Upleganan acetate | CAS#2408422-41-1 | Polymyxin

MedKoo Cat#: 145008 | Name: Upleganan acetate

Description:

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

SPR206 is a next-generation polymyxin used for treatment of multidrug-resistant (MDR) Gram-negative infections. SPR206 has potent in vitro and in vivo activity against A. baumannii, P. aeruginosa, and multiple clinically important species of Enterobacterales, including multidrug- and extensively drug-resistant strains. SPR206 has shown good in vitro activity against MDR, tigecycline-resistant and non-MDR clinical isolates of Gram-negative pathogens.

Chemical Structure

Upleganan acetate

CAS#2408422-41-1

Theoretical Analysis

MedKoo Cat#: 145008

Name: Upleganan acetate

CAS#: 2408422-41-1

Chemical Formula: C54H86ClN15O14

Exact Mass: 1203.6167

Molecular Weight: 1204.82

Elemental Analysis: C, 53.83; H, 7.20; Cl, 2.94; N, 17.44; O, 18.59

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Upleganan acetate; SPR-206 acetate; SPR206 acetate; SPR 206 acetate; SPR-206-acetate; SPR 206-acetate;

IUPAC/Chemical Name

(S)-4-amino-N-((2S,3R)-1-(((S)-3-amino-1-oxo-1-(((3S,6S,9S,12S,15R,18S,21S)-6,9,18-tris(2-aminoethyl)-15-benzyl-3-((R)-1-hydroxyethyl)-12-isobutyl-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptaazacyclotricosan-21-yl)amino)propan-2-yl)amino)-3-hydroxy-1-oxobutan-2-yl)-3-(3-chlorophenyl)butanamide acetate

InChi Key

YADKGXKKBAFXFJ-CYMYEOQJSA-N

InChi Code

1S/C52H82ClN15O12.C2H4O2/c1-27(2)21-38-48(76)62-34(13-17-54)44(72)61-36(15-19-56)47(75)68-42(28(3)69)51(79)59-20-16-37(46(74)60-35(14-18-55)45(73)65-39(49(77)64-38)22-30-9-6-5-7-10-30)63-50(78)40(26-58)66-52(80)43(29(4)70)67-41(71)24-32(25-57)31-11-8-12-33(53)23-31;1-2(3)4/h5-12,23,27-29,32,34-40,42-43,69-70H,13-22,24-26,54-58H2,1-4H3,(H,59,79)(H,60,74)(H,61,72)(H,62,76)(H,63,78)(H,64,77)(H,65,73)(H,66,80)(H,67,71)(H,68,75);1H3,(H,3,4)/t28-,29-,32-,34+,35+,36+,37+,38+,39-,40+,42+,43+;/m1./s1

SMILES Code

CC(O)=O.[H][C@]1(NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC2=CC=CC=C2)NC(=O)[C@H](CCN)NC(=O)[C@H](CCNC1=O)NC(=O)[C@H](CN)NC(=O)[C@@H](NC(=O)C[C@H](CN)C3=CC(Cl)=CC=C3)[C@@H](C)O)[C@@H](C)O

