Identification

Name
Gramicidin D
Accession Number
DB00027  (BTD00036, BIOD00036)
Type
Small Molecule
Groups
Approved
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.

Structure
Thumb
Synonyms
  • Bacillus brevis gramicidin D
  • Gramicidin
  • Gramicidin A
  • Gramicidin B
  • Gramicidin C
  • Gramicidine
International/Other Brands
Sofradex (Sanofi)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Antibiotic CreamGramicidin D (0.25 mg) + Polymyxin B Sulfate (10000 unit)CreamTopicalPharmetics (2011) Inc.2009-12-23Not applicableCanada
Antibiotic CreamGramicidin D (0.25 mg) + Polymyxin B Sulfate (10000 unit)CreamTopicalCanadian Custom Packaging Company2012-03-22Not applicableCanada
Antibiotic CreamGramicidin D (0.25 mg) + Polymyxin B Sulfate (10000 unit)CreamTopicalTechnilab Pharma Inc.1998-11-032005-08-05Canada
Antibiotic Cream for KidsGramicidin D (0.25 mg) + Lidocaine hydrochloride (50 mg) + Polymyxin B Sulfate (10000 unit)CreamTopicalPharmetics (2011) Inc.Not applicableNot applicableCanada
Antibiotic Cream for KidsGramicidin D (0.25 mg) + Lidocaine hydrochloride (50 mg) + Polymyxin B Sulfate (10000 unit)CreamTopicalTaro Pharmaceuticals, Inc.2009-07-30Not applicableCanada
Antibiotic Cream Plus Pain ReliefGramicidin D (0.25 mg) + Lidocaine hydrochloride (50 mg) + Polymyxin B Sulfate (10000 unit)CreamTopicalPharmetics (2011) Inc.2009-12-23Not applicableCanada
Antibiotic Cream Plus Pain ReliefGramicidin D (0.25 mg) + Lidocaine hydrochloride (40 mg) + Polymyxin B Sulfate (10000 unit)CreamTopicalCanadian Custom Packaging Company2012-04-09Not applicableCanada
Antibiotic Cream Plus Pain Relief for KidsGramicidin D (0.25 mg) + Lidocaine hydrochloride (40 mg) + Polymyxin B Sulfate (10000 unit)CreamTopicalCanadian Custom Packaging Company2012-07-11Not applicableCanada
Antibiotic DropsGramicidin D (0.025 mg) + Polymyxin B Sulfate (10000 unit)SolutionAuricular (otic); OphthalmicSandoz Canada Incorporated2017-06-01Not applicableCanada
Antibiotic Ear DropsGramicidin D (0.025 mg) + Polymyxin B Sulfate (10000 unit)Solution / dropsAuricular (otic)Sandoz Canada IncorporatedNot applicableNot applicableCanada
Categories
UNII
5IE62321P4
CAS number
1405-97-6
Weight
Average: 1811.253
Monoisotopic: 1810.033419343
Chemical Formula
C96H135N19O16
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[[email protected]@H](NC(=O)CNC(=O)[[email protected]@H](NC=O)C(C)C)C(=O)N[[email protected]@H](C)C(=O)N[[email protected]](C(C)C)C(=O)N[[email protected]@H](C(C)C)C(=O)N[[email protected]](C(C)C)C(=O)N[[email protected]@H](CC1=CNC2=C1C=CC=C2)C(=O)N[[email protected]](CC(C)C)C(=O)N[[email protected]@H](CC1=CNC2=C1C=CC=C2)C(=O)N[[email protected]](CC(C)C)C(=O)N[[email protected]@H](CC1=CNC2=C1C=CC=C2)C(=O)N[[email protected]](CC(C)C)C(=O)N[[email protected]@H](CC1=CNC2=C1C=CC=C2)C(=O)NCCO

Pharmacology

Indication

For treatment of skin lesions, surface wounds and eye infections.

