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Streptomycin sulfate structure
Streptomycin sulfate structure

Streptomycin sulfate

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;sulfuric acid
CAS No.: 3810-74-0
Molecular Weight:1457.38
Modify Date.: 2022-03-06 06:12
Introduction: An antibacterial. White to light gray or pale buff powder with faint amine-like odor. View more+
1. Names and Identifiers
1.1 Name
Streptomycin sulfate
1.2 Synonyms

1,1&rsquo-{1-D-(1,3,5/2,4,6)-4-[5-deoxy-2-O-(2-deoxy-2-methylamino-α-L-glucopyranosyl)-3-C-formyl-α-L-lyxofuranosyloxy]-2,5,6-trihydroxycyclohex-1,3-ylene}diguanidine sulfate (2:3) (salt) 2-[(1S,2R,3S,4S,5R,6S)-5-(diaminomethylideneamino)-2-[(2R,3S,4S,5R)-3-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-methylamino-oxan-2-yl]oxy-4-formyl-4-hydroxy-5-methyl-oxolan-2-yl]oxy-3,4,6-trihydroxy-cyclohexyl]guanidine D-Streptamine, O-2-deoxy-2-(methylamino)-a-L-glucopyranosyl-(1->2)-O-5-deoxy-3-C-formyl-a-L-lyxofuranosyl-(1->4)-N,N'-bis(aminoiminomethyl)-, sulfate (2:3) EINECS 223-286-0 MFCD00037023 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-lyxofuranosyl]oxy]-2,5,6-trihydroxy-1,3-cyclohexanediyl]bis[guanidine] sulfate (2:3) 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 sulfate 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 sulfate (2:3) salt O-2-deoxy-2-methylamino-α-L-glucopyranosyl-(1→2)-O-5-deoxy-3-C-formyl-α-L-lyxofuranosyl-(1→4)-N1,N3-diamidino-D-streptamine sulfate (2:3) (salt) Strep-sol Streptomyc Streptomycin 2/3 Sulfate Streptomycin (sulfate) Streptomycin sulfate salt Streptomycin Sulphate Verstrep

