Product Name

  • Name

    Retapamulin

  • EINECS 639-491-7
  • CAS No. 224452-66-8
  • Article Data4
  • CAS DataBase
  • Density 1.16±0.1 g/cm3(Predicted)
  • Solubility
  • Melting Point
  • Formula C30H47NO4S
  • Boiling Point 623.8 °C at 760 mmHg
  • Molecular Weight 517.773
  • Flash Point 331 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 224452-66-8 (Retapamulin)
  • Hazard Symbols
  • Synonyms Aceticacid, [[(3-exo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl]thio]-,(3aS,4R,5S,6S,8R,9R,9aR,10R)-6-ethenyldecahydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-3a,9-propano-3aH-cyclopentacycloocten-8-ylester (9CI);Altabax;Altargo;Mutilin14-(exo-8-methyl-8-azabicyclo[3.2.1]oct-3-ylsulfanyl)acetate;SB275833;Acetic acid, 2-[[(3-exo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl]thio]-, (3aS,4R,5S,6S,8R,9R,9aR,10R)-6-ethenyldecahydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-3a,9-propano-3aH-cyclopentacycloocten-8-yl ester;(3aS,4R,5S,6S,8R,9R,9aR,10R)-6-ethenyl-5-hydroxy-4,6,9,10-tetramethyl-1-oxodecahydro-3a,9-propano-3aH-cyclopenta[8]annulen-8-yl{[(1R,3s,5S)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl]sulfanyl}acetate;
  • PSA 92.14000
  • LogP 5.18920

Synthetic route

pleuromutilin tosylate
31716-01-5

pleuromutilin tosylate

C8H15NS*(x)ClH

C8H15NS*(x)ClH

retapamulin
224452-66-8

retapamulin

Conditions
ConditionsYield
With potassium carbonate In acetone at 45℃; for 20h; Temperature;91.2%
pleuromutilin tosylate
31716-01-5

pleuromutilin tosylate

C8H15NS*H2O4S

C8H15NS*H2O4S

retapamulin
224452-66-8

retapamulin

Conditions
ConditionsYield
With potassium carbonate In acetone at 50℃; for 12h;87.3%
(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]octane-3-thiol
848130-83-6

(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]octane-3-thiol

{(3aS,4R,5S,6S,8R,9R,9aR,10R)-6-ethenyldeca hydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-3a,9-propano-3aH-cyclopentacyclo-octen-8-yl methanesulfonyloxyacetate}
60924-38-1

{(3aS,4R,5S,6S,8R,9R,9aR,10R)-6-ethenyldeca hydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-3a,9-propano-3aH-cyclopentacyclo-octen-8-yl methanesulfonyloxyacetate}

retapamulin
224452-66-8

retapamulin

Conditions
ConditionsYield
With triethylamine In 4-methyl-2-pentanone at 20 - 40℃; for 2 - 24h; Product distribution / selectivity;80%
With sulfuric acid at 30℃; for 2h; Cooling with ice; Green chemistry;69.2%
With potassium carbonate In acetone at 20 - 40℃; for 2 - 24h; Product distribution / selectivity;
C31H49NO4S

C31H49NO4S

retapamulin
224452-66-8

retapamulin

Conditions
ConditionsYield
With hydrogenchloride; zinc(II) chloride In 1,4-dioxane at 15 - 30℃; Large scale;48.2%
(x)C4H6O6*C11H19NOS2

(x)C4H6O6*C11H19NOS2

retapamulin
224452-66-8

retapamulin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydroxide / ethanol / 2 h / 40 °C
1.2: pH 1 - 2
2.1: potassium carbonate / acetone / 20 h / 45 °C
View Scheme
C11H19NOS2*H2O4S

C11H19NOS2*H2O4S

retapamulin
224452-66-8

retapamulin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydroxide / ethanol / 1 h / 40 °C
1.2: pH 1 - 2
2.1: potassium carbonate / acetone / 12 h / 50 °C
View Scheme
C11H19NOS2*(x)ClH

C11H19NOS2*(x)ClH

retapamulin
224452-66-8

retapamulin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydroxide / ethanol / 1 h / 50 °C
1.2: pH 1 - 2
2.1: potassium carbonate / acetone / 20 h / 45 °C
View Scheme
pleuromutilin

pleuromutilin

retapamulin
224452-66-8

retapamulin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 4 h / 30 °C
2: potassium carbonate / acetone / 12 h / 50 °C
View Scheme
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 4 h / 30 °C
2: potassium carbonate / acetone / 20 h / 45 °C
View Scheme
3-tropanol
120-29-6

3-tropanol

retapamulin
224452-66-8

retapamulin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 5 h / -10 - 0 °C / Inert atmosphere
2.1: water / 2 h / 25 °C
2.2: pH 6 - 7
3.1: sodium hydroxide / ethanol / 1 h / 40 °C
3.2: pH 1 - 2
4.1: potassium carbonate / acetone / 12 h / 50 °C
View Scheme
Multi-step reaction with 4 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 5 h / -10 - 0 °C / Inert atmosphere
2.1: water / 2 h / 25 °C
2.2: pH 6 - 7
3.1: sodium hydroxide / ethanol / 1 h / 50 °C
3.2: pH 1 - 2
4.1: potassium carbonate / acetone / 20 h / 45 °C
View Scheme
Multi-step reaction with 4 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 5 h / -10 - 0 °C / Inert atmosphere
2.1: water / 3 h / 25 °C
2.2: pH 6 - 7
3.1: sodium hydroxide / ethanol / 2 h / 40 °C
3.2: pH 1 - 2
4.1: potassium carbonate / acetone / 20 h / 45 °C
View Scheme
(1R,3R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl-methane sulfonate
35130-97-3

