U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C30H47NO4S
Molecular Weight 517.763
Optical Activity UNSPECIFIED
Defined Stereocenters 11 / 11
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RETAPAMULIN

SMILES

[H][C@@]12C(=O)CC[C@]13CC[C@@H](C)[C@@]2(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]3C)OC(=O)CS[C@H]4C[C@@H]5CC[C@H](C4)N5C

InChI

InChIKey=STZYTFJPGGDRJD-NHUWBDDWSA-N
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

HIDE SMILES / InChI
Molecular Formula C30H47NO4S
Molecular Weight 517.763
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 11 / 11
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Retapamulin is a topical antibiotic which was approved by FDA (Altabax brand name) for the treatment of impetigo due to Staphylococcus aureus (methicillin-susceptible isolates only) or Streptococcus pyogenes. Retapamulin exerts its antibacterial action by binding to 50S subunit of the bacterial ribosome.

Originator

Smithkline Beecham
6
Curator's Comment: Now a part of GlaxoSmithKline.

Approval Year

2007
205
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
ALTABAX

Approved Use

ALTABAX is indicated 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.

Launch Date

2007
Curative
Approved
8429
ALTABAX

Approved Use

ALTABAX is indicated 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.

Launch Date

2007
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.5 ng/mL
REVIEW
https://pubmed.ncbi.nlm.nih.gov/18416589/
1 % 1 times / day multiple, topical
dose: 1 %
route of administration: Topical
experiment type: MULTIPLE
co-administered:
RETAPAMULIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
49.6 ng × h/mL
REVIEW
https://pubmed.ncbi.nlm.nih.gov/18416589/
1 % 1 times / day multiple, topical
dose: 1 %
route of administration: Topical
experiment type: MULTIPLE
co-administered:
RETAPAMULIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
6%
REVIEW
https://pubmed.ncbi.nlm.nih.gov/18416589/
1 % 1 times / day multiple, topical
dose: 1 %
route of administration: Topical
experiment type: MULTIPLE
co-administered:
RETAPAMULIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1 % 2 times / day multiple, topical
Recommended
Dose: 1 %, 2 times / day
Route: topical
Route: multiple
Dose: 1 %, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022055s004lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: impetigo due to Staphylococcus aureus (methicillin-susceptible isolates only) or Streptococcus pyogenes
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022055s004lbl.pdf
Page: p.1
Disc. AE: Skin irritation, Sensitization...
AEs leading to
discontinuation/dose reduction:
Skin irritation (severe)
Sensitization
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022055s004lbl.pdf
Page: p.1
AEs

AEs

AESignificanceDosePopulation
Sensitization Disc. AE
1 % 2 times / day multiple, topical
Recommended
Dose: 1 %, 2 times / day
Route: topical
Route: multiple
Dose: 1 %, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022055s004lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: impetigo due to Staphylococcus aureus (methicillin-susceptible isolates only) or Streptococcus pyogenes
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022055s004lbl.pdf
Page: p.1
Skin irritation severe
Disc. AE
1 % 2 times / day multiple, topical
Recommended
Dose: 1 %, 2 times / day
Route: topical
Route: multiple
Dose: 1 %, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022055s004lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: impetigo due to Staphylococcus aureus (methicillin-susceptible isolates only) or Streptococcus pyogenes
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022055s004lbl.pdf
Page: p.1
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1737

