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Database / Pharmaceutical impurity

Pharmaceutical impurity

Amoxicillin Trihydrate Imp. A (EP): (2S,5R,6R)-6-Amino-3,3- dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]- heptane-2-carboxylic Acid (6-Aminopenicillanic Acid)

Amoxicillin Trihydrate Imp. A (EP): (2S,5R,6R)-6-Amino-3,3- dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]- heptane-2-carboxylic Acid (6-Aminopenicillanic Acid) is listed in the pharmaceutical impurity collection under CAS 551-16-6. Its represented structure has formula C8H12N2O3S and a calculated molecular weight of 216.26 g/mol.

2D chemical structure

S N H 2 O N O O H H ( R ) ( R ) ( S )

Chemical identity

Catalog name
Amoxicillin Trihydrate Imp. A (EP): (2S,5R,6R)-6-Amino-3,3- dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]- heptane-2-carboxylic Acid (6-Aminopenicillanic Acid)
Common name
Amoxicillin Trihydrate Imp. A (EP)
Chemical name
(2S,5R,6R)-6-Amino-3,3- dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]- heptane-2-carboxylic Acid (6-Aminopenicillanic Acid)
CAS
551-16-6
SMILES
CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O
InChI
InChI=1S/C8H12N2O3S/c1-8(2)4(7(12)13)10-5(11)3(9)6(10)14-8/h3-4,6H,9H2,1-2H3,(H,12,13)/t3-,4+,6-/m1/s1
InChIKey
NGHVIOIJCVXTGV-ALEPSDHESA-N
Associated API
Amoxicillin Trihydrate

Record ID: Ac73ac69d0f8c

Computed properties

C8H12N2O3S Molecular formula
216.262 g/molMolecular weight
216.0569 DaMonoisotopic exact mass
83.63 ŲTopological polar surface area
-0.5394 Calculated LogP (Wildman–Crippen)
51.7032 cm³/molMolar refractivity (Wildman–Crippen)
4 countHydrogen-bond acceptors
2 countHydrogen-bond donors

Descriptors are calculated from the displayed SMILES. Calculated LogP is not a measured partition coefficient or a pH-specific LogD.

Molecular descriptor profile

Descriptor radar

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

Structural feature counts

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

Element composition

C H N O S 0 3 6 9 12 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 weight216.26221.52
Calculated LogP (Wildman–Crippen)-0.539410.04
Topological polar surface area83.6360.73
Hydrogen-bond acceptors450.68
Hydrogen-bond donors264.87
Rotatable bonds (strict)112.12

Complete molecular descriptors

PropertyCalculated valueUnit / type
Molecular formulaC8H12N2O3Sdimensionless
Molecular weight216.262g/mol
Monoisotopic exact mass216.0569Da
Topological polar surface area83.63Ų
Calculated LogP (Wildman–Crippen)-0.5394dimensionless
Molar refractivity (Wildman–Crippen)51.7032cm³/mol
Hydrogen-bond acceptors4count
Hydrogen-bond donors2count
Rotatable bonds (strict)1count
Heavy atoms14count
Heteroatoms6count
Rings2count
Aromatic rings0count
Aliphatic rings2count
Saturated rings2count
Aromatic heterocycles0count
Aliphatic heterocycles2count
Saturated heterocycles2count
Aromatic carbocycles0count
Aliphatic carbocycles0count
Fraction of sp³ carbon atoms0.75fraction
Formal charge0e
Disconnected components1count
Isotopically specified atoms0count
Potential atom stereocenters3count
Unspecified atom stereocenters0count
Spiro atoms0count
Bridgehead atoms0count
Labute approximate surface area85.6223Ų
Valence electrons78count
Radical electrons0count
Bertz complexity317.7083index
Balaban J2.3166index

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 Amoxicillin Trihydrate Imp. A (EP): (2S,5R,6R)-6-Amino-3,3- dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]- heptane-2-carboxylic Acid (6-Aminopenicillanic Acid)

Qualification and safety assessment of Amoxicillin Trihydrate Imp. A (EP): (2S,5R,6R)-6-Amino-3,3- dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]- heptane-2-carboxylic Acid (6-Aminopenicillanic Acid)

Explore toxicological qualification of Amoxicillin Trihydrate Imp. A (EP): (2S,5R,6R)-6-Amino-3,3- dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]- heptane-2-carboxylic Acid (6-Aminopenicillanic Acid) and ICH M7 mutagenic impurity assessment of Amoxicillin Trihydrate Imp. A (EP): (2S,5R,6R)-6-Amino-3,3- dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]- heptane-2-carboxylic Acid (6-Aminopenicillanic Acid) for evaluation of this impurity in its pharmaceutical context.

Where data gaps need to be addressed, resources include read-across assessment for Amoxicillin Trihydrate Imp. A (EP): (2S,5R,6R)-6-Amino-3,3- dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]- heptane-2-carboxylic Acid (6-Aminopenicillanic Acid) and acceptable intake and limit justification for Amoxicillin Trihydrate Imp. A (EP): (2S,5R,6R)-6-Amino-3,3- dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]- heptane-2-carboxylic Acid (6-Aminopenicillanic Acid). 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 Amoxicillin Trihydrate Imp. A (EP): (2S,5R,6R)-6-Amino-3,3- dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]- heptane-2-carboxylic Acid (6-Aminopenicillanic Acid)

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