Compound Detail
CHEMBL267345
AMPHOTERICIN B 💊 Approved Drug
Enter ChEMBL ID:
Free Research Context
This compound will appear in recent viewed items on the research home for this browser.
Research home
View demo workspace
💊 Approved Drug
C[C@@H]1[C@H](O)[C@@H](C)/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](O[C@@H]2O[C@H](C)[C@@H](O)[C@H](N)[C@@H]2O)C[C@@H]2O[C@](O)(C[C@@H](O)C[C@@H](O)[C@H](O)CC[C@@H](O)C[C@@H](O)CC(=O)O[C@H]1C)C[C@H](O)[C@H]2C(=O)O
Basic Information
| ChEMBL ID | CHEMBL267345 |
| Name | AMPHOTERICIN B |
| Phase | Approved |
| Structure Type | MOL |
| InChI Key | APKFDSVGJQXUKY-INPOYWNPSA-N |
| Therapeutic | ✓ Yes |
50
Targets
470
Activities
2
Assay Types
30
PK Parameters
20
Publications
28
Known Names
20
Indications
1
Mechanisms
Molecular Properties
924.1
MW (Da)
0.71
ALogP
17
HBA
12
HBD
319.6
PSA (Ų)
0.17
QED
3
Ro5 Violations
3
Rot. Bonds
Drug Information
| Molecule Type | Small molecule |
| First Approval | 1964 |
| Availability | Prescription |
| Chirality | Single Enantiomer |
Mechanism of Action
| Mechanism | Action Type | Target | Direct | Efficacy |
|---|---|---|---|---|
| Ergosterol sequestering agent | SEQUESTERING AGENT | Ergosterol | ✓ | ✓ |
Indications
Aspergillosis Candidiasis Cryptococcosis Histoplasmosis Infections Leishmaniasis, Visceral Meningitis, Cryptococcal Mucormycosis Mycoses Sporotrichosis Zygomycosis Blastomycosis Candidiasis, Vulvovaginal Leishmaniasis Leishmaniasis, Mucocutaneous Leukemia Lung Diseases Lymphoma Multiple Myeloma Myelodysplastic Syndromes
ATC Classification
A01AB04
amphotericin B
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: STOMATOLOGICAL PREPARATIONS
A07AA07
amphotericin B
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: ANTIDIARRHEALS, INTESTINAL ANTIINFLAMMATORY/ANTIINFECTIVE AGENTS
G01AA03
amphotericin B
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
J02AA01
amphotericin B
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIMYCOTICS FOR SYSTEMIC USE
Drug Warnings
Black Box Warning
General Warning
Activity Summary
IC50 387 meas. best 10.46
EC50 83 meas. best 8.0
Target Activity Profile
| Target | Type | Best pChEMBL | Mean pChEMBL | Best (nM) | # Data |
|---|---|---|---|---|---|
| Leishmania major CHEMBL612879 | IC50 | 10.46 | 6.7019 | 0.0 | 26 |
| Cryptococcus neoformans CHEMBL365 | IC50 | 9.7 | 6.5253 | 0.2 | 15 |
| Aspergillus fumigatus CHEMBL363 | IC50 | 9.0 | 6.3058 | 1.0 | 12 |
| Leishmania infantum CHEMBL612848 | IC50 | 8.0 | 6.5726 | 10.0 | 46 |
| Leishmania chagasi CHEMBL612790 | IC50 | 8.0 | 6.88 | 10.0 | 6 |
| Leishmania donovani CHEMBL367 | EC50 | 8.0 | 6.91 | 10.0 | 30 |
| Leishmania donovani CHEMBL367 | IC50 | 8.0 | 6.8359 | 10.0 | 103 |
| Naegleria fowleri CHEMBL3301413 | IC50 | 7.74 | 7.34 | 18.3 | 3 |
| Leishmania orientalis CHEMBL4630671 | IC50 | 7.64 | 7.305 | 23.0 | 2 |
| Leishmania amazonensis CHEMBL612877 | EC50 | 7.62 | 5.9317 | 24.0 | 6 |
| Candida albicans CHEMBL366 | IC50 | 7.52 | 6.4929 | 30.0 | 24 |
| Leishmania martiniquensis CHEMBL4630669 | IC50 | 7.51 | 7.51 | 31.0 | 1 |
| Leishmania infantum CHEMBL612848 | EC50 | 7.46 | 6.6657 | 35.0 | 23 |
| Leishmania major CHEMBL612879 | EC50 | 7.46 | 6.6638 | 35.0 | 8 |
| Leishmania panamensis CHEMBL612882 | EC50 | 7.27 | 7.27 | 54.0 | 1 |
| Leishmania amazonensis CHEMBL612877 | IC50 | 7.22 | 6.515 | 60.0 | 42 |
| Leishmania panamensis CHEMBL612882 | IC50 | 7.16 | 7.16 | 70.0 | 1 |
| Leishmania mexicana CHEMBL612880 | IC50 | 7.1 | 6.8833 | 80.0 | 3 |
| NON-PROTEIN TARGET CHEMBL3879801 | EC50 | 7.05 | 5.37 | 90.0 | 3 |
