CAS 22189-32-8|Spectinomycin dihydrochloride pentahydrate

Introduction：Basic information about CAS 22189-32-8|Spectinomycin dihydrochloride pentahydrate, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Preparation
7. Articles39
8. Synonyms

Common Name	Spectinomycin dihydrochloride pentahydrate
CAS Number	22189-32-8	Molecular Weight	495.348
Density	/	Boiling Point	583.1ºC at 760 mmHg
Molecular Formula	C₁₄H₃₆Cl₂N₂O₁₂	Melting Point	205-207° (dec)
MSDS	ChineseUSA	Flash Point	306.4ºC

Names

Name	spectinomycin hydrochloride hydrate
Synonym	More Synonyms

BiologicalActivity

Description	Spectinomycin dihydrochloride pentahydrate is a broad-spectrum aminocyclitol antibiotic that inhibits the growth of a variety of gram-positive and gram-negative organisms.
Related Catalog	Signaling Pathways >>Anti-infection >>BacterialResearch Areas >>Infection
In Vitro	Spectinomycin selectively inhibits protein synthesis in cells and in extracts of Escherichia coli. When added to an exponentially growing culture, spectinomycin (50 μg/mL) rapidly and reversibly inhibits growth of Escherichia coli. Amino acid incorporation is slowed immediately but RNA synthesis continued. In extracts of Escherichia coli B, spectinomycin inhibits polypeptide synthesis directed either by endogenous messenger RNA or by MS-2 bacteriophage RNA. Maximum inhibition (70 to 80%) is achieved at 1 μg/mL (3 μM). [1]. Spectinomycin blocks the translocation of peptidyl-tRNAs from the A-site to the P-site by inhibiting the binding of elongation factor G to the ribosome. Spectinomycin interacts specifically with the residues G1064 and 01192 in 16S rRNA and potentially change this molecule into an inactive conformation[2]. Spectinomycin acts as a mixed noncompetitive inhibitor for the td intron RNA with a Ki of 7.2 mM. The splicing inhibition by spectinomycin is dependent on pH changes and Mg2+ concentration, indicating electrostatic interactions with the intron RNA[3].
In Vivo	Renal excretion is a major elimination pathway for spectinomycin. Following IV administration, approximately 55% of the drug is excreted into the urine in unchanged form. After IV administration of 10 mg/kg spectinomycin shows a peak plasma concentration of 37.8 μg/mL and a systemic exposure (area-under the curve AUC0-∞) of 15.7 μg/mL. Following single dose intramuscular administration, the overall elimination half-life of spectinomycin is 1.2 h in cattle, 1.0 h in sheep, 1.0 h in pigs, 1.65 h in chicken and 1.85 h in humans[4].
Animal Admin	Rats: Spectinomycin (10 mg/kg) is administered intravenously to rats. Serial blood samples (approx. 250 μL) are collected pre-dose, and at 0.25, 0.5, 0.75, 1.0, 1.5, 2.0, 4.0, 6.0, 8.0, 12.0, 24.0, 36.0 and 48.0 h post-dose. Plasma is separated immediately by centrifugation (10,000g for 5 min at 4°C) and stored at −80°C until analysis. Urine samples are collected at an interval of 0-6, 6-12, 12-24, 24-36 and 36-48 h post-dose and stored at −80°C until analysis[4].
References	[1]. Davies J, et al. Inhibition of protein synthesis by spectinomycin. Science. 1965 Sep 3;149(3688):1096-8. [2]. Brink MF, et al. Spectinomycin interacts specifically with the residues G1064 and C1192 in 16S rRNA, thereby potentially freezing this molecule into an inactive conformation. Nucleic Acids Res. 1994 Feb 11;22(3):325-31. [3]. Park IK, et al. Spectinomycin inhibits the self-splicing of the group 1 intron RNA. Biochem Biophys Res Commun. 2000 Mar 16;269(2):574-9. [4]. Madhura DB, et al. Pharmacokinetic profile of spectinomycin in rats. Pharmazie. 2013 Aug;68(8):675-6.