Structured Indications
Pharmacodynamics

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
Toxicity
Not Available
Affected organisms
  • Pseudomonas aeruginosa
  • Streptococcus pneumoniae
  • Streptococcus agalactiae
  • Neisseria meningitidis
  • Haemophilus influenzae
  • Neisseria gonorrhoeae
  • Escherichia coli
  • Staphylococcus aureus
  • Klebsiella
  • Enterobacter
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Gramicidin D.Approved
AcetaminophenThe serum concentration of Acetaminophen can be increased when it is combined with Gramicidin D.Approved
Acetylsalicylic acidThe serum concentration of Acetylsalicylic acid can be increased when it is combined with Gramicidin D.Approved, Vet Approved
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Gramicidin D.Approved
AldosteroneThe serum concentration of Aldosterone can be increased when it is combined with Gramicidin D.Experimental, Investigational
AlitretinoinThe serum concentration of Alitretinoin can be increased when it is combined with Gramicidin D.Approved, Investigational
AmbrisentanThe serum concentration of Ambrisentan can be increased when it is combined with Gramicidin D.Approved, Investigational
AmitriptylineThe serum concentration of Amitriptyline can be increased when it is combined with Gramicidin D.Approved
ApixabanThe serum concentration of Apixaban can be increased when it is combined with Gramicidin D.Approved
Arsenic trioxideThe serum concentration of Arsenic trioxide can be increased when it is combined with Gramicidin D.Approved, Investigational
AtazanavirThe serum concentration of Atazanavir can be increased when it is combined with Gramicidin D.Approved, Investigational
AtenololThe serum concentration of Atenolol can be increased when it is combined with Gramicidin D.Approved
AxitinibThe serum concentration of Axitinib can be increased when it is combined with Gramicidin D.Approved, Investigational
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Gramicidin D.Investigational
BelinostatThe serum concentration of Belinostat can be increased when it is combined with Gramicidin D.Approved, Investigational
BetamethasoneThe serum concentration of Betamethasone can be increased when it is combined with Gramicidin D.Approved, Vet Approved
BoceprevirThe serum concentration of Boceprevir can be increased when it is combined with Gramicidin D.Approved, Withdrawn
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Gramicidin D.Approved
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Gramicidin D.Approved
BromocriptineThe serum concentration of Bromocriptine can be increased when it is combined with Gramicidin D.Approved, Investigational
CabazitaxelThe serum concentration of Cabazitaxel can be increased when it is combined with Gramicidin D.Approved
CaffeineThe serum concentration of Caffeine can be increased when it is combined with Gramicidin D.Approved
CamptothecinThe serum concentration of Camptothecin can be increased when it is combined with Gramicidin D.Experimental
CanagliflozinThe serum concentration of Canagliflozin can be increased when it is combined with Gramicidin D.Approved
CarbamazepineThe serum concentration of Carbamazepine can be increased when it is combined with Gramicidin D.Approved, Investigational
CarfilzomibThe serum concentration of Carfilzomib can be increased when it is combined with Gramicidin D.Approved
CeritinibThe serum concentration of Ceritinib can be increased when it is combined with Gramicidin D.Approved
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Gramicidin D.Withdrawn
ChlorpromazineThe serum concentration of Chlorpromazine can be increased when it is combined with Gramicidin D.Approved, Vet Approved
CimetidineThe serum concentration of Cimetidine can be increased when it is combined with Gramicidin D.Approved
CiprofloxacinThe serum concentration of Ciprofloxacin can be increased when it is combined with Gramicidin D.Approved, Investigational
CisplatinThe serum concentration of Cisplatin can be increased when it is combined with Gramicidin D.Approved
CitalopramThe serum concentration of Citalopram can be increased when it is combined with Gramicidin D.Approved
ClarithromycinThe serum concentration of Clarithromycin can be increased when it is combined with Gramicidin D.Approved
ClobazamThe serum concentration of Clobazam can be increased when it is combined with Gramicidin D.Approved, Illicit
ClomifeneThe serum concentration of Clomifene can be increased when it is combined with Gramicidin D.Approved, Investigational
ClonidineThe serum concentration of Clonidine can be increased when it is combined with Gramicidin D.Approved
ClopidogrelThe serum concentration of Clopidogrel can be increased when it is combined with Gramicidin D.Approved, Nutraceutical
ClozapineThe serum concentration of Clozapine can be increased when it is combined with Gramicidin D.Approved
CobimetinibThe serum concentration of Cobimetinib can be increased when it is combined with Gramicidin D.Approved
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Gramicidin D.Approved
