Lefamulin free base | BC-3781 | CAS#1061337-51-6

MedKoo Cat#: 326894 | Name: Lefamulin free base

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Lefamulin is an antibiotic medication used it to treat adults with community-acquired bacterial pneumonia. It is a pleuromutilin antibiotic that inhibits the large subunit of bacterial ribosomes Lefamulin is used to treat adults with community-acquired bacterial pneumonia. It was also investigated for treatment of acute bacterial skin and skin-structure infections (ABSSSI). Lefamulin has in vitro activity against Streptococcus viridans, Moraxella catarrhalis, Enterococcus faecium, methicillin-resistant Staphylococcus aureus (MRSA), among other bacteria. . Lefamulin was approved in 2019.

Chemical Structure

Lefamulin free base

CAS#1061337-51-6 (free base)

Theoretical Analysis

MedKoo Cat#: 326894

Name: Lefamulin free base

CAS#: 1061337-51-6 (free base)

Chemical Formula: C28H45NO5S

Exact Mass: 507.3018

Molecular Weight: 507.73

Elemental Analysis: C, 66.24; H, 8.93; N, 2.76; O, 15.76; S, 6.31

Price and Availability

Size	Price	Availability
50mg	USD 450.00	2 Weeks
100mg	USD 750.00	2 Weeks
200mg	USD 1,250.00	2 Weeks
500mg	USD 2,650.00	2 Weeks

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Related CAS #

1061337-51-6 (free base) 1350636-82-6 (acetate)

Synonym

BC-3781; BC 3781; BC3781; Lefamulin; Lefamulin free base; Xenleta

IUPAC/Chemical Name

(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,2R,4R)-4-amino-2-hydroxycyclohexyl)thio)acetate

InChi Key

KPVIXBKIJXZQJX-FCEONZPQSA-N

InChi Code

InChI=1S/C28H45NO5S/c1-6-26(4)14-22(34-23(32)15-35-21-8-7-18(29)13-20(21)31)27(5)16(2)9-11-28(17(3)25(26)33)12-10-19(30)24(27)28/h6,16-18,20-22,24-25,31,33H,1,7-15,29H2,2-5H3/t16-,17+,18-,20-,21-,22-,24+,25+,26-,27+,28+/m1/s1

