CHEBI:17076 - streptomycin

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ChEBI Name streptomycin
ChEBI ID CHEBI:17076
Definition A amino cyclitol glycoside that consists of streptidine having a disaccharyl moiety attached at the 4-position. The parent of the streptomycin class
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:45745, CHEBI:9284, CHEBI:15119, CHEBI:26784
Supplier Information ChemicalBook:CB3462887, ZINC000008214681
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Streptomycin is an antibiotic medication used to treat a number of bacterial infections, including tuberculosis, Mycobacterium avium complex, endocarditis, brucellosis, Burkholderia infection, plague, tularemia, and rat bite fever. For active tuberculosis it is often given together with isoniazid, rifampicin, and pyrazinamide. It is administered by injection into a vein or muscle. Common side effects include vertigo, vomiting, numbness of the face, fever, and rash. Use during pregnancy may result in permanent deafness in the developing baby. Use appears to be safe while breastfeeding. It is not recommended in people with myasthenia gravis or other neuromuscular disorders. Streptomycin is an aminoglycoside. It works by blocking the ability of 30S ribosomal subunits to make proteins, which results in bacterial death. Albert Schatz first isolated streptomycin in 1943 from Streptomyces griseus. It is on the World Health Organization's List of Essential Medicines. The World Health Organization classifies it as critically important for human medicine.
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Formula C21H39N7O12
Net Charge 0
Average Mass 581.57434
Monoisotopic Mass 581.26567
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
InChIKey UCSJYZPVAKXKNQ-HZYVHMACSA-N
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](C)[C@]1(O)C=O)O[C@H]1[C@H](O)[C@@H](O)[C@H](NC(N)=N)[C@@H](O)[C@@H]1NC(N)=N
Metabolite of Species Details
Streptomyces griseus (NCBI:txid1911) See: PubMed
Roles Classification
Biological Role(s): protein synthesis inhibitor
A compound, usually an anti-bacterial agent or a toxin, which inhibits the synthesis of a protein.
antibacterial drug
A drug used to treat or prevent bacterial infections.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via carbohydrate-containing antibiotic )
antimicrobial drug
A drug used to treat or prevent microbial infections.
antifungal agrochemical
Any substance used in acriculture, horticulture, forestry, etc. for its fungicidal properties.
antifungal drug
Any antifungal agent used to prevent or treat fungal infections in humans or animals.
(via antibiotic antifungal drug )
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
(via antibiotic antifungal agent )
fungicide
A substance used to destroy fungal pests.
(via antibiotic fungicide )
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
antimicrobial drug
A drug used to treat or prevent microbial infections.
antifungal agrochemical
Any substance used in acriculture, horticulture, forestry, etc. for its fungicidal properties.
antifungal drug
Any antifungal agent used to prevent or treat fungal infections in humans or animals.
(via antibiotic antifungal drug )
fungicide
A substance used to destroy fungal pests.
(via antibiotic fungicide )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing streptomycin (CHEBI:17076) has functional parent streptidine (CHEBI:27405)
streptomycin (CHEBI:17076) has role antibacterial drug (CHEBI:36047)
streptomycin (CHEBI:17076) has role antifungal agrochemical (CHEBI:86328)
streptomycin (CHEBI:17076) has role antimicrobial agent (CHEBI:33281)
streptomycin (CHEBI:17076) has role antimicrobial drug (CHEBI:36043)
streptomycin (CHEBI:17076) has role bacterial metabolite (CHEBI:76969)
streptomycin (CHEBI:17076) has role protein synthesis inhibitor (CHEBI:48001)
streptomycin (CHEBI:17076) is a antibiotic antifungal drug (CHEBI:87113)
streptomycin (CHEBI:17076) is a antibiotic fungicide (CHEBI:87114)
streptomycin (CHEBI:17076) is a streptomycins (CHEBI:26788)
streptomycin (CHEBI:17076) is conjugate base of streptomycin(3+) (CHEBI:58007)
Incoming 3''-adenylylstreptomycin (CHEBI:29076) has functional parent streptomycin (CHEBI:17076)
5'-hydroxystreptomycin (CHEBI:24750) has functional parent streptomycin (CHEBI:17076)
streptomycin sulfate (CHEBI:32158) has functional parent streptomycin (CHEBI:17076)
streptomycin(3+) (CHEBI:58007) is conjugate acid of streptomycin (CHEBI:17076)
IUPAC Name
N,N'''-[(1R,2R,3S,4R,5R,6S)-4-{5-deoxy-2-O-[2-deoxy-2-(methylamino)-α-L-glucopyranosyl]-3-C-formyl-α-L-lyxofuranosyloxy}-2,5,6-trihydroxycyclohexane-1,3-diyl]diguanidine
INN Source
streptomycin KEGG DRUG
Synonyms Sources
2,4-Diguanidino-3,5,6-trihydroxycyclohexyl 5-deoxy-2-O-(2-deoxy-2-methylamino-alpha-L-glucopyranosyl)-3-C-formyl-beta-L-lyxopentanofuranoside ChemIDplus
[2-deoxy-2-(dimethylamino)-α-L-glucopyranosyl]-(1→2)-[5-deoxy-3-C-formyl-α-L-lyxofuranosyl]-(1→4)-{N',N'''-[(1,3,5/2,4,6)-2,4,5,6-tetrahydroxycyclohexane-1,3-diyl]diguanidine} IUPAC
SM KEGG DRUG
streomycin ChEBI
STREPTOMYCIN PDBeChem
Brand Name Source
Kantrex DrugBank
Manual Xrefs Databases
2481 DrugCentral
C00413 KEGG COMPOUND
D08531 KEGG DRUG
DB01082 DrugBank
HMDB0015214 HMDB
SRY PDBeChem
streptomycin Alan Wood's Pesticides
Streptomycin Wikipedia
STREPTOMYCIN MetaCyc
View more database links
Registry Numbers Types Sources
57-92-1 CAS Registry Number KEGG COMPOUND
57-92-1 CAS Registry Number ChemIDplus
74498 Reaxys Registry Number Reaxys
Citations
Schneider J, Yepes A, Garcia-Betancur JC, Westedt I, Mielich B, López D (2012)
Streptomycin-induced expression in Bacillus subtilis of YtnP, a lactonase-homologous protein that inhibits development and streptomycin production in Streptomyces griseus.
