Drug Details

General Information of the Drug (ID: DR9957)
Name
Ampicillin
Synonyms
69-53-4; Ampicillin; Aminobenzylpenicillin; Ampicillin acid; Amcill; Polycillin; Principen; Omnipen; Ampicilline; Penbritin; Pentrexyl; Synpenin; Tokiocillin; Totacillin; Novo-ampicillin; D-Ampicillin; Ampicillin Anhydrous; D-(-)-Ampicillin; Adobacillin; Amblosin; Ampichel; Ampicilina; Ampicillinum; Ampifarm; Ampipenin; Ampiscel; Amplacilina; Amplipenyl; Amplisom; Amplital; Bonapicillin; Britacil; Campicillin; Copharcilin; Delcillin; Divercillin; Doktacillin; Duphacillin; Grampenil; Guicitrina; Lifeampil; Norobrittin; Orbicilina; Penbristol; Penbrock; Penicline; Pentrexl; Princillin; Racenacillin; Rosampline; Roscillin; Semicillin; Servicillin; Sumipanto; Texcillin; Totalciclina; Trifacilina; Ultrabion; Ultrabron; Viccillin; Acillin; Amfipen; Ampicil; Ampikel; Ampimed; Ampisyn; Ampivax; Ampivet; Amplin; Binotal; Morepen; Nuvapen; Penimic; Pensyn; Pentrex; Ponecil; Tolomol; Totapen; Vampen; Cimex; Supen; anhydrous ampicillin; Ampicillin anhydrate; Pfizerpen A; Amipenix S; Ampi-bol; SK-Ampicillin; Amfipen V; Pen Ampil; QIDamp; Ampi-Tab; D-Cillin; Olin Kid; Ro-Ampen; Ampi-Co; Austrapen; Pen A; Ampicillina [DCIT]; Bayer 5427; D-(-)-alpha-Aminobenzylpenicillin; ABPC; Ampicilina [INN-Spanish]; Ampicilline [INN-French]; Ampicillinum [INN-Latin]; Ampicin; D-(-)-alpha-Aminopenicillin; Deripen; Wypicil; Alpen; Ampicillin A; Polycillin-N; Totacillin-N; Penbritin-S; AY-6108; Omnipen-N; BRL 1341; Penbritin syrup; Semicillin R; D-(-)-6-(alpha-Aminophenylacetamido)penicillanic acid; P-50; KS-R1; Penbritin paediatric; NSC-528986; AB-PC; BRL-1341; 6-(D(-)-alpha-Aminophenylacetamido)penicillanic acid; Guicitrine; Ampen; NSC 528986; AB-PC Sol; Ampicillin, anhydrous; UNII-7C782967RD; C16H19N3O4S; CHEBI:28971; MFCD00005175; Alpha-Aminobenzylpenicillin; 6-(D-(2-Amino-2-phenylacetamido))-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid; MLS000028405; (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; Ampicillina; HI 63; Ukapen; Pfizerpen-A; WY-5103; AMPI; 7C782967RD; (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; P 50; SQ 17382; Penicillin, (aminophenylmethyl)-; SMR000058352; Ampicillin Base; DSSTox_CID_2602; AY 6108; DSSTox_RID_76654; DSSTox_GSID_22602; (2S,5R,6R)-6-((R)-2-Amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid; (2S,5R,6R)-6-[(R)-2-Amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; Polyflex (Veterinary); ampicillanyl; Ampicillin [USAN:BAN:INN:JAN]; CAS-69-53-4; (2S,5R,6R)-6-{[(2R)-2-AMINO-2-PHENYLETHANOYL]AMINO}-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID; 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[[(2R)-aminophenylacetyl]amino]-3,3-dimethyl-7-oxo-, trihydrate,(2S,5R,6R)-; Omnipen (TN); Totacillin (sodium); BA 7305; HSDB 3009; AMPICILLIN/AMPICILLIN TRIHYDRATE; Ampicillin (USP/INN); EINECS 200-709-7; vidopen; Vidocillin; Marcillin; Pentritin; NSC528986; D-(-)-.alpha.-Aminobenzylpenicillin; Ampicillin,(S); NCGC00018160-02; (2s,5r,6r)-6-((r)-2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (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-carboxylic acid; 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta(S*)))-; Ampicillin [USAN:USP:INN:BAN:JAN]; Ampicillin (anhydrous); Spectrum_000050; 1h8s; AY 6108; D-a-Aminobenzylpenicillin; Opera_ID_1630; Prestwick0_000114; Prestwick1_000114; Prestwick2_000114; Prestwick3_000114; Spectrum2_000769; Spectrum3_000301; Spectrum4_000149; Spectrum5_000814; CHEMBL174; Epitope ID:115008; Epitope ID:116057; EC 200-709-7; SCHEMBL3526; BSPBio_000128; BSPBio_001862; KBioGR_000598; KBioSS_000430; Anhydrous ampicillin (JP17); MLS001074168; BIDD:GT0184; DivK1c_000466; SPBio_000818; SPBio_002067; Ampicillin, analytical standard; BPBio1_000142; DTXSID4022602; CHEBI:53713; GTPL10896; KBio1_000466; KBio2_000430; KBio2_002998; KBio2_005566; KBio3_001362; NINDS_000466; HMS2090I11; HMS2233H23; Ampicillin acid; Principen; Amcill; HY-B0522; ZINC3830218; Tox21_113049; Tox21_301416; BDBM50350465; SBB063111; AKOS015888156; Tox21_113049_1; AC-8805; DB00415; VA10275; WY 5103; 6beta-[(2R)-2-amino-2-phenylacetamido]-2,2-dimethylpenam-3alpha-carboxylic acid; IDI1_000466; SMP1_000211; NCGC00023282-05; NCGC00023282-06; NCGC00023282-21; NCGC00178944-03; NCGC00248937-01; NCGC00255127-01; 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-, D-(-)-; ST077148; SBI-0051283.P003; 6-(a-Aminophenylacetamido)penicillanic acid; C06574; D00204; AMPICILLIN ANHYDROUS, PHARMACEUTICAL GRADE; Q244150; 6-D(-)-alpha-Aminophenylacetamido-penicillanic acid; BRD-K68432770-001-08-0; Ampicillin, anhydrous, 96.0-100.5% (anhydrous basis); Ampicillin, United States Pharmacopeia (USP) Reference Standard; Anhydrous ampicillin, British Pharmacopoeia (BP) Reference Standard; Ampicillin, anhydrous, European Pharmacopoeia (EP) Reference Standard; (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; (2S,5R,6R)-6-{[(2R)-2-AMINO-2-PHENYLETHANOYL]AMINO}-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC; 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((2R)-aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, (2S,5R,6R)-; 6-((2R)-2-amino-2-phenylacetylamino)(2S,5R,6R)-3,3-dimethyl-7-oxo-4-thia-1-aza bicyclo[3.2.0]heptane-2-carboxylic acid; 6-((2R)-2-amino-2-phenylacetylamino)(2S,5R,6R)-3,3-dimethyl-7-oxo-4-thia-1-aza bicyclo[3.2.0]heptane-2-carboxylic acid, oxamethane, oxamethane, oxamethane; 6-[(Aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 9CI; AMPICILLIN; D(-)-ALPHA-AMINOBENZYLPENICILLIN; 6-[D(-)-ALPHA-AMINOPHENYLLACETAMIDO]PENICILLANIC ACID
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Molecular Type
Small molecule
Disease Bacterial infection [ICD-11: 1A00-1C4Z] Approved [1]
Structure
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2D MOL

