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Identification
NameGramicidin D
Accession NumberDB00027  (BIOD00036, BTD00036)
Typebiotech
Groupsapproved
Description

Gramcidin D is a heterogeneous mixture of three antibiotic compounds, gramicidins A, B and C, making up 80%, 6%, and 14% respectively all of which are obtained from the soil bacterial species Bacillus brevis and called collectively gramicidin D. Gramcidins are 15 residue peptides with alternating D and L amino acids. The peptides assemble inside of the hydrophobic interior of the cellular lipid bilayer to form a β-helix. The helix itself is not long enough to span the membrane but it dimerizes to form the elongated channel needed to span the whole membrane. Gramicidin D is used primarily as a topical antibiotic and is one of the three constituents of consumer antibiotic polysporin ophthalmic solution.

Protein structureNo structure small
Protein chemical formulaC99H140N20O17
Protein average weight1882.2947
Sequences
Synonyms
SynonymLanguageCode
GramicidinNot AvailableNot Available
Gramicidin ANot AvailableNot Available
Gramicidin BNot AvailableNot Available
Gramicidin CNot AvailableNot Available
GramicidineNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
NeosporinPfizer
SofradexSanofi
Brand mixtures
Brand NameIngredients
NEOCIDINGramicidin D + Polymyxin B Sulfate + Neomycin
NeocidinGramicidin D + Polymyxin B Sulfate + Neomycin
Categories
CAS number1405-97-6
Taxonomy
KingdomOrganic Compounds
SuperclassOrganic Acids
ClassCarboxylic Acids and Derivatives
SubclassAmino Acids, Peptides, and Analogues
Direct parentPeptides
Alternative parentsNot Available
SubstituentsNot Available
Classification descriptionNot Available
Pharmacology
IndicationFor treatment of skin lesions, surface wounds and eye infections
PharmacodynamicsGramicidin is particularly effective against gram-positive bacteria. Because the drug is highly hemolytic, it cannot be administered internally and so is used only on the skin as a lotion or ointment. It is used primarily in the treatment of infected surface wounds, and in eye, nose, and throat infections. It is normally given with two other antibiotics (neomycin and polymixin B) as an ophthalmic solution
Mechanism of actionGramicidin D binds to and inserts itself into bacterial membranes (with a strong preference to gram-positive cell membranes). This results in membrane disruption and permeabilization (it acts as a channel). This leads to (i) loss of intracellular solutes (e.g., K+ and amino acids); (ii) dissipation of the transmembrane potential; (iii) inhibition of respiration; (iv) a reduction in ATP pools; and (v) inhibition of DNA, RNA, and protein synthesis, which leads to cell death.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Gramicidin d powder240.0USDg
Neosporin gu irr 40 mg/ml amp23.12USDml
Neosporin + pain relief cream0.32USDg
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Stateliquid
Experimental Properties
PropertyValueSource
melting point229 °CNot Available
References
Synthesis Reference

U.S.Patent 2,534,541.

General Reference
  1. Ketchem RR, Lee KC, Huo S, Cross TA: Macromolecular structural elucidation with solid-state NMR-derived orientational constraints. J Biomol NMR. 1996 Jul;8(1):1-14. Pubmed
  2. Townsley LE, Tucker WA, Sham S, Hinton JF: Structures of gramicidins A, B, and C incorporated into sodium dodecyl sulfate micelles. Biochemistry. 2001 Oct 2;40(39):11676-86. Pubmed
  3. Burkhart BM, Gassman RM, Langs DA, Pangborn WA, Duax WL, Pletnev V: Gramicidin D conformation, dynamics and membrane ion transport. Biopolymers. 1999;51(2):129-44. Pubmed
External Links
ResourceLink
PharmGKBPA449808
Drug Product Database422908
WikipediaGramicidin_D
ATC CodesR02AB30
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSshow(71.9 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Transporters

1. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

References:

  1. Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on July 31, 2014 14:14