(1R,3R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl-methane sulfonate

retapamulin
224452-66-8

retapamulin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: water / 2 h / 25 °C
1.2: pH 6 - 7
2.1: sodium hydroxide / ethanol / 1 h / 40 °C
2.2: pH 1 - 2
3.1: potassium carbonate / acetone / 12 h / 50 °C
View Scheme
Multi-step reaction with 3 steps
1.1: water / 2 h / 25 °C
1.2: pH 6 - 7
2.1: sodium hydroxide / ethanol / 1 h / 50 °C
2.2: pH 1 - 2
3.1: potassium carbonate / acetone / 20 h / 45 °C
View Scheme
Multi-step reaction with 3 steps
1.1: water / 3 h / 25 °C
1.2: pH 6 - 7
2.1: sodium hydroxide / ethanol / 2 h / 40 °C
2.2: pH 1 - 2
3.1: potassium carbonate / acetone / 20 h / 45 °C
View Scheme
Multi-step reaction with 3 steps
1: N,N-dimethyl-formamide / 1 h / 120 °C / Green chemistry
2: sodium hydroxide / ethanol / 24 h / Reflux; Green chemistry
3: sulfuric acid / 2 h / 30 °C / Cooling with ice; Green chemistry
View Scheme
(3aS,4R,5S,6S,8R,9R,9aR,10R)-4,6,9,10-tetramethyloctahydro-8-hydroxy-6-ethenyl-1-methoxy-3a,9-propano-3aH-cyclopentacycloocten-5-one

(3aS,4R,5S,6S,8R,9R,9aR,10R)-4,6,9,10-tetramethyloctahydro-8-hydroxy-6-ethenyl-1-methoxy-3a,9-propano-3aH-cyclopentacycloocten-5-one

retapamulin
224452-66-8

retapamulin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: pyridine / tert-butyl methyl ether / -15 - -10 °C / Large scale
1.2: -25 - -10 °C / Large scale
2.1: tetrabutylammomium bromide; sodium hydroxide / tert-butyl methyl ether; water / 10 - 30 °C / Large scale
3.1: zinc(II) chloride; hydrogenchloride / 1,4-dioxane / 15 - 30 °C / Large scale
View Scheme
tiamulin

tiamulin

retapamulin
224452-66-8

retapamulin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sulfuric acid / methanol / 0 - 50 °C / Inert atmosphere; Large scale
2.1: pyridine / tert-butyl methyl ether / -15 - -10 °C / Large scale
2.2: -25 - -10 °C / Large scale
3.1: tetrabutylammomium bromide; sodium hydroxide / tert-butyl methyl ether; water / 10 - 30 °C / Large scale
4.1: zinc(II) chloride; hydrogenchloride / 1,4-dioxane / 15 - 30 °C / Large scale
View Scheme

Retapamulin Specification

The Retapamulin, with the CAS registry number 224452-66-8, is also known as Acetic acid, 2-[[(3-exo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl]thio]-, (3aS,4R,5S,6S,8R,9R,9aR,10R)-6-ethenyldecahydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-3a,9-propano-3aH-cyclopentacycloocten-8-yl ester. This chemical's molecular formula is C30H47NO4S and molecular weight is 516.76. What's more, its systematic name is (3aS,4R,5S,6S,8R,9R,9aR,10R)-6-ethenyl-5-hydroxy-4,6,9,10-tetramethyl-1-oxodecahydro-3a,9-propano-3aH-cyclopenta[8]annulen-8-yl{[(1R,3s,5S)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl]sulfanyl}acetate. Its classification codes is Topical antibiotic for secondarily infected traumatic lesions (SITL) and secondarily infected dermatoses (SID) or impetigo. This chemical is approved by the United States Food and Drug Administration in April 2007 for the treatment of bacterial skin infections such as impetigo. In May 2007, it received approval in the EU from the European Medicines Agency for the same indication. It is a synthetic pleuromutilin.

Physical properties of Retapamulin are: (1)ACD/LogP: 5.006; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 2.50; (4)ACD/LogD (pH 7.4): 2.51; (5)ACD/BCF (pH 5.5): 11.79; (6)ACD/BCF (pH 7.4): 11.87; (7)ACD/KOC (pH 5.5): 39.54; (8)ACD/KOC (pH 7.4): 39.82; (9)#H bond acceptors: 5; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 105.97 Å2; (13)Flash Point: 331.042 °C; (14)Enthalpy of Vaporization: 105.899 kJ/mol; (15)Boiling Point: 623.766 °C at 760 mmHg; (16)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: CN5[C@H]1CC[C@@H]5C[C@@H](C1)SC(C([O-])=O)[C@@H]4C[C@@](C)(C=C)[C@@H](O)[C@H](C)[C@@]32CCC(=O)[C@H]2[C@@]4(C)[C@H](C)CC3
(2)Std. InChI: InChI=1S/C30H47NO4S/c1-7-28(4)16-22(24(27(34)35)36-21-14-19-8-9-20(15-21)31(19)6)29(5)17(2)10-12-30(18(3)26(28)33)13-11-23(32)25(29)30/h7,17-22,24-26,33H,1,8-16H2,2-6H3,(H,34,35)/p-1/t17-,18+,19-,20+,21+,22+,24?,25+,26+,28-,29+,30+/m1/s1
(3)Std. InChIKey: BTPDCEBXECTAID-CLLJVQIRSA-M

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