Conjugated estrogensThe serum concentration of Conjugated estrogens can be increased when it is combined with Gramicidin D.Approved
CopanlisibThe serum concentration of Copanlisib can be increased when it is combined with Gramicidin D.Approved
CrizotinibThe serum concentration of Crizotinib can be increased when it is combined with Gramicidin D.Approved
CyclosporineThe serum concentration of Cyclosporine can be increased when it is combined with Gramicidin D.Approved, Investigational, Vet Approved
Dabigatran etexilateThe serum concentration of the active metabolites of Dabigatran etexilate can be increased when Dabigatran etexilate is used in combination with Gramicidin D.Approved
DabrafenibThe serum concentration of Dabrafenib can be increased when it is combined with Gramicidin D.Approved
DactinomycinThe serum concentration of Dactinomycin can be increased when it is combined with Gramicidin D.Approved
DapagliflozinThe serum concentration of Dapagliflozin can be increased when it is combined with Gramicidin D.Approved
DasatinibThe serum concentration of Dasatinib can be increased when it is combined with Gramicidin D.Approved, Investigational
DaunorubicinThe serum concentration of Daunorubicin can be increased when it is combined with Gramicidin D.Approved
DebrisoquinThe serum concentration of Debrisoquin can be increased when it is combined with Gramicidin D.Approved, Investigational
DexamethasoneThe serum concentration of Dexamethasone can be increased when it is combined with Gramicidin D.Approved, Investigational, Vet Approved
DiazepamThe serum concentration of Diazepam can be increased when it is combined with Gramicidin D.Approved, Illicit, Vet Approved
DiethylstilbestrolThe serum concentration of Diethylstilbestrol can be increased when it is combined with Gramicidin D.Approved, Investigational
DigitoxinThe serum concentration of Digitoxin can be increased when it is combined with Gramicidin D.Approved, Investigational
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Gramicidin D.Approved
DihydrotestosteroneThe serum concentration of Dihydrotestosterone can be increased when it is combined with Gramicidin D.Illicit
DiltiazemThe serum concentration of Diltiazem can be increased when it is combined with Gramicidin D.Approved
DipyridamoleThe serum concentration of Dipyridamole can be increased when it is combined with Gramicidin D.Approved
DocetaxelThe serum concentration of Docetaxel can be increased when it is combined with Gramicidin D.Approved, Investigational
DomperidoneThe serum concentration of Domperidone can be increased when it is combined with Gramicidin D.Approved, Investigational, Vet Approved
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Gramicidin D.Approved, Investigational
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Gramicidin D.Approved
ElbasvirThe serum concentration of Elbasvir can be increased when it is combined with Gramicidin D.Approved
EletriptanThe serum concentration of Eletriptan can be increased when it is combined with Gramicidin D.Approved, Investigational
EnasidenibThe serum concentration of Enasidenib can be increased when it is combined with Gramicidin D.Approved
EpinastineThe serum concentration of Epinastine can be increased when it is combined with Gramicidin D.Approved, Investigational
ErlotinibThe serum concentration of Erlotinib can be increased when it is combined with Gramicidin D.Approved, Investigational
ErythromycinThe serum concentration of Erythromycin can be increased when it is combined with Gramicidin D.Approved, Vet Approved
EstradiolThe serum concentration of Estradiol can be increased when it is combined with Gramicidin D.Approved, Investigational, Vet Approved
EstriolThe serum concentration of Estriol can be increased when it is combined with Gramicidin D.Approved, Investigational, Vet Approved
EstroneThe serum concentration of Estrone can be increased when it is combined with Gramicidin D.Approved
Ethinyl EstradiolThe serum concentration of Ethinyl Estradiol can be increased when it is combined with Gramicidin D.Approved
EtoposideThe serum concentration of Etoposide can be increased when it is combined with Gramicidin D.Approved
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Gramicidin D.Approved
EzetimibeThe serum concentration of Ezetimibe can be increased when it is combined with Gramicidin D.Approved
FesoterodineThe serum concentration of Fesoterodine can be increased when it is combined with Gramicidin D.Approved
FexofenadineThe serum concentration of Fexofenadine can be increased when it is combined with Gramicidin D.Approved
FidaxomicinThe serum concentration of Fidaxomicin can be increased when it is combined with Gramicidin D.Approved
Fluticasone furoateThe serum concentration of Fluticasone furoate can be increased when it is combined with Gramicidin D.Approved
GefitinibThe serum concentration of Gefitinib can be increased when it is combined with Gramicidin D.Approved, Investigational
GemcitabineThe serum concentration of Gemcitabine can be increased when it is combined with Gramicidin D.Approved
