Ampicillin

Details

• Internal ID: b8fa5b62-9ad6-4b98-9cb3-00b6c844bd40
• Taxonomy: Organoheterocyclic compounds > Lactams > Beta lactams > Penams > Penicillins
• 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
• SMILES (Canonical): CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)O)C
• SMILES (Isomeric): 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
• InChI Key: AVKUERGKIZMTKX-NJBDSQKTSA-N
• Popularity: 69,249 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₉N₃O₄S
• Molecular Weight: 349.40 g/mol
• Exact Mass: 349.10962727 g/mol
• Topological Polar Surface Area (TPSA): 138.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): 0.32
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• Ampicillin
• Aminobenzylpenicillin
• Ampicillin acid
• Amcill
• Tokiocillin
• Omnipen
• Ampicillin Anhydrous
• Ampicilline
• Principen
• Semicillin
• Ultrabion
• anhydrous ampicillin
• Ampicillinum
• Pentrexyl
• Synpenin
• Novo-ampicillin
• D-Ampicillin
• Bonapicillin
• Totalciclina
• Adobacillin
• Amblosin
• Ampicilina
• Ampifarm
• Ampipenin
• Ampiscel
• Amplacilina
• Amplipenyl
• Amplisom
• Amplital
• Britacil
• Copharcilin
• D-(-)-Ampicillin
• Delcillin
• Doktacillin
• Duphacillin
• Grampenil
• Guicitrina
• Norobrittin
• Orbicilina
• Penbristol
• Penbrock
• Penicline
• Pentrexl
• Rosampline
• Roscillin
• Servicillin
• Sumipanto
• Texcillin
• Trifacilina
• Ultrabron
• Viccillin
• Amfipen
• Ampicil
• Ampicin
• Ampimed
• Ampisyn
• Ampivax
• Ampivet
• Binotal
• Nuvapen
• Penimic
• Pentrex
• Ponecil
• Tolomol
• Totapen
• Vampen
• Cimex
• Supen
• Ampicillin A
• Ampicillin anhydrate
• Penbritin
• Pfizerpen A
• SK-Ampicillin
• Amipenix S
• Ampi-bol
• Amfipen V
• Pen Ampil
• QIDamp
• Ampi-Tab
• D-Cillin
• Olin Kid
• Ampi-Co
• Ampichel
• Campicillin
• Divercillin
• Lifeampil
• Princillin
• Racenacillin
• Acillin
• Ampikel
• Amplin
• Morepen
• Pensyn
• Semicillin R
• Totacillin
• Ampy-Penyl
• Ro-Ampen
• Ampicillina
• Penbritin paediatric
• Austrapen
• Pen A
• Bayer 5427
• ABPC
• Ampicillin, anhydrous
• Ampicillina [DCIT]
• D-(-)-alpha-Aminobenzylpenicillin
• AB-PC
• D-(-)-alpha-Aminopenicillin
• AY-6108
• Ampicilina [INN-Spanish]
• Ampicilline [INN-French]
• Ampicillinum [INN-Latin]
• AB-PC Sol
• Deripen
• Wypicil
• Alpen
• BRL 1341
• P-50
• Redicilin
• NSC-528986
• KS-R1
• Ampicillin (anhydrous)
• BRL-1341
• D-(-)-6-(alpha-Aminophenylacetamido)penicillanic acid
• HI 63
• 6-(D(-)-alpha-Aminophenylacetamido)penicillanic acid
• NSC 528986
• BA 7305
• WY-5103
• CHEBI:28971
• HSDB 3009
• Penicillin, (aminophenylmethyl)-
• SQ 17382
• EINECS 200-709-7
• Guicitrine
• Ampen
• AY 6108
• 6-(D-(2-Amino-2-phenylacetamido))-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
• DTXSID4022602
• UNII-7C782967RD
• Ampicillin hydrate
• Alpha-Aminobenzylpenicillin
• 7C782967RD
• WY 5103
• MLS000028405
• DTXCID202602
• (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
• 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta(S*)))-
• Ukapen
• EC 200-709-7
• Pfizerpen-A
• AMPI
• NSC528986
• (2S,5R,6R)-6-((R)-2-Amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
• (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
• P 50
• SMR000058352
• Ampicillin Base
• AMPICILLIN (IARC)
• AMPICILLIN [IARC]
• MFCD00005175
• Penicillin, Aminobenzyl
• AMPICILLIN (MART.)
