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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

C[C@@H]1CC[C@@]23CCC(=O)[C@H]2[C@]1(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
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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ALTABAX
Primary
ALTABAX
PubMed

PubMed

TitleDatePubMed
Molecule of the month. Retapamulin.
2006 Dec
Topical retapamulin ointment (1%, wt/wt) twice daily for 5 days versus oral cephalexin twice daily for 10 days in the treatment of secondarily infected dermatitis: results of a randomized controlled trial.
2006 Dec
Activity of retapamulin (SB-275833), a novel pleuromutilin, against selected resistant gram-positive cocci.
2006 Jul
Gateways to clinical trials.
2006 Oct
Retapamulin ointment twice daily for 5 days vs oral cephalexin twice daily for 10 days for empiric treatment of secondarily infected traumatic lesions of the skin.
2006 Sep-Oct
Topical retapamulin ointment, 1%, versus sodium fusidate ointment, 2%, for impetigo: a randomized, observer-blinded, noninferiority study.
2007
In vitro activity against anaerobes of retapamulin, a new topical antibiotic for treatment of skin infections.
2007 Apr
Retapamulin: a semisynthetic pleuromutilin compound for topical treatment of skin infections in adults and children.
2007 Dec
New drugs: retapamulin, bismuth subcitrate potassium, and rotigotine.
2007 Jul-Aug
Gateways to clinical trials.
2007 Jun
Gateways to clinical trials.
2007 May
Altabax approved to treat impetigo.
2007 Oct
[Introduction to cutaneous bacterial infections].
2007 Sep
Altabax (retapamulin ointment), 1%.
2007 Sep-Oct
Current and novel antibiotics against resistant Gram-positive bacteria.
2008
Spotlight on retapamulin in impetigo and other uncomplicated superficial skin infections.
2008
Retapamulin: a review of its use in the management of impetigo and other uncomplicated superficial skin infections.
2008
A primer on topical antibiotics for the skin and eyes.
2008 Apr
Retapamulin: a new topical antibiotic for the treatment of uncomplicated skin infections.
2008 Feb
Retapamulin (Altabax)--a new topical antibiotic.
2008 Feb 25
Clones and drones: do variants of Panton-Valentine leukocidin extend the reach of community-associated methicillin-resistant Staphylococcus aureus?
2008 Jan 15
Drug treatments for skin disease introduced in 2007.
2008 Mar
Efficacy and safety of retapamulin ointment as treatment of impetigo: randomized double-blind multicentre placebo-controlled trial.
2008 May
Local antibiotics in dermatology.
2008 May-Jun
Retapamulin for impetigo and other infections.
2008 Oct
In vitro activity of retapamulin against Staphylococcus aureus isolates resistant to fusidic acid and mupirocin.
2008 Oct
Gateways to clinical trials.
2008 Sep
Microbiological profile of a new topical antibacterial: retapamulin ointment 1%.
2009 Apr
Allergic contact cermatitis to retapamulin ointment.
2009 Aug
Topical retapamulin in the management of infected traumatic skin lesions.
2009 Feb
Lost in translation: differences in antimicrobial indication approval policies between the United States and Europe.
2009 Jul
Allergic contact dermatitis from retapamulin ointment.
2009 Jul-Aug
Agents for the decolonization of methicillin-resistant Staphylococcus aureus.
2009 Mar
[Pediatric dermatology. New aspects of bacterial skin infections in children].
2009 Mar
Mutilins derivatives: from veterinary to human-used antibiotics.
2009 Oct
Daptomycin: a novel lipopeptide antibiotic against Gram-positive pathogens.
2010
The pleuromutilin antibiotics: a new class for human use.
2010 Feb
Retapamulin.
2010 Jan
Retapamulin: what is the role of this topical antimicrobial in the treatment of bacterial infections in atopic dermatitis?
2010 Jan
Retapamulin: a novel topical antibiotic.
2010 Jan-Feb
Retapamulin: an emerging antimicrobial allergen.
2010 May-Jun
Retapamulin: an antibacterial with a novel mode of action in an age of emerging resistance to Staphylococcus aureus.
2010 Oct
Patents