GlecaprevirThe serum concentration of Glecaprevir can be increased when it is combined with Gramicidin D.Approved
GrazoprevirThe serum concentration of Grazoprevir can be increased when it is combined with Gramicidin D.Approved
GrepafloxacinThe serum concentration of Grepafloxacin can be increased when it is combined with Gramicidin D.Investigational, Withdrawn
HaloperidolThe serum concentration of Haloperidol can be increased when it is combined with Gramicidin D.Approved
HydrocortisoneThe serum concentration of Hydrocortisone can be increased when it is combined with Gramicidin D.Approved, Vet Approved
IbuprofenThe serum concentration of Ibuprofen can be increased when it is combined with Gramicidin D.Approved
IdelalisibThe serum concentration of Idelalisib can be increased when it is combined with Gramicidin D.Approved
ImatinibThe serum concentration of Imatinib can be increased when it is combined with Gramicidin D.Approved
ImipramineThe serum concentration of Imipramine can be increased when it is combined with Gramicidin D.Approved
IndacaterolThe serum concentration of Indacaterol can be increased when it is combined with Gramicidin D.Approved
IndinavirThe serum concentration of Indinavir can be increased when it is combined with Gramicidin D.Approved
IndomethacinThe serum concentration of Indomethacin can be increased when it is combined with Gramicidin D.Approved, Investigational
Inotuzumab ozogamicinThe serum concentration of Inotuzumab ozogamicin can be increased when it is combined with Gramicidin D.Approved
IrinotecanThe serum concentration of Irinotecan can be increased when it is combined with Gramicidin D.Approved, Investigational
IvermectinThe serum concentration of Ivermectin can be increased when it is combined with Gramicidin D.Approved, Vet Approved
KetazolamThe serum concentration of Ketazolam can be increased when it is combined with Gramicidin D.Approved
KetoconazoleThe serum concentration of Ketoconazole can be increased when it is combined with Gramicidin D.Approved, Investigational
LamivudineThe serum concentration of Lamivudine can be increased when it is combined with Gramicidin D.Approved, Investigational
LamotrigineThe serum concentration of Lamotrigine can be increased when it is combined with Gramicidin D.Approved, Investigational
LansoprazoleThe serum concentration of Lansoprazole can be increased when it is combined with Gramicidin D.Approved, Investigational
LedipasvirThe serum concentration of Ledipasvir can be increased when it is combined with Gramicidin D.Approved
LenalidomideThe serum concentration of Lenalidomide can be increased when it is combined with Gramicidin D.Approved
LenvatinibThe serum concentration of Lenvatinib can be increased when it is combined with Gramicidin D.Approved
LevetiracetamThe serum concentration of Levetiracetam can be increased when it is combined with Gramicidin D.Approved, Investigational
LevofloxacinThe serum concentration of Levofloxacin can be increased when it is combined with Gramicidin D.Approved, Investigational
LevomilnacipranThe serum concentration of Levomilnacipran can be increased when it is combined with Gramicidin D.Approved
LinagliptinThe serum concentration of Linagliptin can be increased when it is combined with Gramicidin D.Approved
LoperamideThe serum concentration of Loperamide can be increased when it is combined with Gramicidin D.Approved
LosartanThe serum concentration of Losartan can be increased when it is combined with Gramicidin D.Approved
MannitolThe serum concentration of Mannitol can be increased when it is combined with Gramicidin D.Approved, Investigational
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Gramicidin D.Approved
MethylprednisoloneThe serum concentration of Methylprednisolone can be increased when it is combined with Gramicidin D.Approved, Vet Approved
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Gramicidin D.Approved, Investigational
MidazolamThe serum concentration of Midazolam can be increased when it is combined with Gramicidin D.Approved, Illicit
MirabegronThe serum concentration of Mirabegron can be increased when it is combined with Gramicidin D.Approved
MitoxantroneThe serum concentration of Mitoxantrone can be increased when it is combined with Gramicidin D.Approved, Investigational
MorphineThe serum concentration of Morphine can be increased when it is combined with Gramicidin D.Approved, Investigational
Mycophenolate mofetilThe serum concentration of Mycophenolate mofetil can be increased when it is combined with Gramicidin D.Approved, Investigational
NadololThe serum concentration of Nadolol can be increased when it is combined with Gramicidin D.Approved
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Gramicidin D.Approved
NaloxoneThe serum concentration of Naloxone can be increased when it is combined with Gramicidin D.Approved, Vet Approved
NelfinavirThe serum concentration of Nelfinavir can be increased when it is combined with Gramicidin D.Approved
NicardipineThe serum concentration of Nicardipine can be increased when it is combined with Gramicidin D.Approved
