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Compound Detail

CHEMBL125

MILTEFOSINE
💊 Approved Drug
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💊 Approved Drug
CCCCCCCCCCCCCCCCOP(=O)([O-])OCC[N+](C)(C)C

Basic Information

ChEMBL ID CHEMBL125
Name MILTEFOSINE
Phase Approved
Structure Type MOL
InChI Key PQLXHQMOHUQAKB-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

D-18506 Impavido Miltefosina Miltefosine Miltex NSC-605583 NSC-758968
47
Targets
548
Activities
2
Assay Types
9
PK Parameters
20
Publications
7
Known Names
7
Indications
1
Mechanisms

Molecular Properties

407.6
MW (Da)
5.68
ALogP
4
HBA
0
HBD
58.6
PSA (Ų)
0.15
QED
1
Ro5 Violations
20
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2014
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Black Box Warning Natural Product First in Class
USAN Stem -fos-; -fosine

Extended Properties

Molecular Formula C21H46NO4P
MW 407.58
Aromatic Rings 0
Heavy Atoms 27
NP-Likeness 0.44

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Unknown - -

Indications

Leishmaniasis Leishmaniasis, Cutaneous Leishmaniasis, Mucocutaneous Leishmaniasis, Visceral Trypanosomiasis Bipolar Disorder Urticaria

ATC Classification

P01CX04
miltefosine
Level 1: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Level 2: ANTIPROTOZOALS

Drug Warnings

Black Box Warning
teratogenicity
Country: United States

Activity Summary

IC50 464 meas. best 9.57
EC50 84 meas. best 8.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Leishmania donovani
CHEMBL367
IC50 9.57 5.7255 0.3 198
Human immunodeficiency virus 1
CHEMBL378
EC50 8.0 8.0 10.0 1
Leishmania donovani
CHEMBL367
EC50 6.57 5.4388 270.0 33
Unchecked
CHEMBL612545
IC50 6.36 5.6536 437.2 11
Leishmania amazonensis
CHEMBL612877
EC50 6.36 6.0417 440.0 6
Leishmania infantum
CHEMBL612848
EC50 6.3 5.5352 500.0 25
Leishmania infantum
CHEMBL612848
IC50 6.3 5.2886 500.0 72
Leishmania braziliensis
CHEMBL612878
IC50 6.16 5.212 700.0 10
Trypanosoma cruzi
CHEMBL368
EC50 6.04 5.47 920.0 2
Leishmania tropica
CHEMBL612881
IC50 5.94 5.24 1150.0 4
Leishmania amazonensis
CHEMBL612877
IC50 5.87 5.0455 1350.0 40
Leishmania major
CHEMBL612879
IC50 5.84 5.0544 1440.0 16
NON-PROTEIN TARGET
CHEMBL3879801
IC50 5.82 5.03 1500.0 8
Leishmania mexicana
CHEMBL612880
IC50 5.69 5.435 2030.0 2
MDA-MB-231
CHEMBL400
IC50 5.68 4.8533 2075.0 3
Leishmania mexicana
CHEMBL612880
EC50 5.55 5.505 2800.0 2
RBL-2H3
CHEMBL614632
IC50 5.34 5.34 4600.0 2
THP-1
CHEMBL614245
EC50 5.33 4.754 4670.0 5
MDA-MB-435
CHEMBL614697
IC50 5.3 4.97 5000.0 2
Leishmania guyanensis
CHEMBL612793
IC50 5.3 4.8378 5000.0 9
Leishmania major
CHEMBL612879
EC50 5.28 4.874 5310.0 5
MES-SA/Dx5
CHEMBL613827
IC50 5.27 5.27 5350.0 1
HT-29
CHEMBL384
IC50 5.21 4.76 6150.0 2
NCI-H460
CHEMBL396
IC50 5.18 5.18 6620.0 1
THP-1
CHEMBL614245
IC50 5.16 4.6013 7000.0 15
Leishmania aethiopica
CHEMBL612651
IC50 5.11 4.775 7832.0 2
A549
CHEMBL392
IC50 5.07 4.902 8500.0 5
A2780
CHEMBL614004
IC50 5.05 5.05 8870.0 1
MCF7
CHEMBL387
IC50 5.04 4.6663 9200.0 8
RAC-alpha serine/threonine-protein kinase
CHEMBL4282
IC50 5.02 5.02 9600.0 1
Jurkat
CHEMBL397
IC50 5.0 4.74 10000.0 2
A-431
CHEMBL614069
IC50 4.92 4.595 12000.0 2
Homo sapiens
CHEMBL372
IC50 4.9 4.9 12500.0 1
CCRF-CEM
CHEMBL382
IC50 4.87 4.775 13500.0 2
Trichomonas vaginalis
CHEMBL612884
IC50 4.84 4.7467 14500.0 3
Leishmania martiniquensis
CHEMBL4630669
IC50 4.8 4.8 15790.0 1
HeLa
CHEMBL399
IC50 4.78 4.43 16500.0 3
Trypanosoma cruzi
CHEMBL368
IC50 4.73 4.549 18800.0 10
Giardia intestinalis
CHEMBL612652
IC50 4.7 4.7 20000.0 1
RAW264.7
CHEMBL612557
IC50 4.7 4.525 20000.0 2
HL-60
CHEMBL383
IC50 4.69 4.69 20400.0 1
Vero
CHEMBL391
IC50 4.67 4.43 21600.0 2
Leishmania panamensis
CHEMBL612882
IC50 4.67 4.67 21300.0 1
M-phase inducer phosphatase 1
CHEMBL3775
IC50 4.6 4.6 25000.0 1
J774.A1
CHEMBL614040
IC50 4.6 4.6 25350.0 1
DU-145
CHEMBL613508
IC50 4.6 4.6 24920.0 1
HepG2
CHEMBL395
IC50 4.58 4.58 26300.0 1
ADMET
CHEMBL612558
EC50 4.52 4.52 30000.0 1
Trypanosoma brucei
CHEMBL612849
EC50 4.47 4.47 34000.0 1
Naegleria fowleri
CHEMBL3301413
EC50 4.45 4.45 35700.0 2

