GRAMICIDIN
- Product Name
- GRAMICIDIN
- CAS No.
- 1405-97-6
- Chemical Name
- GRAMICIDIN
- Synonyms
- GRAMICIDIN D;Aids002001;GRAMICIDIN;Aids-002001;Gramicidine;GRAMACIDIN D;Gramicidinum;GRAMICIDIN,USP;Gramicidin CRS;Gramicidin TFA
- CBNumber
- CB1431216
- Molecular Formula
- C99H140N20O17
- Formula Weight
- 1882.2947
- MOL File
- 1405-97-6.mol
GRAMICIDIN Property
- Melting point:
- 229-230℃
- storage temp.
- 2-8°C
- solubility
- Practically insoluble in water, soluble in methanol, sparingly soluble in alcohol
- form
- Solid
- color
- White to Off-White
- Water Solubility
- Soluble in acetic acid and lower alcohols. Practically insoluble in water.
- InChI
- 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
- InChIKey
- ZWCXYZRRTRDGQE-SORVKSEFSA-N
- SMILES
- O=C([C@@]([H])(C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])N([H])C([C@]([H])(C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12)N([H])C([C@]([H])(C([H])(C([H])([H])[H])C([H])([H])[H])N([H])C([C@]([H])(C([H])(C([H])([H])[H])C([H])([H])[H])N([H])C([C@@]([H])(C([H])(C([H])([H])[H])C([H])([H])[H])N([H])C([C@]([H])(C([H])([H])[H])N([H])C([C@@]([H])(C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])N([H])C([C@]([H])(C([H])([H])[H])N([H])C(C([H])([H])N([H])C([C@]([H])(C([H])(C([H])([H])[H])C([H])([H])[H])N([H])C([H])=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)N([H])[C@]([H])(C(N([H])[C@@]([H])(C(N([H])[C@]([H])(C(N([H])[C@@]([H])(C(N([H])[C@]([H])(C(N([H])C([H])([H])C([H])([H])O[H])=O)C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12)=O)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])=O)C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12)=O)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])=O)C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12
- CAS DataBase Reference
- 1405-97-6
Safety
- Hazard Codes
- Xn
- Risk Statements
- 20/21-36/37/38
- Safety Statements
- 26-36-24/25-22
- WGK Germany
- 3
- RTECS
- MD8225000
- HS Code
- 2941906000
- Toxicity
- mouse,LD50,intravenous,1500ug/kg (1.5mg/kg),Science. Vol. 103, Pg. 419, 1946.
N-Bromosuccinimide Price
- Product number
- G5002
- Product name
- Gramicidin from Bacillus aneurinolyticus (Bacillus brevis)
- Purity
- Linear polypeptide antibiotic complex. A mixture of gramicidins A, B, C, and D.
- Packaging
- 1g
- Price
- $124
- Updated
- 2025/07/31
- Product number
- G0550000
- Product name
- Gramicidin
- Purity
- European Pharmacopoeia (EP) Reference Standard
- Packaging
- 250 mg
- Price
- $236
- Updated
- 2025/07/31
- Product number
- 1298004
- Product name
- Gramicidin
- Packaging
- 200mg
- Price
- $431
- Updated
- 2025/07/31
- Product number
- 28251
- Product name
- Gramicidin
- Packaging
- 250mg
- Price
- $214
- Updated
- 2024/03/01
- Product number
- G5002
- Product name
- Gramicidin from Bacillus aneurinolyticus (Bacillus brevis)
- Purity
- Linear polypeptide antibiotic complex. A mixture of gramicidins A, B, C, and D.
- Packaging
- 100mg
- Price
- $22.99
- Updated
- 2025/07/31
GRAMICIDIN Chemical Properties,Usage,Production
Description
Gramicidin is a polypeptide antibiotic mixture of gramicidin A , gramicidin B, and gramicidin C originally isolated from B. brevis. It is also a component of the antibiotic tyrothricin . Gramicidin is active against the Gram-positive bacterium S. aureus but not Gram-negative E. coli. It also protects mice from Pneumococcus infection in vivo when administered at a dose of 0.002 mg/animal. Gramicidin inhibits growth of bacteria by forming pores and channels in the cell wall, which increases its permeability to monovalent cations. Formulations containing gramicidin have been used as topical agents in the treatment of bacterial skin infections.
Chemical Properties
White, crystalline platelets. Soluble in lower alcohols, acetic acid, and pyridine; moderately soluble in dry acetone and dioxane; almost insoluble in water, ether, and hydrocarbons. Depresses surface tension, forms a fairly stable colloidal emulsion in distilled water.
Uses
Medicine (antibacterial).
Uses
Targets primarily the cell membrane of Gram-positive bacteria and shows little effect against Gram-negative bacteria. Gramicidin is typically used as a topical antimicrobial agent because it also causes hemolysis of red blood cells.
Uses
Gramicidins are a family of linear pentadecapeptides isolated from Bacillus brevis by Dubos at the Rockefeller Institute in 1939. Gramicidin is a complex of six closely related analogues A1, A2, B1, B2, C1 and C2 where A1 and A2 are the dominant components. Gramidicins act by forming channels in cell membranes causing ion leakage, and is an essential bioprobe for understanding the nature of the cell membranes.