Chemical & Physical Properties

Boiling Point	583.1ºC at 760 mmHg
Melting Point	205-207° (dec)
Molecular Formula	C₁₄H₃₆Cl₂N₂O₁₂
Molecular Weight	495.348
Flash Point	306.4ºC
Exact Mass	494.164520
PSA	175.66000
Vapour Pressure	5.05E-16mmHg at 25°C
InChIKey	UJEMGEUVWHFXGB-XYQGXRRISA-N
SMILES	CNC1C(O)C(NC)C2OC3(O)C(=O)CC(C)OC3OC2C1O.Cl.O
Storage condition	2~8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: WG7400000

CHEMICAL NAME :: Spectinomycin, dihydrochloride, pentahydrate

CAS REGISTRY NUMBER :: 22189-32-8

LAST UPDATED :: 199706

DATA ITEMS CITED :: 13

MOLECULAR FORMULA :: C14-H24-N2-O7.2Cl-H.5H2-O

MOLECULAR WEIGHT :: 494.41

WISWESSER LINE NOTATION :: T C666 BO DO GV IOTJ E1 HQ KM1 LQ MM1 NQ &GH 2 &QH 5

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity)

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 29,43,1976

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2020 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 29,43,1976

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 29,43,1976

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >2500 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity)

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 29,43,1976

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >10 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity)

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 29,43,1976

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2350 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 29,43,1976

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 8400 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 29,43,1976

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity)

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 29,43,1976 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 6800 mg/kg/39D-I

TOXIC EFFECTS :: Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Kidney, Ureter, Bladder - other changes

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 29,43,1976

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2800 mg/kg/32D-I

TOXIC EFFECTS :: Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Endocrine - changes in adrenal weight

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 29,43,1976 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 2400 mg/kg

SEX/DURATION :: female 9-14 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 8,3018,1974

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 2400 mg/kg

SEX/DURATION :: female 7-12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - eye/ear

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 8,3008,1974 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X6089 No. of Facilities: 17 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 958 (estimated) No. of Female Employees: 434 (estimated)

Safety Information

Personal Protective Equipment	Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes	T+
Safety Phrases	24/25
RIDADR	NONH for all modes of transport
WGK Germany	2
RTECS	WG7400000
HS Code	29419090

Preparation

Articles39

Aminoglycoside analysis in food of animal origin with a zwitterionic stationary phase and liquid chromatography-tandem mass spectrometry.

Anal. Chim. Acta 882 , 127-39, (2015)

In this study, fourteen highly polar aminoglycoside (AGs) antibiotics were selected. Various stationary phases were tested, including Obelisc R, ZIC-HILIC, BEH amide and aminopropyl. The nature of the...

DrugBank 3.0: a comprehensive resource for 'omics' research on drugs.

Nucleic Acids Res. 39 , D1035-41., (2011)

DrugBank (http://www.drugbank.ca) is a richly annotated database of drug and drug target information. It contains extensive data on the nomenclature, ontology, chemistry, structure, function, action, ...

Molecular epidemiology of Neisseria gonorrhoeae isolates from Saskatchewan, Canada: utility of NG-MAST in predicting antimicrobial susceptibility regionally.

Sex. Transm. Infect. 90(4) , 297-302, (2014)

To investigate the molecular epidemiology of isolates of Neisseria gonorrhoeae from Saskatchewan, Canada, using Neisseria gonorrhoeae multi antigen sequence typing (NG-MAST), and to assess association...

Synonyms

4H-Pyrano[2,3-b][1,4]benzodioxin-4-one, decahydro-4a,7,9-trihydroxy-2-methyl-6,8-bis(methylamino)-, (2S,6R,7R,8S,9S)-, hydrochloride, hydrate (1:2:5)

4H-Pyrano[2,3-b][1,4]benzodioxin-4-one, decahydro-4a,7,9-trihydroxy-2-methyl-6,8-bis(methylamino)-, (2R,4aR,5aR,6S,7S,8R,9S,9aR,10aS)-, hydrochloride, hydrate (1:2:5)

MFCD00150886

spectogard

EINECS 244-554-3

(2R,4aR,5aR,6S,7S,8R,9S,9aR,10aS)-4a,7,9-Trihydroxy-2-methyl-6,8-bis(methylamino)decahydro-4H-pyrano[2,3-b][1,4]benzodioxin-4-one dihydrochloride pentahydrate

Spectinomycin pentahydrate dihydrochloride

ACTINOSPECTACIN DIHYDROCHLORIDE

Spectinomycin HCL USP/BP

Spectinomycin dihydrochloride pentahydrate

SPECTINOMYCIN 2HCL

(2S,6R,7R,8S,9S)-4a,7,9-Trihydroxy-2-methyl-6,8-bis(methylamino)decahydro-4H-pyrano[2,3-b][1,4]benzodioxin-4-one dihydrochloride pentahydrate

Trobicin (tn)

SPECTINOMYCIN HCL

Spectinomycin hydrochloride

SpectinomycinHydrochloride

Recommended......