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Substance Name: Gramicidin [USP:INN:BAN]
RN: 1405-97-6
UNII: 5IE62321P4
InChIKey: ZWCXYZRRTRDGQE-SORVKSEFSA-N

Note

  • A group of peptide antibiotics from BACILLUS brevis. Gramicidin C or S is a cyclic, ten-amino acid polypeptide and gramicidins A, B, D are linear. Gramicidin is one of the two principal components of TYROTHRICIN.

Molecular Formula

  • C148-H210-N30-O26

Molecular Weight

  • 1882.318
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Anti-Infective Agents, Local
  • Antibacterial
  • Drug / Therapeutic Agent
  • Mutation Data

Names and Synonyms

Name of Substance

  • Gramicidin
  • Gramicidin [USP:INN:BAN]

MeSH Heading

  • Gramicidin

Synonyms

  • EINECS 215-790-4
  • Gramicidin
  • Gramicidina
  • Gramicidina [INN-Spanish]
  • Gramicidine
  • Gramicidine [INN-French]
  • Gramicidinum
  • Gramicidinum [INN-Latin]
  • Gramoderm
  • UNII-5IE62321P4

Systematic Name

  • Gramicidin

Mixture Names

  • Neo-Polycin
  • Neosporin Ophthalmic Solution
  • Spectrocin

Registry Numbers

CAS Registry Number

  • 1405-97-6

FDA UNII

  • 5IE62321P4

System Generated Number

  • 0001405976

Structure Descriptors

InChI

1S/C99H140N20O17/c1-51(2)37-73(109-86(123)59(17)107-81(122)49-105-96(133)82(55(9)10)106-50-121)89(126)108-60(18)87(124)117-84(57(13)14)98(135)119-85(58(15)16)99(136)118-83(56(11)12)97(134)116-80(44-64-48-104-72-34-26-22-30-68(64)72)95(132)112-76(40-54(7)8)92(129)115-79(43-63-47-103-71-33-25-21-29-67(63)71)94(131)111-75(39-53(5)6)91(128)114-78(42-62-46-102-70-32-24-20-28-66(62)70)93(130)110-74(38-52(3)4)90(127)113-77(88(125)100-35-36-120)41-61-45-101-69-31-23-19-27-65(61)69/h19-34,45-48,50-60,73-80,82-85,101-104,120H,35-44,49H2,1-18H3,(H,100,125)(H,105,133)(H,106,121)(H,107,122)(H,108,126)(H,109,123)(H,110,130)(H,111,131)(H,112,132)(H,113,127)(H,114,128)(H,115,129)(H,116,134)(H,117,124)(H,118,136)(H,119,135)/t59-,60-,73+,74+,75+,76+,77-,78-,79-,80-,82-,83-,84+,85-/m0/s1

InChIKey

ZWCXYZRRTRDGQE-SORVKSEFSA-N

Smiles

N([C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@@H]([C@@H](C)C)C(=O)N[C@@H]([C@H](C)C)C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)NCCO)Cc1c[nH]c2c1cccc2)CC(C)C)Cc1c[nH]c2c1cccc2)CC(C)C)Cc1c[nH]c2c1cccc2)CC(C)C)Cc1c[nH]c2c1cccc2)[C@@H](C)C)C)CC(C)C)C)[C@@H](C)C)C=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 1500ug/kg (1.5mg/kg)   Science. Vol. 103, Pg. 419, 1946.
mouse LD50 parenteral 17ug/kg (0.017mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 3, Pg. 1542, 1978.
mouse LDLo intraperitoneal 20mg/kg (20mg/kg) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Journal of Pharmacology and Experimental Therapeutics. Vol. 74, Pg. 75, 1942.