NAV

TNP-470

Identification

Generic Name
TNP-470
DrugBank Accession Number
DB08633
Background

O-(chloroacetylcarbamoyl)fumagillol (TNP-470) has been used in trials studying the treatment of HIV Infections, Sarcoma, Kaposi, and Pancreatic Neoplasms.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 401.882
Monoisotopic: 401.16051534
Chemical Formula
C19H28ClNO6
Synonyms
  • O-(chloroacetylcarbamoyl)fumagillol
  • O-chloroacetylcarbamoylfumagillol
External IDs
  • AGM 1470
  • AGM-1470
  • DRG-0148
  • NSC-642492
  • TNP 470
  • TNP-470
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UMethionine aminopeptidase 2Not 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
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
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
Integrate drug-drug
interactions in your software
Alendronic acidThe risk or severity of jaw osteonecrosis and anti-angiogenesis can be increased when TNP-470 is combined with Alendronic acid.
AmbroxolThe risk or severity of methemoglobinemia can be increased when TNP-470 is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when TNP-470 is combined with Articaine.
BenzocaineThe risk or severity of methemoglobinemia can be increased when TNP-470 is combined with Benzocaine.
Benzyl alcoholThe risk or severity of methemoglobinemia can be increased when TNP-470 is combined with Benzyl alcohol.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as carbamate esters. These are compounds containing an ester of carbamic acid with the general structure R2NC(=O)OR' (R' not H). They are esters of carbamic acids.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Carbamate esters
Alternative Parents
Dicarboximides / Organic carbonic acids and derivatives / Oxacyclic compounds / Epoxides / Dialkyl ethers / Organopnictogen compounds / Organonitrogen compounds / Organochlorides / Organic oxides / Hydrocarbon derivatives
show 2 more
Substituents
Aliphatic heteropolycyclic compound / Alkyl chloride / Alkyl halide / Carbamic acid ester / Carbonic acid derivative / Carbonyl group / Dialkyl ether / Dicarboximide / Ether / Hydrocarbon derivative
show 11 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
X47GR46481
CAS number
129298-91-5
InChI Key
MSHZHSPISPJWHW-PVDLLORBSA-N
InChI
InChI=1S/C19H28ClNO6/c1-11(2)5-6-13-18(3,27-13)16-15(24-4)12(7-8-19(16)10-25-19)26-17(23)21-14(22)9-20/h5,12-13,15-16H,6-10H2,1-4H3,(H,21,22,23)/t12-,13-,15-,16-,18+,19+/m1/s1
IUPAC Name
(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl N-(2-chloroacetyl)carbamate
SMILES
[H][C@]1(CC=C(C)C)O[C@]1(C)[C@@]1([H])[C@]([H])(OC)[C@@]([H])(CC[C@]11CO1)OC(=O)NC(=O)CCl

References

General References
Not Available
PubChem Compound
369976
PubChem Substance
99445104
ChemSpider
328427
BindingDB
17446
ChEBI
90748
ChEMBL
CHEMBL424278
ZINC
ZINC000003914617
PDBe Ligand
TN4

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2TerminatedTreatmentPancreatic Neoplasms1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Kaposi's Sarcoma1

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 Solubility0.0234 mg/mLALOGPS
logP2.52ALOGPS
logP2.24Chemaxon
logS-4.2ALOGPS
pKa (Strongest Acidic)9.71Chemaxon
pKa (Strongest Basic)-3.7Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area89.69 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity98.45 m3·mol-1Chemaxon
Polarizability41.46 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9886
Blood Brain Barrier+0.7707
Caco-2 permeable-0.5611
P-glycoprotein substrateSubstrate0.647
P-glycoprotein inhibitor IInhibitor0.7156
P-glycoprotein inhibitor IIInhibitor0.5513
Renal organic cation transporterNon-inhibitor0.8603
CYP450 2C9 substrateNon-substrate0.8027
CYP450 2D6 substrateNon-substrate0.8334
CYP450 3A4 substrateSubstrate0.7758
CYP450 1A2 substrateNon-inhibitor0.6951
CYP450 2C9 inhibitorNon-inhibitor0.7222
CYP450 2D6 inhibitorNon-inhibitor0.8919
CYP450 2C19 inhibitorNon-inhibitor0.6379
CYP450 3A4 inhibitorNon-inhibitor0.5666
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7177
Ames testAMES toxic0.5347
CarcinogenicityNon-carcinogens0.828
BiodegradationNot ready biodegradable0.9852
Rat acute toxicity2.8117 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9776
hERG inhibition (predictor II)Non-inhibitor0.8006
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uxr-2277900000-ec80becff2f2b42429b4
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0089-1095000000-cd7bb16fd6f42550b76d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f89-4966400000-8ef54061dd009b49836f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-1090000000-c90afe1e0a4fc992dfba
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a5c-8924000000-a9a9f20edbe77ad0215b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01ec-7954000000-05701a1b1d079480f79c
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-206.6340444
predicted
DarkChem Lite v0.1.0
[M-H]-197.82173
predicted
DeepCCS 1.0 (2019)
[M+H]+205.7970444
predicted
DarkChem Lite v0.1.0
[M+H]+199.64664
predicted
DeepCCS 1.0 (2019)
[M+Na]+207.0979444
predicted
DarkChem Lite v0.1.0
[M+Na]+205.25246
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Details1. Methionine aminopeptidase 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Poly(a) rna binding
Specific Function
Cotranslationally removes the N-terminal methionine from nascent proteins. The N-terminal methionine is often cleaved when the second residue in the primary sequence is small and uncharged (Met-Ala...
Gene Name
METAP2
Uniprot ID
P50579
Uniprot Name
Methionine aminopeptidase 2
Molecular Weight
52891.145 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:33 / Updated at June 12, 2020 16:52