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
Structure for Vintafolide (DB05168)
- 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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism UFolate receptor beta Not Available Humans UFolate receptor gamma Not Available Humans UFolate receptor alpha Not Available Humans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAmbroxol The risk or severity of methemoglobinemia can be increased when Vintafolide is combined with Ambroxol. Ancestim The risk or severity of peripheral neuropathy can be increased when Ancestim is combined with Vintafolide. Articaine The risk or severity of methemoglobinemia can be increased when Vintafolide is combined with Articaine. Benzocaine The risk or severity of methemoglobinemia can be increased when Vintafolide is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Vintafolide is combined with Benzyl alcohol. - 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
- 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]
- 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]
- External Links
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 3 Terminated Treatment Ovarian Cancer 1 2 Completed Treatment Adenocarcinoma of the Lung 1 2 Completed Treatment Endometrial Cancer / Ovarian Cancer 1 2 Completed Treatment Non-Small Cell Lung Cancer (NSCLC) 1 2 Completed Treatment Ovarian Cancer 1
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
Property Value Source Water Solubility 0.0133 mg/mL ALOGPS logP 1.42 ALOGPS logP -12 Chemaxon logS -5.2 ALOGPS pKa (Strongest Acidic) 2.47 Chemaxon pKa (Strongest Basic) 11.9 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 36 Chemaxon Hydrogen Donor Count 23 Chemaxon Polar Surface Area 716.39 Å2 Chemaxon Rotatable Bond Count 44 Chemaxon Refractivity 492.22 m3·mol-1 Chemaxon Polarizability 192.53 Å3 Chemaxon Number of Rings 12 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
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 January 14, 2023 19:03