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Miocamycin

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Chemical compound

Pharmaceutical compound

Miocamycin
Clinical data

AHFS/Drugs.com	International Drug Names
ATC code	J01FA11 (WHO)
Identifiers
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
CAS Number	55881-07-7
PubChemCID	6475694
ChemSpider	16735908^Y
UNII	3T48CPS7U2
ChEMBL	ChEMBL1091024^Y
CompTox Dashboard(EPA)	DTXSID60905087
ECHA InfoCard	100.054.418
Chemical and physical data
Formula	C₄₅H₇₁NO₁₇
Molar mass	898.053 g·mol⁻¹
3D model (JSmol)	Interactive image
Melting point	220 °C (428 °F)
Solubility in water	Slightly soluble in water; Soluble in methanol, acetone and chloroform. mg/mL (20 °C)
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
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Miocamycin is amacrolide antibiotic.^[1] It has a spectrum activity similar to that ofErythromycin, but shows higher antimicrobial effect against certain bacteria includingLegionella pneumophila (the causative agent ofLegionnaires' Disease),Mycoplasma hominis, andUreaplasma urealyticum.^[1] In-vivo studies have further expounded on Miocamycin's efficacy, reporting that the medication is more effective than in-vitro data suggests.^[2]

^^a ^bHolliday SM, Faulds D (October 1993). "Miocamycin. A review of its antimicrobial activity, pharmacokinetic properties and therapeutic potential".Drugs.46 (4):720–45.doi:10.2165/00003495-199346040-00008.PMID 7506653.S2CID 195692285.
^Lyseng-Williamson, Katherine A (June 2006)."Miocamycin is an effective option in the treatment of various bacterial infections".Drugs & Therapy Perspectives.22 (6):1–6.doi:10.2165/00042310-200622060-00001.ISSN 1172-0360.S2CID 72178165.

-mycin (Streptomyces)	Streptomycin^# Dihydrostreptomycin Neomycin^# Framycetin Paromomycin^# Ribostamycin Kanamycin Amikacin^# Arbekacin Bekanamycin Dibekacin Tobramycin (+loteprednol) Spectinomycin^# Hygromycin B Totomycin Apramycin Nourseothricin
-micin (Micromonospora)	Gentamicin^# Netilmicin Sisomicin Micronomicin Plazomicin^# Isepamicin Verdamicin Astromicin
other	Butirosin

Tetracyclines	Doxycycline^# Chlortetracycline Clomocycline Demeclocycline Eravacycline Lymecycline Meclocycline^‡ Metacycline Minocycline Omadacycline Oxytetracycline Penimepicycline Rolitetracycline Sarecycline Tetracycline^#
Glycylcyclines	Tigecycline

Amphenicols	Chloramphenicol^# Azidamfenicol Thiamphenicol Florfenicol

Macrolides	Boromycin Carbomycin Carrimycin Clarithromycin^# Dirithromycin Erythromycin^# Flurithromycin Josamycin Kitasamycin Midecamycin Miocamycin Nafithromycin Oleandomycin Rokitamycin Roxithromycin Spiramycin Tildipirosin Tilmicosin Troleandomycin Tylosin Tylvalosin
Azalides	Azithromycin^# Gamithromycin Tulathromycin
Ketolides	Telithromycin^‡ Cethromycin Solithromycin^†
Lincosamides	Clindamycin^# Lincomycin Pirlimycin
Oxepanoprolinamides	Cresomycin Iboxamycin
Streptogramins	Pristinamycin (IA,IIA,IIB) NXL103 (Flopristin,Linopristin) Quinupristin/dalfopristin (Dalfopristin,Quinupristin) Streptogramin A Streptogramin B Virginiamycin (S1)

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