WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 100520
CAS#: 6035-45-6 (calcium hydrate)
Description: Leucovorin calcium is a n active metabolite of folic acid (also called folinic acid and citrovorum factor), which does not require metabolism by dihydrofolate reductase, the molecular target of folate antagonist-type chemotherapeutic drugs. Leucovorin calcium counteracts the toxic effects of these medications, 'rescuing' the patient while permitting the antitumor activity of the folate antagonist. This agent also potentiates the effects of fluorouracil and its derivatives by stabilizing the binding of the drug's metabolite to its target enzyme, thus prolonging drug activity.
MedKoo Cat#: 100520
Name: Leucovorin calcium hydrate
CAS#: 6035-45-6 (calcium hydrate)
Chemical Formula: C20H31CaN7O12
Exact Mass:
Molecular Weight: 601.58
Elemental Analysis: C, 39.93; H, 5.19; Ca, 6.66; N, 16.30; O, 31.91
Related CAS #: 58-05-9 (free acid) 1492-18-8 (calcium) 6035-45-6 (calcium hydrate) 163254-40-8 (sodium) 1141892-29-6 (sodium)
Synonym: Folinic acid calcium salt pentahydrate; Leucovorin calcium hydrate;
IUPAC/Chemical Name: L-Glutamic acid, N-(4-(((2-amino-5-formyl-1,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl)methyl)amino)benzoyl)-, calcium salt (1:1), pentahydrate
InChi Key: NPPBLUASYYNAIG-ZIGBGYJWSA-L
InChi Code: InChI=1S/C20H23N7O7.Ca.5H2O/c21-20-25-16-15(18(32)26-20)27(9-28)12(8-23-16)7-22-11-3-1-10(2-4-11)17(31)24-13(19(33)34)5-6-14(29)30;;;;;;/h1-4,9,12-13,22H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,23,25,26,32);;5*1H2/q;+2;;;;;/p-2/t12?,13-;;;;;;/m0....../s1
SMILES Code: O=C([O-])CC[C@@H](C([O-])=O)NC(C1=CC=C(NCC2N(C=O)C3=C(NC(N)=NC3=O)NC2)C=C1)=O.[H]O[H].[H]O[H].[H]O[H].[H]O[H].[H]O[H].[Ca+2]
Appearance: white to light yellow 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, not in water
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
The following data is based on the product molecular weight 601.58 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: Schwartzman AD, Sethi R, Smith R. Multiorgan failure in a patient treated with the 5-fluorouracil, leucovorin, oxaliplatin, and irinotecan regimen. Clin Colorectal Cancer. 2013 Jun;12(2):136-9. doi: 10.1016/j.clcc.2012.09.005. Epub 2012 Oct 24. Review. PubMed PMID: 23098664.
2: Chuang VT, Suno M. Levoleucovorin as replacement for leucovorin in cancer treatment. Ann Pharmacother. 2012 Oct;46(10):1349-57. doi: 10.1345/aph.1Q677. Epub 2012 Oct 2. Review. PubMed PMID: 23032661.
3: Kovoor PA, Karim SM, Marshall JL. Is levoleucovorin an alternative to racemic leucovorin? A literature review. Clin Colorectal Cancer. 2009 Oct;8(4):200-6. doi: 10.3816/CCC.2009.n.034. Review. PubMed PMID: 19822510.
4: Sterba J, ValÃk D, Bajciová V, Kadlecová V, Gregorová V, Mendelová D. High-dose methotrexate and/or leucovorin rescue for the treatment of children with lymphoblastic malignancies: do we really know why, when and how? Neoplasma. 2005;52(6):456-63. Review. PubMed PMID: 16284689.
5: Kauh J, Johnstone P. Commentary on Wang et al., "Pre-operative chemotherapy with oral tegafur-uracil and leucovorin for rectal cancer" (J Surg Oncol 89: 256-263). J Surg Oncol. 2005 May 1;90(2):106-7. Review. PubMed PMID: 15844186.
6: Hwang JJ. Irinotecan and 5-FU/ leucovorin in metastatic colorectal cancer: balancing efficacy, toxicity, and logistics. Oncology (Williston Park). 2004 Dec;18(14 Suppl 14):26-34. Review. PubMed PMID: 15685831.
