Details of the Drug

General Information of Drug (ID: DMHWE7P)

Drug Name

Ampicillin

Synonyms

ABPC; Acillin; Adobacillin; Alpen; Amblosin; Amcill; Amfipen; Aminobenzylpenicillin; Ampen; Ampichel; Ampicil; Ampicilina; Ampicillanyl; Ampicillina; Ampicilline; Ampicillinum; Ampicin; Ampifarm; Ampikel; Ampimed; Ampipenin; Ampiscel; Ampisyn; Ampivax; Ampivet; Amplacilina; Amplin; Amplipenyl; Amplisom; Amplital; Austrapen; Binotal; Bonapicillin; Britacil; Campicillin; Cimex; Copharcilin; Delcillin; Deripen; Divercillin; Doktacillin; Duphacillin; Grampenil; Guicitrina; Guicitrine; Lifeampil; Morepen; Norobrittin; Nuvapen; Omnipen; Orbicilina; Penbristol; Penbritin; Penbrock; Penicline; Penimic; Pensyn; Pentrex; Pentrexl; Pentrexyl; Polycillin; Ponecil; Princillin; Principen; QIDamp; Racenacillin; Rosampline;Roscillin; Semicillin; Servicillin; Sumipanto; Supen; Synpenin; Texcillin; Tokiocillin; Tolomol; Totacillin; Totalciclina; Totapen; Trifacilina; Ukapen; Ultrabion; Ultrabron; Vampen; Viccillin; Wypicil; Amfipen V; Amipenix S; Ampicillin A; Ampicillin Anhydrous; Ampicillin Base; Ampicillin acid; Ampicillin anhydrate; Ampicillina [DCIT]; Anhydrous ampicillin; Olin Kid; Pen A; Pen A Oral; Pen Ampil;Penbritin paediatric; Penbritin syrup; Pfizerpen A; Semicillin R; Viccillin S; AY 6108; BA 7305; BRL 1341; Bayer 5427; HI 63; P 50; Principen 125; Principen 250; Principen 500; SQ 17382; AB-PC; AB-PCSol; AY-6108; Ambidrin (TN); Ampi-Co; Ampi-Tab; Ampi-bol; Ampicilina [INN-Spanish]; Ampicilline [INN-French]; Ampicillinum [INN-Latin]; Ampipenin, nt3; Ampy-Penyl; Anhydrous ampicillin (JP15); BRL-1341; D-Ampicillin; D-Cillin; KS-R1; Novo-ampicillin; OMNIPEN (AMPICILLIN); Omnipen (TN); Omnipen-N; P-50; Penbritin-S; Penicillin, Aminobenzyl; Pfizerpen-A; Polycillin-N; Polyflex (Veterinary); Ro-Ampen; SK-Ampicillin; Totacillin (sodium); Totacillin-N; WY-5103; Ampicillin (USP/INN); AMPICILLIN (SEE ALSO AMPICILLIN TRIHYDRATE 7177-48-2); Ampicillin [USAN:BAN:INN:JAN]; Ampicillin [USAN:INN:BAN:JAN];D-(-)-Ampicillin; D-(-)-alpha-Aminobenzylpenicillin; D-(-)-alpha-Aminopenicillin; D-(-)-6-(alpha-Aminophenylacetamido)penicillanic acid; 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

Indication

Disease Entry	ICD 11	Status	REF
Acute epiglottitis	N.A.	Approved	[1]
Acute gonococcal cervicitis	N.A.	Approved	[1]
Acute otitis media	AB00	Approved	[1]
Bacillary dysentery	1A02	Approved	[1]
Bacteremia	1A73	Approved	[1]
Bacterial endocarditis	N.A.	Approved	[1]
Bacterial infection	1A00-1C4Z	Approved	[2]
Cholangitis	N.A.	Approved	[1]
Chorioamnionitis	N.A.	Approved	[1]
Dysentery	N.A.	Approved	[1]
Escherichia coli meningitis	N.A.	Approved	[1]
Meningococcal meningitis	N.A.	Approved	[1]
Peritonitis	N.A.	Approved	[1]
Pneumococcal meningitis	N.A.	Approved	[1]
Staphylococcal pneumonia	N.A.	Approved	[1]
Staphylococcus aureus infection	N.A.	Approved	[1]
Streptococcal pneumonia	N.A.	Approved	[1]
Urinary tract infection	GC08	Approved	[1]
Paratyphoid fever	N.A.	Investigative	[1]
Pelvic inflammatory disease	GA05	Investigative	[1]
Sinusitis	CA0A.Z	Investigative	[1]
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Therapeutic Class

