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Pharmaceutical impurity

Itraconazole Imp. A (EP): 4-[4-[4-(4-Methoxyphenyl)piperazin- 1-yl]phenyl]-2-[(1RS)-1-methylpropyl]-2,4-dihydro- 3H-1,2,4-triazol-3-one

Itraconazole Imp. A (EP): 4-[4-[4-(4-Methoxyphenyl)piperazin- 1-yl]phenyl]-2-[(1RS)-1-methylpropyl]-2,4-dihydro- 3H-1,2,4-triazol-3-one is listed in the pharmaceutical impurity collection under CAS 252964-68-4. Its represented structure has formula C23H29N5O2 and a calculated molecular weight of 407.52 g/mol.

2D chemical structure

N N N N N O O

Chemical identity

Catalog name
Itraconazole Imp. A (EP): 4-[4-[4-(4-Methoxyphenyl)piperazin- 1-yl]phenyl]-2-[(1RS)-1-methylpropyl]-2,4-dihydro- 3H-1,2,4-triazol-3-one
Common name
Itraconazole Imp. A (EP)
Chemical name
4-[4-[4-(4-Methoxyphenyl)piperazin- 1-yl]phenyl]-2-[(1RS)-1-methylpropyl]-2,4-dihydro- 3H-1,2,4-triazol-3-one
CAS
252964-68-4
SMILES
CCC(C)n1ncn(-c2ccc(N3CCN(c4ccc(OC)cc4)CC3)cc2)c1=O
InChI
InChI=1S/C23H29N5O2/c1-4-18(2)28-23(29)27(17-24-28)21-7-5-19(6-8-21)25-13-15-26(16-14-25)20-9-11-22(30-3)12-10-20/h5-12,17-18H,4,13-16H2,1-3H3
InChIKey
IVIVGYTUQVJVPF-UHFFFAOYSA-N
Associated API
Itraconazole

Record ID: A5e1a7a741f9e

Computed properties

C23H29N5O2 Molecular formula
407.518 g/molMolecular weight
407.2321 DaMonoisotopic exact mass
55.53 ŲTopological polar surface area
3.3402 Calculated LogP (Wildman–Crippen)
120.246 cm³/molMolar refractivity (Wildman–Crippen)
5 countHydrogen-bond acceptors
0 countHydrogen-bond donors

Descriptors are calculated from the displayed SMILES. Calculated LogP is not a measured partition coefficient or a pH-specific LogD. 1 potential atom stereocenters have unspecified configuration.

Molecular descriptor profile

Descriptor radar

Mol. weight LogP TPSA HBA HBD Rotatable 25 50 75 100

Structural feature counts

0 2 4 6 Count H-bond acceptors H-bond donors Rotatable bonds Rings Aromatic rings Stereo centers

Element composition

C H N O 0 8 16 24 Number of atoms

Radar scale: 0–100 percentile within 25,771 distinct represented structures in this release, using the midpoint rank for ties. Larger values indicate a higher descriptor rank, not greater safety or toxicity. Element counts include hydrogen and combine isotopes under each element.

Radar values and percentile reference
DescriptorValuePercentile
Molecular weight407.51871.07
Calculated LogP (Wildman–Crippen)3.340268.13
Topological polar surface area55.5336.44
Hydrogen-bond acceptors565.12
Hydrogen-bond donors011.28
Rotatable bonds (strict)669.73

Complete molecular descriptors

PropertyCalculated valueUnit / type
Molecular formulaC23H29N5O2dimensionless
Molecular weight407.518g/mol
Monoisotopic exact mass407.2321Da
Topological polar surface area55.53Ų
Calculated LogP (Wildman–Crippen)3.3402dimensionless
Molar refractivity (Wildman–Crippen)120.246cm³/mol
Hydrogen-bond acceptors5count
Hydrogen-bond donors0count
Rotatable bonds (strict)6count
Heavy atoms30count
Heteroatoms7count
Rings4count
Aromatic rings3count
Aliphatic rings1count
Saturated rings1count
Aromatic heterocycles1count
Aliphatic heterocycles1count
Saturated heterocycles1count
Aromatic carbocycles2count
Aliphatic carbocycles0count
Fraction of sp³ carbon atoms0.3913fraction
Formal charge0e
Disconnected components1count
Isotopically specified atoms0count
Potential atom stereocenters1count
Unspecified atom stereocenters1count
Spiro atoms0count
Bridgehead atoms0count
Labute approximate surface area176.6558Ų
Valence electrons158count
Radical electrons0count
Bertz complexity1,014.9971index
Balaban J1.4155index

Ring categories overlap and should not be summed. No toxicity result, PDE, HBEL or acceptable intake is inferred from these descriptors.

Toxicological services and resources for Itraconazole Imp. A (EP): 4-[4-[4-(4-Methoxyphenyl)piperazin- 1-yl]phenyl]-2-[(1RS)-1-methylpropyl]-2,4-dihydro- 3H-1,2,4-triazol-3-one

Qualification and safety assessment of Itraconazole Imp. A (EP): 4-[4-[4-(4-Methoxyphenyl)piperazin- 1-yl]phenyl]-2-[(1RS)-1-methylpropyl]-2,4-dihydro- 3H-1,2,4-triazol-3-one

Explore toxicological qualification of Itraconazole Imp. A (EP): 4-[4-[4-(4-Methoxyphenyl)piperazin- 1-yl]phenyl]-2-[(1RS)-1-methylpropyl]-2,4-dihydro- 3H-1,2,4-triazol-3-one and ICH M7 mutagenic impurity assessment of Itraconazole Imp. A (EP): 4-[4-[4-(4-Methoxyphenyl)piperazin- 1-yl]phenyl]-2-[(1RS)-1-methylpropyl]-2,4-dihydro- 3H-1,2,4-triazol-3-one for evaluation of this impurity in its pharmaceutical context.

Where data gaps need to be addressed, resources include read-across assessment for Itraconazole Imp. A (EP): 4-[4-[4-(4-Methoxyphenyl)piperazin- 1-yl]phenyl]-2-[(1RS)-1-methylpropyl]-2,4-dihydro- 3H-1,2,4-triazol-3-one and acceptable intake and limit justification for Itraconazole Imp. A (EP): 4-[4-[4-(4-Methoxyphenyl)piperazin- 1-yl]phenyl]-2-[(1RS)-1-methylpropyl]-2,4-dihydro- 3H-1,2,4-triazol-3-one. The relevant approach depends on the available evidence, exposure and duration of use.

Related Altox services and technical resources

Other catalogue designations with the same represented structure

These are separate catalogue entries; shared structure does not establish interchangeable pharmacopoeial designations.

Identity sources and calculation method

Identifiers originate from the source catalogues and available public identity records. InChI and InChIKey on this page are generated from the displayed SMILES. RDKit validation checks the molecular representation; it does not independently verify every catalogue assignment.

Discuss an assessment for Itraconazole Imp. A (EP): 4-[4-[4-(4-Methoxyphenyl)piperazin- 1-yl]phenyl]-2-[(1RS)-1-methylpropyl]-2,4-dihydro- 3H-1,2,4-triazol-3-one

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