Details
| Stereochemistry | EPIMERIC |
| Molecular Formula | C58H91N13O20 |
| Molecular Weight | 1290.4205 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 12 / 13 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]1(CCCN1C(=O)[C@@H](NC(=O)[C@H](NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)C\C=C\CCCCCC(C)CC)C(C)C(O)=O)[C@H](C)N)C(C)C)C(=O)N[C@@H](C)[C@]2([H])NC(=O)[C@@]3([H])CCCCN3C2=O
InChI
InChIKey=XBNDESPXQUOOBQ-LSMLZNGOSA-N
InChI=1S/C58H91N13O20/c1-8-30(4)18-13-11-9-10-12-14-21-39(72)63-36(26-44(79)80)51(83)68-46(31(5)58(90)91)54(86)65-35(25-43(77)78)50(82)60-27-40(73)64-34(24-42(75)76)49(81)61-28-41(74)66-47(32(6)59)55(87)67-45(29(2)3)56(88)71-23-17-20-38(71)52(84)62-33(7)48-57(89)70-22-16-15-19-37(70)53(85)69-48/h12,14,29-38,45-48H,8-11,13,15-28,59H2,1-7H3,(H,60,82)(H,61,81)(H,62,84)(H,63,72)(H,64,73)(H,65,86)(H,66,74)(H,67,87)(H,68,83)(H,69,85)(H,75,76)(H,77,78)(H,79,80)(H,90,91)/b14-12+/t30?,31-,32+,33+,34+,35+,36+,37-,38+,45+,46+,47-,48+/m1/s1
| Molecular Formula | C58H91N13O20 |
| Molecular Weight | 1290.4205 |
| Charge | 0 |
| Count |
|
| Stereochemistry | EPIMERIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 12 / 13 |
| E/Z Centers | 1 |
| Optical Activity | UNSPECIFIED |
Amphomycin is a natural antibacterial lipopeptide initially reported by researchers at Bristol-Myers in 1953 from Streptomyces canus. Lipopeptides are cyclic depsipeptides with a peptidyl side chain capped with a saturated alkyl tail. They preferentially target Gram-positive bacteria and may be useful against drug resistant strains. Amphomycin is closely related to a number of "lost" antibiotics, such as aspartocin, crystallomycin, glumamycin, friulimicin, laspartocin, tsushimycin and zaomycin. Interest in amphomycin was re-awakened with the discovery of friulimicin activity against antibiotic resistant strains. Whole cell analysis by solid-state NMR indicates that in vivo mode of action for amphomycin is complex. While the downstream effect of purine biosynthesis inhibition by amphomycin is unknown, presumably it would directly alter the overall metabolism of bacteria.
Approval Year
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | Kanamycin, amphomycin, and hydrocortisone ointment Approved UseFor the treatment of acute otitis externa, furunculosis, folliculitis, pruritus, anal gland infections, erythema, decubital ulcers, superficial wounds, and superficial abscesses associated with bacterial infections caused by organisms susceptible to one or both antibiotics. |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:49:06 GMT 2025
by
admin
on
Mon Mar 31 18:49:06 GMT 2025
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| Record UNII |
4P63B997RT
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| Record Status |
FAILED
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NCI_THESAURUS |
C258
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CFR |
21 CFR 524.1204
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m1851
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DB11499
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C004423
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C81441
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DTXSID101017657
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ACTIVE MOIETY |