7: André T, Noirclerc M, Hammel P, Meckenstock R, Landi B, Cattan S, Selle F, Codoul JF, Guerrier-Parmentier B, Mokhtar R, Louvet C; GERCOR. Phase II study of leucovorin, 5-fluorouracil and gemcitabine for locally advanced and metastatic pancreatic cancer (FOLFUGEM 2). Gastroenterol Clin Biol. 2004 Aug-Sep;28(8-9):645-50. Review. PubMed PMID: 15646530.
8: Reddy GK. Intergroup trial fails to demonstrate a benefit with the addition of irinotecan to bolus 5-fluorouracil/leucovorin in stage III colon cancer. Clin Colorectal Cancer. 2004 Nov;4(4):230-2. Review. PubMed PMID: 15555203.
9: Di Leo A, Buyse M, Bleiberg H. Is overall survival a realistic primary end point in advanced colorectal cancer studies? A critical assessment based on four clinical trials comparing fluorouracil plus leucovorin with the same treatment combined either with oxaliplatin or with CPT-11. Ann Oncol. 2004 Apr;15(4):545-9. Review. PubMed PMID: 15033657.
10: Hwang JJ, Eisenberg SG, Marshall JL. Improving the toxicity of irinotecan/5-FU/leucovorin: a 21-day schedule. Oncology (Williston Park). 2003 Sep;17(9 Suppl 8):37-43. Review. PubMed PMID: 14569847.
11: Saad ED, Hoff PM. UFT and oral leucovorin as radiation sensitizers in rectal and other gastrointestinal malignancies. Cancer Invest. 2003;21(4):624-9. Review. PubMed PMID: 14533450.
12: Kuebler JP, de Gramont A. Recent experience with oxaliplatin or irinotecan combined with 5-fluorouracil and leucovorin in the treatment of colorectal cancer. Semin Oncol. 2003 Aug;30(4 Suppl 15):40-6. Review. PubMed PMID: 14523794.
13: Ghosh A, Boyd R. Leucovorin (calcium folinate) in "antifreeze" poisoning. Emerg Med J. 2003 Sep;20(5):466. Review. PubMed PMID: 12954693; PubMed Central PMCID: PMC1726214.
14: Twelves C. Can capecitabine replace 5-FU/leucovorin in combination with oxaliplatin for the treatment of advanced colorectal cancer? Oncology (Williston Park). 2002 Dec;16(12 Suppl No 14):23-6. Review. PubMed PMID: 12520636.
15: Fisher MD. Irinotecan/5-FU/leucovorin, oxaliplatin/5-FU/leucovorin, and oxaliplatin/irinotecan are each effective in the treatment of 5-FU-resistant advanced colorectal cancer. Clin Colorectal Cancer. 2001 Aug;1(2):85-6. Review. PubMed PMID: 12445365.
16: Fisher MD. Recommendation for irinotecan, 5-fluorouracil, and leucovorin as first-line therapy for colorectal cancer. Clin Colorectal Cancer. 2001 Aug;1(2):82-4. Review. PubMed PMID: 12445364.
17: Langer CJ. The role of UFT and the combination of UFT/leucovorin in non-small cell lung cancer. Lung Cancer. 2001 Nov;34(2):297-303. Review. PubMed PMID: 11679189.
18: Minsky BD. UFT plus oral leucovorin calcium (Orzel) and radiation in combined modality therapy: a comprehensive review. Int J Cancer. 2001 Feb 20;96(1):1-10. Review. PubMed PMID: 11241325.
19: Douillard JY; V-303 Study Group. Irinotecan and high-dose fluorouracil/leucovorin for metastatic colorectal cancer. Oncology (Williston Park). 2000 Dec;14(12 Suppl 14):51-5. Review. PubMed PMID: 11200150.
20: Hoff PM. The tegafur-based dihydropyrimidine dehydrogenase inhibitory fluoropyrimidines, UFT/leucovorin (ORZEL) and S-1: a review of their clinical development and therapeutic potential. Invest New Drugs. 2000 Nov;18(4):331-42. Review. PubMed PMID: 11081569.
