Pirlimycin
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Basic information
- CAS
78822-40-9- Standard SMILES
CC[C@@H]1CCN[C@H](C(=O)N[C@@H]([C@H]2O[C@H](SC)[C@H](O)[C@@H](O)[C@H]2O)[C@H](C)Cl)C1- InChIKey
HBJOXQRURQPDEX-MHXMMLMNSA-N- Molecular formula
- C17H31ClN2O5S
- Average molar mass
- 410.964 g/mol
- Monoisotopic mass
- 410.16422077
Names & identifiers
- Preferred name
- Pirlimycin
- IUPAC
- Methyl 7-chloro-6,7,8-trideoxy-6-{[(2S,4R)-4-ethylpiperidine-2-carbonyl]amino}-1-thio-L-threo-alpha-D-galacto-octopyranoside
- English name
- Pirlimycin
- Molecular formula
- C17H31ClN2O5S
- Molecular weight
- 410.96
Names & synonyms
pyrimycinPirlimycinPirlimycinaPirlimycinePirlimycinumPirlimycine [inn-french]Pirlimycinum [inn-latin]Pirlimycina [inn-spanish]Dexamethasone-4,6α,21,21-dMethyl 7-chloro-6,7,8-trideoxy-6-[[[(2S,4R)-4-ethyl-2-piperidinyl]carbonyl]amino]-1-thio-L-threo-α-D-galacto-octopyranoside
Database identifiers
- CAS
78822-40-9、79548-73-5- PubChem CID
- 157385
- DTXSID
DTXSID30904249- ChEMBL
CHEMBL1652611- UNII
- LM19JT6G5K
- Nikkaji
- J32.482E
Properties
Physicochemical properties
- Boiling point
- 643.9 · 643.9±55.0 °C(Predicted)
- Density
- 1.31 · 1.31
- storage temp.
- -20 °C · Store at -20°C
- solubility
- Soluble in ethanol;Soluble in methanol;Soluble in DMSO;Soluble in dimethyl formamide
- form
- solid
- pka
- 12.88 · 12.88±0.70(Predicted)
- Stability
- Hygroscopic
- FDA 21 CFR
- 556.515 · 556.515
- FDA UNII
- 19 JT6G5K · LM19JT6G5K
Chemistry & industry
Applications
UsesPirlimycin is a semi-synthetic lincosamide prepared from clindamycin by hydrolysing the propyl N-methylproline and re-annealing a 4-ethylpipecolic acid. Pirlimycin is more hydrophobic than clindamycin and is more potent against a number of important pathogens. Like other members of the lincosamide family, pirlimycin is a broad spectrum antibiotic with activity against anaerobic bacteria and protozoans. Pirlimycin acts by binding to the 23S ribosomal subunit, blocking protein synthesis. Pirlimycin has been less extensively researched than the older lincosamides.
Upstream & downstream products
Upstream raw materials
Downstream products
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