inhibitor
1587
substrate
1037

inhibitor
1767
substrate
1217

inhibitor
1852
inhibitor
1612

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
1524

CYP2A6
707

CYP2B6
810

CYP2C8
911

CYP2C19
1478

P-gp
1461
CYP3A5
395

CYP1A2
1054

CYP2C19
991

CYP2C8
693

P-gp
1537
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
1925
 weak [IC50 1.1 uM]
unlikely (co-administration study)
Comment: retapamulin inhibited CYP3A4 isoenzyme activity, IC50 ranged from 1.1 uM with midazolam to 6.2 uM with nifedipine; I/Ki ratios are less than 0.1 for all CYP P450 isoenzymes and no clinically relevant DDI are anticipated when retapamulin is coadministered with other drugs metabolized by CYPs
Page: 6.0
P-gp
1650
 weak [IC50 28.2 uM]
unlikely (co-administration study)
Comment: in vitro inhibitor of digoxin transport by P-gp with a calculated IC50 value of 28.2 uM; it is unlikely that retapamulin will inhibit P-gp mediated transport of co-administered drugs
Page: 5, 6
CYP1A2
1692
 weak [IC50 >99 uM]
CYP2A6
739
 weak [IC50 >99 uM]
CYP2B6
1001
 weak [IC50 >99 uM]
CYP2C19
1553
 weak [IC50 >99 uM]
CYP2C8
965
 weak [IC50 >99 uM]
CYP2C9
1819
 weak [IC50 >99 uM]
CYP2D6
1891
 weak [IC50 >99 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
1737
 major
yes (co-administration study)
Comment: coadministration with ketaconazole increased retapamulin Cmax by 80% and AUC by 77%
Page: 5.0
CYP2C8
693
 minor
CYP2D6
1217
 minor
CYP1A2
1054
 no
CYP2C19
991
 no
CYP2C9
1037
 no
CYP3A5
395
 yes
P-gp
1537
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1647
Sourcing

Sourcing

Vendor/AggregatorIDURL
AA Blocks
AA0039HR
https://www.aablocks.com/goods/Goods/detail?id=AA0039HR
AEchem Scientific Corp., USA
AE1-017412
http://www.aechemsc.com/info_products/AE1-017412.php
AK Scientific, Inc. (AKSCI)
66719
http://www.aksci.com/item_detail.php?cat=66719
Aaron Chemicals
AR003A9J
http://www.aaronchem.com/224452-66-8
AbMole Bioscience
M2974
http://www.abmole.com/products/retapamulin.html
Achemtek
0102-014536
http://www.achemtek.com/224452-66-8
Ambeed
A195059
https://www.ambeed.com/products/224452-66-8.html
ApexBio Technology
B2019
http://www.apexbt.com/retapamulin.html
AstaTech, Inc.
36342
http://www.astatechinc.com/CPSResult.php?CRNO=36615
Aurora Fine Chemicals LLC
A13.110.966
http://online.aurorafinechemicals.com/info?ID=A13.110.966
Aurora Fine Chemicals LLC
A24.091.139
http://online.aurorafinechemicals.com/info?ID=A24.091.139
Aurum Pharmatech LLC
MP-0763
http://www.Aurumpharmatech.com/Product/ProductDetails/MP_0763
BLD Pharm
BD223980
http://www.bldpharm.com/products/224452-66-8.html
Boerchem
BC677692
http://www.boerchem.com/?product_39573.html
CSNpharm
CSN12909
https://www.csnpharm.com/products/retapamulin.html
Chem Scene
CS-0618
http://www.chemscene.com/224452-66-8.html
ChemMol
44009997
http://www.chemmol.com/chemmol/44009997.html
ChemMol
99062376
http://www.chemmol.com/chemmol/99062376.html
Chemspace
CSSB00020618600
https://chem-space.com/CSSB00020618600
Chemspace
CSSB00020629312
https://chem-space.com/CSSB00020629312
Combi-Blocks
QB-7392
http://www.combi-blocks.com/cgi-bin/find.cgi?QB-7392
Glentham Life Sciences
GA4340
http://www.glentham.com/products/product/GA4340/
Hairui
HR34097
http://www.hairuichem.com/en/product/224452-66-8.html
Lab Network
LN02127170
https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN02127170
Matrix Scientific
98144
https://www.matrixscientific.com/098144.html
MedChem Express
HY-17010
https://www.medchemexpress.com/Retapamulin.html
MolPort
MolPort-006-167-754
https://www.molport.com/shop/molecule-link/MolPort-006-167-754
MolPort
MolPort-023-220-081
https://www.molport.com/shop/molecule-link/MolPort-023-220-081
MuseChem
A000673
https://www.musechem.com/product/A000673.html
OChem
25925
http://www.ocheminc.com/index.php?act=psearch&pid=452R668
Oakwood
361956
http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=150814&ExtHyperLink=1
Renno Tech
RL02708
http://www.rennotech.com/product_show.asp?id=2957
Selleck Chemicals
S4056
http://www.selleckchem.com/products/retapamulin.html
Sigma-Aldrich
CDS023386_ALDRICH
https://www.sigmaaldrich.com/catalog/product/aldrich/cds023386?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
TripleBond
CR0022
http://www.triplebond-canada.com/prod/1562/
Yuhao Chemical
LX2351
http://www.chemyuhao.com/224452-66-8.html
abcr GmbH
AB450172
http://www.abcr.com/shop/en/AB450172
eNovation Chemicals
D320205
https://www.enovationchem.com/ProductDetails.asp?ProductID=D320205
iChemical
EBD3585
http://www.ichemical.com/products/224452-66-8.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
PubMed