Applied and environmental microbiology 78, 599-603 [PubMed:22101040]
[show Abstract]
Spies FS, Ribeiro AW, Ramos DF, Ribeiro MO, Martin A, Palomino JC, Rossetti ML, da Silva PE, Zaha A (2011)
Streptomycin resistance and lineage-specific polymorphisms in Mycobacterium tuberculosis gidB gene.
Journal of clinical microbiology 49, 2625-2630 [PubMed:21593257]
[show Abstract]
Young H, Swartwood CJ, Jenkins TC, Belknap R (2011)
A successful strategy for the use of synergistic intravenous streptomycin in a hemodialysis patient with refractory Enterococcus faecalis bacteremia.
Journal of infection and chemotherapy : official journal of the Japan Society of Chemotherapy 17, 698-699 [PubMed:21350946]
[show Abstract]
Huang JQ, Lv QL, Wang HY (2011)
Spectroscopic study of the competitive interaction between streptomycin and Evans blue to bovine serum albumin.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 83, 28-33 [PubMed:21937264]
[show Abstract]
Li YP, Shi Q, Xing X, Wang DK, Zhuang Y, Li D (2011)
[Influence of penicillin and streptomycin on gene expression of extracellular secretion from human umbilical cord tissue derived mesenchymal stem cells in vitro].
Zhongguo shi yan xue ye xue za zhi 19, 163-168 [PubMed:21362244]
[show Abstract]
Philippine Nationwide Tuberculosis Drug Resistance Survey Team (2009)
Nationwide drug resistance survey of tuberculosis in the Philippines.
The international journal of tuberculosis and lung disease : the official journal of the International Union against Tuberculosis and Lung Disease 13, 500-507 [PubMed:19335957]
[show Abstract]
Chandra Gupta TS, Rayudu T, Murthy SV (2008)
Donovanosis with auto-amputation of penis in a HIV-2 infected person.
Indian journal of dermatology, venereology and leprology 74, 490-492 [PubMed:19052412]
[show Abstract]
Zetterström R (2007)
Selman A. Waksman (1888-1973) Nobel Prize in 1952 for the discovery of streptomycin, the first antibiotic effective against tuberculosis.
Acta paediatrica (Oslo, Norway : 1992) 96, 317-319 [PubMed:17429930]
Gürcan S (2007)
[Francisella tularensis and tularemia in Turkey].
Mikrobiyoloji bulteni 41, 621-636 [PubMed:18173084]
[show Abstract]
Okamoto S, Tamaru A, Nakajima C, Nishimura K, Tanaka Y, Tokuyama S, Suzuki Y, Ochi K (2007)
Loss of a conserved 7-methylguanosine modification in 16S rRNA confers low-level streptomycin resistance in bacteria.
Molecular microbiology 63, 1096-1106 [PubMed:17238915]
[show Abstract]
Wiuff C, Andersson DI (2007)
Antibiotic treatment in vitro of phenotypically tolerant bacterial populations.
The Journal of antimicrobial chemotherapy 59, 254-263 [PubMed:17105735]
[show Abstract]
Nagel R, Chan A (2006)
Mistranslation and genetic variability: the effect of streptomycin.
Mutation research 601, 162-170 [PubMed:16904706]
[show Abstract]
Qiu J, Zhou D, Han Y, Zhang L, Tong Z, Song Y, Dai E, Li B, Wang J, Guo Z, Zhai J, Du Z, Wang X, Yang R (2005)
Global gene expression profile of Yersinia pestis induced by streptomycin.
FEMS microbiology letters 243, 489-496 [PubMed:15686853]
[show Abstract]
Granados O, Meza G (2005)
Streptidine, a metabolic derivative produced after administration of streptomycin in vivo, is vestibulotoxic in rats.
