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Substance Name: Streptomycin [INN:BAN]
RN: 57-92-1
UNII: Y45QSO73OB
InChIKey: UCSJYZPVAKXKNQ-HZYVHMACSA-N

Note

  • An antibiotic produced by the soil actinomycete Streptomyces griseus. It acts by inhibiting the initiation and elongation processes during protein synthesis.

Molecular Formula

  • C21-H39-N7-O12

Molecular Weight

  • 581.5761
 

Classification Codes

  • Agricultural Chemical
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Fungicide, Bactericide, Wood Preservative
  • Human Data
  • Mutation Data
  • Natural Product
  • Protein Synthesis Inhibitors
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Streptomycin
  • Streptomycin [INN:BAN]

MeSH Heading

  • Streptomycin

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
  • 4-18-00-07540 (Beilstein Handbook Reference)
  • Agrept
  • Agrimycin
  • BRN 0074498
  • Caswell No. 804
  • CCRIS 5730
  • D-Streptamine, O-2-deoxy-2-(methylamino)-alpha-L-glucopyranosyl-(1-2)-O-5-deoxy-3-C-formyl-alpha-L-lyxofuranosyl-(1-4)-N,N'-bis(aminoiminomethyl)-
  • EINECS 200-355-3
  • EPA Pesticide Chemical Code 006306
  • Estreptomicina
  • Estreptomicina [INN-Spanish]
  • Gerox
  • Hokko-mycin
  • HSDB 1768
  • Neodiestreptopab
  • NSC 14083
  • Strepcen
  • Streptomicina
  • Streptomicina [Italian]
  • Streptomycin
  • Streptomycin A
  • Streptomycine
  • Streptomycinum
  • Streptomyzin
  • Streptomyzin [German]
  • UNII-Y45QSO73OB

Systematic Names

  • D-Streptamine, O-2-deoxy-2-(methylamino)-alpha-L-glucopyranosyl-(1-2)-O-5-deoxy-3-C-formyl-alpha-L-lyxofuranosyl-(1-4)-N,N'-bis(aminoiminomethyl)-
  • D-Streptamine, O-2-deoxy-2-(methylamino)-alpha-L-glucopyranosyl-(1.fwdarw.2)-O-5-deoxy-3-C-formyl-alpha-L-lyxofuranosyl-(1.fwdarw.4)-N,N'-bis(aminoiminomethyl)-
  • Streptomycin

Superlist Name

  • Streptomycin

Registry Numbers

CAS Registry Number

  • 57-92-1

FDA UNII

  • Y45QSO73OB

Other Registry Numbers

  • 12672-24-1
  • 47814-83-5
  • 47816-81-9
  • 82958-69-8

Related Registry Number

  • 3810-74-0 (sulfate (2:3) salt)

System Generated Number

  • 0000057921

Structure Descriptors

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]2[C@H](O[C@H]3[C@H](O)[C@@H](O)[C@H](NC(=N)N)[C@@H](O)[C@@H]3NC(=N)N)O[C@@H](C)[C@]2(O)C=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 150mg/kg (150mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 570, 1978.
cat LDLo oral 2gm/kg (2000mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 570, 1978.
cat LDLo subcutaneous 600mg/kg (600mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 570, 1978.
dog LDLo subcutaneous 300mg/kg (300mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 570, 1978.
guinea pig LDLo subcutaneous 600mg/kg (600mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 570, 1978.
human TDLo intraperitoneal 143mg/kg (143mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION		 British Medical Journal. Vol. 1, Pg. 556, 1961.
human TDLo oral 400mg/kg/28D- (400mg/kg) SENSE ORGANS AND SPECIAL SENSES: CHANGES IN VESTIBULAR FUNCTIONS: EAR Revue Medicale de la Suisse Romande. Vol. 73, Pg. 854, 1953.
human TDLo parenteral 28mg/kg/D (28mg/kg) BLOOD: EOSINOPHILIA Revue Medicale de la Suisse Romande. Vol. 73, Pg. 820, 1953.
monkey LDLo subcutaneous 400mg/kg (400mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 570, 1978.
mouse LD50 intraperitoneal 525mg/kg (525mg/kg)   Strahlentherapie. Vol. 127, Pg. 245, 1965.
mouse LD50 intravenous 90200ug/kg (90.2mg/kg)   Antibiotiki. Vol. 18, Pg. 249, 1973.
mouse LD50 oral 500mg/kg (500mg/kg)   Yakkyoku. Pharmacy. Vol. 38, Pg. 1493, 1987.
mouse LD50 subcutaneous 520mg/kg (520mg/kg)   British Journal of Pharmacology and Chemotherapy. Vol. 15, Pg. 496, 1960.
mouse LD50 unreported 90mg/kg (90mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 213, 1955.
rabbit LDLo intravenous 175mg/kg (175mg/kg)   Naturwissenschaften. Vol. 43, Pg. 183, 1956.
rabbit LDLo subcutaneous 600mg/kg (600mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 570, 1978.
rat LD50 oral 9gm/kg (9000mg/kg)   "Agricultural Chemicals," Thomson, W.T., 4 vols., Fresno, CA, Thomson Publications, 1976/77 revisionVol. 4, Pg. 35, 1976/1977.
rat LDLo intravenous 175mg/kg (175mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 570, 1978.
rat LDLo subcutaneous 600mg/kg (600mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 570, 1978.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -7.530 (none)   EST
Water Solubility 1.00E+06 mg/L 25 EST
Vapor Pressure 5.82E-28 mm Hg 25 EST
Henry's Law Constant 8.41E-44 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 5.51E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.