N-[4-(9-acridinylmethyl)-3-methoxyphenyl]methanesulfonamide
Basic information
- CAS
51264-14-3- Standard SMILES
COc1cc(NS(C)(=O)=O)ccc1Cc1c2ccccc2nc2ccccc12- InChIKey
JRNUZHHDXNSOMO-UHFFFAOYSA-N- Molecular formula
- C22H20N2O3S
- Average molar mass
- 392.5 g/mol
- Monoisotopic mass
- 392.11946368
Overview
N-[4-(9-acridinylmethyl)-3-methoxyphenyl]methanesulfonamide is a member of acridines.
Names & identifiers
- Preferred name
- N-[4-(9-acridinylmethyl)-3-methoxyphenyl]methanesulfonamide
- IUPAC
- N-[4-(acridin-9-ylmethyl)-3-methoxyphenyl]methanesulfonamide
- English name
- Amsacrine
- Molecular formula
- C21H19N3O3S
- Molecular weight
- 393.46
Names & synonyms
N-[4-(9-acridinylmethyl)-3-methoxyphenyl]methanesulfonamideKBio3_002781N-[4-(acridin-9-ylmethyl)-3-methoxyphenyl]methanesulfonamideSpectrum3_001860BSPBio_003280CHEMBL1624239SCHEMBL14479866CHEBI:93727HMS2093A11Pharmakon1600-01503256NSC758423CCG-213145
Show more names
AMSACI-880m-AMSAC01553AmekrinAmsidylAmsakrinAMSIDINELamasineSN 11841
NSC-758423SBI-0206714.P001AB01562989_01SR-05000001846SR-05000001846-1BRD-K98490050-001-01-8BRD-K98490050-003-01-4Q27165420
Database identifiers
- CAS
51264-14-3- PubChem CID
- 3926765
- ChEMBL
CHEMBL1624239
Properties
Computed structural properties
- XLogP
- 4.4
- Topological polar surface area
- 76.7 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 5
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 598
Physicochemical properties
- Melting point
- 230 · 230-240 °C
- Boiling point
- 563 · 563.0±60.0 °C(Predicted)
- Density
- 1.2205 · 1.2205 (rough estimate)
- refractive index
- 1.674 · 1.6740 (estimate)
- storage temp.
- 2 · 2-8°C(protect from light)
- solubility
- Soluble in DMSO
- form
- Powder
- pka
- 8.55 · 8.55±0.10(Predicted)
- color
- Orange to red
- CAS DataBase Reference
- 51264 · 51264-14-3
- NCI Dictionary of Cancer Terms
- amsacrine
- FDA UNII
- 0 DPD30SOY · 00DPD30SOY
- NCI Drug Dictionary
- amsacrine
- ATC code
- 1 XX01 · L01XX01
- Proposition 65 List
- Amsacrine
- IARC
- 2 B · 2B (Vol. 76) 2000
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- ridadr
- 3249
- Toxicity
- LD50 in male, female CDF1 mice: 810 mg/m2; 729 mg/m2 orally (Pavkov)
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_class
- 6.1(b)
- packing_group
- III
- Hazard statements
- H315-H319-H227
- Precautionary statements
- P501-P210-P264-P280-P302+P352-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313-P403+P235
- Hazardous Substances Data
- 51264-14-3(Hazardous Substances Data)
Chemistry & industry
Applications
DescriptionAmsacrine is a cytostatic reported to be active against adult lymphoblastic leukemia which has failed primary treatment or become resistant. Its clinical use, however, is associated with significant neuro-, gastro- and hepatotoxicity.
UsesAmsacrine (Amsidyl) is used as an Investigational drug.
UsesAmsacrine is a drug undergoing intensive trials for severe leukemia and lymphoma. It is a cytotoxic drug that binds with DNA with expressed specificity to the adenosine–tyrosine pair, thus inhibiting DNA synthesis. It has been suggested to be used for severe leukemia. A synonym of this drug is amsidyl.
UsesAntineoplastic.
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: A sulfonamide that is N-phenylmethanesulfonamide substituted by a methoxy group at position 3 and an acridin-9-ylamino group at position 4. It exhibits antineoplastic activity.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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