3D MOL

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Formula
C16H19N3O4S
PubChem CID
6249
Canonical SMILES
CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)O)C
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
CAS Number
CAS 69-53-4
ChEBI ID
CHEBI:28971
TTD Drug ID
D0YA9Z
DrugBank ID
DB00415
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Amentoflavone      Gingko biloba     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Enterococcus faecium ATCC 19434 Microorganism model Enterococcus faecium
Staphylococcus aureus ATCC 25923 Microorganism model Staphylococcus aureus
Streptococcus mutans ATCC 3065 Microorganism model Streptococcus mutans
Escherichia coli ATCC 43895 Microorganism model Escherichia coli
Escherichia coli ATCC 25922 Microorganism model Escherichia coli
Pseudomonas aeruginosa ATCC 27853 Microorganism model Pseudomonas aeruginosa
                    Experimental
                    Result(s)		 Amentoflavone had a considerable antibacterial effect and synergistic interaction with antibiotics against various bacterial strains. The formation of hydroxyl radical would be a cause of the synergistic effect and that this oxidative stress originated from a transient NADH depletion. .
          Bisdemethoxycurcumin      Curcumin     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression UL54  Molecule Info 
Pathway MAP
                    In-vitro Model Staphylococcus aureus strains Microorganism model Staphylococcus aureus
                    Experimental
                    Result(s)		 Antimicrobial effect of BDMC combined with antibiotics was superior to treatment with that of a single agent alone.
          Retinol      Daucus carota     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Staphylococcus aureus strains Microorganism model Staphylococcus aureus
Staphylococcus aureus ATCC 33591 Microorganism model Staphylococcus aureus
Staphylococcus aureus ATCC 25923 Microorganism model Staphylococcus aureus
                    Experimental
                    Result(s)		 Rhein in combination with AM or OX could lead to the development of new combinations of antibiotics against MRSA infection.
Target and Pathway
Target(s) Bacterial Penicillin binding protein (Bact PBP)  Molecule Info  [5]
References
Reference 1 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 061936.
Reference 2 Antibacterial effect of amentoflavone and its synergistic effect with antibiotics. J Microbiol Biotechnol. 2013;23(7):953-8.
Reference 3 The Mechanism of Bisdemethoxycurcumin Enhances Conventional Antibiotics against Methicillin-Resistant Staphylococcus aureus. Int J Mol Sci. 2020 Oct 26;21(21):7945.
Reference 4 Synergistic effect of rhein in combination with ampicillin or oxacillin against methicillin-resistant Staphylococcus aureus. Exp Ther Med. 2012 Apr;3(4):608-612.
Reference 5 Effects of amino acid alterations in penicillin-binding proteins (PBPs) 1a, 2b, and 2x on PBP affinities of penicillin, ampicillin, amoxicillin, cefditoren, cefuroxime, cefprozil, and cefaclor in 18 clinical isolates of penicillin-susceptible, -intermediate, and -resistant pneumococci. Antimicrob Agents Chemother. 2002 May;46(5):1273-80.
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