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Streptomycin
Identification
- Name
- Streptomycin
- Accession Number
- DB01082
- 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.
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
Structure for Streptomycin (DB01082)
- Weight
- Average: 581.5741
Monoisotopic: 581.265669747 - Chemical Formula
- C21H39N7O12
- Synonyms
- 2,4-diguanidino-3,5,6-trihydroxycyclohexyl 5-deoxy-2-O-(2-deoxy-2-methylamino-alpha-L-glucopyranosyl)-3-C-formyl-beta-L-lyxopentanofuranoside
- Estreptomicina
- Streptomicina
- Streptomycin
- Streptomyzin
- External IDs
- NSC-14083
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).
- Associated Conditions
- Bacteremia
- Bacterial Infections
- Chancroid
- Disseminated mycobacterium avium complex infection
- Flu caused by Influenza
- Granuloma Inguinale
- Menière's Disease
- Mycobacterium avium complex infection
- Mycobacterium kansasii infection
- Mycobacterium marinum infection
- Plague
- Pneumonia
- Tuberculosis (TB)
- Tularemia
- Urinary Tract Infection
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
Streptomycin is an aminoglycoside antibiotic that works 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.
Target Actions Organism A30S ribosomal protein S12 inhibitorEscherichia coli (strain K12) A16S ribosomal RNA inhibitorEnteric bacteria and other eubacteria UProtein-arginine deiminase type-4 Not Available Humans - 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
- Not Available
- 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
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- 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
- Mycobacteria
- Mycobacterium tuberculosis
- Yersinia pestis
- Francisella tularensis
- Staphylococcus aureus
- Enterococcus faecalis
- Pathways
Pathway Category Streptomycin Action Pathway Drug action - 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 Unlock Additional DataAbacavir Streptomycin may decrease the excretion rate of Abacavir which could result in a higher serum level. Acarbose Streptomycin may decrease the excretion rate of Acarbose which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Streptomycin which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Streptomycin which could result in a higher serum level. Acenocoumarol The risk or severity of bleeding can be increased when Streptomycin is combined with Acenocoumarol. Acetaminophen Streptomycin may decrease the excretion rate of Acetaminophen which could result in a higher serum level. Acetylcholine The therapeutic efficacy of Acetylcholine can be decreased when used in combination with Streptomycin. Acetyldigitoxin The risk or severity of adverse effects can be increased when Streptomycin is combined with Acetyldigitoxin. Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Streptomycin which could result in a higher serum level. Aclidinium Streptomycin may decrease the excretion rate of Aclidinium which could result in a higher serum level. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- No interactions found.
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Streptomycin Sulfate CW25IKJ202 3810-74-0 CFCMMYICHMLDCC-QXQFOYBSSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataStreptomycin for Injection USP Powder, for solution Intramuscular Sterimax Inc 2001-10-15 Not applicable Canada 
Streptomycin Sulfate Injection USP 1g/2.5ml Liquid Intramuscular Pfizer Canada Ulc 1993-12-31 2000-07-26 Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataStreptomycin Injection, powder, lyophilized, for solution 1 g/1 Intramuscular X-GEN Pharmaceuticals, Inc. 1998-06-30 Not applicable US 
Streptomycin Sulfate Injection, solution 1 g/2.5mL Intramuscular Roerig 1952-03-01 2001-09-01 US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
Categories
- ATC Codes
- J04AM01 — Streptomycin and isoniazid
- J04AM — Combinations of drugs for treatment of tuberculosis
- J04A — DRUGS FOR TREATMENT OF TUBERCULOSIS
- J04 — ANTIMYCOBACTERIALS
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- J01GA — Streptomycins
- J01G — AMINOGLYCOSIDE ANTIBACTERIALS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- A07AA — Antibiotics
- A07A — INTESTINAL ANTIINFECTIVES
- A07 — ANTIDIARRHEALS, INTESTINAL ANTIINFLAMMATORY/ANTIINFECTIVE AGENTS
- A — ALIMENTARY TRACT AND METABOLISM
- Drug Categories
- Agents that produce neuromuscular block (indirect)
- Alimentary Tract and Metabolism
- Aminoglycoside Antibacterials
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antidiarrheals, Intestinal Antiinflammatory/antiinfective Agents
- Antiinfectives for Systemic Use
- Antimycobacterials
- Carbohydrates
- Drugs for Treatment of Tuberculosis
- Drugs that are Mainly Renally Excreted
- Drugs that are Mainly Renally Excreted with Narrow Therapeutic Index
- Enzyme Inhibitors
- Glycosides
- Intestinal Antiinfectives
- Narrow Therapeutic Index Drugs
- Nephrotoxic agents
- OAT1/SLC22A6 inhibitors
- Protein Synthesis Inhibitors
- Streptomycins
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as aminocyclitol glycosides. These are organic compounds containing an amicocyclitol moiety glycosidically linked to a carbohydrate moiety. There are two major classes of aminoglycosides containing a 2-streptamine core. They are called 4,5- and 4,6-disubstituted 2-deoxystreptamines.