Appearance

To be determined

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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 1,204.82 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: Bruss JB, Bader J, Hamed KA. Safety and pharmacokinetics of SPR206 in subjects with varying degrees of renal impairment. Antimicrob Agents Chemother. 2023 Nov 15;67(11):e0050523. doi: 10.1128/aac.00505-23. Epub 2023 Oct 12. PMID: 37823647; PMCID: PMC10648942. 2: Rodvold KA, Bader J, Bruss JB, Hamed K. Pharmacokinetics of SPR206 in Plasma, Pulmonary Epithelial Lining Fluid, and Alveolar Macrophages following Intravenous Administration to Healthy Adult Subjects. Antimicrob Agents Chemother. 2023 Jul 18;67(7):e0042623. doi: 10.1128/aac.00426-23. Epub 2023 Jun 20. PMID: 37338378; PMCID: PMC10353446. 3: Bruss J, Lister T, Gupta VK, Stone E, Morelli L, Lei Y, Melnick D. Single- and Multiple-Ascending-Dose Study of the Safety, Tolerability, and Pharmacokinetics of the Polymyxin Derivative SPR206. Antimicrob Agents Chemother. 2021 Sep 17;65(10):e0073921. doi: 10.1128/AAC.00739-21. Epub 2021 Aug 2. PMID: 34339267; PMCID: PMC8448162. 4: Brown P, Abbott E, Abdulle O, Boakes S, Coleman S, Divall N, Duperchy E, Moss S, Rivers D, Simonovic M, Singh J, Stanway S, Wilson A, Dawson MJ. Design of Next Generation Polymyxins with Lower Toxicity: The Discovery of SPR206. ACS Infect Dis. 2019 Oct 11;5(10):1645-1656. doi: 10.1021/acsinfecdis.9b00217. Epub 2019 Sep 24. PMID: 31525992; PMCID: PMC8152168. 5: Zhang Y, Zhao C, Wang Q, Wang X, Chen H, Li H, Zhang F, Wang H. Evaluation of the in vitro activity of new polymyxin B analogue SPR206 against clinical MDR, colistin-resistant and tigecycline-resistant Gram-negative bacilli. J Antimicrob Chemother. 2020 Sep 1;75(9):2609-2615. doi: 10.1093/jac/dkaa217. PMID: 32591806. 6: Aslan AT, Akova M, Paterson DL. Next-Generation Polymyxin Class of Antibiotics: A Ray of Hope Illuminating a Dark Road. Antibiotics (Basel). 2022 Nov 27;11(12):1711. doi: 10.3390/antibiotics11121711. PMID: 36551367; PMCID: PMC9774142. 7: Lim JS, Chai YY, Ser WX, Haeren AV, Lim YH, Raja T, Foo JB, Hamzah S, Sellappans R, Yow HY. Novel drug candidates against antibiotic-resistant microorganisms: A review. Iran J Basic Med Sci. 2024;27(2):134-150. doi: 10.22038/IJBMS.2023.71672.15593. PMID: 38234674; PMCID: PMC10790292. 8: Abdul-Mutakabbir JC, Opoku NS, Tan KK, Jorth P, Nizet V, Fletcher HM, Kaye KS, Rybak MJ. Determining Susceptibility and Potential Mediators of Resistance for the Novel Polymyxin Derivative, SPR206, in Acinetobacter baumannii. Antibiotics (Basel). 2024 Jan 4;13(1):47. doi: 10.3390/antibiotics13010047. PMID: 38247606; PMCID: PMC10812597. 9: Akhoundsadegh N, Belanger CR, Hancock REW. Outer Membrane Interaction Kinetics of New Polymyxin B Analogs in Gram-Negative Bacilli. Antimicrob Agents Chemother. 2019 Sep 23;63(10):e00935-19. doi: 10.1128/AAC.00935-19. PMID: 31332075; PMCID: PMC6761527. 10: Li S, Zhu X, Cao G, Shen J, Zhu X, Yu J, Wu X, Wu J, Yang H, Li N, Hu Y, Wang J, Huang H, Zhang J. Pharmacokinetics and safety of EVER206, a novel polymyxin antimicrobial, in healthy Chinese subjects. Antimicrob Agents Chemother. 2024 Apr 22:e0156323. doi: 10.1128/aac.01563-23. Epub ahead of print. PMID: 38647294. 11: Gill CM, Nicolau DP. In Vivo Pharmacodynamic Profile of EVER206, a Novel Polymyxin Antimicrobial, against Gram-Negative Bacteria in the Murine Thigh Infection Model. Antimicrob Agents Chemother. 