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Substance Name: Sinefungin [USAN:INN]
RN: 58944-73-3
UNII: W2U467CIIL
InChIKey: LMXOHSDXUQEUSF-YECHIGJVSA-N

Note

  • Antifungal antibiotic containing adenine, sugar hydroxyl & amino groups; isolated from Streptomyces griseolus.

Molecular Formula

  • C15-H23-N7-O5

Molecular Weight

  • 381.3907
 

Classification Codes

  • Anti-Infective Agents
  • Antibiotics, Antifungal
  • Antifungal
  • Antifungal Agents
  • Antimalarials
  • Antiparasitic Agents
  • Antiprotozoal Agents
  • Drug / Therapeutic Agent
  • Natural Product
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Names and Synonyms

Name of Substance

  • Sinefungin
  • Sinefungin [USAN:INN]

Synonyms

  • 6,9-Diamino-1-(6-amino-9H-purin-9-yl)-1,5,6,7,8,9-hexadeoxy-beta-D-ribo-decofuranuronic acid
  • 6,9-Diamino-1-(6-amino-9H-purin-9-yl)-1,5,6,7,8,9-hexadeoxydecofuranuronic acid
  • A 9145
  • Antibiotic 32232 RP
  • Antibiotic A 9145
  • BRN 3574678
  • Compound 57926
  • LY 57926
  • RP 32232
  • Sinefungin
  • Sinefungina
  • Sinefungina [INN-Spanish]
  • Sinefungine
  • Sinefungine [INN-French]
  • Sinefunginum
  • Sinefunginum [INN-Latin]
  • UNII-W2U467CIIL

Systematic Names

  • D-glycero-alpha-L-talo-Decofuranuronic acid, 6,9-diamino-1-(6-amino-9H-purin-9-yl)-1,5,6,7,8,9-hexadeoxy-
  • Decofuranuronic acid, 6,9-diamino-1-(6-amino-9H-purin-9-yl)-1,5,6,7,8,9-hexadeoxy-
  • Decofuranuronic acid, 6,9-diamino-1-(6-amino-9H-purin-9-yl)-1,5,6,7,8,9-hexadeoxy-, (beta-D-ribo)-

Registry Numbers

CAS Registry Number

  • 58944-73-3

FDA UNII

  • W2U467CIIL

Other Registry Number

  • 39315-74-7

System Generated Number

  • 0058944733

Structure Descriptors

InChI

1S/C15H23N7O5/c16-6(1-2-7(17)15(25)26)3-8-10(23)11(24)14(27-8)22-5-21-9-12(18)19-4-20-13(9)22/h4-8,10-11,14,23-24H,1-3,16-17H2,(H,25,26)(H2,18,19,20)/t6-,7-,8+,10+,11+,14+/m0/s1

InChIKey

LMXOHSDXUQEUSF-YECHIGJVSA-N

Smiles

c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)C[C@H](CC[C@@H](C(=O)O)N)N)O)O)N

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 1gm/kg (1000mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 5, Pg. 298, 1981.
mouse LD50 subcutaneous 185mg/kg (185mg/kg)   Journal of Antibiotics. Vol. 26, Pg. 463, 1973.