(2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

• ChemBase编号: 298
• 分子式: C16H19N3O4S
• 平均质量: 349.40476
• 单一同位素质量: 349.1096271
• SMILES: S1[C@H]2N([C@H](C1(C)C)C(=O)O)C(=O)[C@H]2NC(=O)[C@H](N)c1ccccc1
• Canonical SMILES: N[C@H](c1ccccc1)C(=O)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C
• 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
• InChIKey: AVKUERGKIZMTKX-NJBDSQKTSA-N

名称和登记号

名称

• IUPAC标准名: (2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• IUPAC传统名: ampicillin
• 商标名: AB-PC; Ab-Pc Sol; Acillin; Adobacillin; Alpen; Amblosin; Amcill; Amfipen; Amfipen V; Amipenix S; Ampen; Ampi; Ampi-Bol; Ampi-Co; Ampi-Tab; Ampichel; Ampicil; Ampicillin A; Ampicin; Ampifarm; Ampikel; Ampimed; Ampipenin; Ampipenin, Nt3; Ampiscel; Ampisyn; Ampivax; Ampivet; Amplacilina; Amplin; Amplipenyl; Amplisom; Amplital; Ampy-Penyl; Austrapen; BRL; Binotal; Bonapicillin; Britacil; Campicillin; Cimex; Copharcilin; D-Cillin; Delcillin; Deripen; Divercillin; Doktacillin; Duphacillin; Geocillin; Grampenil; Guicitrina; Guicitrine; Lifeampil; Morepen; Norobrittin; Novo-Ampicillin; Nuvapen; Olin Kid; Omnipen; Omnipen-N; Orbicilina; Pen A; Pen Ampil; Pen a Oral; Penbristol; Penbritin; Penbritin Paediatric; Penbritin Syrup; Penbritin-S; Penbrock; Penicline; Penimic; Pensyn; Pentrex; Pentrexl; Pentrexyl; Pfizerpen A; Pfizerpen-A; Polycillin; Polycillin-N; Ponecil; Princillin; Principen; Principen '125'; Principen '250'; Principen '500'; Qidamp; Racenacillin; Ro-Ampen; Rosampline; Roscillin; Semicillin; Semicillin R; Servicillin; Sk-Ampicillin; Spectrobid; Sumipanto; Supen; Synpenin; Texcillin; Tokiocillin; Tolomol; Totacillin; Totacillin-N; Totalciclina; Totapen; Trifacilina; Ultrabion; Ultrabron; Vampen; Viccillin; Viccillin S; Wypicil
• 别名: 氨苄青霉素; 氨苄西林; Ampicilline [INN-French]; Ampicillinum [INN-Latin]; Ampicilline; Ampicillina [Dcit]; Ampicillin [Usan:Ban:Inn:Jan]; Ampicillin Trihydrate; Ampicillin Sodium; Ampicillin Base; Ampicillin Anhydrous; Ampicillin Anhydrate; Ampicillin Acid; Ampicilina [INN-Spanish]; Anhydrous Ampicillin; Bayer 5427; D-Ampicillin; Aminobenzylpenicillin; Ampicillin; Ampicillin; Amplital; Penicline; (2S,5R,6R)-6-[[(2RS)-2-Amino-2-(phenyl-d5)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid; AY 6108-d5; Albipen-d5; Amfipen-d5; Amplital-d5; Penicline-d5; Ampicillin-d5(Mixture of Diastereomers); (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; AY 6108; Albipen; Amfipen; D-(-)-α-Aminobenzylpenicillin; AMPICILLIN ANHYDROUS

登记号

• CAS号: 69-53-4
• EC号: 200-709-7
• MDL号: MFCD00005175
• Beilstein号: 1090925
• PubChem SID: 160963761; 24891442; 46505346
• PubChem CID: 6249
• CHEBI ID: 28971
• ATC码: QJ51CA01; J01CA01; S01AA19
• CHEMBL: 174
• Chemspider ID: 6013
• DrugBank ID: DB00415
• KEGG ID: D00204
• 美国药典/FDA物质标识码: 7C782967RD
• 维基百科标题: Ampicillin
• Medline Plus: a685002

理论计算性质

JChem

• Acid pKa: 3.2380536
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): -2.0056438
• LogD (pH = 7.4): -2.2605202
• Log P: -2.0066502
• 摩尔折射率: 87.5235 cm^3
• 极化性: 34.874416 Å^3
• 极化表面积: 112.73 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.88
• LOG S: -2.76
• 溶解度: 6.05e-01 g/l

