Ampicillin

Ampicillin
	Skeletal formula of ampicillin
	Ball-and-stick model of the zwitterionic form of ampicillin found in the crystal structure of the trihydrate
Clinical data
Trade names	Principen, others
Other names	AM/AMP
AHFS/Drugs.com	Monograph
MedlinePlus	a685002
License data	US DailyMed: Ampicillin;
Pregnancy; category	AU: A; ;
Routes of; administration	By mouth, intravenous, intramuscular
Drug class	Aminopenicillins
ATC code	J01CA01 (WHO) S01AA19 (WHO) QJ51CA01 (WHO) J01CR50 (WHO) J01CA51 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: WARNINGRx-only;
Pharmacokinetic data
Bioavailability	62% ±17% (parenteral); < 30–55% (oral)
Protein binding	15 to 25%
Metabolism	12 to 50%
Metabolites	Penicilloic acid
Elimination half-life	Approx. 1 hour
Excretion	75 to 85% kidney
Identifiers
	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;
CAS Number	69-53-4 ;
PubChem CID	6249;
DrugBank	DB00415 ;
ChemSpider	6013 ;
UNII	7C782967RD;
KEGG	D00204 ; C06574 ;
ChEBI	CHEBI:28971 ;
ChEMBL	ChEMBL174 ;
PDB ligand	AIC (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID4022602 ;
ECHA InfoCard	100.000.645
Chemical and physical data
Formula	C16H19N3O4S
Molar mass	349.41 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:AVKUERGKIZMTKX-NJBDSQKTSA-N ;
	(verify)

Ampicillin is an antibiotic belonging to the aminopenicillin class of the penicillin family. The drug is used to prevent and treat several bacterial infections, such as respiratory tract infections, urinary tract infections, meningitis, salmonellosis, and endocarditis.^[7] It may also be used to prevent group B streptococcal infection in newborns.^[7] It is used by mouth, by injection into a muscle, or intravenously.^[7]

Common side effects include rash, nausea, and diarrhea.^[7] It should not be used in people who are allergic to penicillin.^[7] Serious side effects may include Clostridioides difficile colitis or anaphylaxis.^[7] While usable in those with kidney problems, the dose may need to be decreased.^[7] Its use during pregnancy and breastfeeding appears to be generally safe.^[7]^[8]

Ampicillin was discovered in 1958 and came into commercial use in 1961.^[9]^[10] It is on the World Health Organization's List of Essential Medicines.^[11] The World Health Organization classifies ampicillin as critically important for human medicine.^[12] It is available as a generic medication.^[7]

^ Burley JC, Van De Streek J, Stephens PW (2006). "CSD Entry: AMPCIH01". Cambridge Structural Database: Access Structures. Cambridge Crystallographic Data Centre. doi:10.5517/ccb0nkj. Retrieved 28 June 2022.
^ Burley JC, van de Streek J, Stephens PW (2006). "Ampicillin trihydrate from synchrotron powder diffraction data". Acta Crystallographica Section E. 62 (2): o797 – o799. Bibcode:2006AcCrE..62O.797B. doi:10.1107/S1600536806001371.
^ "Ampicillin - international drug names". Drugs.com. 30 November 2019. Archived from the original on 30 November 2019. Retrieved 26 January 2020.
^ "Antibiotic abbreviations list". Retrieved 22 June 2023.
^ "Ampicillin Use During Pregnancy". Drugs.com. 2 May 2019. Archived from the original on 22 August 2019. Retrieved 26 January 2020.
^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j "Ampicillin". The American Society of Health-System Pharmacists. Archived from the original on 12 July 2015. Retrieved 1 August 2015.
^ "Ampicillin use while Breastfeeding". March 2015. Archived from the original on 23 September 2015. Retrieved 1 August 2015.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 490. ISBN 9783527607495. Archived from the original on 20 December 2016.
^ Ravina E (2011). The evolution of drug discovery : from traditional medicines to modern drugs (1 ed.). Weinheim: Wiley-VCH. p. 262. ISBN 9783527326693. Archived from the original on 9 August 2016.
^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
^ World Health Organization (2019). Critically important antimicrobials for human medicine (6th revision ed.). Geneva: World Health Organization. hdl:10665/312266. ISBN 9789241515528.

[1] Burley JC, Van De Streek J, Stephens PW (2006). "CSD Entry: AMPCIH01". Cambridge Structural Database: Access Structures. Cambridge Crystallographic Data Centre. doi:10.5517/ccb0nkj. Retrieved 28 June 2022.

[2] Burley JC, van de Streek J, Stephens PW (2006). "Ampicillin trihydrate from synchrotron powder diffraction data". Acta Crystallographica Section E. 62 (2): o797 – o799. Bibcode:2006AcCrE..62O.797B. doi:10.1107/S1600536806001371.

[drugs.comINT-3] "Ampicillin - international drug names". Drugs.com. 30 November 2019. Archived from the original on 30 November 2019. Retrieved 26 January 2020.

[4] "Antibiotic abbreviations list". Retrieved 22 June 2023.

[Drugs.com_pregnancy-5] "Ampicillin Use During Pregnancy". Drugs.com. 2 May 2019. Archived from the original on 22 August 2019. Retrieved 26 January 2020.

[FDA-AllBoxedWarnings-6] "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.

[AHFS2015-7] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j "Ampicillin". The American Society of Health-System Pharmacists. Archived from the original on 12 July 2015. Retrieved 1 August 2015.

[8] "Ampicillin use while Breastfeeding". March 2015. Archived from the original on 23 September 2015. Retrieved 1 August 2015.

[9] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 490. ISBN 9783527607495. Archived from the original on 20 December 2016.

[10] Ravina E (2011). The evolution of drug discovery : from traditional medicines to modern drugs (1 ed.). Weinheim: Wiley-VCH. p. 262. ISBN 9783527326693. Archived from the original on 9 August 2016.

[WHO23rd-11] World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.

[12] World Health Organization (2019). Critically important antimicrobials for human medicine (6th revision ed.). Geneva: World Health Organization. hdl:10665/312266. ISBN 9789241515528.

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