MedKoo Cat#: 413557 | Name: Vintafolide

Description:

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

Vintafolide (also known as EC145) is a folate-targeted conjugate of the chemotherapeutic agent vinblastine and a folate moiety, designed to selectively deliver cytotoxic payloads to cancer cells overexpressing folate receptor alpha (FRα), such as in ovarian, endometrial, and non-small cell lung cancers. In preclinical models, Vintafolide showed potent antitumor activity with nanomolar IC₅₀ values (typically 1–10 nM) in FRα-positive cell lines while sparing normal tissues.

Chemical Structure

Vintafolide
Vintafolide
CAS#742092-03-1

Theoretical Analysis

MedKoo Cat#: 413557

Name: Vintafolide

CAS#: 742092-03-1

Chemical Formula: C86H109N21O26S2

Exact Mass: 1915.7294

Molecular Weight: 1917.06

Elemental Analysis: C, 53.88; H, 5.73; N, 15.34; O, 21.70; S, 3.34

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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Related CAS #
No Data
Synonym
Vintafolide; EC-145; EC 145; EC145
IUPAC/Chemical Name
(2R,5S,8S,11S,14S,19S)-19-(4-(((2-amino-4-oxo-3,4-dihydropteridin-6-yl)methyl)amino)benzamido)-5,8,14-tris(carboxymethyl)-2-(((2-((2-((3aR,3a1R,4R,5S,5aR,10bR)-3a-ethyl-9-((5S,7R,9S)-5-ethyl-5-hydroxy-9-(methoxycarbonyl)-1,4,5,6,7,8,9,10-octahydro-2H-3,7-methano[1]azacycloundecino[5,4-b]indol-9-yl)-4,5-dihydroxy-8-methoxy-6-methyl-3a,3a1,4,5,5a,6,11,12-octahydro-1H-indolizino[8,1-cd]carbazole-5-carbonyl)hydrazine-1-carbonyl)oxy)ethyl)disulfanyl)methyl)-11-(3-guanidinopropyl)-4,7,10,13,16-pentaoxo-3,6,9,12,15-pentaazaicosanedioic acid
InChi Key
KUZYSQSABONDME-QRLOMCMNSA-N
InChi Code
InChI=1S/C86H109N21O26S2/c1-6-82(129)35-42-36-85(78(127)132-5,64-47(21-26-106(39-42)41-82)46-12-8-9-13-50(46)95-64)49-30-48-57(34-58(49)131-4)105(3)75-84(48)23-27-107-25-11-22-83(7-2,74(84)107)76(125)86(75,130)77(126)103-104-81(128)133-28-29-134-135-40-56(73(123)124)100-70(119)55(33-62(113)114)99-69(118)54(32-61(111)112)98-67(116)51(14-10-24-90-79(87)88)96-68(117)53(31-60(109)110)94-59(108)20-19-52(72(121)122)97-66(115)43-15-17-44(18-16-43)91-37-45-38-92-65-63(93-45)71(120)102-80(89)101-65/h8-9,11-13,15-18,22,30,34,38,42,51-56,74-76,91,95,125,129-130H,6-7,10,14,19-21,23-29,31-33,35-37,39-41H2,1-5H3,(H,94,108)(H,96,117)(H,97,115)(H,98,116)(H,99,118)(H,100,119)(H,103,126)(H,104,128)(H,109,110)(H,111,112)(H,113,114)(H,121,122)(H,123,124)(H4,87,88,90)(H3,89,92,101,102,120)/t42-,51-,52-,53-,54-,55-,56-,74-,75+,76+,82-,83+,84+,85-,86-/m0/s1
SMILES Code
CC[C@@]1(C[C@@H]2CN(C1)CCc(c([C@@](C(OC)=O)(c3c(OC)cc(N([C@H]4[C@]([C@@H]([C@@]5(C=CCN6CC[C@]74[C@H]56)CC)O)(C(NNC(OCCSSC[C@@H](C(O)=O)NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC(CC[C@@H](C(O)=O)NC(c8ccc(NCc9nc%10c(N=C(NC%10=O)N)nc9)cc8)=O)=O)CC(O)=O)=O)CCCNC(N)=N)=O)CC(O)=O)=O)CC(O)=O)=O)=O)=O)O)C)c7c3)C2)[nH]%11)c%12c%11cccc%12)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
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