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Carbohydrates and carbohydrate conjugates
- Direct Parent
- Aminocyclitol glycosides
- Alternative Parents
- O-glycosyl compounds / Cyclohexanols / Cyclitols and derivatives / Monosaccharides / Oxanes / Tetrahydrofurans / Tertiary alcohols / Guanidines / 1,2-aminoalcohols / Oxacyclic compounds show 10 more
- Substituents
- 1,2-aminoalcohol / Acetal / Alcohol / Aldehyde / Aliphatic heteromonocyclic compound / Amine / Amino cyclitol glycoside / Carbonyl group / Carboximidamide / Cyclic alcohol show 23 more
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- antibiotic antifungal drug, antibiotic fungicide, streptomycins (CHEBI:17076) / Streptidines, Antibiotic fungicides (C00413)
Chemical Identifiers
- UNII
- Y45QSO73OB
- CAS number
- 57-92-1
- InChI Key
- 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
- IUPAC Name
- N-[(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[[email protected]]1[[email protected]](O)[[email protected]@H](O)[[email protected]](CO)O[[email protected]]1O[[email protected]]1[[email protected]](O[[email protected]]2[[email protected]](O)[[email protected]@H](O)[[email protected]](NC(N)=N)[[email protected]@H](O)[[email protected]@H]2NC(N)=N)O[[email protected]@H](C)[[email protected]]1(O)C=O
References
- Synthesis Reference
Arnold L. Demain, Kozo Nagaoka, "Derivatives of streptomycin and method of producing streptomycin derivatives by mutational biosynthesis." U.S. Patent US3993544, issued November 23, 1976.
US3993544- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015214
- KEGG Compound
- C00413
- PubChem Compound
- 19649
- PubChem Substance
- 46506845
- ChemSpider
- 18508
- BindingDB
- 50103513
- 10109
- ChEBI
- 17076
- ChEMBL
- CHEMBL372795
- ZINC
- ZINC000008214681
- Therapeutic Targets Database
- DAP000144
- PharmGKB
- PA451512
- PDBe Ligand
- SRY
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Streptomycin
- AHFS Codes
- 08:12.02 — Aminoglycosides
- PDB Entries
- 1fjg / 1nta / 1ntb / 3hav / 4dr3 / 4dr5 / 4dr6 / 4dr7 / 4duz / 4dv1 … show 13 more
- MSDS
- Download (73.7 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Unknown Status Treatment Reinfection Pulmonary Tuberculosis 1 3 Recruiting Treatment Plague, Bubonic / Plague, Pneumonic 1 2 Completed Treatment Infection, Mycobacterium Avium-Intracellulare 1 2, 3 Completed Treatment Mycobacterium Ulcerans Infection 1 2, 3 Completed Treatment Plague 1 1 Completed Treatment Healthy Volunteers 1 0 Recruiting Treatment Osteomyelitis 1 Not Available Completed Not Available Colorectal Cancers / Surgical Site Infections 1 Not Available Completed Not Available Patients Colonized by Klebsiella Pneumoniae 1 Not Available Completed Treatment Human Immunodeficiency Virus (HIV) Infections / Tuberculosis (TB) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Ben Venue Laboratories Inc.
