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MedKoo Cat#: 573675 | Name: Cephalotaxine
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Description:

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

Cephalotaxine is an antiviral and antitumor agent.

Chemical Structure

Cephalotaxine
CAS#24316-19-6

Theoretical Analysis

MedKoo Cat#: 573675

Name: Cephalotaxine

CAS#: 24316-19-6

Chemical Formula: C18H21NO4

Exact Mass: 315.1471

Molecular Weight: 315.37

Elemental Analysis: C, 68.55; H, 6.71; N, 4.44; O, 20.29

Price and Availability

Size Price Availability Quantity
25mg USD 250.00 2 Weeks
50mg USD 450.00 2 Weeks
100mg USD 750.00 2 Weeks
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Related CAS #
No Data
Synonym
(-)-Cephalotaxine; Alkaloid A from Cephalotaxus; Cephalotaxine; Omacetaxine; NSC 128487; NSC-128487; NSC128487; NSC 245454; NSC245454; NSC-245454; ZINC19795976; ZINC 19795976; ZINC-19795976;
IUPAC/Chemical Name
(11bS,12S,14aR)-13-methoxy-2,3,5,6,11b,12-hexahydro-1H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]cyclopenta[b]pyrrolo[1,2-a]azepin-12-ol
InChi Key
YMNCVRSYJBNGLD-KURKYZTESA-N
InChi Code
1S/C18H21NO4/c1-21-15-9-18-4-2-5-19(18)6-3-11-7-13-14(23-10-22-13)8-12(11)16(18)17(15)20/h7-9,16-17,20H,2-6,10H2,1H3/t16-,17-,18+/m1/s1
SMILES Code
C1Oc2c(O1)cc1c(c2)CCN2[C@@]3([C@H]1[C@@H](C(=C3)OC)O)CCC2
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 315.37 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: Yu GX, Yu Y, Jing-Wu, Zeng LH, Schinnerl J, Cai XH. Cephalotaxine homologous alkaloids from seeds of Cephalotaxus oliveri Mast. Phytochemistry. 2022 Aug;200:113220. doi: 10.1016/j.phytochem.2022.113220. Epub 2022 May 2. PMID: 35513135. 2: Zhao CX, Liu H, Zhang X, Yang MY, Wang YT, Xing YJ, Hua JX, Zhang Q, Li DH, Bai J, Jing YK, Hua HM. Cephalotaxine-type and homoerythrina-type alkaloids with antiproliferative effects from Cephalotaxus fortunei. Org Biomol Chem. 2022 Sep 14;20(35):7076-7084. doi: 10.1039/d2ob01242a. PMID: 36004441. 3: Cai YX, Xie XY, Zhou QQ, Huang X, Xu JB. [Two novel cephalotaxine-type alkaloids from Cephalotaxus sinensis]. Zhongguo Zhong Yao Za Zhi. 2022 Jun;47(11):2994-2999. Chinese. doi: 10.19540/j.cnki.cjcmm.20220307.202. PMID: 35718522. 4: Zhu L, Gong LJ, Zhu DR, Zhu JM, Li Y, Kong LY, Luo JG. Cephalotaxine-type alkaloids from the seeds of Cephalotaxus fortunei and their cytotoxic activities. Phytochemistry. 2021 Nov;191:112903. doi: 10.1016/j.phytochem.2021.112903. Epub 2021 Aug 9. PMID: 34384922. 5: Cortes J, Lang F. Third-line therapy for chronic myeloid leukemia: current status and future directions. J Hematol Oncol. 2021 Mar 18;14(1):44. doi: 10.1186/s13045-021-01055-9. PMID: 33736651; PMCID: PMC7976694. 6: Lai ZZ, Ho YJ, Lu JW. Cephalotaxine inhibits Zika infection by impeding viral replication and stability. Biochem Biophys Res Commun. 2020 Feb 19;522(4):1052-1058. doi: 10.1016/j.bbrc.2019.12.012. Epub 2019 Dec 7. PMID: 31818462; PMCID: PMC7092853. 7: Yang Y, Yu Q, Hu L, Dai B, Qi R, Chang Y, Zhang Q, Zhang Z, Li Y, Zhang X. Enantioselective semisynthesis of novel cephalotaxine esters with potent antineoplastic activities against leukemia. Eur J Med Chem. 2022 Dec 15;244:114731. doi: 10.1016/j.ejmech.2022.114731. Epub 2022 Sep 7. PMID: 36242991. 8: Mill CP, Fiskus W, DiNardo CD, Birdwell C, Davis JA, Kadia TM, Takahashi K, Short N, Daver N, Ohanian M, Borthakur G, Kornblau SM, Green MR, Qi Y, Su X, Khoury JD, Bhalla KN. Effective therapy for AML with RUNX1 mutation by cotreatment with inhibitors of protein translation and BCL2. Blood. 