SMILES Code

O=C(O[C@H]1[C@@]([C@H](C)CC2)(C)[C@@](C(CC3)=O)([H])[C@]32[C@@H](C)[C@H](O)[C@](C)(C=C)C1)CS[C@H]4[C@H](O)C[C@H](N)CC4

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 507.73 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Tang HJ, Lai CC. Lefamulin for treating community-acquired bacterial pneumonia in adult patients aged < 65 years. Clin Infect Dis. 2019 Dec 11. pii: ciz1173. doi: 10.1093/cid/ciz1173. [Epub ahead of print] PubMed PMID: 31822903. 2: Lee YR, Jacobs KL. Leave it to Lefamulin: A Pleuromutilin Treatment Option in Community-Acquired Bacterial Pneumonia. Drugs. 2019 Nov;79(17):1867-1876. doi: 10.1007/s40265-019-01219-5. Review. PubMed PMID: 31705486. 3: Lefamulin (Xenleta) for Community-Acquired Bacterial Pneumonia. JAMA. 2019 Nov 5;322(17):1709-1710. doi: 10.1001/jama.2019.16482. PubMed PMID: 31688883. 4: File TM, Goldberg L, Das A, Sweeney C, Saviski J, Gelone SP, Seltzer E, Paukner S, Wicha WW, Talbot GH, Gasink LB. Efficacy and Safety of Intravenous-to-oral Lefamulin, a Pleuromutilin Antibiotic, for the Treatment of Community-acquired Bacterial Pneumonia: The Phase III Lefamulin Evaluation Against Pneumonia (LEAP 1) Trial. Clin Infect Dis. 2019 Oct 18. pii: ciz710. doi: 10.1093/cid/ciz710. [Epub ahead of print] PubMed PMID: 31626688. 5: Lefamulin (Xenleta) for community-acquired bacterial pneumonia. Med Lett Drugs Ther. 2019 Sep 23;61(1581):145-148. Review. PubMed PMID: 31599865. 6: Alexander E, Goldberg L, Das AF, Moran GJ, Sandrock C, Gasink LB, Spera P, Sweeney C, Paukner S, Wicha WW, Gelone SP, Schranz J. Oral Lefamulin vs Moxifloxacin for Early Clinical Response Among Adults With Community-Acquired Bacterial Pneumonia: The LEAP 2 Randomized Clinical Trial. JAMA. 2019 Sep 27. doi: 10.1001/jama.2019.15468. [Epub ahead of print] PubMed PMID: 31560372. 7: Malani PN. Lefamulin-A New Antibiotic for Community-Acquired Pneumonia. JAMA. 2019 Sep 27. doi: 10.1001/jama.2019.16215. [Epub ahead of print] PubMed PMID: 31560367. 8: Koulenti D, Xu E, Yin Sum Mok I, Song A, Karageorgopoulos DE, Armaganidis A, Lipman J, Tsiodras S. Lefamulin. Comment on: "Novel Antibiotics for Multidrug-Resistant Gram-Positive Microorganisms. Microorganisms, 2019, 7, 270". Microorganisms. 2019 Sep 24;7(10). pii: E386. doi: 10.3390/microorganisms7100386. PubMed PMID: 31554342; PubMed Central PMCID: PMC6843636. 9: Perry W, Golan Y. Therapeutic potential of lefamulin in the treatment of community-acquired pneumonia. Future Microbiol. 2019 Jul;14:927-939. doi: 10.2217/fmb-2019-0027. Epub 2019 Jul 23. PubMed PMID: 31333062. 10: Rodvold KA. Introduction: lefamulin and pharmacokinetic/pharmacodynamic rationale to support the dose selection of lefamulin. J Antimicrob Chemother. 2019 Apr 1;74(Supplement_3):iii2-iii4. doi: 10.1093/jac/dkz084. PubMed PMID: 30949709; PubMed Central PMCID: PMC6449571. 11: Zhang L, Wicha WW, Bhavnani SM, Rubino CM. Prediction of lefamulin epithelial lining fluid penetration after intravenous and oral administration using Phase 1 data and population pharmacokinetics methods. J Antimicrob Chemother. 2019 Apr 1;74(Supplement_3):iii27-iii34. doi: 10.1093/jac/dkz088. PubMed PMID: 30949708; PubMed Central PMCID: PMC6449575. 12: Wicha WW, Strickmann DB, Paukner S. Pharmacokinetics/pharmacodynamics of lefamulin in a neutropenic murine pneumonia model with Staphylococcus aureus and Streptococcus pneumoniae. J Antimicrob Chemother. 2019 Apr 1;74(Supplement_3):iii11-iii18. doi: 10.1093/jac/dkz086. PubMed PMID: 30949707; PubMed Central PMCID: PMC6449573. 13: Wicha WW, Craig WA, Andes D. In vivo pharmacodynamics of lefamulin, the first systemic pleuromutilin for human use, in a neutropenic murine thigh infection model. J Antimicrob Chemother. 2019 Apr 1;74(Supplement_3):iii5-iii10. doi: 10.1093/jac/dkz085. PubMed PMID: 30949706; PubMed Central PMCID: PMC6449574. 14: Bhavnani SM, Zhang L, Hammel JP, Rubino CM, Bader JC, Sader HS, Gelone SP, Wicha WW, Ambrose PG. Pharmacokinetic/pharmacodynamic target attainment analyses to support intravenous and oral lefamulin dose selection for the treatment of patients with community-acquired bacterial pneumonia. J Antimicrob Chemother. 2019 Apr 1;74(Supplement_3):iii35-iii41. doi: 10.1093/jac/dkz089. PubMed PMID: 30949705; PubMed Central PMCID: PMC6449570. 15: Wicha WW, Prince WT, Lell C, Heilmayer W, Gelone SP. Pharmacokinetics and tolerability of lefamulin following intravenous and oral dosing. J Antimicrob Chemother. 2019 Apr 1;74(Supplement_3):iii19-iii26. doi: 10.1093/jac/dkz087. PubMed PMID: 30949704; PubMed Central PMCID: PMC6449572. 16: File TM, Goldberg L, Das A, Sweeney C, Saviski J, Gelone SP, Seltzer E, Paukner S, Wicha WW, Talbot GH, Gasink LB. Efficacy and Safety of Intravenous-to-oral Lefamulin, a Pleuromutilin Antibiotic, for the Treatment of Community-acquired Bacterial Pneumonia: The Phase III Lefamulin Evaluation Against Pneumonia (LEAP 1) Trial. Clin Infect Dis. 2019 Nov 13;69(11):1856-1867. doi: 10.1093/cid/ciz090. PubMed PMID: 30722059; PubMed Central PMCID: PMC6853694. 17: Mendes RE, Paukner S, Doyle TB, Gelone SP, Flamm RK, Sader HS. Low Prevalence of Gram-Positive Isolates Showing Elevated Lefamulin MIC Results during the SENTRY Surveillance Program for 2015-2016 and Characterization of Resistance Mechanisms. Antimicrob Agents Chemother. 2019 Mar 27;63(4). pii: e02158-18. doi: 10.1128/AAC.02158-18. Print 2019 Apr. PubMed PMID: 30670418; PubMed Central PMCID: PMC6437497. 18: Paukner S, Gelone SP, Arends SJR, Flamm RK, Sader HS. Antibacterial Activity of Lefamulin against Pathogens Most Commonly Causing Community-Acquired Bacterial Pneumonia: SENTRY Antimicrobial Surveillance Program (2015-2016). Antimicrob Agents Chemother. 2019 Mar 27;63(4). pii: e02161-18. doi: 10.1128/AAC.02161-18. Print 2019 Apr. PubMed PMID: 30670415; PubMed Central PMCID: PMC6437505. 19: Dillon C, Guarascio AJ, Covvey JR. Lefamulin: a promising new pleuromutilin antibiotic in the pipeline. Expert Rev Anti Infect Ther. 2019 Jan;17(1):5-15. doi: 10.1080/14787210.2019.1554431. Epub 2018 Dec 7. Review. PubMed PMID: 30513017. 20: Veve MP, Wagner JL. Lefamulin: Review of a Promising Novel Pleuromutilin Antibiotic. Pharmacotherapy. 2018 Sep;38(9):935-946. doi: 10.1002/phar.2166. Epub 2018 Aug 20. Review. PubMed PMID: 30019769.