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Identification
NameGramicidin D
Accession NumberDB00027  (BTD00036, BIOD00036)
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 structureDb00027
Related Articles
Protein chemical formulaC99H140N20O17
Protein average weight1882.2947 Da
SequencesNot Available
Synonyms
Bacillus brevis gramicidin D
Gramicidin
Gramicidin A
Gramicidin B
Gramicidin C
Gramicidine
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
SofradexSanofi
Brand mixtures
NameLabellerIngredients
Antibiotic CreamPharmetics (2011) Inc
Antibiotic Cream for KidsTaro Pharmaceuticals Inc
Antibiotic Cream Plus Pain ReliefPharmetics (2011) Inc
Antibiotic Cream Plus Pain Relief for KidsCanadian Custom Packaging Company
Antibiotic Plus Pain Relief CreamTaro Pharmaceuticals Inc
Complete Antibiotic OintmentTaro Pharmaceuticals Inc
Kenacomb CreamWestwood Squibb, Division Of Bristol Myers Squibb Canada Inc.
Kenacomb Mild CreamWestwood Squibb, Division Of Bristol Myers Squibb Canada Inc.
Kenacomb Mild OintmentWestwood Squibb, Division Of Bristol Myers Squibb Canada Inc.
Kenacomb OintmentWestwood Squibb, Division Of Bristol Myers Squibb Canada Inc.
Kenacomb OntSquibb Canada Inc., Division Of Bristol Myers Squibb Canada Inc.
Lidecomb CreamMedicis Canada Ltd.
Lidosporin CreamGlaxo Wellcome Inc.
Mecomb Crm 0.1%Medic Laboratory LtÉe
NeocidinMajor Pharmaceuticals
Neomycin and Polymyxin B Sulfates and GramicidinRebel Distributors Corp
NeosporinMonarch Pharmaceuticals, Inc.
Neosporin Antibiotic CreamGlaxosmithkline Inc
Neosporin Eye-ear SolutionGlaxosmithkline Inc
Odan-sporOdan Laboratories Ltd
OptimyxinSandoz Canada Incorporated
Optimyxin Plus Oto-opht GtteSandoz Canada Incorporated
Original Antibiotic CreamTaro Pharmaceuticals Inc
Polycidin Eye, Ear DropsNovartis Ophthalmics Novartis Pharmaceuticals (Canada) Inc
Polysporin Antibiotic Burn CreamWarner Lambert Canada Inc.
Polysporin Antibiotic CreamJohnson & Johnson Inc
Polysporin Burn Formula CreamGlaxo Wellcome Inc.
Polysporin Cold Sore OintmentJohnson & Johnson Inc
Polysporin CompleteJohnson & Johnson Inc
Polysporin CreamGlaxo Wellcome Inc.
Polysporin Eye and Ear Drops SterileJohnson & Johnson Inc
Polysporin for KidsJohnson & Johnson Inc
Polysporin for StitchesJohnson & Johnson Inc
Polysporin Plus Pain ReliefJohnson & Johnson Inc
Polysporin Triple Antibiotic OintmentGlaxo Wellcome Inc.
Polytopic CreamSandoz Canada Incorporated
Ratio-triacombTeva Canada Limited
Sandoz OpticortSandoz Canada Incorporated
Sofracort Ear/eye OintmentRoussel Canada Inc.
Sofracort Sterile Ear/eye DropsSanofi Aventis Canada Inc
Sofracort Sterile Ear/eye OintmentHoechst Roussel Canada Inc.
Soframycin Nasal SprayErfa Canada 2012 Inc
Soframycin OintmentRoussel Canada Inc.
Soframycin Skin OintmentErfa Canada 2012 Inc
Theraderm CreamBimeda Mtc Animal Health Inc
Triple Antibiotic OintmentTaro Pharmaceuticals Inc
Viaderm Kc CrmTaro Pharmaceuticals Inc
Viaderm Kc OntTaro Pharmaceuticals Inc
SaltsNot Available
Categories
UNII5IE62321P4
CAS number1405-97-6
Taxonomy
DescriptionNot Available
KingdomOrganic Compounds
Super ClassOrganic Acids
ClassCarboxylic Acids and Derivatives
Sub ClassAmino Acids, Peptides, and Analogues
Direct ParentPeptides
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkNot Available
External DescriptorsNot 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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Pseudomonas aeruginosa
  • Streptococcus pneumoniae
  • Streptococcus agalactiae
  • Neisseria meningitidis
  • Haemophilus influenzae
  • Neisseria gonorrhoeae
  • Escherichia coli
  • Staphylococcus aureus
  • Klebsiella
  • Enterobacter
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Solution/ dropsophthalmic
Solutionophthalmic
Liquidophthalmic
Dropsophthalmic; otic
Liquidophthalmic; otic
Creamtopical
Solutionophthalmic; otic
Ointmentophthalmic; otic
Dropstopical
Spraynasal
Ointmenttopical
Prices
Unit descriptionCostUnit
Gramicidin d powder240.0USD g
Neosporin gu irr 40 mg/ml amp23.12USD ml
Neosporin + pain relief cream0.32USD g
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 References
  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:8810522 ]
  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:11570868 ]
  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:10397797 ]
External Links
ATC CodesR02AB30
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (71.9 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
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:14985103 ]
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Drug created on June 13, 2005 07:24 / Updated on March 14, 2016 09:57