Verdamicin

Verdamicin
Systematic (IUPAC) name

(1S,2S,3R,4S,6R)-4,6-diamino-3-({(2S,3R)-3-amino-6-[(1S)-1-aminoethyl]-3,4-dihydro-2H-pyran-2-yl}oxy)-2-hydroxycyclohexyl 3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranoside
Identifiers
CAS Number	49863-48-1^Y
ATC code	none
PubChem	CID 512877
ChemSpider	447461
ChEMBL	CHEMBL1276546^N
Synonyms	(2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[[(2S,3R)-3-amino-6-[(1S)-1-aminoethyl]-3,4-dihydro-2H-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-5-methyl-4-methylaminooxane-3,5-diol
Chemical data
Formula	C₂₀H₃₉N₅O₇
Molar mass	461.55 g/mol
SMILES C[C@@H](C1=CC[C@H]([C@H](O1)O[C@@H]2[C@H](C[C@H]([C@@H]([C@H]2O)O[C@@H]3[C@@H]([C@H]([C@@](CO3)(C)O)NC)O)N)N)N)N
InChI InChI=1S/C20H39N5O7/c1-8(21)12-5-4-9(22)18(30-12)31-15-10(23)6-11(24)16(13(15)26)32-19-14(27)17(25-3)20(2,28)7-29-19/h5,8-11,13-19,25-28H,4,6-7,21-24H2,1-3H3/t8-,9+,10-,11+,13-,14+,15+,16-,17+,18+,19+,20-/m0/s1 Key:XUSXOPRDIDWMFO-CTMSJIKGSA-N
^NY (what is this?) (verify)

Verdamicin is an aminoglycoside antibiotic produced by Micromonospora grisea.^[1]

References

↑ Wagman, G.H.; Weinstein, M.J. (1980). "Antibiotic from Micromonospora.". Annual Review of Microbiology 34: 537–557. doi:10.1146/annurev.mi.34.100180.002541. PMID 6159822.

Antibacterials: protein synthesis inhibitors (J01A, J01B, J01F, J01G, QJ01XQ)

30S

Aminoglycosides
(initiation inhibitors)

-mycin (Streptomyces)	Streptomycin^# Dihydrostreptomycin Neomycin^# Framycetin Paromomycin Ribostamycin Kanamycin^# Amikacin Arbekacin Bekanamycin Dibekacin Tobramycin Spectinomycin^# Hygromycin B Paromomycin

-micin (Micromonospora)	Gentamicin^# Netilmicin Sisomicin Isepamicin Verdamicin Astromicin

Tetracycline antibiotics
(tRNA binding)

Tetracyclines	Doxycycline^# Chlortetracycline Clomocycline Demeclocycline Lymecycline Meclocycline Metacycline Minocycline Oxytetracycline Penimepicycline Rolitetracycline Tetracycline

Glycylcyclines	Tigecycline

50S

Oxazolidinone
(initiation inhibitors)

Peptidyl transferase

Amphenicols	Chloramphenicol^# Azidamfenicol Thiamphenicol Florfenicol

Pleuromutilins	Retapamulin Tiamulin Valnemulin

MLS (transpeptidation/translocation)

Macrolides	Azithromycin^# Clarithromycin Dirithromycin Erythromycin^# Flurithromycin Josamycin Midecamycin Miocamycin Oleandomycin Rokitamycin Roxithromycin Spiramycin Troleandomycin Tylosin Ketolides Telithromycin Cethromycin Solithromycin^†

Lincosamides	Clindamycin^# Lincomycin Pirlimycin

Streptogramins	Pristinamycin Quinupristin/dalfopristin Virginiamycin

EF-G

Steroid antibacterials	Fusidic acid

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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