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MedKoo Cat#: 412282 | Name: CPZEN 45

Description:

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

CPZEN 45 is a caprazamycin derivative that shows antibacterial activity against M. tuberculosis and MDR-TB strains.

Chemical Structure

CPZEN 45
CPZEN 45
CAS#737759-36-3

Theoretical Analysis

MedKoo Cat#: 412282

Name: CPZEN 45

CAS#: 737759-36-3

Chemical Formula: C32H44N6O11

Exact Mass: 688.3068

Molecular Weight: 688.74

Elemental Analysis: C, 55.81; H, 6.44; N, 12.20; O, 25.55

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.
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Synonym
CPZEN 45; CPZEN-45; CPZEN45; Caprazene45; Caprazene-45; Caprazene 45
IUPAC/Chemical Name
(2S)-2-((((2S,3R,4S,5R)-5-(aminomethyl)-3,4-dihydroxytetrahydrofuran-2-yl)oxy)((2S,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)-N-(4-butylphenyl)-1,4-dimethyl-3-oxo-2,3,4,7-tetrahydro-1H-1,4-diazepine-5-carboxamide
InChi Key
RQVDLVWYEOCAJE-HLFJJHGGSA-N
InChi Code
InChI=1S/C32H44N6O11/c1-4-5-6-16-7-9-17(10-8-16)34-28(44)18-11-13-36(2)21(29(45)37(18)3)26(49-31-25(43)22(40)19(15-33)47-31)27-23(41)24(42)30(48-27)38-14-12-20(39)35-32(38)46/h7-12,14,19,21-27,30-31,40-43H,4-6,13,15,33H2,1-3H3,(H,34,44)(H,35,39,46)/t19-,21+,22-,23+,24-,25-,26?,27+,30-,31+/m1/s1
SMILES Code
CCCCc1ccc(NC(C2=CCN([C@H](C(N2C)=O)C([C@H]3O[C@@H](N4C=CC(NC4=O)=O)[C@@H]([C@@H]3O)O)O[C@@H]5O[C@@H]([C@H]([C@H]5O)O)CN)C)=O)cc1
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
>3 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

Preparing Stock Solutions

The following data is based on the product molecular weight 688.74 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.

Recalculate based on batch purity %
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: Kimura KI. Liposidomycin, the first reported nucleoside antibiotic inhibitor of peptidoglycan biosynthesis translocase I: The discovery of liposidomycin and related compounds with a perspective on their application to new antibiotics. J Antibiot (Tokyo). 2019 Dec;72(12):877-889. doi: 10.1038/s41429-019-0241-5. Epub 2019 Oct 4. PMID: 31582803. 2: Ishizaki Y, Takahashi Y, Kimura T, Inoue M, Hayashi C, Igarashi M. Synthesis and biological activity of analogs of CPZEN-45, a novel antituberculosis drug. J Antibiot (Tokyo). 2019 Dec;72(12):970-980. doi: 10.1038/s41429-019-0225-5. Epub 2019 Aug 30. PMID: 31471594. 3: Watanabe T. Chemical Studies on Bioactive Natural Products Directed toward Development of Novel Antiinfective and Anticancer Medicines. Chem Pharm Bull (Tokyo). 2019;67(7):620-631. doi: 10.1248/cpb.c19-00215. PMID: 31257316. 4: Pitner RA, Durham PG, Stewart IE, Reed SG, Cassell GH, Hickey AJ, Carter D. A Spray-Dried Combination of Capreomycin and CPZEN-45 for Inhaled Tuberculosis Therapy. J Pharm Sci. 2019 Oct;108(10):3302-3311. doi: 10.1016/j.xphs.2019.05.024. Epub 2019 May 29. PMID: 31152746; PMCID: PMC6759370. 5: Pstragowski M, Zbrzezna M, Bujalska-Zadrozny M. ADVANCES IN PHARMACOTHERAPY OF TUBERCULOSIS. Acta Pol Pharm. 2017 Jan;74(1):3-11. PMID: 29474756. 6: Huszár S, Singh V, Polčicová A, Baráth P, Barrio MB, Lagrange S, Leblanc V, Nacy CA, Mizrahi V, Mikušová K. N-Acetylglucosamine-1-Phosphate Transferase, WecA, as a Validated Drug Target in Mycobacterium tuberculosis. Antimicrob Agents Chemother. 2017 Oct 24;61(11):e01310-17. doi: 10.1128/AAC.01310-17. PMID: 28874370; PMCID: PMC5655080. 7: Nakamura H, Yoshida T, Tsukano C, Takemoto Y. Synthesis of CPZEN-45: Construction of the 1,4-Diazepin-2-one Core by the Cu-Catalyzed Intramolecular Amidation of a Vinyl Iodide. Org Lett. 2016 May 6;18(9):2300-3. doi: 10.1021/acs.orglett.6b00943. Epub 2016 Apr 18. PMID: 27088563. 8: Soni I, De Groote MA, Dasgupta A, Chopra S. Challenges facing the drug discovery pipeline for non-tuberculous mycobacteria. J Med Microbiol. 2016 Jan;65(1):1-8. doi: 10.1099/jmm.0.000198. Epub 2015 Oct 29. PMID: 26515915. 9: Kumar D, Negi B, Rawat DS. The anti-tuberculosis agents under development and the challenges ahead. Future Med Chem. 2015;7(15):1981-2003. doi: 10.4155/fmc.15.128. Epub 2015 Oct 27. PMID: 26505682. 10: Hanif SN, Hickey AJ, Garcia-Contreras L. Liquid chromatographic determination of CPZEN-45, a novel anti-tubercular drug, in biological samples. J Pharm Biomed Anal. 2014 Jan;88:370-6. doi: 10.1016/j.jpba.2013.09.014. Epub 2013 Oct 6. PMID: 24176740; PMCID: PMC4026256. 11: Ishizaki Y, Hayashi C, Inoue K, Igarashi M, Takahashi Y, Pujari V, Crick DC, Brennan PJ, Nomoto A. Inhibition of the first step in synthesis of the mycobacterial cell wall core, catalyzed by the GlcNAc-1-phosphate transferase WecA, by the novel caprazamycin derivative CPZEN-45. J Biol Chem. 2013 Oct 18;288(42):30309-19. doi: 10.1074/jbc.M113.492173. Epub 2013 Aug 28. PMID: 23986448; PMCID: PMC3798496. 12: Salomon JJ, Galeron P, Schulte N, Morow PR, Severynse-Stevens D, Huwer H, Daum N, Lehr CM, Hickey AJ, Ehrhardt C. Biopharmaceutical in vitro characterization of CPZEN-45, a drug candidate for inhalation therapy of tuberculosis. Ther Deliv. 2013 Aug;4(8):915-23. doi: 10.4155/tde.13.62. PMID: 23919471. 13: Takahashi Y, Igarashi M, Miyake T, Soutome H, Ishikawa K, Komatsuki Y, Koyama Y, Nakagawa N, Hattori S, Inoue K, Doi N, Akamatsu Y. Novel semisynthetic antibiotics from caprazamycins A-G: caprazene derivatives and their antibacterial activity. J Antibiot (Tokyo). 2013 Mar;66(3):171-8. doi: 10.1038/ja.2013.9. PMID: 23532021. 14: Engohang-Ndong J. Antimycobacterial drugs currently in Phase II clinical trials and preclinical phase for tuberculosis treatment. Expert Opin Investig Drugs. 2012 Dec;21(12):1789-800. doi: 10.1517/13543784.2012.724397. Epub 2012 Sep 19. PMID: 22991970.