NifedipineThe serum concentration of Nifedipine can be increased when it is combined with Gramicidin D.Approved
NilotinibThe serum concentration of Nilotinib can be increased when it is combined with Gramicidin D.Approved, Investigational
NintedanibThe serum concentration of Nintedanib can be increased when it is combined with Gramicidin D.Approved
NizatidineThe serum concentration of Nizatidine can be increased when it is combined with Gramicidin D.Approved
OdanacatibThe serum concentration of Odanacatib can be increased when it is combined with Gramicidin D.Investigational
OlanzapineThe serum concentration of Olanzapine can be increased when it is combined with Gramicidin D.Approved, Investigational
OmbitasvirThe serum concentration of Ombitasvir can be increased when it is combined with Gramicidin D.Approved
OsimertinibThe serum concentration of Osimertinib can be increased when it is combined with Gramicidin D.Approved
PaclitaxelThe serum concentration of Paclitaxel can be increased when it is combined with Gramicidin D.Approved, Vet Approved
PanobinostatThe serum concentration of Panobinostat can be increased when it is combined with Gramicidin D.Approved, Investigational
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Gramicidin D.Approved
PhenobarbitalThe serum concentration of Phenobarbital can be increased when it is combined with Gramicidin D.Approved
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Gramicidin D.Approved, Vet Approved
PibrentasvirThe serum concentration of Pibrentasvir can be increased when it is combined with Gramicidin D.Approved
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Gramicidin D.Approved
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Gramicidin D.Approved
PomalidomideThe serum concentration of Pomalidomide can be increased when it is combined with Gramicidin D.Approved
PonatinibThe serum concentration of Ponatinib can be increased when it is combined with Gramicidin D.Approved
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Gramicidin D.Approved
PrazosinThe serum concentration of Prazosin can be increased when it is combined with Gramicidin D.Approved
PrednisoloneThe serum concentration of Prednisolone can be increased when it is combined with Gramicidin D.Approved, Vet Approved
PrednisoneThe serum concentration of Prednisone can be increased when it is combined with Gramicidin D.Approved, Vet Approved
ProgesteroneThe serum concentration of Progesterone can be increased when it is combined with Gramicidin D.Approved, Vet Approved
PropranololThe serum concentration of Propranolol can be increased when it is combined with Gramicidin D.Approved, Investigational
PrucaloprideThe serum concentration of Prucalopride can be increased when it is combined with Gramicidin D.Approved
QuetiapineThe serum concentration of Quetiapine can be increased when it is combined with Gramicidin D.Approved
QuinidineThe serum concentration of Quinidine can be increased when it is combined with Gramicidin D.Approved
QuinineThe serum concentration of Quinine can be increased when it is combined with Gramicidin D.Approved
RanitidineThe serum concentration of Ranitidine can be increased when it is combined with Gramicidin D.Approved
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Gramicidin D.Approved, Investigational
ReserpineThe serum concentration of Reserpine can be increased when it is combined with Gramicidin D.Approved, Investigational
RifampicinThe serum concentration of Rifampicin can be increased when it is combined with Gramicidin D.Approved
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Gramicidin D.Approved, Investigational
RisperidoneThe serum concentration of Risperidone can be increased when it is combined with Gramicidin D.Approved, Investigational
RitonavirThe serum concentration of Ritonavir can be increased when it is combined with Gramicidin D.Approved, Investigational
RivaroxabanThe serum concentration of Rivaroxaban can be increased when it is combined with Gramicidin D.Approved
RomidepsinThe serum concentration of Romidepsin can be increased when it is combined with Gramicidin D.Approved, Investigational
Salicylic acidThe serum concentration of Salicylic acid can be increased when it is combined with Gramicidin D.Approved, Vet Approved
SaquinavirThe serum concentration of Saquinavir can be increased when it is combined with Gramicidin D.Approved, Investigational
SelexipagThe serum concentration of Selexipag can be increased when it is combined with Gramicidin D.Approved
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Gramicidin D.Approved
SimeprevirThe serum concentration of Simeprevir can be increased when it is combined with Gramicidin D.Approved
SitagliptinThe serum concentration of Sitagliptin can be increased when it is combined with Gramicidin D.Approved, Investigational
SofosbuvirThe serum concentration of Sofosbuvir can be increased when it is combined with Gramicidin D.Approved
SorafenibThe serum concentration of Sorafenib can be increased when it is combined with Gramicidin D.Approved, Investigational
