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Details

Stereochemistry EPIMERIC
Molecular Formula C58H91N13O20
Molecular Weight 1290.4182
Optical Activity UNSPECIFIED
Defined Stereocenters 12 / 13
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of Amphomycin

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

HIDE SMILES / InChI
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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Kanamycin, amphomycin, and hydrocortisone ointment

Approved Use

For 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.
Name Type Language
Amphomycin
MART.   MI   USAN  
USAN  
Official Name English
AMPHOMYCIN [MART.]
Common Name English
Amfomycin [WHO-DD]
Common Name English
AMPHOMYCIN [MI]
Common Name English
GLUMAMYCIN
Common Name English
AMFOMYCIN
INN   WHO-DD  
INN  
Official Name English
AMPHOMYCIN [USAN]
Common Name English
amfomycin [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C258
Created by admin on Fri Dec 15 17:35:52 GMT 2023 , Edited by admin on Fri Dec 15 17:35:52 GMT 2023
CFR 21 CFR 524.1204
Created by admin on Fri Dec 15 17:35:51 GMT 2023 , Edited by admin on Fri Dec 15 17:35:51 GMT 2023
Code System Code Type Description
MERCK INDEX
m1851
Created by admin on Fri Dec 15 17:35:51 GMT 2023 , Edited by admin on Fri Dec 15 17:35:51 GMT 2023
PRIMARY Merck Index
PUBCHEM
91663250
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PRIMARY
FDA UNII
4P63B997RT
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PRIMARY
ECHA (EC/EINECS)
215-760-0
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PRIMARY
DRUG BANK
DB11499
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PRIMARY
SMS_ID
100000085150
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PRIMARY
EVMPD
SUB00440MIG
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PRIMARY
ChEMBL
CHEMBL2103921
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PRIMARY
INN
1119
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PRIMARY
CAS
1402-82-0
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PRIMARY
MESH
C004423
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PRIMARY
NCI_THESAURUS
C81441
Created by admin on Fri Dec 15 17:35:52 GMT 2023 , Edited by admin on Fri Dec 15 17:35:52 GMT 2023
PRIMARY
EPA CompTox
DTXSID101017657
Created by admin on Fri Dec 15 17:35:51 GMT 2023 , Edited by admin on Fri Dec 15 17:35:51 GMT 2023
PRIMARY