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Retapamulin

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Synopsis

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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, 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 Formula	C₃₀H₄₇NO₄S
Molecular Weight	517.8 g/mol
XLogP3	6.1
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	6
Exact Mass	517.32258015 g/mol
Monoisotopic Mass	517.32258015 g/mol
Topological Polar Surface Area	92.1 Å²
Heavy Atom Count	36
Formal Charge	0
Complexity	895
Isotope Atom Count	0
Defined Atom Stereocenter Count	10
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Altabax
PubMed Health	Retapamulin (On the skin)
Drug Classes	Antibacterial
Drug Label	ALTABAX 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 Ingredient	Retapamulin
Dosage Form	Ointment
Route	Topical
Strength	1%
Market Status	Prescription
Company	Glaxo Grp

2 of 2
Drug Name	Altabax
PubMed Health	Retapamulin (On the skin)
Drug Classes	Antibacterial
Drug Label	ALTABAX 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 Ingredient	Retapamulin
Dosage Form	Ointment
Route	Topical
Strength	1%
Market Status	Prescription
Company	Glaxo 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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