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Midecamycin

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Chemical compound

Pharmaceutical compound

Midecamycin
Clinical data

AHFS/Drugs.com	International Drug Names
ATC code	J01FA03 (WHO)
Identifiers
IUPAC name (2S,3S,4R,6S)-6-{[(2R,3S,4R,5R,6S)-4-(dimethylamino)-5-hydroxy-6-{[(4R,6S,7R,9R,10R,11E,13E,16R)-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-4-(propanoyloxy)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy}-2-methyloxan-3-yl]oxy}-4-hydroxy-2,4-dimethyloxan-3-yl propanoate
CAS Number	35457-80-8^Y
PubChemCID	5382853
ChemSpider	4445365^Y
UNII	N34Z0Y5UH7
KEGG	D01339^Y
CompTox Dashboard(EPA)	DTXSID5045463
ECHA InfoCard	100.047.784
Chemical and physical data
Formula	C₄₁H₆₇NO₁₅
Molar mass	813.979 g·mol⁻¹
3D model (JSmol)	Interactive image
Melting point	155 to 156 °C (311 to 313 °F)
Solubility in water	Soluble inacidic/low pH water; Very soluble in methanol, chloroform, ethyl acetate, benzene, ethyl ether; Almost completely in ethanol(>95.5) mg/mL (20 °C)
SMILES O=CC[C@H]3C[C@@H](C)[C@@H](O)/C=C/C=C/C[C@H](OC(=O)C[C@@H](OC(=O)CC)[C@H](OC)[C@H]3O[C@@H]2O[C@@H]([C@@H](O[C@@H]1O[C@H]([C@H](OC(=O)CC)[C@](O)(C1)C)C)[C@H](N(C)C)[C@H]2O)C)C
InChI InChI=1S/C41H67NO15/c1-11-30(45)54-29-21-32(47)51-24(4)16-14-13-15-17-28(44)23(3)20-27(18-19-43)37(38(29)50-10)57-40-35(48)34(42(8)9)36(25(5)53-40)56-33-22-41(7,49)39(26(6)52-33)55-31(46)12-2/h13-15,17,19,23-29,33-40,44,48-49H,11-12,16,18,20-22H2,1-10H3/b14-13+,17-15+/t23-,24-,25-,26+,27+,28+,29-,33+,34-,35-,36-,37+,38+,39+,40+,41-/m1/s1^Y Key:DMUAPQTXSSNEDD-QALJCMCCSA-N^Y
(verify)

Midecamycin is amacrolide antibiotic^[1] that is synthesized fromStreptomyces mycarofaciens.^[2]

Physical Properties

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Itsmelting point may vary depending on the compound type and the source consulted. For example, the Merck Index gives a melting point of 155-156Celsius for the A₁ type while theJapanese Pharmacopoeia reports 153-158 Celsius. The Merck Index also gives a melting point of 122-125 Celsius for the A₃ type.^{[citation needed]}

References

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^Salhi A, Vindel JA, Brunaud M, Berceaux G, Marin A, Wuatelet C (1977). "Properties of midecamycin, a new macrolide antibiotic".Giornale Italiano di Chemioterapia.24 (1–2):67–76.PMID 308022.
^Wang YG, Hutchinson CR (1989). "Cloning of midecamycin biosynthetic genes from Streptomyces mycarofaciens 1748".Chinese Journal of Biotechnology.5 (4):191–201.PMID 2491329.

This systemicantibiotic-related article is astub. You can help Wikipedia byexpanding it.

Antibacterials thatinhibit protein synthesis (J01A,J01B,J01F,J01G,QJ01XQ)

30S

Aminoglycosides
(initiation inhibitors)

-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

Tetracycline antibiotics
(tRNA binding)

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

50S

Oxazolidinone
(initiation inhibitors)

Peptidyl transferase

Amphenicols	Chloramphenicol^# Azidamfenicol Thiamphenicol Florfenicol

MLS (transpeptidation/translocation)

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)

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

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