Definition
An antibiotic produced by the metabolic processes of the bacteria Bacillus brevis. It is a polypeptide that is active against most Gram-positive pathogenic bacteria. It is one of the two antibiotic components of tyrothricin but has been isolated and used
brand name
Gramoderm (Schering).
Antimicrobial activity
Gramicidin is highly active against many Gram-positive bacteria. Neisseria spp. are relatively resistant. Gram-negative bacilli including Pseudomonas aeruginosa are susceptible although conflicting data exist about the degree of susceptibility. Gramicidin has a bactericidal activity against Mycoplasma spp. and several pathogenic fungi, including Candida albicans. Interestingly, it also appears to have antiviral activity against HIV and herpes simplex viruses (HSV-1, HSV-2).
General Description
Gramicidin is obtained from tyrothricin, a mixture ofpolypeptides usually obtained by extraction of cultures of B.brevis. Tyrothricin was isolated in 1939 by Dubos in aplanned search to find an organism growing in soil that wouldhave antibiotic activity against human pathogens. With onlylimited use in therapy now, it is of historical interest as thefirst in the series of modern antibiotics. Tyrothricin is a whiteto slightly gray or brown-white powder, with little or no odoror taste. It is practically insoluble in water and is soluble in alcoholand dilute acids. Suspensions for clinical use can beprepared by adding an alcoholic solution to calculatedamounts of distilled water or isotonic saline solutions.
Gramicidin acts as an ionophore in bacterial cell membranesto cause the loss of potassium ion from the cell. Itis bactericidal.Tyrothricin and gramicidin are effective primarilyagainst Gram-positive organisms. Their use is restricted tolocal applications. Tyrothricin can cause lysis of erythrocytes,which makes it unsuitable for the treatment of systemicinfections. Its applications should avoid direct contactwith the bloodstream through open wounds or abrasions. Itis ordinarily safe to use tyrothricin in troches for throat infections,as it is not absorbed from the GI tract. Gramicidinis available in various topical preparations containing otherantibiotics, such as bacitracin and neomycin.
Pharmaceutical Applications
Gramicidin as used in topical formulations is a mixture of
several closely related compounds, of which about 80% is in
the form of gramicidin A. It is part of the tyrothricin complex
originally isolated from B. brevis.
It is active against most species of Gram-positive bacteria,
including mycobacteria. Gram-negative bacilli are completely
insensitive.
It is highly toxic to erythrocytes, liver and kidney, and is
used only in topical formulations, usually as one of several
components.
Biochem/physiol Actions
Linear polypeptide antibiotic mixture of gramicidin A, B, C, and D. Gramicidin A acts as neutral carrier and helps in the establishment of ion flux across the lipid bilayer.
Mechanism of action
The mechanisms of gramicidin’s bactericidal activity have not been fully elucidated. Gramicidin is known to alter the function of the bacterial cytoplasmic membrane by forming channels that destroy the ion gradient and make it permeable for inorganic cations . It may also be a potent and specific inhibitor of the transcription reaction and inhibit the binding of DNA-dependent RNA polymerase (transcriptase) to DNA . Gramicidin appears to have antiviral activity against HIV, HSV-1, and HSV-2 viruses and is also used as a contraceptive due to its spermostatic properties.
Clinical Use
The use of gramicidin is restricted to topical applications on wounds or as ear and eye drops. Currently, much research is being invested to generate less toxic analogs that still exhibit the same wide range of bactericidal activity. To date, no new gramicidin-like polypeptides are available for clinical use. Gramicidin is used in some countries as a topical contraceptive, because it has spermostatic activity.
References
[1] WALLACE B A. Gramicidin channels and pores.[J]. Annual review of biophysics and biophysical chemistry, 1990, 19: 127-157. DOI: 10.1146/annurev.bb.19.060190.001015
[2] KILLIAN J A. Gramicidin and gramicidin-lipid interactions[J]. Biochimica et Biophysica Acta (BBA) - Reviews on Biomembranes, 1992, 1113 3: Pages 391-425. DOI: 10.1016/0304-4157(92)90008-x
[3] R J DUBOS R D H. THE PRODUCTION OF BACTERICIDAL SUBSTANCES BY AEROBIC SPORULATING BACILLI.[J]. Journal of Experimental Medicine, 1941, 73 5: 629-640. DOI: 10.1084/jem.73.5.629
GRAMICIDIN Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from GRAMICIDIN manufacturers
- Product
- GRAMICIDIN 1405-97-6
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- 98%
- Supply Ability
- 20T
- Release date
- 2025-08-30
- Product
- Gramicidin 1405-97-6
- Price
- US $100.00-80.00/KG
- Min. Order
- 10KG
- Purity
- 99%
- Supply Ability
- 10000kg
- Release date
- 2024-08-22
- Product
- GRAMICIDIN 1405-97-6
- Price
- US $1.10/g
- Min. Order
- 1g
- Purity
- 99.9%
- Supply Ability
- 100 Tons Min
- Release date
- 2021-07-16