Lodamin
Basic information
- CAS
129298-91-5- Standard SMILES
CO[C@@H]1[C@H](OC(=O)NC(=O)CCl)CC[C@]2(CO2)[C@H]1[C@@]1(C)O[C@@H]1CC=C(C)C- InChIKey
MSHZHSPISPJWHW-PVDLLORBSA-N- Molecular formula
- C19H28ClNO6
- Average molar mass
- 401.9 g/mol
- Monoisotopic mass
- 401.1605153
Overview
O-(chloroacetylcarbamoyl)fumagillol is a carbamate ester that is fumagillol in which the hydroxy group has been converted to the corresponding N-(chloroacetyl)carbamate derivative. It has a role as an antineoplastic agent, an angiogenesis inhibitor, an EC 1.5.1.3 (dihydrofolate reductase) inhibitor, a methionine aminopeptidase 2 inhibitor and a retinoic acid receptor alpha antagonist. It is a spiro-epoxide, a carbamate ester, a sesquiterpenoid, an organochlorine compound and a semisynthetic derivative. It is functionally related to a fumagillol.
Names & identifiers
- Preferred name
- Lodamin
- IUPAC
- [(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl] N-(2-chloroacetyl)carbamate
- English name
- AGM-1470
- Molecular formula
- C19H28ClNO6
- Molecular weight
- 401.88
Names & synonyms
Tnp-470129298-91-5O-(chloroacetylcarbamoyl)fumagillolO-ChloroacetylcarbamoylfumagillolNSC642492DRG-0148LODAMINDTXSID0041141NSC-642492X47GR46481CHEBI:90748DTXCID00819891
Show more names
AGM-1470TNP470,TNP 470Fumagillin Impurity 1O-Chloracetyl-carbamoyl fumagillol6-O-chloroacetylcarbamoylfumagillolTNP-470 - CAS 129298-91-5 - CalbiochemO-(chloroacetyl-carbaMoyl) fuMagillol,TNP-470
(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 (chloroacetyl)carbamate[(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl] N-(2-chloroacetyl)carbamate((3R,4S,5S,6R)-5-methoxy-4-((2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl)-1-oxaspiro(2.5)octan-6-yl) N-(2-chloroacetyl)carbamate(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 (chloroacetyl)carbamateRefChem:898528mPEG-PLA-TNP-470TNP470AGM1470
Properties
Computed structural properties
- XLogP
- 2.5
- Topological polar surface area
- 89.7 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 7
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 636
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Melting point
- 90 · 90-93°C
- alpha
- 24 · D24 -46.6° (c = 0.44 in CHCl3)
- Density
- 1.26 · 1.26±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- 15 mg/mL · DMSO: >15mg/mL
- form
- White to light yellow solid
- pka
- 7.19 · 7.19±0.46(Predicted)
- color
- White to Pale Yellow Waxy
- Stability
- Hygroscopic
- InChIKey
- MSHZHSPISPJWHW-PVDLLORBSA-N
- SMILES
- ClCC(=O)NC(=O)O[C@H]1[C@H]([C@@H]([C@]3(OC3)CC1)[C@]2(O[C@@H]2CC=C(C)C)C)OC
- NCI Dictionary of Cancer Terms
- -470 · TNP-470
- FDA UNII
- 47 GR46481 · X47GR46481
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (97.4%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (97.4%)
Safety data
- wgk
- 2
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms.
Agents and endogenous substances that antagonize or inhibit the development of new blood vessels.
Applications
DescriptionTNP-470 is a synthetic analog of fumagillin that inhibits angiogenesis. It irreversibly inactivates methionine aminopeptidase-2 (MetAP2; IC50 = 2 μM), blocking endothelial cell proliferation in vitro and angiogenesis in vivo. It is without effect on MetAP1. TNP-470 has therapeutic potential in cancer and microsporidiosis.
UsesTNP-470 is a synthetic analog of fumagillin that inhibits angiogenesis. It irreversibly inactivates methionine aminopeptidase-2 (MetAP2; IC50 = 2 μM), blocking endothelial cell proliferation in vitro and angiogenesis in vivo. It is without effect on MetAP1. TNP-470 has therapeutic potential in cancer and microsporidiosis.
UsesTNP-470 is a synthetic analog of Fumagillin (F862650); a compound isolated from the fungus Aspergillus fumigatus. Fumagillin is an antimicrobial agent used in the treatment of microsporidiosis and shows promise as both an anti-infective and antiangiogenic agent.
General DescriptionTNP-470 is a synthetic analogue of fumagillin. It is a natural product of Aspergillus fumigatus. TNP-470 serves as an angiogenesis inhibitor.
Additional notes
DefinitionChEBI: A carbamate ester that is fumagillol in which the hydroxy group has been converted to the corresponding N-(chloroacetyl)carbamate derivative.
Related reactions
1 records
Compound notes
Loading…