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Details

Stereochemistry ABSOLUTE
Molecular Formula C99H140N20O17
Molecular Weight 1882.2947
Optical Activity UNSPECIFIED
Defined Stereocenters 14 / 14
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VALINEGRAMICIDIN A

SMILES

CC(C)C[C@@H](NC(=O)[C@H](C)NC(=O)CNC(=O)[C@@H](NC=O)C(C)C)C(=O)N[C@@H](C)C(=O)N[C@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(C)C)C(=O)N[C@@H](CC1=CNC2=C1C=CC=C2)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CC3=CNC4=C3C=CC=C4)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CC5=CNC6=CC=CC=C56)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CC7=CNC8=C7C=CC=C8)C(=O)NCCO

InChI

InChIKey=ZWCXYZRRTRDGQE-LUPIJMBPSA-N
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

HIDE SMILES / InChI

Description

Linear gramicidin is a hydrophobic antibiotic polypeptide composed of 15 hydrophobic amino acids in D- and L-alternate conformers with the following sequence: formyl-L-X-gly-L-ala-D-leu-L-ala-D-val-L-val-D-val-L-trp-D-leu-Ltrp-D-leu-L-trp-D-leu-L-trp-ethanolamine where X represents either valine or isoleucine. Whether amino acid 11 is tryptophan, phenylalanine, or tyrosine, gramicidins are called A, B, or C, respectively. A mixture of three pairs of antibacterial substances (Gramicidin A, B, and C) is also called Gramicidin D and is produced by the growth of Bacillus brevis Dubos (Fam. Bacillaceae). Gramicidin is bactericidal for a variety of gram-positive organisms. It increases the permeability of the bacterial cell membrane to inorganic cations by forming a network of channels through the normal lipid bilayer of the membrane. Gramicidin is used in the combination with neomycin sulfate and polymyxin B sulfate (NEOSPORIN®) for the topical treatment of superficial infections of the external eye and its adnexa caused by susceptible bacteria.

Originator

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
NEOSPORIN
Primary
NEOSPORIN
Primary
NEOSPORIN
Primary
NEOSPORIN
Primary
NEOSPORIN
PubMed

PubMed

TitleDatePubMed
Spectroscopic [correction of eSpectroscopic] and structural properties of valine gramicidin A in monolayers at the air-water interface.
2002 Dec
René Dubos: unearthing antibiotics.
2006 Feb 20
Patents

Sample Use Guides

In Vivo Use Guide
Instill one or two drops of NEOSPORIN® into the affected eye every 4 hours for 7 to 10 days. In severe infections, dosage may be increased to as much as two drops every hour.
Route of Administration: Topical
In Vitro Use Guide
The K+ transport in erythrocytes induced by gramicidin A or valinomycin is a first-order reaction. The activation energy of the induced transport is low and amounts to 6 and 10 kcal/mole, respectively. The indirect method for calculation of the driving force of diffusion, c, is given; in pig erythrocytes, the c value for gramicidin A is 21.7, and for valinomycin 35.4 mM-KCl. The gramicidin A-induced transport corresponds to that of a single gramicidin channel, and not to the multichannel transport observed in the model systems.
Name Type Language
VALINEGRAMICIDIN A
Common Name English
1-L-VALINEGRAMICIDIN A
Common Name English
L-TRYPTOPHANAMIDE, N-FORMYL-L-VALYLGLYCYL-L-ALANYL-D-LEUCYL-L-ALANYL-D-VALYL-L-VALYL-D-VALYL-L-TRYPTOPHYL-D-LEUCYL-L-TRYPTOPHYL-D-LEUCYL-L-TRYPTOPHYL-D-LEUCYL-N-(2-HYDROXYETHYL)-
Systematic Name English
GRAMICIDIN A, 1-L-VALINE-
Common Name English
Code System Code Type Description
CAS
4419-81-2
Created by admin on Tue Mar 06 15:54:25 UTC 2018 , Edited by admin on Tue Mar 06 15:54:25 UTC 2018
PRIMARY