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Substance Name: Sisomicin [USAN:INN:BAN]
RN: 32385-11-8
UNII: X55XSL74YQ
InChIKey: URWAJWIAIPFPJE-YFMIWBNJSA-N

Note

  • Antibiotic produced by Micromonospora inyoensis. It is closely related to gentamicin C1A, one of the components of the gentamicin complex (GENTAMICINS).

Molecular Formula

  • C19-H37-N5-O7

Molecular Weight

  • 447.529
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Protein Synthesis Inhibitors
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Sisomicin
  • Sisomicin [USAN:INN:BAN]

MeSH Heading

  • Sisomicin

Synonyms

  • (2S-cis)-4-O-(3-Amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl)-2-deoxy-6-O-(3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl)-D-streptamine
  • Antibiotic 66-40
  • BRN 1357913
  • EINECS 251-018-2
  • O-2,6-Diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1-4)-O-(3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-6)-2-deoxy-D-streptamine
  • O-3-Deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-4)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1-6))-2-deoxy-L-streptamine
  • Rickamicin
  • Sch 13475
  • Siseptin
  • Sisomicin
  • Sisomicina
  • Sisomicina [INN-Spanish]
  • Sisomicine
  • Sisomicine [INN-French]
  • Sisomicinum
  • Sisomicinum [INN-Latin]
  • Sisomycin
  • Sissomicin
  • UNII-X55XSL74YQ

Systematic Names

  • (2S-cis)-4-O-(3-Amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl)-2-deoxy-6-O-(3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl)-D-streptamine
  • D-Streptamine, O-3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-6)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1-4))-2-deoxy-
  • Sisomicin

Registry Numbers

CAS Registry Number

  • 32385-11-8

FDA UNII

  • X55XSL74YQ

Other Registry Numbers

  • 34406-63-8
  • 37332-59-5
  • 53179-08-1

Related Registry Number

  • 53179-09-2 (sulfate (2:5) (salt))

System Generated Number

  • 0032385118

Structure Descriptors

InChI

InChI=1S/C19H37N5O7/c1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17/h3,9-18,24-27H,4-7,20-23H2,1-2H3/t9-,10+,11-,12+,13-,14-,15+,16-,17-,18-,19+/m1/s1

InChIKey

URWAJWIAIPFPJE-YFMIWBNJSA-N

Smiles

CN[C@@H]1[C@@H](O)[C@@H](O[C@H]2[C@H](N)C[C@H](N)[C@@H](O[C@H]3OC(=CC[C@H]3N)CN)[C@@H]2O)OC[C@]1(C)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 221mg/kg (221mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 1, Pg. 178, 1980.
mouse LD50 intravenous 34mg/kg (34mg/kg)   "Structure-Activity Relationship among the Semisynthetic Antibiotics," Perlman, D., ed., New York, Academic Press, 1977Vol. -, Pg. 239, 1977.
mouse LD50 oral > 5gm/kg (5000mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. Vol. 4, Pg. 107, 1978.
mouse LD50 subcutaneous 177mg/kg (177mg/kg)   Chemotherapy Vol. 26(Suppl,
rat LD50 intravenous 32mg/kg (32mg/kg)   Archives of Toxicology. Vol. 54, Pg. 275, 1983.
rat LD50 oral > 5gm/kg (5000mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. Vol. 4, Pg. 107, 1978.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -3.450 (none)   EST
Atmospheric OH Rate Constant 5.35E-10 cm3/molecule-sec 25 EST

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