Identification
- Summary
Gramicidin D is a bactericidal antibiotic used in the treatment of dermatological and ophthalmic infections.
- Brand Names
- Sofracort, Soframycin, Triple Antibiotic, Viaderm Kc
- Generic Name
- Gramicidin D
- DrugBank Accession Number
- DB00027
- Background
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, which assemble inside of the hydrophobic interior of the cellular lipid bilayer to form a β-helix. Active against most Gram-positive bacteria and some Gram-negative organisms, Gramicidin D is used primarily as a topical antibiotic and is also found in Polysporin ophthalmic solution.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Gramicidin D (DB00027)
- Weight
- Average: 1811.253
Monoisotopic: 1810.033419343 - Chemical Formula
- C96H135N19O16
- Synonyms
- Bacillus brevis gramicidin D
- Gramicidin
- Gramicidin A
- Gramicidin B
- Gramicidin C
- Gramicidina
- Gramicidine
Pharmacology
- Indication
For treatment of skin lesions, surface wounds and eye infections.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Allergic skin reaction Combination Product in combination with: Framycetin (DB00452), Desoximetasone (DB00547) •••••••••••• •••••••••• •• ••••••••••••••• ••••• Used in combination to treat Conjunctivitis Combination Product in combination with: Neomycin (DB00994), Polymyxin B (DB00781) ••• ••• Used in combination to treat Conjunctivitis allergic Combination Product in combination with: Framycetin (DB00452), Dexamethasone (DB01234) •••••••••••• •••••••• • ••••• Used in combination to treat Conjunctivitis infective Combination Product in combination with: Dexamethasone (DB01234), Framycetin (DB00452) •••••••••••• •••••••• • ••••• Used in combination to treat Corneal inflammation Combination Product in combination with: Polymyxin B (DB00781), Neomycin (DB00994) ••• ••• - Contraindications & Blackbox Warnings
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Gramicidin 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 action
Gramicidin 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.
- Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcenocoumarol The risk or severity of bleeding can be increased when Gramicidin D is combined with Acenocoumarol. Ambroxol The risk or severity of methemoglobinemia can be increased when Gramicidin D is combined with Ambroxol. Articaine The risk or severity of methemoglobinemia can be increased when Gramicidin D is combined with Articaine. BCG vaccine The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Gramicidin D. Benzocaine The risk or severity of methemoglobinemia can be increased when Gramicidin D is combined with Benzocaine. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Sofradex (Sanofi)
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Antibiotic Cream Gramicidin D (0.25 mg / g) + Polymyxin B sulfate (10000 unit / g) Cream Topical Technilab Pharma Inc. 1998-11-03 2005-08-05 Canada 
Antibiotic Cream Gramicidin D (0.25 mg / g) + Polymyxin B sulfate (10000 unit / g) Cream Topical Canadian Custom Packaging Company 2012-03-22 2020-09-11 Canada Antibiotic Cream Gramicidin D (0.25 mg / g) + Polymyxin B sulfate (10000 unit / g) Cream Topical Cellchem Pharmaceuticals Inc. 2009-12-23 Not applicable Canada Antibiotic Cream for Kids Gramicidin D (0.25 mg / g) + Lidocaine hydrochloride (50 mg / g) + Polymyxin B sulfate (10000 unit / g) Cream Topical Cellchem Pharmaceuticals Inc. Not applicable Not applicable Canada Antibiotic Cream for Kids Gramicidin D (0.25 mg / g) + Lidocaine hydrochloride (50 mg / g) + Polymyxin B sulfate (10000 unit / g) Cream Topical Taro Pharmaceuticals, Inc. 2009-07-30 Not applicable Canada
Categories
- ATC Codes
- R02AB30 — Gramicidin
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues.
