ampicillin (CHEBI:28971)

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CHEBI:28971 - ampicillin

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ChEBI Name	ampicillin

ChEBI ID	CHEBI:28971

Definition	A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-phenylacetamido group.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:40648, CHEBI:45042, CHEBI:2683, CHEBI:22536

Supplier Information	ChemicalBook:CB03374713, ChemicalBook:CB3263316, eMolecules:538632, Selleckchem:Gabapentin(Neurontin), ZINC000000004949

Download	Molfile XML SDF

more structures >>

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43 45 0 0 0 0 999 V2000

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3.3295 0.5806 0.3292 C 0 0 1 0 0 0 0 0 0 0 0 0

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3.9371 2.8925 -0.4253 C 0 0 0 0 0 0 0 0 0 0 0 0

1.7515 2.5059 0.5420 N 0 0 2 0 0 0 0 0 0 0 0 0

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4.3438 0.8376 1.4447 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.9366 0.6603 -0.7493 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.9688 -2.8512 -1.0762 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.2990 -3.9390 0.5896 C 0 0 0 0 0 0 0 0 0 0 0 0

-4.0092 -2.7691 0.7861 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.6948 -1.6399 0.0537 C 0 0 0 0 0 0 0 0 0 0 0 0

2.8054 1.9083 -0.2831 C 0 0 2 0 0 0 0 0 0 0 0 0

0.9660 1.5606 1.3719 C 0 0 1 0 0 0 0 0 0 0 0 0

-0.2537 1.8906 0.5085 C 0 0 1 0 0 0 0 0 0 0 0 0

0.6149 2.9483 -0.1394 C 0 0 0 0 0 0 0 0 0 0 0 0

3.9062 -0.3447 -0.7446 C 0 0 0 0 0 0 0 0 0 0 0 0

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4.1450 3.7045 0.4449 O 0 0 0 0 0 0 0 0 0 0 0 0

4.7137 2.8694 -1.5194 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.7748 1.4216 -0.3161 O 0 0 0 0 0 0 0 0 0 0 0 0

0.4049 3.8432 -0.9298 O 0 0 0 0 0 0 0 0 0 0 0 0

1.7323 -0.0669 0.9965 S 0 0 0 0 0 0 0 0 0 0 0 0

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5.2291 1.3166 1.0286 H 0 0 0 0 0 0 0 0 0 0 0 0

3.8988 1.4878 2.1973 H 0 0 0 0 0 0 0 0 0 0 0 0

2.4008 1.6868 -1.2703 H 0 0 0 0 0 0 0 0 0 0 0 0

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2 10 4 0 0 0 0

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3 8 1 0 0 0 0

3 14 1 0 0 0 0

3 18 1 0 0 0 0

3 24 1 0 0 0 0

4 9 1 0 0 0 0

4 16 1 0 0 0 0

4 37 1 0 0 0 0

5 14 1 0 0 0 0

5 20 2 0 0 0 0

5 21 1 0 0 0 0

6 14 1 0 0 0 0

6 15 1 0 0 0 0

6 17 1 0 0 0 0

7 9 1 0 0 0 0

7 19 1 0 0 0 0

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8 30 1 0 0 0 0

8 31 1 0 0 0 0

8 32 1 0 0 0 0

9 22 2 0 0 0 0

10 26 1 0 0 0 0

11 12 4 0 0 0 0

11 27 1 0 0 0 0

12 13 4 0 0 0 0

12 43 1 0 0 0 0

13 29 1 0 0 0 0

14 33 1 0 0 0 0

15 16 1 0 0 0 0

15 24 1 0 0 0 0

15 40 1 0 0 0 0

16 17 1 0 0 0 0

16 38 1 0 0 0 0

17 23 2 0 0 0 0

18 34 1 0 0 0 0

18 35 1 0 0 0 0

18 36 1 0 0 0 0

19 41 1 0 0 0 0

19 42 1 0 0 0 0

21 39 1 0 0 0 0

M END): 25 ms

reading 43 atoms

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43 atoms created

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Wikipedia	License
Gabapentin, sold under the brand name Neurontin among others, is an anticonvulsant medication primarily used to treat neuropathic pain and also for partial seizures of epilepsy. It is a commonly used medication for the treatment of neuropathic pain caused by diabetic neuropathy, postherpetic neuralgia, and central pain. It is moderately effective: about 30–40% of those given gabapentin for diabetic neuropathy or postherpetic neuralgia have a meaningful benefit. Gabapentin, like other gabapentinoid drugs, acts by decreasing activity of the α2δ-1 protein, coded by the CACNA2D1 gene, first known as an auxiliary subunit of voltage gated calcium channels. However, see Pharmacodynamics, below. By binding to α2δ-1, gabapentin reduces the release of excitatory neurotransmitters (primarily glutamate) and as a result, reduces excess excitation of neuronal networks in the spinal cord and brain. Sleepiness and dizziness are the most common side effects. Serious side effects include respiratory depression, and allergic reactions. As with all other antiepileptic drugs approved by the FDA, gabapentin is labeled for an increased risk of suicide. Lower doses are recommended in those with kidney disease. Gabapentin was first approved for use in the United Kingdom in 1993. It has been available as a generic medication in the United States since 2004. It is the first of several other drugs that are similar in structure and mechanism, called gabapentinoids. In 2022, it was the tenth most commonly prescribed medication in the United States, with more than 40 million prescriptions. During the 1990s, Parke-Davis, a subsidiary of Pfizer, used a number of illegal techniques to encourage physicians in the United States to prescribe gabapentin for unapproved uses. They have paid out millions of dollars to settle lawsuits regarding these activities.
Read full article at Wikipedia