Histology and histopathology 20, 357-364 [PubMed:15736038]
[show Abstract]
Alcalá Minagorre PJ, Fernández Bernal A, Sánchez Bautista A, Loeda Ozores C (2004)
[Francisella tularensis infection transmitted by prairie dog].
Anales de pediatria (Barcelona, Spain : 2003) 60, 583-584 [PubMed:15207172]
[show Abstract]
Babalola CP, Patel KB, Nightingale CH, Nicolau DP (2004)
Synergistic activity of vancomycin and teicoplanin alone and in combination with streptomycin against Enterococcus faecalis strains with various vancomycin susceptibilities.
International journal of antimicrobial agents 23, 343-348 [PubMed:15081082]
[show Abstract]
Kassa-Kelembho E, Bobossi-Serengbe G, Takeng EC, Nambea-Koisse TB, Yapou F, Talarmin A (2004)
Surveillance of drug-resistant childhood tuberculosis in Bangui, Central African Republic.
The international journal of tuberculosis and lung disease : the official journal of the International Union against Tuberculosis and Lung Disease 8, 574-578 [PubMed:15137533]
[show Abstract]
Shen MR, Chou CY, Chiu WT (2003)
Streptomycin and its analogues are potent inhibitors of the hypotonicity-induced Ca2+ entry and Cl- channel activity.
FEBS letters 554, 494-500 [PubMed:14623118]
[show Abstract]
Higa M, Saitoh H, Yamane N, Nakasone I, Miyagi C (2002)
[Interpretive compatibility of antimycobacterial susceptibility for Mycobacterium tuberculosis determined by proportion test method on egg-based Ogawa media and broth microdilution test, BrothMIC MTB].
Kekkaku : [Tuberculosis] 77, 61-66 [PubMed:11905029]
[show Abstract]
Ruiz P, Rodríguez-Cano F, Zerolo FJ, Casal M (2002)
Investigation of the in vitro activity of streptomycin against Mycobacterium tuberculosis.
Microbial drug resistance (Larchmont, N.Y.) 8, 147-149 [PubMed:12118520]
[show Abstract]
Thompson S, Omphroy L, Oetting T (2001)
Parinaud's oculoglandular syndrome attributable to an encounter with a wild rabbit.
American journal of ophthalmology 131, 283-284 [PubMed:11228320]
[show Abstract]
SPRADBROW PB (1963)
Chemotherapy of experimental leptospiral infection in mice.
British journal of pharmacology and chemotherapy 20, 237-244 [PubMed:13990247]
[show Abstract]
TODOROFF T, FRANZOSI P (1962)
[Pyrazinamide in association with streptomycin, PAS and isoniazid in the therapy of pulmonary tuberculosis].
Minerva medica 53, 2667-2673 [PubMed:13985260]
CATTANEO C, IPATA PL (1960)
[The action of streptomycin, kanamycin and isoniazid on the breakdown of ATP in mycobacteria].
Annali dell'Istituto "Carlo Forlanini" 20, 315-324 [PubMed:13691614]
BARTMANN K, VILLNOW J, SCHWARZ C (1958)
[Animal experimental studies on an intermittent chemotherapy and prevention of tuberculosis. VII. Success of continuous and intermittent doses of isoniazid and the triple combination isoniazid, streptomycin, PAS in a therapeutic test in guinea pigs].
Beitrage zur Klinik der Tuberkulose und spezifischen Tuberkulose-Forschung 118, 297-313 [PubMed:13596285]
CAPON AW (1954)
Streptomycin and PAS vs. streptomycin, PAS and isoniazid in the treatment of pulmonary tuberculosis.
Canadian Medical Association journal 70, 62-67 [PubMed:13116094]
VICHER EE, SOSKA JW, JACKSON GG (1953)
Microbiologic flora of chronic cutaneous ulcers; in vitro sensitivity of microbiologic flora to three antibiotics, penicillin, streptomycin, and bacitracin.
A.M.A. archives of surgery 66, 283-291 [PubMed:13030054]
NAGAO I (1953)
Three basic antibiotics, streptomycin, roseomycin and No. 259 in experimental typhoid infection.
The Tohoku journal of experimental medicine 58, 169-173 [PubMed:13136149]
WALTHER G, WINTER KA (1952)
[The effect of streptomycin, PAS and TB6 on blood coagulation and its different phases; experimental study].
Klinische Wochenschrift 30, 25-28 [PubMed:14939639]
ILLERA PAISAN C (1951)
[What can be expected of streptomycin, PAS and TB 1 in the treatment of tuberculosis].
Medicamenta 9, 251-253 [PubMed:14852338]
GRUMBACH A (1950)
[Mode of action of the antibiotics; penicillin and streptomycin].
Schweizerische Zeitschrift fur Pathologie und Bakteriologie. Revue suisse de pathologie et de bacteriologie 13, 586-593 [PubMed:14828344]
MATHUR YS (1947)
Streptomycin, an antibiotic.
Clinical Society journal 11, 61-67 [PubMed:18916143]
Last Modified
22 February 2017