分子性质

理化性质

• 溶解度: 1 M NH4OH: soluble50 mg/mL; 1 M NH4OH: soluble50 mg/mL, clear, colorless; 1.01E+004 mg/L; DMSO; Water
• 外观: Off-White to Pale Yellow Solid; White Solid
• 熔点: 196-198°C (dec.); 199-202°C (dec.); 208 °C decomposes; 208 °C (dec.)(lit.)
• 比旋光度: [α]20/D +295±5°, c = 0.2% in H2O
• 疏水性(logP): 0.4

安全信息

• 保存条件: -20°C Freezer, Under Inert Atmosphere; 2-8°C; Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• RTECS编号: XH8350000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 2
• 危险公开号: 36/37/38-42/43
• 安全公开号: 22-26-36/37
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Danger
• GHS危险声明: H315-H317-H319-H334-H335
• GHS警示性声明: P261-P280-P305 + P351 + P338-P342 + P311
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• 保存温度: 2-8°C

药理学性质

• 给药途径: Oral, intravenous
• 生物利用度: 40% (oral)
• 排泄: 75 to 85% renal
• 半衰期: approx 1 hour
• 代谢: 12 to 50%
• 蛋白结合率: 15 to 25%
• 妊娠期药物分类: A (Au), B (U.S.)

产品相关信息

• 纯度: ≥98.0% (NT); 96.0-100.5% (anhydrous basis)
• 适用性: suitable for 1694 per US EPA
• 杂质: ≤1% water
• Empirical Formula (Hill Notation): C16H19N3O4S

详细说明

MP Biomedicals - 02190146

Crystalline

DrugBank - DB00415

• Drug Groups: approved
• Description: Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic. [PubChem]
• Indication: For treatment of infection (Respiratory, GI, UTI and meningitis) due to E. coli, P. mirabilis, enterococci, Shigella, S. typhosa and other Salmonella, nonpenicillinase-producing N. gononhoeae, H. influenzae, staphylococci, streptococci including streptoc
• Pharmacology: Ampicillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Ampicillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Ampicillin results from the inhibition of cell wall synthesis and is mediated through Ampicillin binding to penicillin binding proteins (PBPs). Ampicillin is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases.
• Affected Organisms: Enteric bacteria and other eubacteria
• Elimination: Ampicillin is excreted largely unchanged in the urine.
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - A9393

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
A β-lactam antibiotic with an amino group attached to the penicillin structure. Inhibits bacterial cell-wall synthesis (peptidoglycan cross-linking) by inactivating transpeptidases on the inner surface of the bacterial cell membrane. Bactericidal only to growing Escherichia coli. Mode of resistance: Cleavage of β-lactam ring of ampicillin by β-lactamase. Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Application
Ampicillin is used to select bacteria cells with specific resistance during general microbiology studies. It is used to study antibiotic resistance and penetration limitations, the synergy between multiple antibiotics, certain bloodstream infections, and has been used to develop PCR assays to detect resistance genes in cerebrospinal fluid 1,2,3,4.

Sigma Aldrich - 10047

Biochem/physiol Actions
A β-lactam antibiotic with an amino group attached to the penicillin structure. Inhibits bacterial cell-wall synthesis (peptidoglycan cross-linking) by inactivating transpeptidases on the inner surface of the bacterial cell membrane. Bactericidal only to growing Escherichia coli. Mode of resistance: Cleavage of β-lactam ring of ampicillin by β-lactamase. Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Inhibits cell wall synthesis in Escherichia coli1; In the purification of penicillin acylase2; Enhances luminol chemiluminescence.3

Toronto Research Chemicals - A634300

Orally active, semi-synthetic antibiotic; structurally related to penicillin. Antibacterial.

Toronto Research Chemicals - A634302

Labelled Ampicillin. Orally active, semi-synthetic antibiotic; structurally related to penicillin. Antibacterial.

参考文献

• Ivashkiv, E., et al.: Anal. Profiles Drug Subs., 2, 1 (1973)
• Campoli-Richards, D.M., et al.: Drugs, 33, 577 (1973)
• Sill, M. L., et al.: Antimicrob. Agents Chemother., 52, 1551 (1973)
• Ivashkiv, E., et al.: Anal. Profiles Drug Subs., 2, 1 (1973)
• Campoli-Richards, D.M., et al.: Drugs, 33, 577 (1973)
• Sill, M. L., et al.: Antimicrob. Agents Chemother., 52, 1551 (1973)