Leucovorin | CAS#58-05-9 | metabolite of folic acid

MedKoo Cat#: 584331 | Name: Leucovorin

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Description:

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

Leucovorin (also known as folinic acid) is a folate derivative that acts by enhancing the bioactivity of chemotherapy agents like methotrexate, aiding in the recovery of normal cells. It bypasses dihydrofolate reductase inhibition, providing tetrahydrofolate for DNA synthesis, thus supporting cell division and repair. Additionally, leucovorin potentiates 5-fluorouracil's efficacy in treating colorectal cancer by enhancing its cytotoxic effects on tumor cells.

Chemical Structure

Leucovorin

CAS#58-05-9 (free acid)

Theoretical Analysis

MedKoo Cat#: 584331

Name: Leucovorin

CAS#: 58-05-9 (free acid)

Chemical Formula: C20H23N7O7

Exact Mass: 473.1659

Molecular Weight: 473.45

Elemental Analysis: C, 50.74; H, 4.90; N, 20.71; O, 23.65

Price and Availability

Size	Price	Availability
100mg	USD 350.00	2 Weeks
250mg	USD 500.00	2 Weeks
1g	USD 850.00	2 Weeks

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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

Leucovorin; HSDB 6544

IUPAC/Chemical Name

5-Formyltetrahydrofolic acid

InChi Key

VVIAGPKUTFNRDU-UHFFFAOYSA-N

InChi Code

InChI=1S/C20H23N7O7/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)

SMILES Code

O=C(O)C(NC(C1=CC=C(NCC2N(C=O)C3=C(NC2)N=C(N)NC3=O)C=C1)=O)CCC(O)=O

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Folinic acid (Leucovorin) is a biological folic acid and is generally administered along with Methotrexate (MTX) (HY-14519) as a rescue agent to decrease MTX-induced toxicity.

In vitro activity:

Folinic acid (Leucovorin) is generally administered along with MTX as a rescue agent to decrease MTX-induced toxicity. The addition of FA (folinic acid) at 50 micrograms ml-1 significantly reduced % MNBN (40-68%) and % Abs (36-77%). Inhibition was also seen at 5 micrograms FA (12 to 54% for MNBN and 20 to 61% for Abs). These results indicate that FA is capable of reducing the cytogenetic damage induced by MTX and appears to be an anticlastogenic agent. Reference: Mutat Res. 1998 Feb 2;397(2):221-8. https://pubmed.ncbi.nlm.nih.gov/9541646/

In vivo activity:

These data show that chronic administration of MTX induces suppression of skeletal growth in mice, possibly through the inhibition of the pathway of de novo DNA synthesis. Folinic acid treatment following MTX administration appears to reverse this growth inhibition. Reference: Acta Paediatr. 2003 Dec;92(12):1438-44. https://pubmed.ncbi.nlm.nih.gov/14971796/

	Solvent	mg/mL	mM	comments
Solubility
	DMSO	172.5	364.35

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 473.45 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

Formulation protocol:

1. Tedeschi PM, Kathari YK, Farooqi IN, Bertino JR. Leucovorin rescue allows effective high-dose pralatrexate treatment and an increase in therapeutic index in mesothelioma xenografts. Cancer Chemother Pharmacol. 2014 Nov;74(5):1029-32. doi: 10.1007/s00280-014-2580-z. Epub 2014 Sep 9. PMID: 25205429; PMCID: PMC4209237. 2. Keshava C, Keshava N, Whong WZ, Nath J, Ong TM. Inhibition of methotrexate-induced chromosomal damage by folinic acid in V79 cells. Mutat Res. 1998 Feb 2;397(2):221-8. doi: 10.1016/s0027-5107(97)00216-9. PMID: 9541646. 3. Iqbal MP, Ahmed M, Umer M, Mehboobali N, Qureshi AA. Effect of methotrexate and folinic acid on skeletal growth in mice. Acta Paediatr. 2003 Dec;92(12):1438-44. PMID: 14971796. 4. Van der Wilt CL, Pinedo HM, Smid K, Peters GJ. Elevation of thymidylate synthase following 5-fluorouracil treatment is prevented by the addition of leucovorin in murine colon tumors. Cancer Res. 1992 Sep 15;52(18):4922-8. PMID: 1516048.