Antibiotics

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

349.4

Logarithm of the Partition Coefficient (xlogp)

-1.1

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [3]
Bioavailability: 62% of drug becomes completely available to its intended biological destination(s) [4]
Clearance: The drug present in the plasma can be removed from the body at the rate of 2.8 mL/min/kg [5]
Elimination: 88% of drug is excreted from urine in the unchanged form [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 1.4 hours [5]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 166.85196 micromolar/kg/day [6]
Unbound Fraction: The unbound fraction of drug in plasma is 0.85% [5]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.22 L/kg [5]
Water Solubility: The ability of drug to dissolve in water is measured as 7.8 mg/mL [3]

Chemical Identifiers

Formula: C16H19N3O4S
IUPAC Name: (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
Canonical SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](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

Cross-matching ID

PubChem CID: 6249
ChEBI ID: CHEBI:28971
CAS Number: 69-53-4
DrugBank ID: DB00415
TTD ID: D0YA9Z
VARIDT ID: DR00712
INTEDE ID: DR2177
ACDINA ID: D00037

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Bacterial Penicillin binding protein (Bact PBP)	TTJP4SM	NOUNIPROTAC	Binder	[7]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Peptide transporter 2 (SLC15A2)	DT8QKNP	S15A2_HUMAN	Substrate	[8]
Peptide transporter 1 (SLC15A1)	DT9G7XN	S15A1_HUMAN	Substrate	[9]
Multidrug resistance-associated protein 2 (ABCC2)	DTFI42L	MRP2_HUMAN	Substrate	[10]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
N-acylhomoserine lactone acylase (lacA)	DEIU0XN	A0A0A1VBK6_9BURK	Substrate	[11]
Beta-lactamase (blaB)	DET9I1W	BLAC_BACUN	Substrate	[12]
Beta-lactamase (blaB)	DETDS7E	A0A2S0LB67_9FLAO	Substrate	[13]
Beta-lactamase (blaB)	DEC7JEF	A0A1S1G219_9NEIS	Substrate	[13]
Beta-lactamase (blaB)	DEBKS91	A0A1B1FBM9_ACIBA	Substrate	[14]
AmpC beta-lactamase (ampC)	DERI7LO	A0A0H3KQ39_BURM1	Substrate	[15]
Beta-lactamase (blaB)	DEWYT5M	D4HFC4_CUTAS	Substrate	[13]
Beta-lactamase (blaB)	DE3FVRW	BLA2_BAC17	Substrate	[13]
Beta-lactamase (blaB)	DEG5Y4W	A0A344X3A2_STASP	Substrate	[13]
Beta-lactamase (blaB)	DEQX0DG	Q8RIK5_FUSNN	Substrate	[13]
Beta-lactamase (blaB)	DEXB2A9	A0A379CPC3_PLESH	Substrate	[16]
Beta-lactamase (blaB)	DEWMGC3	A0A2U9SV73_9BURK	Substrate	[13]
Beta-lactamase (blaB)	DE52KD0	Q6EZ46_RALPI	Substrate	[13]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrial (CYP24A1)	OTG2T749	CP24A_HUMAN	Gene/Protein Processing	[17]
6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 3 (PFKFB3)	OT25JBA3	F263_HUMAN	Gene/Protein Processing	[17]
Aldo-keto reductase family 1 member B10 (AKR1B10)	OTOA4HTH	AK1BA_HUMAN	Gene/Protein Processing	[17]
Aldo-keto reductase family 1 member C2 (AKR1C2)	OTQ2XMO3	AK1C2_HUMAN	Gene/Protein Processing	[17]
Angiomotin (AMOT)	OTWHDG9B	AMOT_HUMAN	Gene/Protein Processing	[17]
Ankyrin repeat domain-containing protein 1 (ANKRD1)	OTHJ7JV9	ANKR1_HUMAN	Gene/Protein Processing	[17]
Aquaporin-3 (AQP3)	OT2J7JPD	AQP3_HUMAN	Gene/Protein Processing	[17]
Arginase-1 (ARG1)	OTHZITAM	ARGI1_HUMAN	Gene/Protein Processing	[17]
Arrestin domain-containing protein 3 (ARRDC3)	OTAKW7R9	ARRD3_HUMAN	Gene/Protein Processing	[17]
Arrestin domain-containing protein 4 (ARRDC4)	OTINJ0FX	ARRD4_HUMAN	Gene/Protein Processing	[17]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Ampicillin (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Clindamycin	DM15HL8	Minor	Increased risk of intestinal flora disorders by the combination of Ampicillin and Clindamycin.	Acne vulgaris [ED80]	[18]
Anisindione	DM2C48U	Moderate	Increased risk of bleeding by the combination of Ampicillin and Anisindione.	Coagulation defect [3B10]	[19]
Mycophenolic acid	DMRBMAU	Moderate	Altered absorption of Ampicillin due to GI flora changes caused by Mycophenolic acid.	Crohn disease [DD70]	[20]
Dexlansoprazole	DM1DBV5	Moderate	Decreased absorption of Ampicillin due to altered gastric pH caused by Dexlansoprazole.	Gastro-oesophageal reflux disease [DA22]	[21]
Probenecid	DMMFWOJ	Minor	Decreased elimination of Ampicillin caused by Probenecid mediated competitive inhibition of renal tubular secretion.	Inborn purine/pyrimidine/nucleotide metabolism error [5C55]	[22]
Methotrexate	DM2TEOL	Major	Decreased elimination of Ampicillin caused by Methotrexate mediated competitive inhibition of renal tubular secretion.	Leukaemia [2A60-2B33]	[23]
Warfarin	DMJYCVW	Moderate	Increased risk of bleeding by the combination of Ampicillin and Warfarin.	Supraventricular tachyarrhythmia [BC81]	[19]
Mycophenolate mofetil	DMPQAGE	Moderate	Altered absorption of Ampicillin due to GI flora changes caused by Mycophenolate mofetil.	Transplant rejection [NE84]	[20]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
D&C red no. 28	E00491	6097185	Colorant
FD&C blue no. 1	E00263	19700	Colorant
Isopropyl alcohol	E00070	3776	Antimicrobial preservative; Solvent
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Ammonia	E00007	222	Alkalizing agent
Butyl alcohol	E00011	263	Flavoring agent; Solvent
Ferrosoferric oxide	E00231	14789	Colorant
Magnesium stearate	E00208	11177	lubricant
Potassium hydroxide	E00233	14797	Alkalizing agent
Propylene glycol	E00040	1030	Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Ampicillin 250 mg capsule	250 mg	Oral Capsule	Oral
Ampicillin 500 mg capsule	500 mg	Oral Capsule	Oral