Preparing Stock Solutions

The following data is based on the product molecular weight 1,917.06 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: Ambrosio AJ, Suzin D, Palmer EL, Penson RT. Vintafolide (EC145) for the treatment of folate-receptor-α positive platinum-resistant ovarian cancer. Expert Rev Clin Pharmacol. 2014 Jul;7(4):443-50. doi: 10.1586/17512433.2014.909723. Epub 2014 Apr 18. PMID: 24742319. 2: Vergote I, Leamon CP. Vintafolide: a novel targeted therapy for the treatment of folate receptor expressing tumors. Ther Adv Med Oncol. 2015 Jul;7(4):206-18. doi: 10.1177/1758834015584763. PMID: 26136852; PMCID: PMC4480526. 3: Luyckx M, Votino R, Squifflet JL, Baurain JF. Profile of vintafolide (EC145) and its use in the treatment of platinum-resistant ovarian cancer. Int J Womens Health. 2014 Mar 31;6:351-8. doi: 10.2147/IJWH.S39696. PMID: 24729732; PMCID: PMC3976235. 4: Graybill WS, Coleman RL. Vintafolide: a novel targeted agent for epithelial ovarian cancer. Future Oncol. 2014 Mar;10(4):541-8. doi: 10.2217/fon.14.8. PMID: 24754586. 5: Reddy JA, Dorton R, Bloomfield A, Nelson M, Vetzel M, Guan J, Leamon CP. Rational combination therapy of vintafolide (EC145) with commonly used chemotherapeutic drugs. Clin Cancer Res. 2014 Apr 15;20(8):2104-14. doi: 10.1158/1078-0432.CCR-13-2423. Epub 2014 Jan 15. PMID: 24429878. 6: Serpe L, Gallicchio M, Canaparo R, Dosio F. Targeted treatment of folate receptor-positive platinum-resistant ovarian cancer and companion diagnostics, with specific focus on vintafolide and etarfolatide. Pharmgenomics Pers Med. 2014 Jan 29;7:31-42. doi: 10.2147/PGPM.S58374. PMID: 24516337; PMCID: PMC3917542. 7: Assaraf YG, Leamon CP, Reddy JA. The folate receptor as a rational therapeutic target for personalized cancer treatment. Drug Resist Updat. 2014 Oct-Dec;17(4-6):89-95. doi: 10.1016/j.drup.2014.10.002. Epub 2014 Oct 8. PMID: 25457975. 8: Guertin AD, O'Neil J, Stoeck A, Reddy JA, Cristescu R, Haines BB, Hinton MC, Dorton R, Bloomfield A, Nelson M, Vetzel M, Lejnine S, Nebozhyn M, Zhang T, Loboda A, Picard KL, Schmidt EV, Dussault I, Leamon CP. High Levels of Expression of P-glycoprotein/Multidrug Resistance Protein Result in Resistance to Vintafolide. Mol Cancer Ther. 2016 Aug;15(8):1998-2008. doi: 10.1158/1535-7163.MCT-15-0950. Epub 2016 Jun 2. PMID: 27256377. 9: Naumann RW, Coleman RL, Burger RA, Sausville EA, Kutarska E, Ghamande SA, Gabrail NY, Depasquale SE, Nowara E, Gilbert L, Gersh RH, Teneriello MG, Harb WA, Konstantinopoulos PA, Penson RT, Symanowski JT, Lovejoy CD, Leamon CP, Morgenstern DE, Messmann RA. PRECEDENT: a randomized phase II trial comparing vintafolide (EC145) and pegylated liposomal doxorubicin (PLD) in combination versus PLD alone in patients with platinum-resistant ovarian cancer. J Clin Oncol. 2013 Dec 10;31(35):4400-6. doi: 10.1200/JCO.2013.49.7685. Epub 2013 Oct 14. PMID: 24127448. 10: Razzak M. Gynaecological cancer: vintafolide--targeting the folate receptor with a cytotoxic offers hope. Nat Rev Clin Oncol. 2013 Dec;10(12):668. doi: 10.1038/nrclinonc.2013.201. Epub 2013 Oct 29. PMID: 24165951.