2023 May 17;67(5):e0173822. doi: 10.1128/aac.01738-22. Epub 2023 Apr 6. PMID: 37022170; PMCID: PMC10190685. Sent by NCBI 9:13 AM (0 minutes ago) to me This message contains search results from the National Center for Biotechnology Information (NCBI) at the U.S. National Library of Medicine (NLM). Do not reply directly to this message Sent On: Tue Jun 04 09:13:15 2024 Search: spr206 From: karsen.willard@medkoo.com 11 selected items PubMed Results Items 1-11 of 11 (Display the 11 citations in PubMed) 1. Safety and pharmacokinetics of SPR206 in subjects with varying degrees of renal impairment. Bruss JB, Bader J, Hamed KA. Antimicrob Agents Chemother. 2023 Nov 15;67(11):e0050523. doi: 10.1128/aac.00505-23. Epub 2023 Oct 12. PMID: 37823647 Free PMC article. 2. Pharmacokinetics of SPR206 in Plasma, Pulmonary Epithelial Lining Fluid, and Alveolar Macrophages following Intravenous Administration to Healthy Adult Subjects. Rodvold KA, Bader J, Bruss JB, Hamed K. Antimicrob Agents Chemother. 2023 Jul 18;67(7):e0042623. doi: 10.1128/aac.00426-23. Epub 2023 Jun 20. PMID: 37338378 Free PMC article. 3. Single- and Multiple-Ascending-Dose Study of the Safety, Tolerability, and Pharmacokinetics of the Polymyxin Derivative SPR206. Bruss J, Lister T, Gupta VK, Stone E, Morelli L, Lei Y, Melnick D. Antimicrob Agents Chemother. 2021 Sep 17;65(10):e0073921. doi: 10.1128/AAC.00739-21. Epub 2021 Aug 2. PMID: 34339267 Free PMC article. Clinical Trial. 4. Design of Next Generation Polymyxins with Lower Toxicity: The Discovery of SPR206. Brown P, Abbott E, Abdulle O, Boakes S, Coleman S, Divall N, Duperchy E, Moss S, Rivers D, Simonovic M, Singh J, Stanway S, Wilson A, Dawson MJ. ACS Infect Dis. 2019 Oct 11;5(10):1645-1656. doi: 10.1021/acsinfecdis.9b00217. Epub 2019 Sep 24. PMID: 31525992 Free PMC article. 5. Evaluation of the in vitro activity of new polymyxin B analogue SPR206 against clinical MDR, colistin-resistant and tigecycline-resistant Gram-negative bacilli. Zhang Y, Zhao C, Wang Q, Wang X, Chen H, Li H, Zhang F, Wang H. J Antimicrob Chemother. 2020 Sep 1;75(9):2609-2615. doi: 10.1093/jac/dkaa217. PMID: 32591806 6. Next-Generation Polymyxin Class of Antibiotics: A Ray of Hope Illuminating a Dark Road. Aslan AT, Akova M, Paterson DL. Antibiotics (Basel). 2022 Nov 27;11(12):1711. doi: 10.3390/antibiotics11121711. PMID: 36551367 Free PMC article. Review. 7. Novel drug candidates against antibiotic-resistant microorganisms: A review. Lim JS, Chai YY, Ser WX, Haeren AV, Lim YH, Raja T, Foo JB, Hamzah S, Sellappans R, Yow HY. Iran J Basic Med Sci. 2024;27(2):134-150. doi: 10.22038/IJBMS.2023.71672.15593. PMID: 38234674 Free PMC article. Review. 8. Determining Susceptibility and Potential Mediators of Resistance for the Novel Polymyxin Derivative, SPR206, in Acinetobacter baumannii. Abdul-Mutakabbir JC, Opoku NS, Tan KK, Jorth P, Nizet V, Fletcher HM, Kaye KS, Rybak MJ. Antibiotics (Basel). 2024 Jan 4;13(1):47. doi: 10.3390/antibiotics13010047. PMID: 38247606 Free PMC article. 9. Outer Membrane Interaction Kinetics of New Polymyxin B Analogs in Gram-Negative Bacilli. Akhoundsadegh N, Belanger CR, Hancock REW. Antimicrob Agents Chemother. 2019 Sep 23;63(10):e00935-19. doi: 10.1128/AAC.00935-19. Print 2019 Oct. PMID: 31332075 Free PMC article. 10. Pharmacokinetics and safety of EVER206, a novel polymyxin antimicrobial, in healthy Chinese subjects. Li S, Zhu X, Cao G, Shen J, Zhu X, Yu J, Wu X, Wu J, Yang H, Li N, Hu Y, Wang J, Huang H, Zhang J. Antimicrob Agents Chemother. 2024 Apr 22:e0156323. doi: 10.1128/aac.01563-23. Online ahead of print. PMID: 38647294 11. In Vivo Pharmacodynamic Profile of EVER206, a Novel Polymyxin Antimicrobial, against Gram-Negative Bacteria in the Murine Thigh Infection Model. Gill CM, Nicolau DP. Antimicrob Agents Chemother. 2023 May 17;67(5):e0173822. doi: 10.1128/aac.01738-22. Epub 2023 Apr 6. PMID: 37022170 Free PMC article.