Miocamycin

Miocamycin
Systematic (IUPAC) name

(2S,3S,4R,6S)-6-{[(2R,3S,4R,5R,6S)-6-{[(4S,5R,6S,7R,9R,10R,11E,13E,16R)-10-(acetyloxy)-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-4-propoxy-1-oxacyclohexadeca-11,13-dien-6-yl]oxy}-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy}-2,4-dimethyl-3-propoxyoxan-4-yl acetate
Clinical data
AHFS/Drugs.com	International Drug Names
Identifiers
CAS Number	55881-07-7
ATC code	J01FA11
PubChem	CID 6475694
ChemSpider	16735908^Y
ChEMBL	CHEMBL1091024^Y
Chemical data
Formula	C₄₅H₇₅NO₁₅
Molar mass	870.075 g/mol
SMILES CC(=O)O[C@H]3/C=C/C=C/C[C@@H](C)OC(=O)C[C@@H](OC(=O)CC)[C@H](OC)[C@@H](O[C@@H]2O[C@H](C)[C@@H](O[C@H]1C[C@@](C)(OC(C)=O)[C@@H](OC(=O)CC)[C@H](C)O1)[C@H](N(C)C)[C@H]2O)[C@@H](CC=O)C[C@H]3C
InChI InChI=1S/C45H71NO17/c1-13-34(50)59-33-23-36(52)55-26(4)18-16-15-17-19-32(58-29(7)48)25(3)22-31(20-21-47)41(42(33)54-12)62-44-39(53)38(46(10)11)40(27(5)57-44)61-37-24-45(9,63-30(8)49)43(28(6)56-37)60-35(51)14-2/h15-17,19,21,25-28,31-33,37-44,53H,13-14,18,20,22-24H2,1-12H3/b16-15+,19-17+/t25-,26-,27-,28+,31+,32+,33-,37+,38-,39-,40-,41+,42+,43+,44+,45-/m1/s1^Y Key:GQNZGCARKRHPOH-RQIKCTSVSA-N^Y
Physical data
Melting point	220 °C (428 °F)
Solubility in water	Slightly soluble in water; Soluble in methanol, acetone and chloroform. mg/mL (20 °C)
(verify)

Miocamycin is a macrolide antibiotic.

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

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

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

Steroid antibacterials	Fusidic acid

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^‡Withdrawn from market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

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