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targets (2) transporters (1)
for drugs
Identification
Name Streptomycin
Accession Number DB01082 (APRD00412)
Type small molecule
Groups approved
Description

Streptomycin is an aminoglycoside antibiotic produced by the soil actinomycete Streptomyces griseus. It acts by binding to the 30S ribosomal subunit of susceptible organisms and disrupting the initiation and elongation steps in protein synthesis. It is bactericidal due to effects that are not fully understood.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Streptomycin a Sulfate
  • Streptomycin Sesquisulfate Hydrate
  • Streptomycin Sulfate
  • Streptomycin Sulphate
  • Streptomycin, Sulfate Salt
Brand names
  • Kantrex
Brand name mixtures
  • Aurex Rotenone Drops (Bacitracin + Penicillin + Rotenone + Streptomycin (Streptomycin Sulfate) + Undecylenic Acid)
  • Combiotic Vitamin Booster Pws (Calcium D-Pantothenate + Menadione + Nicotinic Acid + Penicillin G Potassium + Pyridoxine Hydrochloride + Streptomycin (Streptomycin Sulfate) + Vitamin a + Vitamin B12 + Vitamin B2 + Vitamin D3 + Vitamin E)
  • Dp Booster Pws (D-Pantothenic Acid (Calcium D-Pantothenate) + Menadione + Nicotinic Acid + Penicillin G Potassium + Pyridoxine Hydrochloride + Streptomycin (Streptomycin Sulfate) + Vitamin a + Vitamin B1 + Vitamin B12 + Vitamin B2 + Vitamin D3 + Vitamin E)
  • Mastitis Care (Neomycin (Neomycin Sulfate) + Penicillin G Potassium + Polymyxin B (Polymyxin B Sulfate) + Streptomycin (Streptomycin Sulfate))
  • Medic Aid 2-50 (Menadione Sodium Bisulfite + Penicillin (Penicillin G Potassium) + Penicillin (Penicillin G Procaine) + Streptomycin Sulfate + Vitamin a + Vitamin D3)
  • Medivit (Calcium D-Pantothenate + Menadione + Nicotinamide + Penicillin G Potassium + Pyridoxine Hydrochloride + Streptomycin Sulfate + Vitamin a + Vitamin B1 + Vitamin B12 + Vitamin B2 + Vitamin D3 + Vitamin E)
  • Neospan Mastitis Treatment (Neomycin (Neomycin Sulfate) + Penicillin G Potassium + Polymyxin B (Polymyxin B Sulfate) + Streptomycin (Streptomycin Sulfate))
  • P.T. Booster (Calcium D-Pantothenate + Neomycin (Neomycin Sulfate) + Nicotinic Acid + Pyridoxine Hydrochloride + Streptomycin (Streptomycin Sulfate) + Vitamin a + Vitamin B1 + Vitamin B12 + Vitamin B2 + Vitamin D3)
  • Parvit Plus (Penicillin G Procaine + Streptomycin Sulfate + Vitamin a + Vitamin C + Vitamin D3 + Vitamin E + Vitamin K1)
  • Pig Booster Liq Coop (Calcium D-Pantothenate + Neomycin + Nicotinic Acid + Streptomycin + Vitamin a + Vitamin B1 + Vitamin B12 + Vitamin B2 + Vitamin B6 + Vitamin D)
  • Pig Starter Liq (Calcium D-Pantothenate + Neomycin Sulfate + Nicotinic Acid + Pyridoxine Hydrochloride + Streptomycin Sulfate + Vitamin a + Vitamin B1 + Vitamin B12 + Vitamin B2 + Vitamin D)
  • Pig Zest (Calcium D-Pantothenate + Neomycin (Neomycin Sulfate) + Nicotinic Acid + Pyridoxine Hydrochloride + Streptomycin (Streptomycin Sulfate) + Vitamin a + Vitamin B1 + Vitamin B12 + Vitamin B2 + Vitamin D3)
  • Poly Tonine a Super Booster No.1 (Calcium D-Pantothenate + Menadione + Nicotinamide + Penicillin G Potassium + Pyridoxine Hydrochloride + Streptomycin Sulfate + Vitamin a + Vitamin B12 + Vitamin B2 + Vitamin D3 + Vitamin E (Dl-Alpha Tocopheryl Acetate))
  • Poly Vita Pen Strep (Calcium D-Pantothenate + Menadione Sodium Bisulfite + Nicotinic Acid + Penicillin G Procaine + Streptomycin (Streptomycin Sulfate) + Vitamin a + Vitamin B12 + Vitamin B2 + Vitamin D3 + Vitamin E)
  • Polytonine a Super Booster No 1 Pws (Calcium D-Pantothenate + Menadione + Nicotinamide + Penicillin G Potassium + Pyridoxine Hydrochloride + Streptomycin (Streptomycin Sulfate) + Vitamin a + Vitamin B12 + Vitamin B2 + Vitamin D3 + Vitamin E (Dl-Alpha Tocopheryl Acetate))
  • Poultry Rx Pwr (Calcium D-Pantothenate + Folic Acid + Menadione Sodium Bisulfite + Nicotinic Acid + Penicillin G Potassium + Streptomycin (Streptomycin Sulfate) + Vitamin a + Vitamin B1 + Vitamin B12 + Vitamin B2 + Vitamin B6 + Vitamin D3 + Vitamin E)
