Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR2177)
Drug Name
Ampicillin
Synonyms
Acillin; Adobacillin; Ambidrin (TN); Amblosin; Amcill; Amfipen; Amfipen V; Aminobenzylpenicillin; Amipenix S; Ampi-Co; Ampi-Tab; Ampi-bol; Ampichel; Ampicil; Ampicilina; Ampicilina [INN-Spanish]; Ampicillanyl; Ampicillin (USP/INN); Ampicillin A; Ampicillin Anhydrous; Ampicillin Base; Ampicillin [USAN:BAN:INN:JAN]; Ampicillin acid; Ampicillin anhydrate; Ampicillina; Ampicillina [DCIT]; Ampicilline; Ampicilline [INN-French]; Ampicillinum; Ampicillinum [INN-Latin]; Ampicin; Ampifarm; Ampikel; Ampimed; Ampipenin; Ampipenin, nt3; Ampiscel; Ampisyn; Ampivax; Ampivet; Amplacilina; Amplin; Amplipenyl; Amplisom; Amplital; Ampy-Penyl; Anhydrous ampicillin; Anhydrous ampicillin (JP15); Austrapen; BRL 1341; Binotal; Bonapicillin; Britacil; Campicillin; Copharcilin; D-(-)-alpha-Aminobenzylpenicillin; D-(-)-alpha-Aminopenicillin; D-Ampicillin; D-Cillin; Delcillin; Deripen; Divercillin; Doktacillin; Duphacillin; Grampenil; Guicitrina; Guicitrine; Lifeampil; Morepen; Norobrittin; Novo-ampicillin; Nuvapen; OMNIPEN (AMPICILLIN); Olin Kid; Omnipen; Omnipen (TN); Omnipen-N; Orbicilina; Pen A Oral; Pen Ampil;Penbritin paediatric; Penbristol; Penbritin; Penbritin syrup; Penbritin-S; Penbrock; Penicillin, Aminobenzyl; Penicline; Penimic; Pensyn; Pentrex; Pentrexl; Pentrexyl; Pfizerpen A; Pfizerpen-A; Polycillin; Polycillin-N; Polyflex (Veterinary); Ponecil; Princillin; Principen; Principen 125; Principen 250; Principen 500; QIDamp; Racenacillin; Ro-Ampen; Rosampline;Roscillin; SK-Ampicillin; SQ 17382; Semicillin; Semicillin R; Servicillin; Sumipanto; Synpenin; Texcillin; Tokiocillin; Tolomol; Totacillin; Totacillin (sodium); Totacillin-N; Totalciclina; Totapen; Trifacilina; Ukapen; Ultrabion; Ultrabron; Vampen; Viccillin; Viccillin S; WY-5103; Wypicil; 6-(D(-)-alpha-Aminophenylacetamido)penicillanic acid; 6beta-[(2R)-2-amino-2-phenylacetamido]-2,2-dimethylpenam-3alpha-carbonyl; 6beta-[(2R)-2-amino-2-phenylacetamido]-2,2-dimethylpenam-3alpha-carboxylic acid; AB-PC; AB-PCSol; ABPC; AMPICILLIN (SEE ALSO AMPICILLIN TRIHYDRATE 7177-48-2); AY 6108; AY-6108; Alpen; Ampen; Ampicillin [USAN:INN:BAN:JAN];D-(-)-Ampicillin; BA 7305; BRL-1341; Bayer 5427; Cimex; D-(-)-6-(alpha-Aminophenylacetamido)penicillanic acid; HI 63; KS-R1; P 50; P-50; Pen A; Supen
Indication Endocarditis [ICD11: 1B12] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 349.4 Topological Polar Surface Area 138
Heavy Atom Count 24 Rotatable Bond Count 4
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
6249
PubChem SID
8803 ; 612819 ; 855874 ; 7847272 ; 7978702 ; 8153929 ; 11335641 ; 11360880 ; 11362844 ; 11365406 ; 11367968 ; 11371462 ; 11373737 ; 11376130 ; 11461852 ; 11466142 ; 11467262 ; 11484554 ; 11485803 ; 11488585 ; 11490117 ; 11491964 ; 11493864 ; 14802821 ; 14827659 ; 24891442 ; 26706523 ; 29215015 ; 29225245 ; 46392100 ; 46484751 ; 46505346 ; 47291088 ; 47440199 ; 47810705 ; 47885360 ; 47959687 ; 48035057 ; 48035058 ; 48184948 ; 48415562 ; 49698352 ; 49855717 ; 50064028 ; 50104132 ; 50930328 ; 53789146 ; 53801116 ; 56312591 ; 56314308
ChEBI ID
ChEBI:28971
CAS Number
69-53-4
TTD Drug ID
D0YA9Z
Formula
C16H19N3O4S
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
5R,6R-penicilloic acid DM000864 N. A. Unclear 1 [9] , [10]
5S,6R-penicilloic acid DM000865 N. A. Unclear 1 [9] , [10]
Ampicillin penicilloic acid DM000863
53364402
Unclear 1 [9] , [10]
Ampicillin piperazine-2,5- dione DM000866
338751
