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Chemistry

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Also known as: 224452-66-8, Altabax, Altargo, Sb-275833, Sb 275833, Sb275833
Molecular Formula
C30H47NO4S
Molecular Weight
517.8  g/mol
InChI Key
STZYTFJPGGDRJD-FJJJPKKESA-N
FDA UNII
4MG6O8991R

Retapamulin
Retapamulin, marketed by GlaxoSmithKline as the ointment Altabax, is an antibiotic for skin infections like impetigo. It was approved by the FDA in April 2007.
Retapamulin is a Pleuromutilin Antibacterial.
1 2D Structure

Retapamulin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[(1S,2R,3S,4S,6R,7R,8R,14R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]sulfanyl]acetate
2.1.2 InChI
InChI=1S/C30H47NO4S/c1-7-28(4)16-24(35-25(33)17-36-22-14-20-8-9-21(15-22)31(20)6)29(5)18(2)10-12-30(19(3)27(28)34)13-11-23(32)26(29)30/h7,18-22,24,26-27,34H,1,8-17H2,2-6H3/t18-,19+,20-,21+,22?,24-,26+,27+,28-,29+,30+/m1/s1
2.1.3 InChI Key
STZYTFJPGGDRJD-FJJJPKKESA-N
2.1.4 Canonical SMILES
CC1CCC23CCC(=O)C2C1(C(CC(C(C3C)O)(C)C=C)OC(=O)CSC4CC5CCC(C4)N5C)C
2.1.5 Isomeric SMILES
C[C@@H]1CC[C@@]23CCC(=O)[C@H]2[C@@]1([C@@H](C[C@@]([C@H]([C@@H]3C)O)(C)C=C)OC(=O)CSC4C[C@H]5CC[C@@H](C4)N5C)C
2.2 Other Identifiers
2.2.1 UNII
4MG6O8991R
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 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

2. Altabax

3. Altargo

4. Sb 275833

5. Sb-275833

6. Sb275833

2.3.2 Depositor-Supplied Synonyms

1. 224452-66-8

2. Altabax

3. Altargo

4. Sb-275833

5. Sb 275833

6. Sb275833

7. Rebapamulin

8. 4mg6o8991r

9. Nsc-759885

10. [(1s,2r,3s,4s,6r,7r,8r,14r)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[[(1r,5s)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]sulfanyl]acetate

11. (3as,4r,5s,6s,8r,9r,9ar,10r)-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-6-vinyldecahydro-3a,9-propanocyclopenta[8]annulen-8-yl {[(3-exo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl]thio}acetate

12. (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

13. Acetic Acid, (((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

14. Unii-4mg6o8991r

15. Retapamulin [usan:inn:ban]

16. Retapamulin [mi]

17. Retapamulin [inn]

18. Retapamulin [usan]

19. Retapamulin [vandf]

20. Chembl1658

21. Retapamulin [mart.]

22. Retapamulin [who-dd]

23. Schembl365459

24. Retapamulin [ema Epar]

25. Gtpl11035

26. Retapamulin [orange Book]

27. Chebi:166679

28. (3as,4r,5s,6s,8r,9r,9ar,10r)-2-(exo-8-methyl-8-azabicyclo[3.2.1]octan-3-ylsulfanyl)acetic Acid 5-hydroxy-4,6,9,10-tetramethyl-1-oxo-6-vinylperhydro-3a,9-propanocyclopentacycloocten-8-yl Ester

29. Zinc3931840

30. Mfcd11045316

31. S4056

32. Akos016008865

33. Akos030485971

34. Zinc100013500

35. Zinc103660515

36. Ccg-269837

37. Cs-0618

38. Db01256

39. Nsc 759885

40. Ncgc00386248-01

41. Ac-26826

42. As-11455

43. Hy-17010

44. Ab01566905_01

45. 452r668

46. A851322

47. Q7316645

48. Brd-k33082088-001-03-3

49. (1s,2r,3s,4s,6r,7r,8r,14r)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0^{1,8}]tetradecan-6-yl 2-{[(1r,5s)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]sulfanyl}acetate

50. (3ar,4r,5r,7s,8s,9r,9as,12r)-8-hydroxy-4,7,9,12-tetramethyl-5-((3-(((3-exo)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl)thio)prop-1-en-2-yl)oxy)-7-vinyloctahydro-4,9a-propanocyclopenta[8]annulen-3(3ah)-one