  • Previte (Neomycin (Neomycin Sulfate) + Selenium (Selenium Sulfide) + Streptomycin (Streptomycin Sulfate) + Vitamin a + Vitamin D + Vitamin E + Vitamin K1)
  • Scour Bolus Plus (Calcium Carbonate + Magnesium Oxide + Menadione (Menadione Sodium Bisulfite) + Neomycin (Neomycin Sulfate) + Potassium Acetate + Sodium Acetate + Sodium Chloride + Streptomycin (Streptomycin Sulfate) + Sulfamerazine + Sulfamethazine + Sulfanilamide + Sulfathiazole + Vitamin a + Vitamin D)
  • Stimu-Pig (Calcium D-Pantothenate + Neomycin (Neomycin Sulfate) + Nicotinic Acid + Pyridoxine Hydrochloride + Streptomycin (Streptomycin Sulfate) + Vitamin a + Vitamin B1 + Vitamin B12 + Vitamin B2 + Vitamin D3)
  • Streptocilline - Sp Pws (Calcium D-Pantothenate + Menadione + Nicotinamide + Penicillin G Potassium + Pyridoxine Hydrochloride + Streptomycin Sulfate + Thiamine Hydrochloride + Vitamin a + Vitamin B12 + Vitamin B2 + Vitamin D3 + Vitamin E)
  • Sul Dyo Strep (Aluminum Hydroxide + Kaolin + Pectin + Streptomycin Sulfate + Sulfamethazine)
  • Sulectim Plus Scour Boluses (Calcium Carbonate + Magnesium Oxide + Menadione Sodium Bisulfite + Neomycin (Neomycin Sulfate) + Potassium Acetate + Sodium Acetate + Sodium Chloride + Streptomycin (Streptomycin Sulfate) + Sulfamerazine + Sulfamethazine + Sulfanilamide + Sulfathiazole Sodium + Vitamin a + Vitamin D)
  • Vibiomed Fmx (Calcium D-Pantothenate + Dl-Alpha Tocopheryl Acetate + Menadione + Nicotinamide + Penicillin G Potassium + Pyridoxine Hydrochloride + Streptomycin Sulfate + Vitamin a + Vitamin B12 + Vitamin B2 + Vitamin D3)
Categories
  • Anti-Bacterial Agents
  • Protein Synthesis Inhibitors
  • Aminoglycosides
CAS number 57-92-1
Weight Average: 581.5741
Monoisotopic: 581.265669747
Chemical Formula C21H39N7O12
InChI Key InChIKey=UCSJYZPVAKXKNQ-HZYVHMACSA-N
InChI
InChI=1S/C21H39N7O12/c1-5-21(36,4-30)16(40-17-9(26-2)13(34)10(31)6(3-29)38-17)18(37-5)39-15-8(28-20(24)25)11(32)7(27-19(22)23)12(33)14(15)35/h4-18,26,29,31-36H,3H2,1-2H3,(H4,22,23,27)(H4,24,25,28)/t5-,6-,7+,8-,9-,10-,11+,12-,13-,14+,15+,16-,17-,18-,21+/m0/s1
Plain Text
IUPAC Name
1-[(1S,2R,3R,4S,5R,6R)-3-carbamimidamido-6-{[(2R,3R,4R,5S)-3-{[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy}-4-formyl-4-hydroxy-5-methyloxolan-2-yl]oxy}-2,4,5-trihydroxycyclohexyl]guanidine
SMILES
CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@H]1[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](NC(N)=N)[C@@H](O)[C@@H]2NC(N)=N)O[C@@H](C)[C@]1(O)C=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Amynoglycosides
Substructures
  • Carbohydrates
  • Aminoglycosides
  • Glycerol and Derivatives
  • Hydroxy Compounds
  • Pyrans
  • Acetals and Derivatives
  • Aliphatic and Aryl Amines
  • Ethers
  • Aldehydes
  • Alcohols and Polyols
  • Amino Alcohols
  • Heterocyclic compounds
  • Guanidines
  • Carboxamidines
  • Furans
  • Amynoglycosides
Pharmacology
Indication For the treatment of tuberculosis. May also be used in combination with other drugs to treat tularemia (Francisella tularensis), plague (Yersia pestis), severe M. avium complex, brucellosis, and enterococcal endocarditis (e.g. E. faecalis, E. faecium).
Pharmacodynamics Streptomycin is an aminoglycoside antibiotic. Aminoglycosides work by binding to the bacterial 30S ribosomal subunit, causing misreading of t-RNA, leaving the bacterium unable to synthesize proteins vital to its growth. Aminoglycosides are useful primarily in infections involving aerobic, Gram-negative bacteria, such as Pseudomonas, Acinetobacter, and Enterobacter. In addition, some mycobacteria, including the bacteria that cause tuberculosis, are susceptible to aminoglycosides. Infections caused by Gram-positive bacteria can also be treated with aminoglycosides, but other types of antibiotics are more potent and less damaging to the host. In the past the aminoglycosides have been used in conjunction with penicillin-related antibiotics in streptococcal infections for their synergistic effects, particularly in endocarditis. Aminoglycosides are mostly ineffective against anaerobic bacteria, fungi and viruses.