1.3 CAS No.
3810-74-0
1.4 CID
19648
1.5 EINECS(EC#)
223-286-0
1.6 Molecular Formula
C42H84N14O36S3 (isomer)
1.7 Inchi
InChI=1S/2C21H39N7O12.3H2O4S/c2*1-5-21(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;3*1-5(2,3)4/h2*4-18,26,29,31-36H,3H2,1-2H3,(H4,22,23,27)(H4,24,25,28);3*(H2,1,2,3,4)/t2*5-,6-,7+,8-,9-,10-,11+,12-,13-,14+,15+,16-,17-,18-,21+;;;/m00.../s1
1.8 InChkey
QTENRWWVYAAPBI-YCRXJPFRSA-N
1.9 Canonical Smiles
CC1C(C(C(O1)OC2C(C(C(C(C2O)O)N=C(N)N)O)N=C(N)N)OC3C(C(C(C(O3)CO)O)O)NC)(C=O)O.CC1C(C(C(O1)OC2C(C(C(C(C2O)O)N=C(N)N)O)N=C(N)N)OC3C(C(C(C(O3)CO)O)O)NC)(C=O)O.OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O
1.10 Isomers 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.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.OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O
2. Properties
3.1 Density
1.2302 (rough estimate)
3.1 Boiling point
948.2 °C at 760 mmHg
3.1 Refractive index
-85 ° (C=1, H2O)
3.1 Flash Point
527.3 °C
3.1 PSA
911.80000
3.1 logP
-8.65400
3.1 Solubility
H2O: 0.1?g/mL, clear
3.2 Appearance
White to off-white powder
3.3 Storage
Store at -20°C.
3.4 Chemical Properties
White or white-like powder, odorless, slightly bitter taste, hygroscopic, soluble in water, easily soluble in water and relatively stable, insoluble in ethanol or chloroform, be stable under dry condition, can be sealed from light for more than four years with efficacy unchanged, the aqueous solution can be stored at room temperature pH3~7 for 2 to 4 weeks, in the case of acid, alkali, oxidizing agents, it is easily damaged and lose effect.
3.5 Color/Form
white to off-white
3.6 PH
pH (100g/l, 25℃) : 4.5~7.0
3.7 Water Solubility
Water solubility: 0.1 g/mL, clear
3.8 Spectral Properties
MAX ABSORPTION (0.2 M H3BO3): 280 NM (A= 2, 1%, 1 CM); (PH 9.4 BORATE BUFFER): 318 NM (A= 2, 1%, 1 CM)
3.9 Stability
Stable. Incompatible with strong oxidizing agents.
3.10 StorageTemp
2-8°C
3. Use and Manufacturing
4.1 General Description
An antibacterial. White to light gray or pale buff powder with faint amine-like odor.
4.2 Purification Methods
The sulfate is recrystallised from H2O/EtOH, washed with a little EtOH, Et2O and dried in a vacuum. [UV and IR: Grove & Randall Antibiotics Monographs 2 163 1855, Heuser et al. J Am Chem Soc 75 4013 1953, Kuehl et al. J Am Chem Soc 68 1460 1946, Regna et al. J Biol Chem 165 631 1946.] During protein synthesis it inhibits initiation and causes misreading of mRNA [Zierhut et al. Eur J Biochem 98 577 1979, Chandra & Gray Methods Enzymol 184 70 1990]. [Beilstein 18/11 V 82.] Streptomycin sulfate Preparation Products And Raw materials Raw materials
4.3 Usage
It is used for treating tuberculosis, Brinell and non-hemolytic hammer bacillus caused infectious endocarditis, plague and tularemia, Haemophilus influenzae and gram-negative bacilli caused infections.
4. Safety and Handling
5.1 Symbol
GHS07, GHS08
5.1 Hazard Codes
Xn,Xi
5.1 Signal Word
Warning
5.1 Risk Statements
22-36/37/38-63-42/43
5.1 Safety Statements
26-36-36/37-45-22-60
5.1 Exposure Standards and Regulations
A tolerance of zero is established for residues of streptomycin in the uncooked edible tissues of chickens, turkeys, and swine, and in eggs.
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
5.2 Fire Hazard
Flash point data for Streptomycin sulfate are not available, however Streptomycin sulfate is probably combustible.
5.3 Hazard Declaration
H302-H361
5.3 DisposalMethods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Streptomycin is unstable to heat and does not accumulate in the soil. Therefore, disposal by incineration or burial should not result in harm to the environment. Recommendable methods: Incineration & landfill. Not recommendable method: Discharge to sewer. Peer review: Do not landfill in a recognizable form. (Peer-review conclusions of an IRPTC expert consultation (May 1985))
5.4 RIDADR
OTH
5.4 Safety Profile
Poison by ingestion and intravenous routes. Moderately toxic by subcutaneous route. An experimental teratogen. Human systemic effects by intraperitoneal route: flaccid paralysis without anesthesia, motor activity changes and pulmonary changes. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and SOx. See also STREPTOMYCIN and SULFATES.
5.5 Caution Statement
P281
5.5 Formulations/Preparations
STREPTOMYCIN SULFATE, USP, IS SUPPLIED FOR PARENTERAL INJECTION EITHER AS A STERILE DRY POWDER OR IN STERILE SOLN. EACH VIAL CONTAINS THE EQUIV OF 1 OR 5 G OF THE BASE; SOLN, WHICH ARE STABLE FOR MONTHS, CONTAIN 500 MG/ML. /STREPTOMYCIN SULFATE/
Streptomycin is usually avail as the trihydrochloride, trihydrochloride-calcium chloride double salt, phosphate, or sesquisulfate, which occurs as granules or powder.
Agrimycin 100: 15% streptomycin, 1.5% Terramycin (Oxytetracycline)... Dusts, 0.1-0.2%; Wettable powder 8.5-62.5%. May be combined with copper.
This antibiotic is marketed as the sulfate or nitrate under the trade names Agrimycin 17, AG-Strep, and Phytomycin by Pfizer, Merck, and Olin Mathieson.
Units: one unit equals one microgram of pure crystalline streptomycin base.
Combinations: Streptomycin-oxytetracycline mixture; streptomycin-tetracycline hydrochloride mixture
Agri-Mycin 17, Agri-Strep, Plantomycin
5.6 WGK Germany
3
5.6 RTECS
WK4990000
5.6 Safety

