Basic information
- CAS
37661-08-8- Standard SMILES
CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@H](N)c3ccccc3)[C@H]2SC1(C)C.Cl- InChIKey
IWVTXAGTHUECPN-ANBBSHPLSA-N- Molecular formula
- C21H28ClN3O7S
- Average molar mass
- 502 g/mol
- Monoisotopic mass
- 501.1336491
Names & identifiers
- Preferred name
- Bacampicillin Hydrochloride
- IUPAC
- 1-ethoxycarbonyloxyethyl (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;hydrochloride
- English name
- Bacampicillin hydrochloride
- Molecular formula
- C21H28ClN3O7S
- Molecular weight
- 501.98
Names & synonyms
Bacampicillin hydrochloride37661-08-8bacampicillin HClSpectrobidAmbaxinDTXSID0045466Becampicillin hydrochloridePM034U953TNSC-758228CHEBI:2969DTXCID80254661-ethoxycarbonyloxyethyl (2S,5R,6R)-6-(((2R)-2-amino-2-phenyl-acetyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate;hydrochloride
Show more names
bapcbacacilPengoodpenglobeBacampicinebecampicillin
1-ethoxycarbonyloxyethyl (2S,5R,6R)-6-[[(2R)-2-amino-2-phenyl-acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;hydrochlorideRefChem:57086Bacampicillin-hydrochloride1-Ethoxycarbonyloxyethyl (2S,5R,6R)-6-((2R)-2-amino-2-phenylacetylamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate monohydrochlorideBacampicillin (hydrochloride)1-ethoxycarbonyloxyethyl (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;hydrochloride4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-,1-[(ethoxycarbonyl)oxy]ethyl ester, hydrochloride (1:1), (2S,5R,6R)-Ambacamp
Properties
Computed structural properties
- Topological polar surface area
- 163 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 10
- Heavy atoms
- 33
- Formal charge
- 0
- Complexity
- 756
Experimental & physicochemical properties
Collision Cross Section199 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；220.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 171 · 171-176° (dec)
- alpha
- 20 · D20 +161.5°
- storage temp.
- -20 °C · Store at -20°C
- solubility
- Soluble in water, freely soluble in ethanol (96 per cent), soluble in methylene chloride.
- form
- Solid
- color
- 2 CO · Crystals from Me2CO pet ether
- FDA UNII
- 34 U953T · PM034U953T
- Symbol(GHS)
- 8 · GHS08
- Signal word
- Danger
- Hazard statements
- 317 · H317-H334
- Precautionary statements
- 261 · P261-P280-P284-P304+P340-P342+P311
- Toxicity
- 50 in · LD50 in mice (mg/kg): 8529 orally; 176 i.p.; 9475 s.c.; 184 i.v. (Edanaga)
Safety & regulation
Safety data
- Toxicity
- LD50 in mice (mg/kg): 8529 orally; 176 i.p.; 9475 s.c.; 184 i.v. (Edanaga)
- Signal word
- Danger
- Symbol(GHS)
- GHS08
- Hazard statements
- H317-H334
- Precautionary statements
- P261-P280-P284-P304+P340-P342+P311
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Applications
DescriptionBacampicillin was synthesized by Ekstrom¨ et al. of Astra Lakemedel in 1975. It is ¨ more stable against acid than ampicillin and more rapidly absorbed orally; its absorption is less affected by a patient’s most recent meal than is the case for ampicillin. Bacampicillin is hydrolyzed by intestinal esterase after oral administration and then behaves the same as ampicillin. In double-blind comparison studies, bacampicillin was shown to be as effective as ampicillin when administered at half the dose.
UsesBacampicillin is a penicillin class of antibiotic. Bacampicillin is a prodrug of ampicillin (A634300) with improved oral bioavailability.
Upstream & downstream products
Upstream raw materials
Suppliers29 total
国药集团化学试剂有限公司86-21-63210123 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
安耐吉化学&3A（安徽泽升科技有限公司）021-58432009 400-005-6266 · [email protected]
ChemeGen 中国
Related reactions
1 records
Compound notes
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