Mechanism of action Aminoglycosides like Streptomycin "irreversibly" bind to specific 30S-subunit proteins and 16S rRNA. Specifically Streptomycin binds to four nucleotides of 16S rRNA and a single amino acid of protein S12. This interferes with decoding site in the vicinity of nucleotide 1400 in 16S rRNA of 30S subunit. This region interacts with the wobble base in the anticodon of tRNA. This leads to interference with the initiation complex, misreading of mRNA so incorrect amino acids are inserted into the polypeptide leading to nonfunctional or toxic peptides and the breakup of polysomes into nonfunctional monosomes.
Absorption Rapidly absorbed after intramuscular injection with peak serum concentrations attained after 1 - 2 hours. Not absorbed in the GI tract.
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Route of elimination Small amounts are excreted in milk, saliva, and sweat. Streptomycin is excreted by glomerular filtration.
Half life 5 - 6 hours in adults with normal renal function
Clearance Not Available
Toxicity Nephrotoxic and ototoxic potential. Nephrotoxicity is caused by accumulation of the drug in proximal renal tubular cells, which results in cellular damage. Tubular cells may regenerate despite continued exposure and nephrotoxicity is usually mild and reversible. Streptomycin is the least nephrotoxic of the aminoglycosides owing to the small number of cationic amino groups in its structure. Otoxocity occurs via drug accumulation in the endolymph and perilymph of the inner ear. Accumulation causes irreversible damage to hair cells of the cochlea or summit of the ampullar cristae of the vestibular complex. High frequency hearing loss precedes low frequency hearing loss. Further toxicity may result in retrograde degeneration of the auditory nerve. Vestibular toxicity may result in vertigo, nausea and vomiting, dizziness and loss of balance. LD50=430 mg/kg (Orally in rats with Streptomycin Sulfate); Side effects include nausea, vomiting, and vertigo, paresthesia of face, rash, fever, urticaria, angioneurotic edema, and eosinophilia.
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways
Pathway Name SMPDB ID
Smp00259 Streptomycin Pathway SMP00259
Pharmacoeconomics
Manufacturers
  • John d copanos and co inc
  • Eli lilly and co
  • Pfizer laboratories div pfizer inc
  • X gen pharmaceuticals inc
Packagers
Dosage forms
Form Route Strength
Powder, for solution Intramuscular
Prices
Unit description Cost Unit
Streptomycin sulf 1 gm vial 14.65 USD vial
Streptomycin sulfate powder 0.82 USD g
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties
Property Value Source
logP -6.4 PhysProp
Predicted Properties
Property Value Source
water solubility 1.28e+01 g/l ALOGPS
logP -2.61 ALOGPS
logP -7.77 ChemAxon Molconvert
logS -1.66 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 19 ChemAxon Molconvert
hydrogen donor count 14 ChemAxon Molconvert
polar surface area 331.43 ChemAxon Molconvert
rotatable bond count 9 ChemAxon Molconvert
refractivity 149.47 ChemAxon Molconvert
polarizability 55.76 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C00413 Link_out
PubChem Compound 19649 Link_out
PubChem Substance 46506845 Link_out
ChemSpider 18508 Link_out
ChEBI 17076 Link_out
ChEMBL 17076 Link_out
Therapeutic Targets Database DAP000144 Link_out
PharmGKB PA451512 Link_out
HET SRY Link_out
Drug Product Database 2243660 Link_out
RxList http://www.rxlist.com/cgi/generic2/streptomycin.htm Link_out
Drugs.com http://www.drugs.com/cdi/streptomycin.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Streptomycin Link_out
ATC Codes
  • A07AA04
  • J01GA01
  • S01AA15
AHFS Codes
  • 08:12.02
PDB Entries
FDA label Not Available
MSDS show (73.7 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. 30S ribosomal protein S12