- Kingdom
- Organic compounds
- Super Class
- Organic Polymers
- Class
- Polypeptides
- Sub Class
- Not Available
- Direct Parent
- Polypeptides
- Alternative Parents
- Peptides / Leucine and derivatives / Valine and derivatives / N-acyl-alpha amino acids and derivatives / Tryptamines and derivatives / N-formyl-alpha amino acids / Alpha amino acid amides / Alanine and derivatives / 3-alkylindoles / N-acylethanolamines show 10 more
- Substituents
- 3-alkylindole / Alanine or derivatives / Alcohol / Alkanolamine / Alpha peptide / Alpha-amino acid amide / Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Benzenoid show 29 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Pseudomonas aeruginosa
- Streptococcus pneumoniae
- Streptococcus agalactiae
- Neisseria meningitidis
- Haemophilus influenzae
- Neisseria gonorrhoeae
- Escherichia coli
- Staphylococcus aureus
- Klebsiella
- Enterobacter
Chemical Identifiers
- UNII
- 5IE62321P4
- CAS number
- 1405-97-6
- InChI Key
- NDAYQJDHGXTBJL-MWWSRJDJSA-N
- InChI
- InChI=1S/C96H135N19O16/c1-50(2)36-71(105-79(118)48-102-93(128)80(54(9)10)103-49-117)86(121)104-58(17)84(119)113-82(56(13)14)95(130)115-83(57(15)16)96(131)114-81(55(11)12)94(129)112-78(43-62-47-101-70-33-25-21-29-66(62)70)92(127)108-74(39-53(7)8)89(124)111-77(42-61-46-100-69-32-24-20-28-65(61)69)91(126)107-73(38-52(5)6)88(123)110-76(41-60-45-99-68-31-23-19-27-64(60)68)90(125)106-72(37-51(3)4)87(122)109-75(85(120)97-34-35-116)40-59-44-98-67-30-22-18-26-63(59)67/h18-33,44-47,49-58,71-78,80-83,98-101,116H,34-43,48H2,1-17H3,(H,97,120)(H,102,128)(H,103,117)(H,104,121)(H,105,118)(H,106,125)(H,107,126)(H,108,127)(H,109,122)(H,110,123)(H,111,124)(H,112,129)(H,113,119)(H,114,131)(H,115,130)/t58-,71+,72+,73+,74+,75-,76-,77-,78-,80-,81+,82+,83-/m0/s1
- IUPAC Name
- (2R)-N-[(1S)-1-{[(1R)-1-{[(1S)-1-{[(1R)-1-{[(1S)-1-{[(1R)-1-{[(1S)-1-{[(1R)-1-{[(1S)-1-{[(1R)-1-{[(1S)-1-[(2-hydroxyethyl)carbamoyl]-2-(1H-indol-3-yl)ethyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-2-methylpropyl]carbamoyl}-2-methylpropyl]carbamoyl}ethyl]-2-{2-[(2S)-2-formamido-3-methylbutanamido]acetamido}-4-methylpentanamide
- SMILES
- CC(C)C[C@@H](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](CC1=CNC2=C1C=CC=C2)C(=O)N[C@H](CC(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](CC1=CNC2=C1C=CC=C2)C(=O)NCCO
References
- Synthesis Reference
U.S.Patent 2,534,541.
- General References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- External Links
- KEGG Drug
- D04369
- PubChem Compound
- 45267103
- PubChem Substance
- 46507412
- ChemSpider
- 24623445
- 5011
- ChEMBL
- CHEMBL557217
- Therapeutic Targets Database
- DAP001327
- PharmGKB
- PA449808
- Wikipedia
- Gramicidin
- MSDS
- Download (71.9 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Unknown Status Treatment Hordeolum 1 Not Available Withdrawn Prevention Bloodstream Infections (BSI) / Skin Diseases, Infectious 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Johnson & Johnson Healthcare
- Monarch Pharmacy
- Professional Co.
- Dosage Forms
Form Route Strength Solution Auricular (otic); Ophthalmic Solution / drops Auricular (otic) Solution / drops Ophthalmic Solution Ophthalmic Solution Ophthalmic 0.025 mg Liquid Auricular (otic); Ophthalmic Ointment Ophthalmic Solution / drops Auricular (otic); Ophthalmic Solution / drops Topical Ointment Auricular (otic); Ophthalmic Spray Nasal Solution Ophthalmic 25.000 mcg Ointment Topical Liquid Ophthalmic Cream Topical - Prices
Unit description Cost Unit Gramicidin d powder 240.0USD g Neosporin gu irr 40 mg/ml amp 23.12USD ml Neosporin + pain relief cream 0.32USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Liquid
- Experimental Properties
Property Value Source melting point (°C) 229 °C Not Available - Predicted Properties
Property Value Source Water Solubility 0.0039 mg/mL ALOGPS logP 4.38 ALOGPS logP 5.96 Chemaxon logS -5.7 ALOGPS pKa (Strongest Acidic) 11.56 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 16 Chemaxon Hydrogen Donor Count 20 Chemaxon Polar Surface Area 519.89 Å2 Chemaxon Rotatable Bond Count 50 Chemaxon Refractivity 492.33 m3·mol-1 Chemaxon Polarizability 194.73 Å3 Chemaxon Number of Rings 8 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- 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. [Article]
- Borgnia MJ, Eytan GD, Assaraf YG: Competition of hydrophobic peptides, cytotoxic drugs, and chemosensitizers on a common P-glycoprotein pharmacophore as revealed by its ATPase activity. J Biol Chem. 1996 Feb 9;271(6):3163-71. [Article]
- Kondratov RV, Komarov PG, Becker Y, Ewenson A, Gudkov AV: Small molecules that dramatically alter multidrug resistance phenotype by modulating the substrate specificity of P-glycoprotein. Proc Natl Acad Sci U S A. 2001 Nov 20;98(24):14078-83. doi: 10.1073/pnas.241314798. Epub 2001 Nov 13. [Article]
Drug created at June 13, 2005 13:24 / Updated at January 02, 2024 23:41