2022 Feb 10;139(6):907-921. doi: 10.1182/blood.2021013156. PMID: 34601571; PMCID: PMC8832475. 9: Zhang J, Gan Y, Li H, Yin J, He X, Lin L, Xu S, Fang Z, Kim BW, Gao L, Ding L, Zhang E, Ma X, Li J, Li L, Xu Y, Horne D, Xu R, Yu H, Gu Y, Huang W. Inhibition of the CDK2 and Cyclin A complex leads to autophagic degradation of CDK2 in cancer cells. Nat Commun. 2022 May 20;13(1):2835. doi: 10.1038/s41467-022-30264-0. PMID: 35595767; PMCID: PMC9122913. 10: Zhang ZW, Zhang XF, Feng J, Yang YH, Wang CC, Feng JC, Liu S. Formal synthesis of cephalotaxine. J Org Chem. 2013 Jan 18;78(2):786-90. doi: 10.1021/jo302608a. Epub 2012 Dec 17. PMID: 23214930. 11: Liu T, Guo Q, Zheng S, Liu Y, Yang H, Zhao M, Yao L, Zeng K, Tu P. Cephalotaxine Inhibits the Survival of Leukemia Cells by Activating Mitochondrial Apoptosis Pathway and Inhibiting Autophagy Flow. Molecules. 2021 May 18;26(10):2996. doi: 10.3390/molecules26102996. PMID: 34070111; PMCID: PMC8158396. 12: Mikolajczak KL, Smith CR Jr, weisleder D. Synthesis of cephalotaxine esters and correlation of their structures with antitumor activity. J Med Chem. 1977 Mar;20(3):328-32. doi: 10.1021/jm00213a002. PMID: 845863. 13: Wang LB, Wang DN, Wu LG, Cao J, Tian JH, Liu R, Ma R, Yu JJ, Wang J, Huang Q, Xiong WY, Zhang X. Homoharringtonine inhibited breast cancer cells growth via miR-18a-3p/AKT/mTOR signaling pathway. Int J Biol Sci. 2021 Mar 2;17(4):995-1009. doi: 10.7150/ijbs.44907. PMID: 33867824; PMCID: PMC8040299. 14: Kim JE, Song YJ. Anti-varicella-zoster virus activity of cephalotaxine esters in vitro. J Microbiol. 2019 Jan;57(1):74-79. doi: 10.1007/s12275-019-8514-z. Epub 2018 Nov 19. PMID: 30456755; PMCID: PMC7090801. 15: Pérard-Viret J, Quteishat L, Alsalim R, Royer J, Dumas F. Cephalotaxus Alkaloids. Alkaloids Chem Biol. 2017;78:205-352. doi: 10.1016/bs.alkal.2017.07.001. Epub 2017 Aug 16. PMID: 28838429; PMCID: PMC7110560. 16: Esmieu WR, Worden SM, Catterick D, Wilson C, Hayes CJ. A formal synthesis of (-)-cephalotaxine. Org Lett. 2008 Jul 17;10(14):3045-8. doi: 10.1021/ol8010166. Epub 2008 Jun 13. PMID: 18549234. 17: Wei W, Huang S, Ling Q, Mao S, Qian Y, Ye W, Li F, Pan J, Lin X, Huang J, Huang X, Zhai Y, Sun J, Jin J. Homoharringtonine is synergistically lethal with BCL-2 inhibitor APG-2575 in acute myeloid leukemia. J Transl Med. 2022 Jul 6;20(1):299. doi: 10.1186/s12967-022-03497-2. PMID: 35794605; PMCID: PMC9258085. 18: Gouthami P, Chegondi R, Chandrasekhar S. Formal Total Synthesis of (±)-Cephalotaxine and Congeners via Aryne Insertion Reaction. Org Lett. 2016 May 6;18(9):2044-6. doi: 10.1021/acs.orglett.6b00659. Epub 2016 Apr 12. PMID: 27070197. 19: Chen XJ, Zhang WN, Chen B, Xi WD, Lu Y, Huang JY, Wang YY, Long J, Wu SF, Zhang YX, Wang S, Li SX, Yin T, Lu M, Xi XD, Li JM, Wang KK, Chen Z, Chen SJ. Homoharringtonine deregulates MYC transcriptional expression by directly binding NF-κB repressing factor. Proc Natl Acad Sci U S A. 2019 Feb 5;116(6):2220-2225. doi: 10.1073/pnas.1818539116. Epub 2019 Jan 18. PMID: 30659143; PMCID: PMC6369765. 20: An XT, Ge XM, Liu XY, Yang YH, Zhao XH, Ma XY, Peng C, Fan YJ, Qin Y, Fan CA. Enantioselective Divergent Syntheses of Cephalotaxus Alkaloids: (-)-Cephalotaxine, (-)-Cephalotine B, and (-)-Fortuneicyclidins A and B. J Am Chem Soc. 2023 Apr 26;145(16):9233-9241. doi: 10.1021/jacs.3c01572. Epub 2023 Apr 12. PMID: 37043290.

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