In vitro protocol:

In vivo protocol:

1. Iqbal MP, Ahmed M, Umer M, Mehboobali N, Qureshi AA. Effect of methotrexate and folinic acid on skeletal growth in mice. Acta Paediatr. 2003 Dec;92(12):1438-44. PMID: 14971796. 2. Van der Wilt CL, Pinedo HM, Smid K, Peters GJ. Elevation of thymidylate synthase following 5-fluorouracil treatment is prevented by the addition of leucovorin in murine colon tumors. Cancer Res. 1992 Sep 15;52(18):4922-8. PMID: 1516048.

1: Damaske A, Ma N, Williams R. Leucovorin-induced hypersensitivity reaction. J Oncol Pharm Pract. 2012 Mar;18(1):136-9. doi: 10.1177/1078155210396577. Epub 2011 Jan 19. PubMed PMID: 21248170. 2: Ishihara S, Hayama T, Yamada H, Nozawa K, Matsuda K, Watanabe T. Benefit of tegafur-uracil and leucovorin in chemoradiotherapy for rectal cancer. Hepatogastroenterology. 2011 May-Jun;58(107-108):756-62. PubMed PMID: 21830385. 3: Saltz L, Badarinath S, Dakhil S, Bienvenu B, Harker WG, Birchfield G, Tokaz LK, Barrera D, Conkling PR, O'Rourke MA, Richards DA, Reidy D, Solit D, Vakiani E, Capanu M, Scales A, Zhan F, Boehm KA, Asmar L, Cohn A. Phase III trial of cetuximab, bevacizumab, and 5-fluorouracil/leucovorin vs. FOLFOX-bevacizumab in colorectal cancer. Clin Colorectal Cancer. 2012 Jun;11(2):101-11. doi: 10.1016/j.clcc.2011.05.006. Epub 2011 Nov 4. PubMed PMID: 22055112. 4: Budai B, Nagy T, Láng I, Hitre E. The use of high dose d,l-leucovorin in first-line bevacizumab+mFOLFIRI treatment of patients with metastatic colorectal cancer may enhance the antiangiogenic effect of bevacizumab. Angiogenesis. 2013 Jan;16(1):113-21. doi: 10.1007/s10456-012-9303-z. Epub 2012 Sep 6. PubMed PMID: 22956187. 5: Ajima H, Ogata H, Fujita K, Miwa K, Sunakawa Y, Mizuno K, Ishida H, Yamashita K, Nakayama H, Kawara K, Takahashi H, Sasaki Y. Clinical and economic evaluation of first-line therapy with FOLFIRI or modified FOLFOX6 for metastatic colorectal cancer. Jpn J Clin Oncol. 2010 Jul;40(7):634-8. doi: 10.1093/jjco/hyq029. PubMed PMID: 20587616. 6: Sadahiro S, Suzuki T, Maeda Y, Tanaka A, Ogoshi K, Kamijo A, Murayama C, Tsukioka S, Sakamoto E, Fukui Y, Oka T. Molecular determinants of folate levels after leucovorin administration in colorectal cancer. Cancer Chemother Pharmacol. 2010 Mar;65(4):735-42. doi: 10.1007/s00280-009-1079-5. Epub 2009 Jul 28. PubMed PMID: 19636555. 7: Sadahiro S, Suzuki T, Tanaka A, Okada K, Kamijo A, Nagase H, Uchida J. Reduction in γ-glutamyl hydrolase expression is associated with response to uracil and tegafur/leucovorin chemotherapy in patients with colorectal cancer. Anticancer Res. 2013 Aug;33(8):3431-8. PubMed PMID: 23898115. 8: Yamazaki K, Kuwano H, Ojima H, Otsuji T, Kato T, Shimada K, Hyodo I, Nishina T, Shirao K, Esaki T, Ohishi T, Denda T, Takeuchi M, Boku N. A randomized phase II study of combination therapy with S-1, oral leucovorin, and oxaliplatin (SOL) and mFOLFOX6 in patients with previously untreated metastatic colorectal cancer. Cancer Chemother Pharmacol. 2015 Mar;75(3):569-77. doi: 10.1007/s00280-015-2676-0. Epub 2015 Jan 10. PubMed PMID: 25575764. 9: Cho YH, Kim SY, Hong Lee M, Yoo MW, Bang HY, Lee KY, Yoon SY. Comparative analysis of the efficacy and safety of chemotherapy with oxaliplatin plus fluorouracil/leucovorin between elderly patients over 65 years and younger patients with advanced gastric cancer. Gastric Cancer. 