PubMed

TitleDatePubMed
Gateways to clinical trials.
2006 Oct
In vitro activity against anaerobes of retapamulin, a new topical antibiotic for treatment of skin infections.
2007 Apr
New drugs: retapamulin, bismuth subcitrate potassium, and rotigotine.
2007 Jul-Aug
Gateways to clinical trials.
2007 May
Altabax (retapamulin ointment), 1%.
2007 Sep-Oct
Spotlight on retapamulin in impetigo and other uncomplicated superficial skin infections.
2008
Retapamulin for impetigo and other infections.
2008 Oct
Agents for the decolonization of methicillin-resistant Staphylococcus aureus.
2009 Mar
The pleuromutilin antibiotics: a new class for human use.
2010 Feb
Patents

Patents

20070116729
157

Sample Use Guides

In Vivo Use Guide
A thin layer of retapamulin (Altabax) should be applied to the affected area (up to 100 cm2 in total area in adults or 2% total body surface area in pediatric patients aged 9 months or older) twice daily for 5 days.
Route of Administration: Topical
In Vitro Use Guide
In vitro activity of retapamulin was determinde against methicillin-susceptible Staphylococcus aureus (MSSA), methicillin-resistant S. aureus (MRSA), and linezolid and methicillin-resistant S. aureus (LR-MRSA). MSSA and MRSA isolates were susceptible to retapamulin, with an MIC90 of 0.094 mg/L and 0.125 mg/L respectively, but retapamulin MICs for the 18 LR-MRSA strains were over 32 mg/L in all cases.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:45:10 GMT 2023
Edited
by admin
on Fri Dec 15 15:45:10 GMT 2023
Record UNII
4MG6O8991R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RETAPAMULIN
EMA EPAR   INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
retapamulin [INN]
Common Name English
RETAPAMULIN [MI]
Common Name English
ALTABAX
Brand Name English
RETAPAMULIN [EMA EPAR]
Common Name English
SB275833
Code English
RETAPAMULIN [MART.]
Common Name English
(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
Common Name English
SB-275833
Code English
RETAPAMULIN [ORANGE BOOK]
Common Name English
RETAPAMULIN [USAN]
Common Name English
RETAPAMULIN [VANDF]
Common Name English
ALTARGO
Brand Name English
Retapamulin [WHO-DD]
Common Name English
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
Common Name English
NSC-759885
Code English
Classification Tree Code System Code
WHO-ATC D06AX13
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
WHO-VATC QD06AX13
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
NDF-RT N0000175434
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
NDF-RT N0000175433
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
NCI_THESAURUS C258
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
EMA ASSESSMENT REPORTS ALTARGO(AUTHORIZED IMPETIGO)
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
Code System Code Type Description
FDA UNII
4MG6O8991R
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
PRIMARY
WIKIPEDIA
RETAPAMULIN
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
