chempirical

Ampicillin

C16H19N3O4SCAS 69-53-4349.41 g/mol

Open in Covalent MOL file
SNHONH2ONOOH
AmideCarboxylic acidLactamPrimary amineSulfide

Properties

Molecular formula
C16H19N3O4S
Molar mass
349.41 g/mol
Exact mass
349.1096 Da
Melting point
202 °C (decomposes)
pKa
2.5, 7.25
logP
1.16Crippen estimate
Polar surface area
116.2 Ų
H-bond donors / acceptors
3 / 5
Rotatable bonds
4
Stereocentres
R, R, R, Sin SMILES atom order

Hazards

Danger
Irritant (GHS07)Health Hazard (GHS08)Environmental Hazard (GHS09)

Aggregated from 167 ECHA notifications, via PubChem; a share says how many notifiers assign that statement.

Precautionary statements

P233, P260, P261, P264, P264+P265, P271, P272, P273, P280, P284, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P391, P403, P403+P233, P405, P501

Identifiers

CAS number
69-53-4
SMILES
CC1(C)S[C@@H]2[C@H](N=C(O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(=O)O
InChIKey
AVKUERGKIZMTKX-NJBDSQKTSA-N
InChI
InChI=1S/C16H19N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10-,11+,14-/m1/s1

Weigh it out

Type any one amount. The others follow from the molar mass.

Names and synonyms

92 names · show all
  • 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-
  • 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-, D-(-)-
  • 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-, [2S-[2α,5α,6β(S*)]]-
  • 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-(D-2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-
  • 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2R)-aminophenylacetyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-
  • (2S,5R,6R)-6-[[(2R)-2-Amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • (-)-6-(2-Amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • 6-[D-(-)-α-Aminophenylacetamido]penicillanic acid
  • Binotal
  • Penbritin
  • Viccillin
  • Penicline
  • Aminobenzylpenicillin
  • Omnipen
  • D-(-)-α-Aminobenzylpenicillin
  • D-(-)-α-Aminopenicillin
  • Penbritin paediatric
  • Penbritin syrup
  • Ampicillin acid
  • Penicillin, (aminophenylmethyl)-
  • Ampicillin A
  • Amblosin
  • Amplital
  • Austrapen
  • Britacil
  • BRL 1341
  • Doktacillin
  • Penbristol
  • Totapen
  • Amfipen
  • Nuvapen
  • Ultrabron
  • Amplisom
  • Ampimed
  • Guicitrina
  • D-Ampicillin
  • D-(-)-Ampicillin
  • 6-[D-(-)-2-Amino-2-phenylacetamido]penicillanic acid
  • Ampicillin anhydrate
  • Wy 5103
  • Penbrock
  • AY 6108
  • Semicillin
  • Viccillin S
  • Tolomol
  • D-(-)-6-(α-Aminophenylacetamido)penicillanic acid
  • Ampivet
  • Amotital
  • Roscillin
  • Synpenin
  • Olin kid
  • Ampisyn
  • Alpen
  • P 50
  • Bonapicillin
  • Grampenil
  • Copharcilin
  • Ultrabion
  • Ampipenin
  • Totalciclina
  • Pentrexyl
  • Totacillin
  • Ampi-bol
  • QIDamp
  • Tokiocillin
  • Marisilan
  • Amipenix S
  • Ponecil
  • Adobacillin
  • Campicillin
  • Ficillin
  • Redicilin
  • Ampi-kel
  • Polyflex
  • Polyflex (antibiotic)
  • Ampicilina
  • Bacipen
  • Amipenix
  • Dumopen
  • Albipen
  • Ampitab
  • Domicillin
  • NSC 528986
  • A-Pen
  • Omnipe
  • Amcillin
  • Reichlin
  • Cincillin
  • Gobemicina
  • Britapen
  • Hiperbiotico
  • Unacim

Work with Ampicillin

Predict the NMR spectrum1H and 13C shifts with multiplicities Make a solutionWhat to weigh for any molarity and volume Check drug-likenessLipinski, Veber and lead-likeness Isotope patternExact mass and the mass spectrum pattern

Stereoisomers, salts and isotopologues

The same compound in another form: other stereochemistry, a salt or hydrate, the free acid or base, or an isotope-labelled version.

Ampicillin trihydrate7177-48-2Hydrate Ampicillin sodium69-52-3Salt

Similar compounds

Amoxicillin26787-78-084 % similar Amoxicillin trihydrate61336-70-780 % similar Carbenicillin4697-36-379 % similar (2R)-2-(4-Hydroxyphenyl)glycyl-N-[(2S,5R,6R)-2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-6-yl]-(2R)-2-(4-hydroxyphenyl)glycinamide188112-75-677 % similar Amoxicillin dimer73590-06-465 % similar Penicillin G61-33-664 % similar Azlocillin37091-66-064 % similar Ticarcillin34787-01-463 % similar

Tanimoto similarity of circular fingerprints over the whole catalogue. All similar compounds

Same formula

Cephradine38821-53-3

Elsewhere

PubChem CAS Common Chemistry NIST WebBook