Basic information
- CAS
7177-48-2- Standard SMILES
CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(=O)O.O.O.O- InChIKey
RXDALBZNGVATNY-CWLIKTDRSA-N- Molecular formula
- C16H25N3O7S
- Average molar mass
- 403.5 g/mol
- Monoisotopic mass
- 403.14132132
Names & identifiers
- Preferred name
- Ampicillin Trihydrate
- IUPAC
- (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;trihydrate
- English name
- Ampicillin trihydrate
- Molecular formula
- C16H25N3O7S
- Molecular weight
- 403.45
Names & synonyms
Show more names
Database identifiers
- CAS
7177-48-2- PubChem CID
- 23565
- DTXSID
DTXSID9020083- ChEMBL
CHEMBL453388- ChEBI
CHEBI:31209- UNII
- HXQ6A1N7R6
- EC Number
- 615-347-9
Properties
Computed structural properties
- Topological polar surface area
- 141 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 4
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 562
Physicochemical properties
- Melting point
- 208 °C · 208 °C (dec.)(lit.)
- Boiling point
- 684 ℃ · 684℃
- refractive index
- 265 ° · 265 ° (C=0.1, H2O)
- Flash point
- 87 °C · 87 °C
- storage temp.
- 2 · Sealed in dry,2-8°C
- solubility
- 4 OH · NH4OH 1 M: 50 mg/mL, clear, colorless
- form
- solid
- color
- white to off-white
- pka
- 2.5 · 2.5 (COOH)(at 25℃)
- Water Solubility
- 0.1 · 0.1-1 g/100 mL at 21 ºC
- Merck
- 14 · 14,586
- BRN
- 5399534 · 5399534
- Stability
- Hygroscopic
- Major Application
- pharmaceutical (small molecule)
- InChIKey
- RXDALBZNGVATNY-CWLIKTDRSA-N
- SMILES
- O.O.O.CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(O)=O
- Toxicology and Carcinogenesis
- Toxicology and Carcinogenesis Studies of Ampicillin Trihydrate (CASRN 7177-48-2) in F344/N Rats and B6C3F1 Mice (Gavage Studies)
- CAS DataBase Reference
- 7177 · 7177-48-2(CAS DataBase Reference)
- FDA UNII
- 6 A1N7R6 · HXQ6A1N7R6
- EPA Substance Registry System
- Ampicillin trihydrate (7177-48-2)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Protein binding
- 20 % · 20%
- Excreted unchanged in urine
- 20 · Oral: 20-60; Parenteral: 60-80%
- Volume of distribution
- 0.17 · 0.17-0.31(L/kg)
- Biological half-life
- 1 · 1-1.5 / 7-20
- Symbol(GHS)
- 8 · GHS08
- Signal word
- Danger
- Hazard statements
- 317 · H317-H334
- Precautionary statements
- 261 · P261-P272-P280-P284-P302+P352-P333+P313
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- Hazard Codes
- Xn,Xi
- Risk Statements
- 36 · 36/37/38-42/43
- Safety Statements
- 22 · 22-26-36/37-36-45-23
- WGK Germany
- 2 · 2
- RTECS
- 8425000 · XH8425000
- F
- 3 · 3-10
- HS Code
- 29411020 · 29411020
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Resp · Eye Irrit. 2Resp. Sens. 1Skin Irrit. 2Skin Sens. 1STOT SE 3
- Toxicity
- 50 orl-rat: · LD50 orl-rat: 10 g/kg ANTBAL 20,653,75
Safety & regulation
Safety data
- F
- 3-10
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 2
- rtecs
- XH8425000
- hs_code
- 29411020
- Toxicity
- LD50 orl-rat: 10 g/kg ANTBAL 20,653,75
- risk_code
- 36/37/38-42/43
- Signal word
- Danger
- Symbol(GHS)
- GHS08
- hazard_code
- Xn,Xi
- safety_code
- 22-26-36/37-36-45-23
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H317-H334
- Hazard Classifications
- Eye Irrit. 2Resp. Sens. 1Skin Irrit. 2Skin Sens. 1STOT SE 3
- Precautionary statements
- P261-P272-P280-P284-P302+P352-P333+P313
Chemistry & industry
Applications
DescriptionAs a penicillin group of beta-lactam antibiotics, Ampicillin is the first broad-spectrum penicillin, which has in vitro activity against Gram-positive and Gram-negative aerobic and anaerobic bacteria, commonly used for preventing and treating bacterial infections of respiratory tract, urinary tract, middle ear, sinuses, stomach and intestines, bladder, and kidney, etc. caused by susceptible bacteria. It is also used to treat uncomplicated gonorrhea, meningitis, endocarditis salmonellosis, and other serious infections through administered by mouth, intramuscular injection or by intravenous infusion. Like all antibiotics, it is not effective for the treatment of viral infections. Ampicillin functions by killing the bacteria or preventing their growth. After penetrating Gram-positive and Gram-negative bacteria, it acts as an irreversible inhibitor of the enzyme transpeptidase needed by bacteria to make the cell wall, which results to the inhibition of cell wall synthesis and eventually leads to cell lysis.
UsesCommonly used to select for ampicillin resistance in mutated and transformed cells
UsesPenicillin antibacterial.
General DescriptionOdorless white microcrystalline powder with a bitter taste. A 0.25% solution in water has a pH of 3.5 to 5.5.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers101 total
Additional notes
DefinitionChEBI: Ampicillin trihydrate is a hydrate. It contains an ampicillin.
Related reactions
Compound notes
Loading…