PRIMARY
EPA CompTox
DTXSID00870265
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
PRIMARY
INN
8494
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
PRIMARY
CAS
224452-66-8
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
PRIMARY
DRUG BANK
DB01256
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
PRIMARY
MESH
C508887
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
PRIMARY
EVMPD
SUB25391
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
PRIMARY
RXCUI
642274
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
PRIMARY RxNorm
SMS_ID
100000089366
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
PRIMARY
MERCK INDEX
m9551
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
PRIMARY Merck Index
USAN
PP-62
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
PRIMARY
NSC
759885
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
PRIMARY
NCI_THESAURUS
C61924
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
PRIMARY
DAILYMED
4MG6O8991R
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
PRIMARY
ChEMBL
CHEMBL409542
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
PRIMARY
DRUG CENTRAL
2371
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
PRIMARY
LACTMED
Retapamulin
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
PRIMARY
Related Record Type Details
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METABOLIC ENZYME -> SUBSTRATE
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TARGET ORGANISM->INHIBITOR
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METABOLIC ENZYME -> SUBSTRATE
MAJOR
STAPHYLOCOCCUS AUREUS
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Related Record Type Details
Structure of (3AR,4R,5S,6S,8R,9R,9AS,10R,12R)-5,12-DIHYDROXY-4,6,9,10-TETRAMETHYL-1-OXO-6-VINYLDECAHYDRO-3A,9-PROPANOCYCLOPENTA(8)ANNULEN-8-YL 2-(((1R,3S,5S)-8-AZABICYCLO(3.2.1)OCTAN-3-YL)THIO)ACETATE
METABOLITE -> PARENT
Structure of (2S,3AR,4R,5S,6S,8R,9R,9AS,10R,12R)-2,5,12-TRIHYDROXY-4,6,9,10-TETRAMETHYL-1-OXO-6-VINYLDECAHYDRO-3A,9-PROPANOCYCLOPENTA(8)ANNULEN-8-YL 2-(((1R,3S,5S)-8-METHYL-8-AZABICYCLO(3.2.1)OCTAN-3-YL)THIO)ACETATE
METABOLITE -> PARENT
Structure of (3AR,4R,5R,7S,8S,9R,9AS,12R)-8-HYDROXY-4,7,9,12-TETRAMETHYL-3-OXO-7-VINYLDECAHYDRO-4,9A-PROPANOCYCLOPENTA(8)ANNULEN-5-YL 2-((R)-((1R,3S,5S)-8-METHYL-8-AZABICYCLO(3.2.1)OCTAN-3-YL)SULFINYL)ACETATE
METABOLITE -> PARENT
Structure of N-DEMETHYL-RETAPAMULIN
METABOLITE -> PARENT
Structure of (3AR,4R,5R,7S,8S,9R,9AS,12R)-8-HYDROXY-4,7,9,12-TETRAMETHYL-3-OXO-7-VINYLDECAHYDRO-4,9A-PROPANOCYCLOPENTA(8)ANNULEN-5-YL 2-(((1R,3S,5S)-8-AZABICYCLO(3.2.1)OCTAN-3-YL)THIO)ACETATE
METABOLITE -> PARENT
Structure of (2S,3AR,4R,5R,7S,8S,9R,9AS,12R)-2,8-DIHYDROXY-4,7,9,12-TETRAMETHYL-3-OXO-7-VINYLDECAHYDRO-4,9A-PROPANOCYCLOPENTA(8)ANNULEN-5-YL 2-(((1R,3S,5S)-8-METHYL-8-AZABICYCLO(3.2.1)OCTAN-3-YL)THIO)ACETATE
METABOLITE -> PARENT
Related Record Type Details
Structure of RETAPAMULIN
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