Drug Information

General Information
Drug ID
DR00712
Drug Name
Ampicillin
Synonyms
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; Acillin; Adobacillin; Alpen; Ambidrin (TN); Amblosin; Amcill; Amfipen; Amfipen V; Aminobenzylpenicillin; Amipenix S; Ampen; 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 [USAN:INN:BAN:JAN];D-(-)-Ampicillin; 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; BA 7305; BRL 1341; BRL-1341; Bayer 5427; Binotal; Bonapicillin; Britacil; Campicillin; Cimex; Copharcilin; D-(-)-6-(alpha-Aminophenylacetamido)penicillanic acid; D-(-)-alpha-Aminobenzylpenicillin; D-(-)-alpha-Aminopenicillin; D-Ampicillin; D-Cillin; Delcillin; Deripen; Divercillin; Doktacillin; Duphacillin; Grampenil; Guicitrina; Guicitrine; HI 63; KS-R1; Lifeampil; Morepen; Norobrittin; Novo-ampicillin; Nuvapen; OMNIPEN (AMPICILLIN); Olin Kid; Omnipen; Omnipen (TN); Omnipen-N; Orbicilina; P 50; P-50; Pen A; 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; Supen; Synpenin; Texcillin; Tokiocillin; Tolomol; Totacillin; Totacillin (sodium); Totacillin-N; Totalciclina; Totapen; Trifacilina; Ukapen; Ultrabion; Ultrabron; Vampen; Viccillin; Viccillin S; WY-5103; Wypicil
Drug Type
Small molecular drug
Indication Bacterial infections [ICD11:1A00-1H0Z] Approved [1]
Therapeutic Class
Antibiotics
Structure
3D MOL 2D MOL
Formula
C16H19N3O4S
Canonical SMILES
CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)O)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
CAS Number
CAS 69-53-4
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
XLogP
-1.1
PubChem CID
6249
PubChem SID
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 ,612819 ,7847272 ,7978702 ,8153929 ,855874 ,8803
ChEBI ID
ChEBI:28971
TTD Drug ID
D0YA9Z
DT(s) Transporting This Drug MRP2 Transporter Info Multidrug resistance-associated protein 2 Substrate [2]
PEPT1 Transporter Info Peptide transporter 1 Substrate [3]
PEPT2 Transporter Info Peptide transporter 2 Substrate [4]
PEPT2 Transporter Info Peptide transporter 2 Substrate [4]
References
1 Ampicillin was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64.
3 Several hPepT1-transported drugs are substrates of the Escherichia coli proton-coupled oligopeptide transporter YdgR. Res Microbiol. 2017 Jun;168(5):443-449.
4 Transport characteristics of a novel peptide transporter 1 substrate, antihypotensive drug midodrine, and its amino acid derivatives. J Pharmacol Exp Ther. 2006 Jul;318(1):455-60.

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