Pharmacological action: yes
Actions: inhibitor

Cryo-EM studies suggest that S12 contacts the EF-Tu bound tRNA in the A-site during codon-recognition. This contact is most likely broken as the aminoacyl-tRNA moves into the peptidyl transferase center in the 50S subunit

Organism class: bacterial
UniProt ID: P0A7S3 Link_out
Gene: rpsL
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Mieskes KT, Rusch-Gerdes S, Truffot-Pernot C, Feldmann K, Tortoli E, Casal M, Loscher T, Rinder H: Rapid, simple, and culture-independent detection of rpsL codon 43 mutations that are highly predictive of streptomycin resistance in Mycobacterium tuberculosis. Am J Trop Med Hyg. 2000 Jul-Aug;63(1-2):56-60. Pubmed
  4. Kenney TJ, Churchward G: Cloning and sequence analysis of the rpsL and rpsG genes of Mycobacterium smegmatis and characterization of mutations causing resistance to streptomycin. J Bacteriol. 1994 Oct;176(19):6153-6. Pubmed
  5. Fukuda M, Koga H, Ohno H, Ogawa K, Yang B, Miyamoto J, Tomono K, Kohno S: [Relationship between streptomycin susceptibility and rpsL mutations of Mycobacterium tuberculosis strains] Kekkaku. 1997 Sep;72(9):507-13. Pubmed

2. 16S rRNA

Pharmacological action: yes
Actions: inhibitor

In prokaryotes, the 16S rRNA is essential for recognizing the 5' end of mRNA and hence positioning it correctly on the ribosome. The 16S rRNA has a characteristic secondary structure in which half of the nucleotides are base-paired. The 16S rRNA sequence has been highly conserved and is often used for evolutionary and species comparative analysis.

Gene Sequence: FASTA

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Okamoto S, Tamaru A, Nakajima C, Nishimura K, Tanaka Y, Tokuyama S, Suzuki Y, Ochi K: Loss of a conserved 7-methylguanosine modification in 16S rRNA confers low-level streptomycin resistance in bacteria. Mol Microbiol. 2007 Feb;63(4):1096-106. Pubmed
  4. Nishimura K, Hosaka T, Tokuyama S, Okamoto S, Ochi K: Mutations in rsmG, encoding a 16S rRNA methyltransferase, result in low-level streptomycin resistance and antibiotic overproduction in Streptomyces coelicolor A3. J Bacteriol. 2007 May;189(10):3876-83. Epub 2007 Mar 23. Pubmed
  5. Vila-Sanjurjo A, Lu Y, Aragonez JL, Starkweather RE, Sasikumar M, O’Connor M: Modulation of 16S rRNA function by ribosomal protein S12. Biochim Biophys Acta. 2007 Jul-Aug;1769(7-8):462-71. Epub 2007 Apr 20. Pubmed
Transporters

1. Solute carrier family 22 member 6

Actions: inhibitor
UniProt ID: Q4U2R8 Link_out
Gene: hROAT1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on November 10, 2010 13:45

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.