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References

1	Ampicillin FDA Label
2	FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 061936.
3	BDDCS applied to over 900 drugs
4	Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
5	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
6	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
7	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.
8	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.
9	Several hPepT1-transported drugs are substrates of the Escherichia coli proton-coupled oligopeptide transporter YdgR. Res Microbiol. 2017 Jun;168(5):443-449.
10	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.
11	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.
12	Purification and characterization of a new beta-lactamase from Bacteroides uniformis. Antimicrob Agents Chemother. 1995 Jul;39(7):1458-61.
13	Beta-lactamase production and antimicrobial susceptibility of subgingival bacteria from refractory periodontitis. Oral Microbiol Immunol. 2004 Oct;19(5):303-8.
14	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.
15	Characterization of the AmpC beta-Lactamase from Burkholderia multivorans. Antimicrob Agents Chemother. 2018 Sep 24;62(10). pii: e01140-18.
16	Beta-lactamase expression in Plesiomonas shigelloides. J Antimicrob Chemother. 2000 Jun;45(6):877-80.
17	Comparison of phenotypic and transcriptomic effects of false-positive genotoxins, true genotoxins and non-genotoxins using HepG2 cells. Mutagenesis. 2011 Sep;26(5):593-604.
18	Brause BD, Romankiewicz JA, Gotz V, Franklin JE Jr, Roberts RB "Comparative study of diarrhea associated with clindamycin and ampicillin therapy." Am J Gastroenterol 73 (1980): 244-8. [PMID: 7405925]
19	Alexander DP, Russo ME, Fohrman DE, Rothstein G "Nafcillin-induced platelet dysfunction and bleeding." Antimicrob Agents Chemother 23 (1983): 59-62. [PMID: 6830209]
20	Product Information. CellCept (mycophenolate mofetil). Roche Laboratories, Nutley, NJ.
21	Product Information. Kapidex (dexlansoprazole). Takeda Pharmaceuticals America, Lincolnshire, IL.
22	Allen MB, Fitzpatrick RW, Barratt A, Cole RB "The use of probenecid to increase the serum amoxycillin levels in patients with bronchiectasis." Respir Med 84 (1990): 143-6. [PMID: 2371437]
23	Kwon OC, Lee JS, Kim YG, Lee CK, Yoo B, Hong S. Safety of the concomitant use of methotrexate and a prophylactic dose of trimethoprim-sulfamethoxazole.?Clin Rheumatol. 2018;37(12):3215-3220. [PMID: 29383453]