Patents

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 Mon Oct 21 21:02:48 UTC 2019
Edited
by admin
on Mon Oct 21 21:02:48 UTC 2019
Record UNII
4MG6O8991R
Record Status Validated (UNII)
Record Version
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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
SB 275833
Common Name 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
RETAPAMULIN [WHO-DD]
Common Name English
ALTARGO
Brand 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
Classification Tree Code System Code
WHO-ATC D06AX13
Created by admin on Mon Oct 21 21:02:48 UTC 2019 , Edited by admin on Mon Oct 21 21:02:48 UTC 2019
WHO-VATC QD06AX13
Created by admin on Mon Oct 21 21:02:48 UTC 2019 , Edited by admin on Mon Oct 21 21:02:48 UTC 2019
NDF-RT N0000175434
Created by admin on Mon Oct 21 21:02:48 UTC 2019 , Edited by admin on Mon Oct 21 21:02:48 UTC 2019
NDF-RT N0000175433
Created by admin on Mon Oct 21 21:02:48 UTC 2019 , Edited by admin on Mon Oct 21 21:02:48 UTC 2019
NCI_THESAURUS C258
Created by admin on Mon Oct 21 21:02:48 UTC 2019 , Edited by admin on Mon Oct 21 21:02:48 UTC 2019
EMA ASSESSMENT REPORTS ALTARGO(AUTHORIZED IMPETIGO)
Created by admin on Mon Oct 21 21:02:48 UTC 2019 , Edited by admin on Mon Oct 21 21:02:48 UTC 2019
Code System Code Type Description
WIKIPEDIA
RETAPAMULIN
Created by admin on Mon Oct 21 21:02:48 UTC 2019 , Edited by admin on Mon Oct 21 21:02:48 UTC 2019
PRIMARY
LactMed
224452-66-8
Created by admin on Mon Oct 21 21:02:48 UTC 2019 , Edited by admin on Mon Oct 21 21:02:48 UTC 2019
PRIMARY
INN
8494
Created by admin on Mon Oct 21 21:02:48 UTC 2019 , Edited by admin on Mon Oct 21 21:02:48 UTC 2019
PRIMARY
CAS
224452-66-8
Created by admin on Mon Oct 21 21:02:48 UTC 2019 , Edited by admin on Mon Oct 21 21:02:48 UTC 2019
PRIMARY
DRUG BANK
DB01256
Created by admin on Mon Oct 21 21:02:48 UTC 2019 , Edited by admin on Mon Oct 21 21:02:48 UTC 2019
PRIMARY
MESH
C508887
Created by admin on Mon Oct 21 21:02:48 UTC 2019 , Edited by admin on Mon Oct 21 21:02:48 UTC 2019
PRIMARY
EVMPD
SUB25391
Created by admin on Mon Oct 21 21:02:48 UTC 2019 , Edited by admin on Mon Oct 21 21:02:48 UTC 2019
PRIMARY
RXCUI
642274
Created by admin on Mon Oct 21 21:02:48 UTC 2019 , Edited by admin on Mon Oct 21 21:02:48 UTC 2019
PRIMARY RxNorm
MERCK INDEX
M9551
Created by admin on Mon Oct 21 21:02:48 UTC 2019 , Edited by admin on Mon Oct 21 21:02:48 UTC 2019
PRIMARY Merck Index
NCI_THESAURUS
C61924
Created by admin on Mon Oct 21 21:02:48 UTC 2019 , Edited by admin on Mon Oct 21 21:02:48 UTC 2019
PRIMARY
ChEMBL
CHEMBL409542
Created by admin on Mon Oct 21 21:02:48 UTC 2019 , Edited by admin on Mon Oct 21 21:02:48 UTC 2019
PRIMARY
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