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Substance Name: Josamycin [USAN:INN:BAN:JAN]
RN: 16846-24-5
UNII: HV13HFS217
InChIKey: XJSFLOJWULLJQS-NGVXBBESSA-N

Note

  • A macrolide antibiotic from Streptomyces narbonensis. The drug has antimicrobial activity against a wide spectrum of pathogens.

Molecular Formula

  • C42-H69-N-O15

Molecular Weight

  • 827.999
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial
  • Drug / Therapeutic Agent
  • Natural Product
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Josamycin
  • Josamycin [USAN:INN:BAN:JAN]

MeSH Heading

  • Josamycin

Synonyms

  • Antibiotic yl-704 A3
  • CCRIS 8511
  • EINECS 240-871-6
  • EN-141
  • Josamicina
  • Josamicina [INN-Spanish]
  • Josamycin
  • Josamycine
  • Josamycine [INN-French]
  • Josamycinum
  • Josamycinum [INN-Latin]
  • Kitasamycin A3
  • Leucomycin A3
  • Stereoisomer of 4-(acetyloxy)-6-((3,6-dideoxy-4-O-(2,6-dideoxy-3-C-methyl-4-O-(3-methyl-1-oxobutyl)-alpha-L-ribo-hexopyranosyl)-3-(dimethylamino)-beta-D-glucopyranosyl)oxy)-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxooxacyclohexadeca-11,13-diene-7-acetaldehyde
  • Stereoisomer of 7-(formylmethyl)-4,10-dihydroxy-5-methoxy-9,16-dimethyl-2-oxooxacyclohexadeca-11,13-dien-6-yl 3,6-dideoxy-4-O-(2,6-dideoxy-3-C-methyl-alpha-L-ribo-hexopyranosyl)-3-(dimethylamino)-beta-D-glucopyranoside 4'-acetate 4''-isovalerate
  • Stereoisomer of 7-(formylmethyl)-4,10-dihydroxy-5-methoxy-9,16-dimethyl-2-oxooxacyclohexadeca-11,13-dien-6-yl 3,6-dideoxy-4-O-(2,6-dideoxy-3-C-methyl-alpha-L-ribo-hexopyranosyl)-3-(dimethylamino)-beta-D-glucopyranoside 4'-acetate 4'-isovalerate
  • Turimycin A5
  • UNII-HV13HFS217
  • Yl-704 A3

Systematic Names

  • Josamycin
  • Leucomycin V, 3-acetate 4(sup B)-(3-methylbutanoate)
  • Leucomycin V, 3-acetate 4(sup beta)-(3-methylbutanoate)
  • Leucomycin V, 3-acetate 4B-(3-methylbutanoate)

Registry Numbers

CAS Registry Number

  • 16846-24-5

FDA UNII

  • HV13HFS217

Other Registry Numbers

  • 11033-18-4
  • 35414-05-2
  • 39416-64-3
  • 56689-45-3
  • 801993-04-4

System Generated Number

  • 0016846245

Structure Descriptors

InChI

InChI=1S/C42H69NO15/c1-23(2)19-32(47)56-40-27(6)53-34(22-42(40,8)50)57-37-26(5)54-41(36(49)35(37)43(9)10)58-38-29(17-18-44)20-24(3)30(46)16-14-12-13-15-25(4)52-33(48)21-31(39(38)51-11)55-28(7)45/h12-14,16,18,23-27,29-31,34-41,46,49-50H,15,17,19-22H2,1-11H3/b13-12+,16-14+/t24-,25-,26-,27+,29+,30+,31-,34+,35-,36-,37-,38+,39+,40+,41+,42-/m1/s1

InChIKey

XJSFLOJWULLJQS-NGVXBBESSA-N

Smiles

CO[C@H]1[C@@H](CC(=O)O[C@H](C)C\C=C\C=C\[C@H](O)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@@H]2O[C@H](C)[C@@H](O[C@H]3C[C@@](C)(O)[C@@H](OC(=O)CC(C)C)[C@H](C)O3)[C@@H]([C@H]2O)N(C)C)OC(=O)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LD50 intraperitoneal 520mg/kg (520mg/kg)   Hindustan Antibiotics Bulletin. Vol. 11, Pg. 26, 1969.
mammal (species unspecified) LD50 intravenous 385mg/kg (385mg/kg)   Hindustan Antibiotics Bulletin. Vol. 11, Pg. 26, 1969.
mammal (species unspecified) LD50 subcutaneous 786mg/kg (786mg/kg)   Hindustan Antibiotics Bulletin. Vol. 11, Pg. 26, 1969.
mouse LD50 intraperitoneal 780mg/kg (780mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 2, Pg. 85, 1980.
mouse LD50 intravenous 385mg/kg (385mg/kg)   Nihon Daigaku No-juigakubu Gakujutsu Kenkyu Hokoku. Research Reports of the College of Agriculture and Veterinary Medicine, Nihon University. Vol. (35), Pg. 41, 1978.
mouse LD50 oral 6400mg/kg (6400mg/kg)   Japanese Journal of Antibiotics. Vol. 37, Pg. 1565, 1984.
mouse LD50 subcutaneous > 3gm/kg (3000mg/kg)   Drugs in Japan Vol. 6, Pg. 364, 1982.
rat LD50 intraperitoneal > 3gm/kg (3000mg/kg)   Drugs in Japan Vol. 6, Pg. 364, 1982.
rat LD50 intravenous 390mg/kg (390mg/kg)   Nihon Daigaku No-juigakubu Gakujutsu Kenkyu Hokoku. Research Reports of the College of Agriculture and Veterinary Medicine, Nihon University. Vol. (35), Pg. 41, 1978.
rat LD50 oral > 7gm/kg (7000mg/kg)   Drugs in Japan Vol. 6, Pg. 364, 1982.
rat LD50 subcutaneous > 3gm/kg (3000mg/kg)   Drugs in Japan Vol. 6, Pg. 364, 1982.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 131.5 deg C   EXP
log P (octanol-water) 3.160 (none)   EST
Atmospheric OH Rate Constant 4.29E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.