Pharmacokinetic Data

Parameter Value Units Species
Cmax 171745.42 nM Homo sapiens
T1/2 100.0 hr Homo sapiens
T1/2 100.0 hr Homo sapiens
T1/2 100.0 hr Homo sapiens
T1/2 1.667 hr Homo sapiens
T1/2 741.6 hr Homo sapiens
T1/2 150.0 hr Homo sapiens
T1/2 144.0 hr Homo sapiens
t1/2 - - Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Leishmania donovani IC50 = 0.27 nM 9.57 Antiprotozoal activity against Leishmania donovani MHOM/ET/67/L82 amastigotes 19364854
Human immunodeficiency virus 1 EC50 = 10.0 nM 8.0 Antiviral activity against HIV-1 3B 31499360
Leishmania donovani IC50 = 120.0 nM 6.92 Antileishmanial activity against Leishmania donovani MHOM/ET/67/L82 axenic amast... 29896963
Leishmania donovani IC50 = 130.0 nM 6.89 Antiprotozoal activity against amastigote form of Leishmania donovani MHOM/ET/67... 28116906
Leishmania donovani IC50 = 142.0 nM 6.85 Antimicrobial activity against Leishmania donovani MHOM/ET/67/L82 axenic amastig... 19817445
Leishmania donovani IC50 = 150.0 nM 6.82 Leishmanicidal activity against promastigote form of Leishmania donovani MHOM/IN... 27318121
Leishmania donovani IC50 = 150.0 nM 6.82 Antileishmanial activity against Leishmania donovani MHOM/IN/80/DD8 promastigote... 30840453
Leishmania donovani IC50 = 150.0 nM 6.82 Antileishmanial activity against Leishmania donovani MHOM/Br/79/Maria promastigo... 33901901
Leishmania donovani IC50 = 156.0 nM 6.81 Antileishmanial activity against axenic amastigote stage of Leishmania donovani ... 27092415
Leishmania donovani IC50 = 156.0 nM 6.81 Antiprotozoal activity against Leishmania donovani MHOM/ET/67/L82 alamar blue st... 27543881
Leishmania donovani IC50 = 162.0 nM 6.79 Antiparasitic activity against axenic amastigote stage of Leishmania donovani MH... 26344593
Leishmania donovani IC50 = 162.0 nM 6.79 Antileishmanial activity against axenic amastigote forms of Leishmania donovani ... 26363868
Leishmania donovani IC50 = 190.0 nM 6.72 Antileishmanial activity against promastigote stage of Leishmania donovani asses... 38107179
Leishmania donovani IC50 = 205.0 nM 6.69 Antileishmanial activity against Leishmania donovani MHOM/ET/67/L82 amastigote a... 19564359
Leishmania donovani IC50 = 220.0 nM 6.66 Antileishmanial activity against Leishmania donovani axenic amastigotes after 72... 18644723
Leishmania donovani IC50 = 250.0 nM 6.6 Antileishmanial activity against Leishmania donovani infected in rat L6 cells 19942439
Leishmania donovani IC50 = 250.0 nM 6.6 Antiparasitic activity against Leishmania donovani MHOM-ET-67/L82 axenic amastig... 28789893
Leishmania donovani IC50 = 260.0 nM 6.58 Antileishmanial activity against Leishmania donovani axenic amastigotes 19781948
Leishmania donovani IC50 = 260.0 nM 6.58 Antileishmanial activity against Leishmania donovani MHOM/ET/67/L82 18989953
Leishmania donovani IC50 = 260.0 nM 6.58 Antiparasitic activity against Leishmania donovani MHOM-ET-67/L82 in amastigotes... 17949068

Literature References

PubMed DOI Target Context # Activities
19015344 10.1128/aac.01233-08 Leishmania donovani 86
17242145 10.1128/aac.01123-06 Leishmania donovani 34
19995922 10.1128/aac.01014-09 ADMET 28
19995922 10.1128/aac.01014-09 Unchecked 19
29294275 10.1021/acs.jmedchem.7b01413 Candida albicans 15
18765686 10.1128/aac.00197-08 Naegleria fowleri 14
31542713 10.1016/j.ejmech.2019.111676 ADMET 14
28059524 10.1021/acs.jmedchem.6b01447 Mus musculus 14
17283192 10.1128/aac.01415-06 Leishmania donovani 13
19752271 10.1128/aac.00866-09 Leishmania donovani 11
18519729 10.1128/aac.00014-08 Homo sapiens 11
28433512 10.1016/j.bmc.2017.03.051 Leishmania amazonensis 11
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
30095915 10.1021/acs.jnatprod.8b00356 Leishmania amazonensis 11
29461823 10.1021/acs.jmedchem.7b01581 Leishmania infantum 10
25128666 10.1016/j.ejmech.2014.08.028 MCF7 10
33148491 10.1016/j.ejmech.2020.112956 ADMET 10
30728107 10.1016/j.bmc.2019.01.033 Unchecked 9
30728107 10.1016/j.bmc.2019.01.033 Trypanosoma cruzi 9
17353242 10.1128/aac.01428-06 Streptococcus pneumoniae 8

Data from ChEMBL 36 via Core Engine