SparfloxacinThe serum concentration of Sparfloxacin can be increased when it is combined with Gramicidin D.Approved, Investigational
SphingosineThe serum concentration of Sphingosine can be increased when it is combined with Gramicidin D.Experimental
TacrolimusThe serum concentration of Tacrolimus can be increased when it is combined with Gramicidin D.Approved, Investigational
TamoxifenThe serum concentration of Tamoxifen can be increased when it is combined with Gramicidin D.Approved
Taurocholic AcidThe serum concentration of Taurocholic Acid can be increased when it is combined with Gramicidin D.Experimental
Technetium Tc-99m sestamibiThe serum concentration of Technetium Tc-99m sestamibi can be increased when it is combined with Gramicidin D.Approved
TelaprevirThe serum concentration of Telaprevir can be increased when it is combined with Gramicidin D.Approved, Withdrawn
TemsirolimusThe serum concentration of Temsirolimus can be increased when it is combined with Gramicidin D.Approved
TicagrelorThe serum concentration of Ticagrelor can be increased when it is combined with Gramicidin D.Approved
TimololThe serum concentration of Timolol can be increased when it is combined with Gramicidin D.Approved
TolvaptanThe serum concentration of Tolvaptan can be increased when it is combined with Gramicidin D.Approved
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Gramicidin D.Approved, Investigational
ToremifeneThe serum concentration of Toremifene can be increased when it is combined with Gramicidin D.Approved, Investigational
Trastuzumab emtansineThe serum concentration of Trastuzumab emtansine can be increased when it is combined with Gramicidin D.Approved
UlipristalThe serum concentration of Ulipristal can be increased when it is combined with Gramicidin D.Approved
UmeclidiniumThe serum concentration of Umeclidinium can be increased when it is combined with Gramicidin D.Approved
VecuroniumThe serum concentration of Vecuronium can be increased when it is combined with Gramicidin D.Approved
VelpatasvirThe serum concentration of Velpatasvir can be increased when it is combined with Gramicidin D.Approved
VenetoclaxThe serum concentration of Venetoclax can be increased when it is combined with Gramicidin D.Approved
VenlafaxineThe serum concentration of Venlafaxine can be increased when it is combined with Gramicidin D.Approved
VerapamilThe serum concentration of Verapamil can be increased when it is combined with Gramicidin D.Approved
VinblastineThe serum concentration of Vinblastine can be increased when it is combined with Gramicidin D.Approved
VincristineThe serum concentration of Vincristine can be increased when it is combined with Gramicidin D.Approved, Investigational
VismodegibThe serum concentration of Vismodegib can be increased when it is combined with Gramicidin D.Approved
VoxilaprevirThe serum concentration of Voxilaprevir can be increased when it is combined with Gramicidin D.Approved
ZidovudineThe serum concentration of Zidovudine can be increased when it is combined with Gramicidin D.Approved
Food Interactions
Not 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
KEGG Drug
D04369
PubChem Compound
45267103
PubChem Substance
46507412
ChemSpider
24623445
ChEMBL
CHEMBL557217
Therapeutic Targets Database
DAP001327
PharmGKB
PA449808
Wikipedia
Gramicidin_D
ATC Codes
R02AB30 — Gramicidin
MSDS
Download (71.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3Unknown StatusTreatmentHordeolum1
Not AvailableCompletedTreatmentNasal Carriers of Staphylococcus Aureus1
Not AvailableWithdrawnPreventionBlood Stream Infections / Skin Diseases, Infectious1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
Solution / dropsAuricular (otic)
Solution / dropsOphthalmic
SolutionOphthalmic
SolutionAuricular (otic); Ophthalmic
LiquidOphthalmic
LiquidAuricular (otic); Ophthalmic
CreamTopical
OintmentAuricular (otic); Ophthalmic
Solution / dropsAuricular (otic); Ophthalmic
Solution / 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.
Patents
Not Available

Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)229 °CNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0039 mg/mLALOGPS
logP4.38ALOGPS
logP5.96ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)11.56ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count20ChemAxon
Polar Surface Area519.89 Å2ChemAxon
Rotatable Bond Count50ChemAxon
Refractivity492.33 m3·mol-1ChemAxon
Polarizability194.73 Å3ChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

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
Polypeptide / Alpha peptide / Leucine or derivatives / Valine or derivatives / N-acyl-alpha amino acid or derivatives / Alpha-amino acid amide / N-formyl-alpha-amino acid / N-formyl-alpha amino acid or derivatives / Triptan / Alanine or derivatives
show 29 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not 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
Uniprot Name
Multidrug resistance protein 1
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]

Drug created on June 13, 2005 07:24 / Updated on November 07, 2017 01:33