- Gallipot
- Sanofi-Aventis Inc.
- X-Gen Pharmaceuticals
- Dosage Forms
Form Route Strength Injection, powder, for solution Intramuscular 1.253 g Injection 1 g Powder Injection, powder, lyophilized, for solution Intramuscular 1 g/1 Powder, for solution Intramuscular Injection, solution Intramuscular 1 g/2.5mL Liquid Intramuscular - Prices
Unit description Cost Unit Streptomycin sulf 1 gm vial 14.65USD vial Streptomycin sulfate powder 0.82USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP -6.4 Not Available - Predicted Properties
Property Value Source Water Solubility 12.8 mg/mL ALOGPS logP -2.6 ALOGPS logP -7.6 ChemAxon logS -1.7 ALOGPS pKa (Strongest Acidic) 11.09 ChemAxon pKa (Strongest Basic) 11.6 ChemAxon Physiological Charge 3 ChemAxon Hydrogen Acceptor Count 19 ChemAxon Hydrogen Donor Count 14 ChemAxon Polar Surface Area 331.43 Å2 ChemAxon Rotatable Bond Count 9 ChemAxon Refractivity 149.47 m3·mol-1 ChemAxon Polarizability 55.87 Å3 ChemAxon Number of Rings 3 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
Property Value Probability Human Intestinal Absorption - 0.8824 Blood Brain Barrier - 0.9712 Caco-2 permeable - 0.6968 P-glycoprotein substrate Substrate 0.5531 P-glycoprotein inhibitor I Non-inhibitor 0.7577 P-glycoprotein inhibitor II Non-inhibitor 0.8382 Renal organic cation transporter Non-inhibitor 0.7782 CYP450 2C9 substrate Non-substrate 0.7053 CYP450 2D6 substrate Non-substrate 0.8177 CYP450 3A4 substrate Non-substrate 0.5275 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9072 CYP450 2D6 inhibitor Non-inhibitor 0.923 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.8867 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8818 Ames test AMES toxic 0.9107 Carcinogenicity Non-carcinogens 0.9528 Biodegradation Not ready biodegradable 0.9821 Rat acute toxicity 1.8409 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9924 hERG inhibition (predictor II) Non-inhibitor 0.9009
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Trna binding
- Specific Function
- With S4 and S5 plays an important role in translational accuracy.Interacts with and stabilizes bases of the 16S rRNA that are involved in tRNA selection in the A site and with the mRNA backbone. Lo...
- Gene Name
- rpsL
- Uniprot ID
- P0A7S3
- Uniprot Name
- 30S ribosomal protein S12
- Molecular Weight
- 13736.995 Da
References
- 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:11357996]
- 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:7928982]
- 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:9364810]
Yes
Inhibitor
References
- 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:17238915]
- 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(2). J Bacteriol. 2007 May;189(10):3876-83. Epub 2007 Mar 23. [PubMed:17384192]
- 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:17512991]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Protein-arginine deiminase activity
- Specific Function
- Catalyzes the citrullination/deimination of arginine residues of proteins such as histones, thereby playing a key role in histone code and regulation of stem cell maintenance. Citrullinates histone...
- Gene Name
- PADI4
- Uniprot ID
- Q9UM07
- Uniprot Name
- Protein-arginine deiminase type-4
- Molecular Weight
- 74078.65 Da
References
- Knuckley B, Luo Y, Thompson PR: Profiling Protein Arginine Deiminase 4 (PAD4): a novel screen to identify PAD4 inhibitors. Bioorg Med Chem. 2008 Jan 15;16(2):739-45. Epub 2007 Oct 13. [PubMed:17964793]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- 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:10411577]
Drug created on June 13, 2005 07:24 / Updated on September 20, 2020 08:49
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