File:Streptomycin2.svg · Wikimedia Commons · See Wikimedia Commons
streptomycin
Sign in to saveAlso known as SM, [2-Deoxy-2-(dimethylamino)-alpha-L-glucopyranosyl]-(1->2)-[5-deoxy-3-C-formyl-alpha-L-lyxofuranosyl]-(1->4)-{n',n'''-[(1,3,5/2,4,6)-2,4,5,6-tetrahydroxycyclohexane-1,3-diyl]diguanidine}, Kantrex, 2,4-Diguanidino-3,5,6-trihydroxycyclohexyl 5-deoxy-2-O-(2-deoxy-2-methylamino-alpha-L-glucopyranosyl)-3-C-formyl-beta-L-lyxopentanofuranoside, streomycin, 2,4-diguanidino-3,5,6-trihydroxycyclohexyl 5-deoxy-2-O-(2-deoxy-2-methylamino-alpha-L-glucopyranosyl)-3-C-formyl-beta-L-lyxopentanofuranoside
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.
OverviewAI-generated
Streptomycin is a chemical compound with the formula C₂₁H₃₉N₇O₁₂. It has a mass of 581.266 and a weight of 581.6. The compound is characterized by a charge of 0, an xlogp of -8, and a topological polar surface area of 336. It contains 12 hydrogen bond donors and 15 hydrogen bond acceptors.
The defined daily dose for streptomycin is 1. In scientific literature, the term is associated with 34,614 entries in PubMed. Additionally, the subject is referenced by 546 other encyclopedia articles.
Synthesized by Vinony from 17 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Key facts
- Drug.Verifiedfields
- changed
- Drug.verifiedrevid
- 470471096
- Drug.StdInChI
- 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
- Drug.StdInChIKey
- UCSJYZPVAKXKNQ-HZYVHMACSA-N
- Drug.melting_point
- 12
- Drug.image
- Streptomycin2.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 209
- Drug.image2
- Streptomycin-1ntb-xtal-3D-balls.png
- Drug.image_class2
- bg-transparent
- Drug.DailyMedID
- Streptomycin
- Drug.routes_of_administration
- Intramuscular, intravenous
- Drug.ATC_prefix
- A07
- Drug.ATC_suffix
- AA04
- Drug.legal_AU
- S4
- Drug.legal_UK
- POM
- Drug.legal_US
- Rx-only
- Drug.bioavailability
- 84% to 88% IM (est.) 0% by mouth
via Wikipedia infobox
Chemical data
- Formula
- C21H39N7O12
- Molecular weight
- 581.6 g/mol
- IUPAC name
- 2-[(1R,2R,3S,4R,5R,6S)-3-(diaminomethylideneamino)-4-[(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-2,5,6-trihydroxycyclohexyl]guanidine
- SMILES
- C[C@H]1[C@@]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H]([C@@H]([C@H]2O)O)N=C(N)N)O)N=C(N)N)O[C@H]3[C@H]([C@@H]([C@H]([C@@H](O3)CO)O)O)NC)(C=O)O
- InChIKey
- UCSJYZPVAKXKNQ-HZYVHMACSA-N
- XLogP
- -8
- Polar surface area
- 336 Ų
- H-bond donors
- 12
- H-bond acceptors
- 15
- Formal charge
- 0
via PubChem
Research
34,614 papers- [Streptomycin].Gazette medicale de France · 1951
- [Streptomycin].Nederlands tijdschrift voor geneeskunde · 1948VAN DONGEN K
- [Streptomycin].Strasbourg medical · 1947
- [Streptomycin].Maroc medical · 1951DEBRE R
- [Streptomycin].Archives hospitalieres · 1947ABAZA A
- [Streptomycin].L'union medicale du Canada · 1947SAUCIER J
- [Streptomycin].Journal de medecine de Lyon · 1948MARAL R, BLANDIN A
- [Streptomycin].Revue medicale de France · 1947LAHAM J
via PubMed
~10 min read
Encyclopedic overview
11 sectionsContents
- Uses
- Medication
- Pesticide
- Cell culture
- Protein purification
- Side effects
- Mechanism of action
- History
- New Jersey
- References
- Further reading
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.
Excerpted from Wikipedia’s “streptomycin” article, available under the CC BY-SA 4.0 licence.