2012 Oct;15(4):389-95. doi: 10.1007/s10120-011-0128-z. Epub 2012 Jan 12. PubMed PMID: 22237658. 10: Mohammad HA, Magdy FM, Mahmoud OM. FOLFOX (oxaliplatin and 5 fluorouracil/leucovorin) in patients with untreated metastatic gastric adenocarcinoma Phase II study. Indian J Cancer. 2011 Oct-Dec;48(4):460-5. doi: 10.4103/0019-509X.92280. PubMed PMID: 22293261. 11: Francois E, Smith D, Dahan L, Michel C, Perrier H, Mari V, Seitz JF, Follana P, Evesque L, Chamorey E. Uracil-tegafur/leucovorin and mitomycin C salvage therapy in patients with advanced colorectal cancer: a phase II study. J Chemother. 2012 Aug;24(4):207-11. doi: 10.1179/1973947812Y.0000000021. PubMed PMID: 23040684. 12: Morak MJ, Richel DJ, van Eijck CH, Nuyttens JJ, van der Gaast A, Vervenne WL, Padmos EE, Schaake EE, Busch OR, van Tienhoven G. Phase II trial of Uracil/Tegafur plus leucovorin and celecoxib combined with radiotherapy in locally advanced pancreatic cancer. Radiother Oncol. 2011 Feb;98(2):261-4. doi: 10.1016/j.radonc.2010.10.016. Epub 2010 Nov 12. PubMed PMID: 21075468. 13: Karbownik A, Szałek E, Urjasz H, Kadziołka M, Grześkowiak E. Stability of calcium folinate (Teva) in concentrate after re-use and in dilute infusions in 0.9% NaCl in polyethylene bags. Acta Pol Pharm. 2013 Mar-Apr;70(2):301-7. PubMed PMID: 23614286. 14: Macy ME, Duncan T, Whitlock J, Hunger SP, Boklan J, Narendren A, Herzog C, Arceci RJ, Bagatell R, Trippett T, Christians U, Rolla K, Ivy SP, Gore L; Pediatric Oncology Experimental Therapeutics Investigators' Consortium (POETIC). A multi-center phase Ib study of oxaliplatin (NSC#266046) in combination with fluorouracil and leucovorin in pediatric patients with advanced solid tumors. Pediatr Blood Cancer. 2013 Feb;60(2):230-6. doi: 10.1002/pbc.24278. Epub 2012 Sep 28. PubMed PMID: 23024067; PubMed Central PMCID: PMC3522763. 15: Kato S, Andoh H, Gamoh M, Yamaguchi T, Murakawa Y, Shimodaira H, Takahashi S, Mori T, Ohori H, Maeda S, Suzuki T, Kato S, Akiyama S, Sasaki Y, Yoshioka T, Ishioka C; Tohoku Clinical Oncology Research and Education. Safety verification trials of mFOLFIRI and sequential IRIS + bevacizumab as first- or second-line therapies for metastatic colorectal cancer in Japanese patients. Oncology. 2012;83(2):101-7. doi: 10.1159/000339541. Epub 2012 Jul 9. PubMed PMID: 22777333. 16: Zittoun J, Tonelli AP, Marquet J, De Gialluly E, Hancock C, Yacobi A, Johnson JB. Pharmacokinetic comparison of leucovorin and levoleucovorin. Eur J Clin Pharmacol. 1993;44(6):569-73. PubMed PMID: 8405015. 17: Grogan L, Sotos GA, Allegra CJ. Leucovorin modulation of fluorouracil. Oncology (Williston Park). 1993 Aug;7(8):63-72; discussion 75-6. Review. PubMed PMID: 8398636. 18: McGuire BW, Sia LL, Leese PT, Gutierrez ML, Stokstad EL. Pharmacokinetics of leucovorin calcium after intravenous, intramuscular, and oral administration. Clin Pharm. 1988 Jan;7(1):52-8. PubMed PMID: 3257913. 19: Yoshida Y, Hasegawa J, Nishimura J, Hirota M, Kim Y, Nezu R. [Clinical significance of bolus 5-fluorouracil for recurrent or metastatic colorectal cancer treated with FOLFOX+ BevacizumabTherapy]. Gan To Kagaku Ryoho. 2011 Aug;38(8):1293-6. Japanese. PubMed PMID: 21829066. 20: Xie Q, Wen F, Wei YQ, Deng HX, Li Q. Cost analysis of adjuvant therapy with XELOX or FOLFOX4 for colon cancer. Colorectal Dis. 2013 Aug;15(8):958-62. doi: 10.1111/codi.12216. PubMed PMID: 23506229.

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