Unclear 1 [9] , [10]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000223 Ampicillin Ampicillin penicilloic acid Unclear blaB [9], [10]
MR000224 Ampicillin 5R,6R-penicilloic acid Unclear blaB [9], [10]
MR000225 Ampicillin 5S,6R-penicilloic acid Unclear blaB [9], [10]
MR000226 Ampicillin Ampicillin piperazine-2,5- dione Unclear blaB [9], [10]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
AmpC beta-lactamase (ampC) DME1192 Burkholderia multivorans
A0A0H3KQ39_BURM1
3.5.2.6
[2]
Beta-lactamase (blaB) DME1563 Ralstonia pickettii
Q6EZ46_RALPI
3.5.2.6
[3]
Beta-lactamase (blaB) DME1214 Bacillus megaterium
BLA2_BAC17
3.5.2.6
[3]
Beta-lactamase (blaB) DME1224 Fusobacterium nucleatum
Q8RIK5_FUSNN
3.5.2.6
[3]
Beta-lactamase (blaB) DME1562 Corynebacterium acnes
D4HFC4_CUTAS
3.5.2.6
[3]
Beta-lactamase (blaB) DME1342 Acinetobacter baumannii
A0A1B1FBM9_ACIBA
3.5.2.6
[4]
Beta-lactamase (blaB) DME1561 Burkholderia pseudomallei
A0A2U9SV73_9BURK
3.5.2.6
[3]
Beta-lactamase (blaB) DME1564 Staphylococcus aureus
A0A344X3A2_STASP
3.5.2.6
[3]
Beta-lactamase (blaB) DME1026 Bacteroides uniformis
BLAC_BACUN
3.5.2.6
[5]
Beta-lactamase (blaB) DME1221 Capnocytophaga haemolytica
A0A2S0LB67_9FLAO
3.5.2.6
[3]
Beta-lactamase (blaB) DME1227 Neisseria sicca
A0A1S1G219_9NEIS
3.5.2.6
[3]
Beta-lactamase (blaB) DME1228 Plesiomonas shigelloides
A0A379CPC3_PLESH
3.5.2.6
[6]
N-acylhomoserine lactone acylase (lacA) DME1021 Acidovorax ebreus
A0A0A1VBK6_9BURK
3.5.1.97
[7]
Unclear metabolic mechanism (DME-unclear) DME1279 Methanobrevibacter oralis Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1280 Methanobrevibacter smithii Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1281 Methanomassiliicoccus luminyensis Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1282 Methanosphaera stadtmanae Not Available Not Available [8]
⏷ Show the Full List of 17  DME(s)
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Beta-lactamase (blaB) DME1026 Km = 4.4 microM
BLAC_BACUN
[5]
References
1 Ampicillin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Characterization of the AmpC beta-Lactamase from Burkholderia multivorans. Antimicrob Agents Chemother. 2018 Sep 24;62(10). pii: e01140-18.
3 Beta-lactamase production and antimicrobial susceptibility of subgingival bacteria from refractory periodontitis. Oral Microbiol Immunol. 2004 Oct;19(5):303-8.
4 Drug-resistant genes carried by Acinetobacter baumanii isolated from patients with lower respiratory tract infection. Chin Med J (Engl). 2010 Sep;123(18):2571-5.
5 Purification and characterization of a new beta-lactamase from Bacteroides uniformis. Antimicrob Agents Chemother. 1995 Jul;39(7):1458-61.
6 Beta-lactamase expression in Plesiomonas shigelloides. J Antimicrob Chemother. 2000 Jun;45(6):877-80.
7 A novel quorum-quenching N-acylhomoserine lactone acylase from Acidovorax sp. strain MR-S7 mediates antibiotic resistance. Appl Environ Microbiol. 2017 Jun 16;83(13). pii: e00080-17.
8 The antimicrobial resistance pattern of cultured human methanogens reflects the unique phylogenetic position of archaea. J Antimicrob Chemother. 2011 Sep;66(9):2038-44.
9 Liquid chromatographic determination of ampicillin and its metabolites in human urine by postcolumn alkaline degradation J Pharm Pharmacol. 1987 Jan;39(1):5-8. doi: 10.1111/j.2042-7158.1987.tb07152.x.
10 Identification of metabolites of ampicillin using liquid chromatography/thermospray mass spectrometry and fast atom bombardment tandem mass spectrometry Biomed Environ Mass Spectrom. 1989 Nov;18(11):983-94. doi: 10.1002/bms.1200181106.

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.