Formula

C16H19N3O4S

Net Charge

Average Mass

349.40500

Monoisotopic Mass

349.10963

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

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)c1ccccc1)C(O)=O

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	antibacterial drug A drug used to treat or prevent bacterial infections. allergen A chemical compound, or part thereof, which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy. (via penicillin allergen ) (via penicillin ) antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. (via heterocyclic antibiotic )

Application(s):	antibacterial drug A drug used to treat or prevent bacterial infections.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	ampicillin (CHEBI:28971) has role antibacterial drug (CHEBI:36047) ampicillin (CHEBI:28971) is a β-lactam antibiotic (CHEBI:27933) ampicillin (CHEBI:28971) is a penicillin (CHEBI:17334) ampicillin (CHEBI:28971) is a penicillin allergen (CHEBI:88187) ampicillin (CHEBI:28971) is conjugate acid of ampicillin(1−) (CHEBI:50658)

Incoming	ampicilloyl-butylamine (CHEBI:55473) has functional parent ampicillin (CHEBI:28971) bacampicillin (CHEBI:2968) has functional parent ampicillin (CHEBI:28971) epicillin (CHEBI:58974) has functional parent ampicillin (CHEBI:28971) lenampicillin (CHEBI:135748) has functional parent ampicillin (CHEBI:28971) pivampicillin (CHEBI:8255) has functional parent ampicillin (CHEBI:28971) sultamicillin (CHEBI:51770) has functional parent ampicillin (CHEBI:28971) talampicillin (CHEBI:9391) has functional parent ampicillin (CHEBI:28971) ampicillin trihydrate (CHEBI:31209) has part ampicillin (CHEBI:28971) ampicillin(1−) (CHEBI:50658) is conjugate base of ampicillin (CHEBI:28971) ampicilloyl group (CHEBI:53704) is substituent group from ampicillin (CHEBI:28971)

IUPAC Name

6β-[(2R)-2-amino-2-phenylacetamido]-2,2-dimethylpenam-3α-carboxylic acid

INNs	Sources
ampicilina	ChemIDplus
ampicillin	ChemIDplus
ampicilline	ChemIDplus
ampicillinum	ChemIDplus

Synonyms	Sources
(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	IUPAC
(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	PDBeChem
(2S,6R)-6-{[(2R)-2-amino-2-phenylethanoyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	PDBeChem
6-(D-(2-amino-2-phenylacetamido))-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid	ChemIDplus
ABPC	ChEBI
aminobenzylpenicillin	DrugBank
AMP	ChEBI
Ampicillin	KEGG COMPOUND
ampicillin acid	DrugBank
ampicillin anhydrous	DrugBank
Anhydrous ampicillin	KEGG COMPOUND
AP	ChEBI
D-(−)-6-(α-aminophenylacetamido)penicillanic acid	ChemIDplus
D-(−)-ampicillin	ChemIDplus

Manual Xrefs	Databases
1849	VSDB
198	DrugCentral
1H8S	PDB
AIC	PDBeChem
Ampicillin	Wikipedia
C06574	KEGG COMPOUND
D00204	KEGG DRUG
DB00415	DrugBank
GB902703	Patent
HMDB0014559	HMDB
LSM-5761	LINCS
PN1	PDBeChem
US2985648	Patent
US3157640	Patent
View more database links

Registry Numbers	Types	Sources
4300240	Reaxys Registry Number	Reaxys
69-53-4	CAS Registry Number	ChemIDplus

Citations	Types	Sources
10930630	PubMed citation	Europe PMC
12562703	PubMed citation	Europe PMC
12569987	PubMed citation	Europe PMC
12833570	PubMed citation	Europe PMC
14139119	PubMed citation	Europe PMC
14455820	PubMed citation	Europe PMC
15768449	PubMed citation	Europe PMC
16033609	PubMed citation	Europe PMC
18611716	PubMed citation	Europe PMC
19967069	PubMed citation	Europe PMC
2083978	PubMed citation	Europe PMC
23568176	PubMed citation	Europe PMC
23861268	PubMed citation	Europe PMC
24474427	PubMed citation	Europe PMC
24666465	PubMed citation	Europe PMC
25998949	PubMed citation	Europe PMC
28543395	PubMed citation	Europe PMC
29017833	PubMed citation	Europe PMC
6176550	PubMed citation	Europe PMC
8020088	PubMed citation	Europe PMC
9433938	PubMed citation	Europe PMC

Last Modified

07 March 2019

CHEBI:28971 - ampicillin

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