• AMPICILLIN [MART.]
• (2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• (2S,5R,6R)-6-[(R)-2-Amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-, D-(-)-
• ampicillanyl
• AMPICILLIN (EP MONOGRAPH)
• AMPICILLIN [EP MONOGRAPH]
• AMPICILLIN (USP MONOGRAPH)
• AMPICILLIN [USP MONOGRAPH]
• Ampicillin [USAN:BAN:INN:JAN]
• 6beta-[(2R)-2-amino-2-phenylacetamido]-2,2-dimethylpenam-3alpha-carboxylic acid
• CAS-69-53-4
• (2S,5R,6R)-6-{[(2R)-2-AMINO-2-PHENYLETHANOYL]AMINO}-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID
• 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((2R)-aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, (2S,5R,6R)-
• Omnipen (TN)
• Totacillin (sodium)
• Aminobenzyl Penicillin
• SULTAMICILLIN IMPURITY C (EP IMPURITY)
• SULTAMICILLIN IMPURITY C [EP IMPURITY]
• C16H19N3O4S
• Ampicillin (USP/INN)
• vidopen
• Vidocillin
• Marcillin
• Pentritin
• D-(-)-.alpha.-Aminobenzylpenicillin
• 6beta-((2R)-2-amino-2-phenylacetamido)-2,2-dimethylpenam-3alpha-carboxylic acid
• Ampicillin,(S)
• D(-)-ALPHA-AMINOBENZYLPENICILLIN
• NCGC00018160-02
• (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
• (2S,5R,6R)-6-(((2R)-2-AMINO-2-PHENYLETHANOYL)AMINO)-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID
• (2s,5r,6r)-6-((r)-2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• (2S,5R,6R)-6-[[(2R)-2-amino-2-phenyl-acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• Ampicillin [USAN:USP:INN:BAN:JAN]
• VICILLIN S
• Spectrum_000050
• 1h8s
• AY 6108
• AMPICILLIN [MI]
• AMPICILLIN [INN]
• D-a-Aminobenzylpenicillin
• Opera_ID_1630
• Prestwick0_000114
• Prestwick1_000114
• Prestwick2_000114
• Prestwick3_000114
• Spectrum2_000769
• Spectrum3_000301
• Spectrum4_000149
• Spectrum5_000814
• AMPICILLIN [HSDB]
• AMPICILLIN [USAN]
• AMPICILLIN [VANDF]
• CHEMBL174
• Epitope ID:115008
• Epitope ID:116057
• SCHEMBL3526
• AMPICILLIN [USP-RS]
• AMPICILLIN [WHO-DD]
• AMPICILLIN [WHO-IP]
• BSPBio_000128
• BSPBio_001862
• KBioGR_000598
• KBioSS_000430
• Anhydrous ampicillin (JP17)
• MLS001074168
• BIDD:GT0184
• DivK1c_000466
• D-(-)--Aminobenzylpenicillin
• SPBio_000818
• SPBio_002067
• Ampicillin, analytical standard
• D-(-)-a-Aminobenzylpenicillin
• BPBio1_000142
• CHEBI:53713
• GTPL10896
• KBio1_000466
• KBio2_000430
• KBio2_002998
• KBio2_005566
• KBio3_001362
• J01CA01
• S01AA19
• NINDS_000466
• ANHYDROUS AMPICILLIN [JAN]
• HMS2090I11
• HMS2233H23
• Ampicillin acid; Principen; Amcill
• AMPICILLINUM [WHO-IP LATIN]
• HY-B0522
• Tox21_113049
• Tox21_301416
• BDBM50350465
• AMPICILLIN ANHYDROUS [WHO-IP]
• AKOS015888156
• Tox21_113049_1
• AC-8805
• DB00415
• IDI1_000466
• SMP1_000211
• AMPICILLIN ANHYDROUS [GREEN BOOK]
• NCGC00023282-05
• NCGC00023282-06
• NCGC00023282-21
• NCGC00178944-03
• NCGC00248937-01
• NCGC00255127-01
• BA166034
• SBI-0051283.P003
• 6-(a-Aminophenylacetamido)penicillanic acid
• C06574
• D00204
• EN300-127654
• 6-[D(-)-a-Aminophenylacetamido]penicillanic acid
• A936108
• AMPICILLIN ANHYDROUS, PHARMACEUTICAL GRADE
• Q244150
• 6-D(-)-alpha-Aminophenylacetamido-penicillanic acid
• Ampicillin 1000 microg/mL in Acetonitrile:Methanol
• PIPERACILLIN SODIUM IMPURITY A [EP IMPURITY]
• BRD-K68432770-001-08-0
• Ampicillin, anhydrous, 96.0-100.5% (anhydrous basis)
• Z1603854590
• Ampicillin, United States Pharmacopeia (USP) Reference Standard
• Anhydrous ampicillin, British Pharmacopoeia (BP) Reference Standard
