Basic information
- CAS
53179-09-2- Standard SMILES
CN[C@@H]1[C@@H](O)[C@@H](O[C@@H]2[C@@H](O)[C@H](O[C@H]3OC(CN)=CC[C@H]3N)[C@@H](N)C[C@H]2N)OC[C@]1(C)O.CN[C@@H]1[C@@H](O)[C@@H](O[C@@H]2[C@@H](O)[C@H](O[C@H]3OC(CN)=CC[C@H]3N)[C@@H](N)C[C@H]2N)OC[C@]1(C)O.O=S(=O)(O)O.O=S(=O)(O)O.O=S(=O)(O)O.O=S(=O)(O)O.O=S(=O)(O)O- InChIKey
CIKNYWFPGZCHDL-ZHFUJENKSA-N- Molecular formula
- C38H84N10O34S5
- Average molar mass
- 1,385.5 g/mol
- Monoisotopic mass
- 1,384.3754956
Overview
Sisomicin Sulfate is the sulfate salt form of sisomicin, a broad-spectrum aminoglycoside antibiotic isolated from Micromonospora inyoensis. Sisomicin is strucurally similar to gentamicin but has a unique unsaturated diamino sugar. Of the aminoglycoside antibiotics, sisomicin has the greatest activity against gram-positive bacteria.
Names & identifiers
- Preferred name
- Sisomicin Sulfate
- IUPAC
- bis((2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol);sulfuric acid
- English name
- Sisomycin Sulfate
- Molecular formula
- C19H39N5O11S
- Molecular weight
- 545.61
Names & synonyms
Sisomicin sulfate53179-09-2Sch 13475 sulfateSisomicin SulphateSissomicin sulfateSch 13475 sulphateSCH-13475 SulfateK14444371CNSC-757315Sisomicin Sulfate (2:5) SaltD-Streptamine, (2S-cis)-4-O-(3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl)-2-deoxy-6-O-(3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl)-, sulfate (2:5) (salt)O-3-Deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-4)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1-6))-2-deoxy-L-streptamine sulfate (2:5) (salt)
Show more names
6)-o-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-d-glycero-hex-4-enopyranosyl-(1-4))sisominBaymicinSisollineextramycinpathomycinSisobioticsisomycinsulfate
DTXCID7025479RefChem:886368DTXSID9045479Sisomycin sulfateSisomicin sulfate saltBaymicineMensisoDisisomicin pentakis(sulphate)
Properties
Computed structural properties
- Topological polar surface area
- 842 Ų
- Hydrogen bond donors
- 26
- Hydrogen bond acceptors
- 44
- Rotatable bonds
- 12
- Heavy atoms
- 87
- Formal charge
- 0
- Complexity
- 724
Physicochemical properties
- Melting point
- 70 · 70-73C
- Boiling point
- 155 ℃ · 155℃
- Flash point
- 110 ° · >110°(230°F)
- storage temp.
- 2 · Keep in dark place,Inert atmosphere,2-8°C
- solubility
- 2 O: · H2O: soluble50mg/mL
- form
- powder
- color
- white to off-white
- optical activity
- 25 · [α]25/D 100 to 110° in water (Specific rotation (anhydrous), C=1)
- Water Solubility
- Soluble in water
- Merck
- 14 · 14,8550
- Stability
- Hygroscopic
- Major Application
- pharmaceutical (small molecule)
- InChIKey
- JVTNJDPXUPRGIE-QNJHHENCNA-N
- FDA UNII
- 14444371 C · K14444371C
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H312 (97.6%): Harmful in contact with skin [Warning Acute toxicity, dermal]
P203, P261, P271, P280, P302+P352, P304+P340, P317, P318, P321, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (97.6%)
Safety data
- wgk
- 3
- rtecs
- WK2288000
- hs_code
- 2941901010
- Toxicity
- LD50 in mice (mg/kg): 34 i.v., 221 i.p., 288 s.c. (Weinstein)
- risk_code
- 61-20/21/22-36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- T,Xi
- safety_code
- 53-22-36/37/39-45-36-26
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard statements
- H312+H332-H360
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationRepr. 1B
- Precautionary statements
- P202-P261-P280-P302+P352+P312-P304+P340+P312-P308+P313
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins.
Substances that inhibit the growth or reproduction of BACTERIA.
Applications
Usesantibacterial, binds to ribosomes
UsesSisomicin Sulfate Salt is an aminoglycoside antibiotic. It can also be used as reactant/reagent in structural and kinetics study of self-assembling macrocyclic dimer natural product aminoglycoside 66-40C and unnatural variants.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
南通飞宇生物科技有限公司
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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