefosine) against drug-resistant strains of Trypanosoma cruzi. Antimicrob Agents Chemother. 2002 Nov;46(11):3472-7. [PubMed:12384352]
  6. Blaha C, Duchene M, Aspock H, Walochnik J: In vitro activity of hexadecylphosphocholine (miltefosine) against metronidazole-resistant and -susceptible strains of Trichomonas vaginalis. J Antimicrob Chemother. 2006 Feb;57(2):273-8. Epub 2005 Dec 12. [PubMed:16344287]
  7. Widmer F, Wright LC, Obando D, Handke R, Ganendren R, Ellis DH, Sorrell TC: Hexadecylphosphocholine (miltefosine) has broad-spectrum fungicidal activity and is efficacious in a mouse model of cryptococcosis. Antimicrob Agents Chemother. 2006 Feb;50(2):414-21. [PubMed:16436691]
External Links
KEGG Drug
D02494
PubChem Compound
3599
PubChem Substance
310264984
ChemSpider
3473
BindingDB
50034220
ChEBI
75283
ChEMBL
CHEMBL125
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Miltefosine
ATC Codes
L01XX09 — Miltefosine
FDA label
Download (389 KB)
MSDS
Download (83.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentLeishmaniasis, Cutaneous2
2CompletedTreatmentLeishmaniasis, Cutaneous / Mucocutaneous Leishmaniasis1
2CompletedTreatmentLeishmaniasis / Mucocutaneous Leishmaniasis1
2CompletedTreatmentPKDL1
2CompletedTreatmentPrimary Visceral Leishmaniasis1
2CompletedTreatmentVisceral Leishmaniasis3
2Not Yet RecruitingTreatmentPKDL - Post-Kala-Azar Dermal Leishmanioid1
2RecruitingTreatmentLeishmaniasis1
2RecruitingTreatmentLeishmaniasis, Cutaneous1
2TerminatedTreatmentChronic Urticaria1
2TerminatedTreatmentLeishmaniasis, Cutaneous1
3Active Not RecruitingTreatmentVisceral Leishmaniasis1
3CompletedTreatmentLeishmaniasis, Cutaneous1
3CompletedTreatmentVisceral Leishmaniasis2
3Not Yet RecruitingTreatmentVisceral Leishmaniasis1
3RecruitingTreatmentPost Kala Azar Dermal Leishmaniasis1
3Unknown StatusTreatmentLeishmaniasis, Cutaneous1
4CompletedTreatmentLeishmaniasis, Cutaneous1
4CompletedTreatmentPost-kala-azar Dermal Leishmaniasis1
Not AvailableRecruitingNot AvailableLeishmaniasis1
Not AvailableRecruitingNot AvailableLeishmaniasis or Other Uses of Miltefosine1
Not AvailableRecruitingNot AvailableMucocutaneous Leishmaniasis2

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
CapsuleOral50 mg/1
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US1999037289No1998-01-222018-01-22Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
pKa~2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00022 mg/mLALOGPS
logP2.68ALOGPS
logP2.25ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)1.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area58.59 Å2ChemAxon
Rotatable Bond Count20ChemAxon
Refractivity125.51 m3·mol-1ChemAxon
Polarizability50.58 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Download (55 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as phosphocholines. These are compounds containing a [2-(trimethylazaniumyl)ethoxy]phosphonic acid or derivative.
Kingdom
Organic compounds
Super Class
Organic nitrogen compounds
Class
Organonitrogen compounds
Sub Class
Quaternary ammonium salts
Direct Parent
Phosphocholines
Alternative Parents
Dialkyl phosphates / Tetraalkylammonium salts / Organopnictogen compounds / Organooxygen compounds / Organic salts / Organic oxides / Hydrocarbon derivatives / Amines
Substituents
Phosphocholine / Dialkyl phosphate / Alkyl phosphate / Phosphoric acid ester / Organic phosphoric acid derivative / Tetraalkylammonium salt / Organic oxygen compound / Organopnictogen compound / Organic oxide / Hydrocarbon derivative
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
phosphocholines, phospholipid (CHEBI:75283)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Rybczynska M, Liu R, Lu P, Sharom FJ, Steinfels E, Pietro AD, Spitaler M, Grunicke H, Hofmann J: MDR1 causes resistance to the antitumour drug miltefosine. Br J Cancer. 2001 May 18;84(10):1405-11. [PubMed:11355955]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Phospholipase d activity
Specific Function
Implicated as a critical step in numerous cellular pathways, including signal transduction, membrane trafficking, and the regulation of mitosis. May be involved in the regulation of perinuclear int...
Gene Name
PLD1
Uniprot ID
Q13393
Uniprot Name
Phospholipase D1
Molecular Weight
124183.135 Da
References
  1. Sindermann H, Engel J: Development of miltefosine as an oral treatment for leishmaniasis. Trans R Soc Trop Med Hyg. 2006 Dec;100 Suppl 1:S17-20. Epub 2006 May 26. [PubMed:16730362]

Drug created on February 17, 2015 15:46 / Updated on February 08, 2018 18:15