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 a number of 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 Clostridium 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 Crystallogr. 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 Crystallogr. 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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