AMPHOTERICIN B

Search structure
Trade Names:
Synonyms:
Status: Approved (1964)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: A01AB04
UNII: 7XU7A7DROE

Structure
InChI Key APKFDSVGJQXUKY-INPOYWNPSA-N
Smile C[C@@H]1OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@]2(O)C[C@H](O)[C@@H](C(=O)O)[C@H](C[C@@H](O[C@@H]3O[C@H](C)[C@@H](O)[C@H](N)[C@@H]3O)/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@H]1C)O2
InChI
InChI=1S/C47H73NO17/c1-27-17-15-13-11-9-7-5-6-8-10-12-14-16-18-34(64-46-44(58)41(48)43(57)30(4)63-46)24-38-40(45(59)60)37(54)26-47(61,65-38)25-33(51)22-36(53)35(52)20-19-31(49)21-32(50)23-39(55)62-29(3)28(2)42(27)56/h5-18,27-38,40-44,46,49-54,56-58,61H,19-26,48H2,1-4H3,(H,59,60)/b6-5+,9-7+,10-8+,13-11+,14-12+,17-15+,18-16+/t27-,28-,29-,30+,31+,32+,33-,34-,35+,36+,37-,38-,40+,41-,42+,43+,44-,46-,47+/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C47H73NO17
Molecular Weight 924.09
AlogP 0.71
Hydrogen Bond Acceptor 17.0
Hydrogen Bond Donor 12.0
Number of Rotational Bond 3.0
Polar Surface Area 319.61
Molecular species ZWITTERION
Aromatic Rings 0.0
Heavy Atoms 65.0

Pharmacology

Action Mechanism of Action Reference
SEQUESTERING AGENT Ergosterol sequestering agent PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C19
- 96000 - - -
Enzyme Hydrolase
- - - - 12
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 100

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Leishmaniasis, Visceral 4 D007898 ClinicalTrials
Leishmaniasis 3 D007896 ClinicalTrials
Myelodysplastic Syndromes 3 D009190 ClinicalTrials
Neoplasms 3 D009369 ClinicalTrials
Leukemia 3 D007938 ClinicalTrials
Lung Diseases 3 D008171 ClinicalTrials
Multiple Myeloma 3 D009101 ClinicalTrials
Myeloproliferative Disorders 3 D009196 ClinicalTrials
Vaginosis, Bacterial 3 D016585 ClinicalTrials
Blastomycosis 3 D001759 ClinicalTrials
Candidiasis, Vulvovaginal 3 D002181 ClinicalTrials
Leishmaniasis, Mucocutaneous 3 D007897 ClinicalTrials
Fuchs' Endothelial Dystrophy 2 D005642 ClinicalTrials
Candidiasis, Invasive 2 D058365 ClinicalTrials
Aspergillosis, Allergic Bronchopulmonary 2 D001229 ClinicalTrials
Leukemia, Myeloid, Acute 2 D015470 ClinicalTrials
Intracranial Hypertension 2 D019586 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 2 D054198 ClinicalTrials
Candidiasis, Chronic Mucocutaneous 2 D002178 ClinicalTrials
Leishmaniasis, Cutaneous 1 D016773 ClinicalTrials

Related Entries

Scaffolds

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
23.43
Injury, poisoning and procedural complications
12.28
Infections and infestations
6.85
Investigations
6.16
Respiratory, thoracic and mediastinal disorders
5.31
Renal and urinary disorders
5.2
Metabolism and nutrition disorders
5.05
Nervous system disorders
4.83
Gastrointestinal disorders
4.15
Skin and subcutaneous tissue disorders
4.12
Blood and lymphatic system disorders
3.88
Immune system disorders
3.64
Cardiac disorders
3.41
Vascular disorders
3.03
Hepatobiliary disorders
2.16

Cross References

Resources Reference
CAS NUMBER 1397-89-3
ChEBI 2682
ChEMBL CHEMBL267345
DrugBank DB00681
DrugCentral 197
EPA CompTox DTXSID9022601
FDA SRS 7XU7A7DROE
Human Metabolome Database HMDB0014819
KEGG C06573
PharmGKB PA448415
PubChem 5280965
SureChEMBL SCHEMBL17973
ZINC ZINC000253387843
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