Dehydronifedipine
Basic information
- CAS
67035-22-7- Standard SMILES
COC(=O)c1c(C)nc(C)c(C(=O)OC)c1-c1ccccc1[N+](=O)[O-]- InChIKey
UMQHJQGNGLQJPF-UHFFFAOYSA-N- Molecular formula
- C17H16N2O6
- Average molar mass
- 344.32 g/mol
- Monoisotopic mass
- 344.10083623
Overview
Dehydronifedipine is a phenylpyridine.
Names & identifiers
- Preferred name
- Dehydronifedipine
- IUPAC
- dimethyl 2,6-dimethyl-4-(2-nitrophenyl)pyridine-3,5-dicarboxylate
- English name
- OXIDIZED NIFEDIPINE
- Molecular formula
- C17H16N2O6
- Molecular weight
- 344.32
Names & synonyms
67035-22-7DehydronifedipineDDNPCDimethyl 2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylateOR3W8GT1C8BAY-b 4759DTXSID90523474-(2-Nitrophenyl)-3,5-bis(carboxymethyl)-2,6-dimethylpyridine2,6-Dimethyl-4-(ortho-nitrophenyl)-3,5-pyridinedicarboxylic aciddimenthyl ester4-(2'-Nitrophenyl)-2,6-dimethylpyridine-3,5-dicarboxylic acid dimethyl esterDNIFRefChem:585660
Show more names
B 4759BAY-b-4759Nifedipine-1NIFEDIPINE EP IMP ANifidipine Impurity ANitrophenyl nifedipineNifedipine impurity A CRSNifedipine impurity A (EP)Desmethyldihydronifedipine
DTXCID9030919Dehydro Nifedipinedimethyl 2,6-dimethyl-4-(2-nitrophenyl)pyridine-3,5-dicarboxylateNifedipine EP Impurity A4-(2-Nitrophenyl)-2,6-dimethylpyridine-3,5-dicarboxylic acid dimethyl esterMFCD00153847Nifedipine M (dehydro)3,5-dimethyl 2,6-dimethyl-4-(2-nitrophenyl)pyridine-3,5-dicarboxylate
Database identifiers
- CAS
67035-22-7- PubChem CID
- 128753
- DTXSID
DTXSID9052347- ChEMBL
CHEMBL1573- ChEBI
CHEBI:168902- UNII
- OR3W8GT1C8
- EC Number
- 620-752-9
- Nikkaji
- J331.420K
Properties
Computed structural properties
- XLogP
- 2.8
- Topological polar surface area
- 111 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 5
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 492
Experimental & physicochemical properties
Chemical ClassesPharmaceutical
DrugsPharmaceuticals -> Metabolite of Nifedipine
Physicochemical properties
- Melting point
- 100 · 100-105 °C
- Boiling point
- 443.7 · 443.7±45.0 °C(Predicted)
- Density
- 1.284 · 1.284±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- pka
- 1.55 · 1.55±0.29(Predicted)
- form
- powder
- color
- yellow
- InChI
- 1S/C17H16N2O6/c1-9-13(16(20)24-3)15(14(10(2)18-9)17(21)25-4)11-7-5-6-8-12(11)19(22)23/h5-8H,1-4H3
- InChIKey
- UMQHJQGNGLQJPF-UHFFFAOYSA-N
- SMILES
- COC(=O)c1c(C)nc(C)c(C(=O)OC)c1-c2ccccc2[N+]([O-])=O
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
Danger
H318 (93.5%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
P264+P265, P280, P305+P354+P338, and P317 (click each P-code to see the statement)
Aggregated GHS information provided per 46 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesEye Dam. 1 (93.5%)
Toxicology
USGS Health-Based Screening Levels for Evaluating Water-Quality
Dehydronifedipine
Pharmaceutical
Smith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 2
- risk_code
- 41
- Signal word
- Danger
- Symbol(GHS)
- GHS05
- hazard_code
- Xi
- safety_code
- 26-39
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H318
- Hazard Classifications
- Eye Dam. 1
Chemistry & industry
Pharmacology
Metabolism/MetabolitesOxidized nifedipine is a known human metabolite of nifedipine.
Tissue LocationsKidney
Cellular LocationsCytoplasm
Applications
DescriptionDehydro nifedipine is an active metabolite of nifedipine , a calcium channel blocker present in formulations used to treat hypertension and angina. Dehydro nifedipine is formed when nifedipine is metabolized by the cytochrome P450 (CYP) isomers CYP3A4 and CYP3A5. Dehydro nifedipine inhibits glucose uptake in PC-12 cells with an IC50 value of 130 μM.
UsesOxidized nifedipine has been used for apoptotic signaling studies in dopaminergic neurons.
UsesThe main Nifedipine metabolite in human plasma
Additional notes
DefinitionChEBI: Dehydronifedipine is a phenylpyridine.
Related reactions
1 records
Compound notes
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