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Substance Name: Guamecycline [INN:BAN:DCF]
RN: 16545-11-2
UNII: 4NQR4R6G3S
InChIKey: DIRJDIBCAHCCFL-AQFAATAFSA-N

Classification Codes

  • Drug / Therapeutic Agent
  • Natural Product

Molecular Formula

  • C29-H38-N8-O8

Molecular Weight

  • 626.6672
 
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Names and Synonyms

Name of Substance

  • Guamecycline
  • Guamecycline [INN:BAN:DCF]

Synonyms

  • EINECS 240-611-1
  • Guameciclina
  • Guameciclina [INN-Spanish]
  • Guameciclina [Italian]
  • Guamecycline
  • Guamecyclinum
  • Guamecyclinum [INN-Latin]
  • N-((4-(((Aminoiminomethyl)amino)iminomethyl)-1-piperazinyl)methyl)-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide (4S-(4alpha,4aalpha,5aalpha,6beta,12aalpha))-
  • N-((4-(Amidinoamidino)-1-piperazinyl)methyl)-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide
  • Tetrabiguanide
  • UNII-4NQR4R6G3S
  • Xanthomycin A
  • Xantomicina

Systematic Names

  • 2-Naphthacenecarboxamide, N-((4-(((aminoiminomethyl)amino)iminomethyl)-1-piperazinyl)methyl)-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, (4S-(4alpha,4aalpha,5aalpha,6beta,12aalpha))-
  • 2-Naphthacenecarboxamide, N-((4-(amidinoamidino)-1-piperazinyl)methyl)-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-
  • Guamecycline
  • N,N-Diethyleneiminobiguanidomethyltetracycline
  • N-((4-(Amidinoamidino)-1-piperazinyl)methyl)-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide

Registry Numbers

CAS Registry Number

  • 16545-11-2

FDA UNII

  • 4NQR4R6G3S

Related Registry Number

  • 13040-98-7 (di-hydrochloride)

System Generated Number

  • 0016545112

Structure Descriptors

InChI

1S/C29H38N8O8/c1-28(44)13-5-4-6-16(38)17(13)21(39)18-14(28)11-15-20(35(2)3)22(40)19(24(42)29(15,45)23(18)41)25(43)33-12-36-7-9-37(10-8-36)27(32)34-26(30)31/h4-6,14-15,20,38,40-41,44-45H,7-12H2,1-3H3,(H,33,43)(H5,30,31,32,34)/t14-,15-,20-,28+,29-/m0/s1

InChIKey

DIRJDIBCAHCCFL-AQFAATAFSA-N

Smiles

CN(C)[C@H]1[C@@H]2C[C@H]3C(=C(O)[C@]2(O)C(=O)C(=C1O)C(=O)NCN4CCN(CC4)C(=N)NC(=N)N)C(=O)c5c(O)cccc5[C@@]3(C)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 250ug/kg (0.25mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 2, Pg. 290, 1980.
mouse LD50 intravenous 160ug/kg (0.16mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 182, 1978.