| Leishmania tropica CHEMBL612881 | IC50 | 7.05 | 6.9167 | 90.0 | 6 |
| Leishmania braziliensis CHEMBL612878 | IC50 | 7.05 | 6.7782 | 90.0 | 11 |
| Leishmania peruviana CHEMBL613215 | IC50 | 7.0 | 7.0 | 100.0 | 2 |
| NON-PROTEIN TARGET CHEMBL3879801 | IC50 | 7.0 | 6.4088 | 100.0 | 8 |
| Candida tropicalis CHEMBL612870 | IC50 | 7.0 | 6.76 | 100.0 | 2 |
| Leishmania aethiopica CHEMBL612651 | IC50 | 6.96 | 6.96 | 110.0 | 1 |
| Human immunodeficiency virus 1 CHEMBL378 | IC50 | 6.87 | 6.815 | 136.0 | 2 |
| Leishmania mexicana CHEMBL612880 | EC50 | 6.82 | 6.82 | 150.0 | 1 |
| Trypanosoma cruzi CHEMBL368 | IC50 | 6.82 | 6.0486 | 152.0 | 7 |
| Pyricularia oryzae CHEMBL612925 | IC50 | 6.8 | 6.8 | 160.0 | 1 |
| Pichia kudriavzevii CHEMBL612841 | IC50 | 6.7 | 6.24 | 200.0 | 5 |
| Nakaseomyces glabratus CHEMBL612647 | IC50 | 6.55 | 6.43 | 280.0 | 3 |
| Candida parapsilosis CHEMBL612868 | IC50 | 6.52 | 6.52 | 300.0 | 1 |
| Vero CHEMBL391 | IC50 | 6.48 | 5.0325 | 330.0 | 4 |
| ADMET CHEMBL612558 | IC50 | 6.28 | 5.2325 | 520.0 | 8 |
| Trichophyton mentagrophytes CHEMBL613162 | IC50 | 6.27 | 6.18 | 540.0 | 3 |
| Saccharomyces cerevisiae CHEMBL361 | IC50 | 6.26 | 6.26 | 550.0 | 5 |
| Trichophyton rubrum CHEMBL612649 | IC50 | 6.22 | 6.22 | 600.0 | 2 |
| Leishmania braziliensis CHEMBL612878 | EC50 | 6.1 | 6.1 | 800.0 | 1 |
| Aspergillus niger CHEMBL358 | IC50 | 6.05 | 6.05 | 900.0 | 1 |
| Lichtheimia corymbifera CHEMBL612369 | IC50 | 6.0 | 6.0 | 1000.0 | 1 |
| Unchecked CHEMBL612545 | EC50 | 5.85 | 5.85 | 1400.0 | 1 |
| Aspergillus flavus CHEMBL614955 | IC50 | 5.82 | 5.65 | 1500.0 | 2 |
| BK polyomavirus CHEMBL4888480 | EC50 | 5.78 | 5.78 | 1670.0 | 1 |
| ADMET CHEMBL612558 | EC50 | 5.7 | 5.42 | 2000.0 | 4 |
| THP-1 CHEMBL614245 | EC50 | 5.7 | 5.03 | 2000.0 | 3 |
| HepG2 CHEMBL395 | IC50 | 5.6 | 5.37 | 2500.0 | 3 |
| Trypanosoma brucei rhodesiense CHEMBL612348 | IC50 | 5.55 | 5.55 | 2800.0 | 1 |
| J774.A1 CHEMBL614040 | IC50 | 5.5 | 5.5 | 3140.0 | 1 |
| THP-1 CHEMBL614245 | IC50 | 5.08 | 4.8657 | 8400.0 | 7 |
| Peritoneal macrophage CHEMBL5314330 | EC50 | 5.04 | 5.04 | 9180.0 | 1 |
Pharmacokinetic Data
| Parameter | Value | Units | Species |
|---|---|---|---|
| AUC | 63983.0 | ng.hr.mL-1 | Mus musculus |
| AUC | 2600.0 | ng.hr.mL-1 | Homo sapiens |
| AUC | 36000.0 | ng.hr.mL-1 | Homo sapiens |
| AUC | 36000.0 | ng.hr.mL-1 | Homo sapiens |
| AUC | 2488.0 | ng.hr.mL-1 | Mus musculus |
| AUC | 4476.0 | ng.hr.mL-1 | Mus musculus |
| AUC | 4.02 | ml/min.kg | Mus musculus |
| CL | 0.4 | mL.min-1.kg-1 | Homo sapiens |
| CL | 0.46 | mL.min-1.kg-1 | Homo sapiens |
| CL | 0.1 | mL.min-1.kg-1 | Canis lupus familiaris |
| CL | 0.1 | mL.min-1.kg-1 | Macaca |
| CL | 0.4 | mL.min-1.kg-1 | Homo sapiens |
| CL | 2.0 | mL.min-1.kg-1 | Rattus norvegicus |
| CL | 0.25 | ml/hr | Mus musculus |
| CL | 1.75 | mL.min-1.kg-1 | Homo sapiens |
| CL | 1.867 | mL.min-1.kg-1 | Homo sapiens |
| CL | 0.4667 | mL.min-1.kg-1 | Homo sapiens |
| Cmax | 2.6 | ug.mL-1 | Homo sapiens |
| Cmax | 2.9 | ug.mL-1 | Homo sapiens |
| Cmax | 2.9 | ug.mL-1 | Homo sapiens |
| Fu | 0.04 | - | Homo sapiens |
| Fu | 0.11 | - | Mus musculus |
| MRT | 9.664 | hr | Mus musculus |
| MRT | 28.8 | hr | Mus musculus |
| t1/2 | - | - | Homo sapiens |
| T1/2 | 15.96 | hr | Mus musculus |
| T1/2 | 0.05833 | hr | Homo sapiens |
| T1/2 | 27.5 | hr | Homo sapiens |
| T1/2 | 0.05833 | hr | Homo sapiens |
| T1/2 | 28.2 | hr | Homo sapiens |
Activity Data Samples
Top measurements by pChEMBL value
Literature References
Data from ChEMBL 36 via Core Engine