• Ampicillin, anhydrous, European Pharmacopoeia (EP) Reference Standard
• (2S,5R,6R)-6-(((R,E)-2-Amino-1-hydroxy-2-phenylethylidene)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• (2S,5R,6R)-6-((2R)-2-Amino-2-phenylacetylamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
• (2S,5R,6R)-6-[(R)-2-Amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid
• (2S,5R,6R)-6-{[(2R)-2-AMINO-2-PHENYLETHANOYL]AMINO}-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC
• 4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-((AMINOPHENYLACETYL)AMINO)-3,3-DIMETHYL-7-OXO-, (2S-(2.ALPHA.,5.ALPHA.,6.BETA.(S*)))-
• 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[[(2R)-aminophenylacetyl]amino]-3,3-dimethyl-7-oxo-, trihydrate,(2S,5R,6R)-
• 6-[(Aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 9CI

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9249	92.49%
Caco-2	-	0.9100	91.00%
Blood Brain Barrier	-	1.0000	100.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Lysosomes	0.5707	57.07%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9316	93.16%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.7239	72.39%
P-glycoprotein inhibitior	-	0.9243	92.43%
P-glycoprotein substrate	-	0.8330	83.30%
CYP3A4 substrate	+	0.5279	52.79%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8352	83.52%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9402	94.02%
CYP2C19 inhibition	-	0.9399	93.99%
CYP2D6 inhibition	-	0.9401	94.01%
CYP1A2 inhibition	-	0.9253	92.53%
CYP2C8 inhibition	-	0.9943	99.43%
CYP inhibitory promiscuity	-	0.9884	98.84%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	+	0.7200	72.00%
Carcinogenicity (trinary)	Non-required	0.6941	69.41%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9916	99.16%
Skin irritation	-	0.7329	73.29%
Skin corrosion	-	0.9229	92.29%
Ames mutagenesis	-	0.9200	92.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8150	81.50%
Micronuclear	+	0.8800	88.00%
Hepatotoxicity	+	1.0000	100.00%
skin sensitisation	-	0.7410	74.10%
Respiratory toxicity	+	0.9778	97.78%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	-	0.6228	62.28%
Acute Oral Toxicity (c)	IV	0.6698	66.98%
Estrogen receptor binding	-	0.6008	60.08%
Androgen receptor binding	-	0.8632	86.32%
Thyroid receptor binding	-	0.6132	61.32%
Glucocorticoid receptor binding	-	0.8662	86.62%
Aromatase binding	-	0.6689	66.89%
PPAR gamma	-	0.7578	75.78%
Honey bee toxicity	-	0.8808	88.08%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.9286	92.86%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	97.26%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.99%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.27%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.73%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.46%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.10%	99.23%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	88.77%	94.62%
CHEMBL5600	P27448	Serine/threonine-protein kinase c-TAK1	87.28%	88.81%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	86.95%	94.08%
CHEMBL340	P08684	Cytochrome P450 3A4	86.75%	91.19%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.01%	82.69%
CHEMBL5028	O14672	ADAM10	83.52%	97.50%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.42%	95.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.29%	85.14%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 6249
• LOTUS: LTS0229974
• wikiData: Q244150