Name: Streptomycin
SKU: 57-92-1

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Basic Information

Molecular Structure:
CAS No.:	57-92-1
Name:	Streptomycin

Formula:	C₂₁H₃₉N₇O₁₂
Molecular Weight:	581.58
Synonyms:	Streptomycin (8CI);2,4-Diguanidino-3,5,6-trihydroxycyclohexyl 5-deoxy-2-O-(2-deoxy-2-methylamino-a-glucopyranosyl)-3-formylpentofuranoside;Agrept;Agrimycin;NSC 14083;Neodiestreptopab;Streptomycin A;
EINECS:	223-286-0
Density:	1.982 g/cm³
Melting Point:	194 °C
Boiling Point:	948.247 °C at 760 mmHg
Flash Point:	527.281 °C
Appearance:	Crystalline powder
PSA:	331.43000
LogP:	-4.96900

Synthetic route

: 54-85-3
isoniazid

: 57-92-1
streptomicin

: 4480-58-4
streptomycin-isonicotinoylhydrazone

Conditions

Conditions	Yield
With water pH 7.0-7.2;
With methanol

: 124-22-1
n-Dodecylamine

: 57-92-1
streptomicin

: 56222-71-0
(1R)-N,N'-dicarbamimidoyl-O4-[3-(dodecylamino-methyl)-O2-(2-methylamino-2-deoxy-α-L-glucopyranosyl)-5-deoxy-α-L-lyxofuranosyl]-streptamine

: 2016-42-4
tetradecylamine

: 57-92-1
streptomicin

: (1R)-N,N'-dicarbamimidoyl-O4-[O2-(2-methylamino-2-deoxy-α-L-glucopyranosyl)-3-(tetradecylamino-methyl)-5-deoxy-α-L-lyxofuranosyl]-streptamine

: 143-27-1
hexadecylamine

: 57-92-1
streptomicin

: 56222-72-1
(1R)-N,N'-dicarbamimidoyl-O4-[3-(hexadecylamino-methyl)-O2-(2-methylamino-2-deoxy-α-L-glucopyranosyl)-5-deoxy-α-L-lyxofuranosyl]-streptamine

: 111-86-4
n-Octylamine

: 57-92-1
streptomicin

: (1R)-N,N'-dicarbamimidoyl-O4-[O2-(2-methylamino-2-deoxy-α-L-glucopyranosyl)-3-(octylamino-methyl)-5-deoxy-α-L-lyxofuranosyl]-streptamine

: 2016-57-1
1-aminodecane

: 57-92-1
streptomicin

: 56222-69-6
(1R)-N,N'-dicarbamimidoyl-O4-[3-(decylamino-methyl)-O2-(2-methylamino-2-deoxy-α-L-glucopyranosyl)-5-deoxy-α-L-lyxofuranosyl]-streptamine

: 5351-23-5
4-hydroxybenzoic acid hydrazide

: 57-92-1
streptomicin

: (1R)-N,N'-dicarbamimidoyl-O4-{3-[(4-hydroxy-benzoylhydrazono)-methyl]-O2-(2-methylamino-2-deoxy-α-L-glucopyranosyl)-5-deoxy-α-L-lyxofuranosyl}-streptamine

Conditions

Conditions	Yield
With water

: 57-92-1
streptomicin

: 140-28-3
N,N'-Dibenzylethylenediamine

: 47896-20-8
(1R)-N,N'-bis-carbamimidoyl-O4-[3-(1,3-dibenzyl-imidazolidin-2-yl)-O2-(2-methylamino-2-deoxy-α-L-glucopyranosyl)-5-deoxy-α-L-lyxofuranosyl]-streptamine

: 57-92-1
streptomicin

: 128-46-1, 82443-21-8
dihydrostreptomycin

Conditions

Conditions	Yield
With sulfuric acid; water bei der elektrochemischen Reduktion an einer Cadmium-Amalgam-Kathode;
With sulfuric acid; water bei der elektrochemischen Reduktion an einer Quecksilber-Kathode;
With sulfuric acid; water bei der elektrochemischen Reduktion an einer Blei-Kathode;
With sulfuric acid; water bei der elektrochemischen Reduktion an einer Blei-Amalgam-Kathode;