51. (3as,4r,5s,6s,8r,9r,9ar,10r)-6-ethenyl-5-hydroxy-4,6,9,10-tetramethyl-1-oxodecahydro-3a,9-propanocyclopenta[8]annulen-8-yl {[(3-exo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl]sulfanyl}acetate

52. [(1s,2r,3s,4s,6r,7r,8r,14r)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[[(1r,5s)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]sulanyl]acetate

2.4 Create Date
2006-07-28
3 Chemical and Physical Properties
Molecular Weight 517.8 g/mol
Molecular Formula C30H47NO4S
XLogP36.1
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count6
Rotatable Bond Count6
Exact Mass517.32258015 g/mol
Monoisotopic Mass517.32258015 g/mol
Topological Polar Surface Area92.1 Ų
Heavy Atom Count36
Formal Charge0
Complexity895
Isotope Atom Count0
Defined Atom Stereocenter Count10
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameAltabax
PubMed HealthRetapamulin (On the skin)
Drug ClassesAntibacterial
Drug LabelALTABAX contains retapamulin, a semisynthetic pleuromutilin antibiotic. The chemical name of retapamulin is acetic acid, [[(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-tetrame...
Active IngredientRetapamulin
Dosage FormOintment
RouteTopical
Strength1%
Market StatusPrescription
CompanyGlaxo Grp

2 of 2  
Drug NameAltabax
PubMed HealthRetapamulin (On the skin)
Drug ClassesAntibacterial
Drug LabelALTABAX contains retapamulin, a semisynthetic pleuromutilin antibiotic. The chemical name of retapamulin is acetic acid, [[(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-tetrame...
Active IngredientRetapamulin
Dosage FormOintment
RouteTopical
Strength1%
Market StatusPrescription
CompanyGlaxo Grp

4.2 Drug Indication

For use in adults and pediatric patients aged 9 months and older for the topical treatment of impetigo (up to 100 cm2 in total area in adults or 2% total body surface area in pediatric patients aged 9 months or older) due to Staphylococcus aureus (methicillin-susceptible isolates only) or Streptococcus pyogenes.


Short term treatment of the following superficial skin infections:

- impetigo;

- infected small lacerations, abrasions or sutured wounds.

See sections 4. 4 and 5. 1 for important information regarding the clinical activity of retapamulin against different types of Staphylococcus aureus.

Consideration should be given to official guidance on the appropriate use of antibacterial agents.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Retapamulin is a semisynthetic pleuromutilin antibiotic. This drug is usually bacteriostatic in action, but may become bactericidal at highed concentrations (when MBC is 1000 times higher than MIC). Retapamulin acts by selectively inhibiting the initiation of protein synthesis in bacteria at the level of bacterial 50S ribosome.


5.2 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
RETAPAMULIN
5.3.2 FDA UNII
4MG6O8991R
5.3.3 Pharmacological Classes
Pleuromutilin Antibacterial [EPC]; Diterpenes [CS]
5.4 ATC Code

D06AX13


D - Dermatologicals

D06 - Antibiotics and chemotherapeutics for dermatological use

D06A - Antibiotics for topical use

D06AX - Other antibiotics for topical use

D06AX13 - Retapamulin


5.5 Metabolism/Metabolites

In vitro studies with human liver microsomes demonstrated that retapamulin is extensively metabolized to numerous metabolites, of which the predominant routes of metabolism were mono-oxygenation and N-demethylation. The major enzyme responsible for metabolism of retapamulin in human liver microsomes was cytochrome P450 3A4 (CYP3A4).


5.6 Mechanism of Action

Retapamulin is a bacterial protein synthesis inhibitor belonging to a class of compounds called pleuromutilins. These compounds inhibit the initiation of protein synthesis by binding to a specific site on the 50S subunit of bacterial ribosome (domain V of 23S rRNA). This binding site involves ribosomal protein L3 and is in the region of the ribosomal P site and peptidyl transferase center. By virtue of binding to this site, pleuromutilins inhibit peptidyl transfer, block P-site interactions, and prevent the normal formation of active 50S ribosomal subunits.


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29-Jun-2022
29-Jun-2022
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