Moderately toxic by ingestion and subcutaneous routes. Human teratogenic effects by intramuscular route: developmental abnormalities of the eye and ear. When heated to decomposition it emits very toxic fumes of SOx and NOx. See also STREPTOMYCIN and SULFATES.

5.7 Specification

?Streptomycin sulfate , ever using CAS.:?298-39-5, its cas register number is 3810-74-0.

5.8 Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
hamster LD50 oral 400mg/kg (400mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: FOOD INTAKE (ANIMAL)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Toxicology and Applied Pharmacology. Vol. 14, Pg. 510, 1969.
infant TDLo intraperitoneal 170mg/kg (170mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
British Medical Journal. Vol. 1, Pg. 557, 1961.
mouse LD50 intravenous 90200ug/kg (90.2mg/kg) ? Antibiotiki. Vol. 18, Pg. 444, 1973.
mouse LD50 oral 430mg/kg (430mg/kg) ? "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 106, 1982.
mouse LD50 subcutaneous 403mg/kg (403mg/kg) ? Antibiotics Annual. Vol. 4, Pg. 574, 1956/1957.
rat LD50 oral 430mg/kg (430mg/kg) ? "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 106, 1982.
rat LD50 subcutaneous 600mg/kg (600mg/kg) ? Arzneimittel-Forschung. Drug Research. Vol. 12, Pg. 597, 1962.

?

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H317 May cause an allergic skin reaction

H335 May cause respiratory irritation

Precautionary statement(s)
Prevention

none

Response

none

Storage

none

Disposal

none

2.3 Other hazards which do not result in classification

none

6. Other Information
6.0 Usage
Inhibits initiation and causes misreading of rRNA in protein synthesis Streptomycin sulfate is used to study the mechanisms of streptomycin resistance. It is used to inhibit bacterial contamination in cell culture applications in association with penicillin. It is an antibiotic drug initially used for tuberculosis treatment. It inhibits protein synthesis by binding to 30S ribosomal subunit, which induces the misreading of the genetic code. It is involved in the initiation of translation of DNA, thereby results in death for a susceptible bacterium. Further, it controls bacterial and fungal diseases of certain fruit, vegetables, seed, ornamental crops and algae in ornamental ponds and aquaria
7. Computational chemical data
  • Molecular Weight: 1457.38g/mol
  • Molecular Formula: C42H84N14O36S3
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 1456.4334786
  • Monoisotopic Mass: 1456.4334786
  • Complexity: 1020
  • Rotatable Bond Count: 18
  • Hydrogen Bond Donor Count: 30
  • Hydrogen Bond Acceptor Count: 42
  • Topological Polar Surface Area: 922
  • Heavy Atom Count: 95
  • Defined Atom Stereocenter Count: 30
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 5
  • CACTVS Substructure Key Fingerprint: AAADcfB//gBgAAAAAAAAAAAAAAAAASJAAAA0aIEAAAAAAAAAAAAAHgAQCAAADHzxgAcDCALABoAoAAgQpDIAAAEAAAAAAIFIAAATEBYAwAAnQAAHMAAXAAHycA8KAAAAAAAAAAACgAAUCACgAAAAAAAAAA==
9. Realated Product Infomation