Identification

Generic Name
Vintafolide
DrugBank Accession Number
DB05168
Background

Vintafolide is a folate-targeted chemotherapeutic conjugate (folate vitamin + vinca alkaloid) in clinical stage development as a treatment for folate-receptor positive cancers.

Type
Small Molecule
Groups
Investigational
Structure
Weight
Average: 1917.06
Monoisotopic: 1915.729405062
Chemical Formula
C86H109N21O26S2
Synonyms
  • Vintafolide
External IDs
  • EC-145
  • EC145

Pharmacology

Indication

Investigated for use/treatment in solid tumors.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

Vintafolide minimizes the off-target toxicity by delivering the vinca molecule directly and specifically to cancer cells that over-express the folate-receptor. Once delivered to the cancer cell surface, Vintafolide is internalized into the cancer cell via endocytosis, a natural cellular process. Once inside the cell, Endocyte’s proprietary linker technology releases the chemotherapy to eliminate the cancer cell.

TargetActionsOrganism
UFolate receptor betaNot AvailableHumans
UFolate receptor gammaNot AvailableHumans
UFolate receptor alphaNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AncestimThe risk or severity of peripheral neuropathy can be increased when Ancestim is combined with Vintafolide.
CandicidinThe serum concentration of Vintafolide can be increased when it is combined with Candicidin.
ClarithromycinThe serum concentration of Vintafolide can be increased when it is combined with Clarithromycin.
ClindamycinThe serum concentration of Vintafolide can be increased when it is combined with Clindamycin.
Darbepoetin alfaThe risk or severity of Thrombosis can be increased when Darbepoetin alfa is combined with Vintafolide.
Epoetin deltaThe risk or severity of peripheral neuropathy can be increased when Epoetin delta is combined with Vintafolide.
ErythromycinThe serum concentration of Vintafolide can be increased when it is combined with Erythromycin.
ErythropoietinThe risk or severity of Thrombosis can be increased when Erythropoietin is combined with Vintafolide.
EverolimusThe serum concentration of Vintafolide can be increased when it is combined with Everolimus.
FilgrastimThe risk or severity of peripheral neuropathy can be increased when Filgrastim is combined with Vintafolide.
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Food Interactions
Not Available

Categories

ATC Codes
L01CA06 — Vintafolide
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as vinca alkaloids. These are alkaloids with a dimeric chemical structure composed of an indole nucleus (catharanthine), and a dihydroindole nucleus (vindoline), joined together.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Vinca alkaloids
Sub Class
Not Available
Direct Parent
Vinca alkaloids
Alternative Parents
Oligopeptides / Hexacarboxylic acids and derivatives / Arginine and derivatives / Glutamine and derivatives / Aspartic acid and derivatives / Carbazoles / Hippuric acids / N-acyl-L-alpha-amino acids / Quinoline carboxamides / Pterins and derivatives
show 43 more
Substituents
1,2-aminoalcohol / 3-alkylindole / Alcohol / Alkyl aryl ether / Alpha peptide / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-oligopeptide / Amine / Amino acid
show 81 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
36O410ZD4I
CAS number
742092-03-1
InChI Key
KUZYSQSABONDME-QRLOMCMNSA-N
InChI
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
IUPAC Name
(2S)-2-[(4-{[(2-amino-4-oxo-4,8-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]-4-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-2-carboxy-1-{[(1S)-2-carboxy-1-{[(1R)-1-carboxy-2-{[2-({N'-[(1R,9R,10S,11R,12R,19R)-12-ethyl-4-[(1R,13S,15R,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0^{4,12}.0^{5,10}]nonadeca-4(12),5,7,9-tetraen-13-yl]-10,11-dihydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,13-tetraene-10-carbonyl]hydrazinecarbonyl}oxy)ethyl]disulfanyl}ethyl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}butyl]carbamoyl}-2-carboxyethyl]carbamoyl}butanoic acid
SMILES
[H][C@@]12N3CC[C@@]11C4=CC(=C(OC)C=C4N(C)[C@@]1([H])[C@](O)([C@H](O)[C@]2(CC)C=CC3)C(=O)NNC(=O)OCCSSC[C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(O)=O)NC(=O)CC[C@H](NC(=O)C1=CC=C(NCC2=CNC3=NC(N)=NC(=O)C3=N2)C=C1)C(O)=O)C(O)=O)[C@]1(C[C@@]2([H])C[N@](C[C@](O)(CC)C2)CCC2=C1NC1=CC=CC=C21)C(=O)OC

References

General References
  1. Leamon CP, Reddy JA, Vlahov IR, Westrick E, Parker N, Nicoson JS, Vetzel M: Comparative preclinical activity of the folate-targeted Vinca alkaloid conjugates EC140 and EC145. Int J Cancer. 2007 Oct 1;121(7):1585-92. [Article]
  2. Reddy JA, Dorton R, Westrick E, Dawson A, Smith T, Xu LC, Vetzel M, Kleindl P, Vlahov IR, Leamon CP: Preclinical evaluation of EC145, a folate-vinca alkaloid conjugate. Cancer Res. 2007 May 1;67(9):4434-42. [Article]
PubChem Compound
122173811
PubChem Substance
347827715
ChemSpider
27444385
ChEBI
134736
ChEMBL
CHEMBL3039521
Wikipedia
EC145

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3TerminatedTreatmentOvarian Cancer1
2CompletedTreatmentAdenocarcinoma of Lung (Disorder)1
2CompletedTreatmentEndometrial Cancer / Ovarian Cancer1
2CompletedTreatmentNon-Small Cell Lung Carcinoma (NSCLC)1
2CompletedTreatmentOvarian Cancer1
2CompletedTreatmentSolid Tumors1
2WithdrawnTreatmentNeoplasms, Breast1
1CompletedTreatmentCancer1
1TerminatedTreatmentCancer, Advanced1
1TerminatedTreatmentSolid Tumors1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0133 mg/mLALOGPS
logP1.42ALOGPS
logP-12ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)2.47ChemAxon
pKa (Strongest Basic)11.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count36ChemAxon
Hydrogen Donor Count23ChemAxon
Polar Surface Area716.39 Å2ChemAxon
Rotatable Bond Count44ChemAxon
Refractivity492.22 m3·mol-1ChemAxon
Polarizability192.53 Å3ChemAxon
Number of Rings12ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Methotrexate binding
Specific Function
Binds to folate and reduced folic acid derivatives and mediates delivery of 5-methyltetrahydrofolate and folate analogs into the interior of cells. Has high affinity for folate and folic acid analo...
Gene Name
FOLR2
Uniprot ID
P14207
Uniprot Name
Folate receptor beta
Molecular Weight
29279.31 Da
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Folic acid binding
Specific Function
Binds to folate and reduced folic acid derivatives and mediates delivery of 5-methyltetrahydrofolate to the interior of cells. Isoform Short does not bind folate.
Gene Name
FOLR3
Uniprot ID
P41439
Uniprot Name
Folate receptor gamma
Molecular Weight
27638.0 Da
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Receptor activity
Specific Function
Binds to folate and reduced folic acid derivatives and mediates delivery of 5-methyltetrahydrofolate and folate analogs into the interior of cells. Has high affinity for folate and folic acid analo...
Gene Name
FOLR1
Uniprot ID
P15328
Uniprot Name
Folate receptor alpha
Molecular Weight
29818.94 Da

Drug created at October 21, 2007 22:23 / Updated at February 21, 2021 18:51