: 119-53-9
2-hydroxy-2-phenylacetophenone

: 57-92-1
streptomicin

: C49H55N7O12

Conditions

Conditions	Yield
With potassium hydroxide; 2-hydroxyethanethiol; sodium sulfite In water at 100℃; for 0.166667h;

Downstream Products

128-46-1

Total:84 Page 1 of 3 1 2 3 Next>>

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History

Streptomycin (CAS NO.57-92-1) was first isolated on October 19, 1943 by Albert Schatz, a graduate student, in the laboratory of Selman Abraham Waksman at Rutgers University. Waksman and his laboratory discovered several antibiotics, including actinomycin, clavacin, streptothricin, streptomycin, grisein, neomycin, fradicin, candicidin and candidin. Of these, streptomycin and neomycin found extensive application in the treatment of numerous infectious diseases. Streptomycin was the first antibiotic that could be used to cure the disease tuberculosis; early production of the drug was dominated by Merck & Co. under George W. Merck.
The first randomized trial of streptomycin against pulmonary tuberculosis was carried out in 1947 by the MRC Tuberculosis Research Unit. Whilst neither double-blind nor placebo-controlled, results showed efficacy against TB, albeit with minor toxicity and acquired bacterial resistance to the drug.

Consensus Reports

EPA Genetic Toxicology Program.

Specification

The Streptomycin, with the CAS registry number 57-92-1, is also known as 2,4-Diguanidino-3,5,6-trihydroxycyclohexyl 5-deoxy-2-O-(2-deoxy-2-methylamino-a-L-glucopyranosyl)-3-C-formyl-b-L-lyxopentanofuranoside. It belongs to the product categories of Oligosaccharide Compounds; Intermediates & Fine Chemicals; Oligosaccharides; Pharmaceuticals. Its EINECS number is 223-286-0. This chemical's molecular formula is C₂₁H₃₉N₇O₁₂ and molecular weight is 581.57. What's more, its systematic name is 5-(2,4-diguanidino-3,5,6-trihydroxy-cyclohexoxy)- 4-[4,5-dihydroxy-6-(hydroxymethyl)-3-methylamino-tetrahydropyran-2-yl] oxy-3-hydroxy-2-methyl-tetrahydrofuran-3-carbaldehyde. Its classification codes are: (1)Agricultural Chemical; (2)Anti-Bacterial Agents; (3)Anti-Infective Agents; (4)Drug / Therapeutic Agent; (5)Enzyme Inhibitors; (6)Fungicide, bactericide, wood preservative; (7)Human Data; (8)Mutation data; (9)Natural Product; (10)Protein synthesis inhibitors; (11)Reproductive Effect. Its storage temperature is 2-8 °C. It is an antibiotic produced by the soil actinomycete Streptomyces griseus. It acts by inhibiting the initiation and elongation processes during protein synthesis. It is also used as a pesticide, to combat the growth of bacteria, fungi and algae.

Physical properties of Streptomycin are: (1)# of Rule of 5 Violations: 3; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 1; (5)ACD/KOC (pH 7.4): 1; (6)#H bond acceptors: 19; (7)#H bond donors: 16; (8)#Freely Rotating Bonds: 16; (9)Polar Surface Area: 336.43 Å²; (10)Index of Refraction: 1.762; (11)Molar Refractivity: 121.037 cm³; (12)Molar Volume: 293.483 cm³; (13)Polarizability: 47.983×10^-24cm³; (14)Surface Tension: 92.673 dyne/cm; (15)Density: 1.982 g/cm³; (16)Flash Point: 527.281 °C; (17)Enthalpy of Vaporization: 156.549 kJ/mol; (18)Boiling Point: 948.247 °C at 760 mmHg; (19)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)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
(2)Std. 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
(3)Std. InChIKey: UCSJYZPVAKXKNQ-HZYVHMACSA-N

The toxicity data is as follows:

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)	VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	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.

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History

Consensus Reports

Specification