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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H19N3O4S
Molecular Weight 349.405
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMPICILLIN

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C3=CC=CC=C3)C(O)=O

InChI

InChIKey=AVKUERGKIZMTKX-NJBDSQKTSA-N
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

HIDE SMILES / InChI
Molecular Formula C16H19N3O4S
Molecular Weight 349.405
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Unknown
123738
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:11:14 UTC 2023
Edited
by admin
on Fri Dec 15 15:11:14 UTC 2023
Record UNII
7C782967RD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMPICILLIN
HSDB   INN   MART.   MI   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN   USAN  
Official Name English
AMPICILLIN [MART.]
Common Name English
AMPICILLIN [EP MONOGRAPH]
Common Name English
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*)))-
Systematic Name English
BRL-1341
Code English
AMPICILLIN ANHYDROUS
GREEN BOOK   WHO-IP  
Common Name English
AMINOBENZYLPENICILLIN
Common Name English
PIPERACILLIN SODIUM IMPURITY A [EP IMPURITY]
Common Name English
AMPICILLIN [MI]
Common Name English
AMPICILLIN ANHYDROUS [WHO-IP]
Common Name English
WY 5103
Code English
REDICILIN
Common Name English
ULTRABION
Common Name English
AMPICILLIN [USP MONOGRAPH]
Common Name English
Ampicillin [WHO-DD]
Common Name English
P-50
Code English
AMPICILLIN (ANHYDROUS)
Common Name English
AMPICILLIN [WHO-IP]
Common Name English
SEMICILLIN
Common Name English
AMPICILLIN [USAN]
Common Name English
ANHYDROUS AMPICILLIN [JAN]
Common Name English
AMPICILLIN ANHYDROUS [GREEN BOOK]
Common Name English
AMPICILLIN, ANHYDROUS
EP  
Common Name English
SULTAMICILLIN IMPURITY C [EP IMPURITY]
Common Name English
ANHYDROUS AMPICILLIN
JAN  
Common Name English
AMPICILLIN [HSDB]
Common Name English
TOKIOCILLIN
Common Name English
AMPICILLIN [USP-RS]
Common Name English
ampicillin [INN]
Common Name English
AMPICILLINUM [WHO-IP LATIN]
Common Name English
AMPICILLIN [IARC]
Common Name English
AY-6108
Code English
AMPICILLIN [VANDF]
Common Name English
NSC-528986
Code English
(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
Systematic Name English
Classification Tree Code System Code
NDF-RT N0000011281
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
WHO-VATC QJ51RC20
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
CFR 21 CFR 522.90
Created by admin on Fri Dec 15 15:11:14 UTC 2023 , Edited by admin on Fri Dec 15 15:11:14 UTC 2023
LIVERTOX NBK547894
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
WHO-ATC J01CR01
Created by admin on Fri Dec 15 15:11:14 UTC 2023 , Edited by admin on Fri Dec 15 15:11:14 UTC 2023
WHO-VATC QJ51CA51
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
WHO-VATC QJ51CA01
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
CFR 21 CFR 520.90E
Created by admin on Fri Dec 15 15:11:14 UTC 2023 , Edited by admin on Fri Dec 15 15:11:14 UTC 2023
NCI_THESAURUS C1500
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
WHO-VATC QJ01CR01
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
WHO-VATC QJ51CR01
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
NDF-RT N0000175497
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
WHO-ATC J01CA51
Created by admin on Fri Dec 15 15:11:14 UTC 2023 , Edited by admin on Fri Dec 15 15:11:14 UTC 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
CFR 21 CFR 520.90B
Created by admin on Fri Dec 15 15:11:14 UTC 2023 , Edited by admin on Fri Dec 15 15:11:14 UTC 2023
WHO-VATC QG51AG04
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
WHO-VATC QJ01CA01
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
WHO-VATC QJ01CA51
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
CFR 21 CFR 520.90F
Created by admin on Fri Dec 15 15:11:14 UTC 2023 , Edited by admin on Fri Dec 15 15:11:14 UTC 2023
WHO-ATC S01AA19
Created by admin on Fri Dec 15 15:11:14 UTC 2023 , Edited by admin on Fri Dec 15 15:11:14 UTC 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
IARC Ampicillin
WHO-VATC QS01AA19
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
CFR 21 CFR 556.40
Created by admin on Fri Dec 15 15:11:14 UTC 2023 , Edited by admin on Fri Dec 15 15:11:14 UTC 2023
WHO-VATC QG51AG05
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 6.2.1
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
CFR 21 CFR 520.90
Created by admin on Fri Dec 15 15:11:14 UTC 2023 , Edited by admin on Fri Dec 15 15:11:14 UTC 2023
CFR 21 CFR 520.90D
Created by admin on Fri Dec 15 15:11:14 UTC 2023 , Edited by admin on Fri Dec 15 15:11:14 UTC 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
WHO-ATC J01CA01
Created by admin on Fri Dec 15 15:11:14 UTC 2023 , Edited by admin on Fri Dec 15 15:11:14 UTC 2023
WHO-VATC QG51AG07
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
CFR 21 CFR 520.90C
Created by admin on Fri Dec 15 15:11:14 UTC 2023 , Edited by admin on Fri Dec 15 15:11:14 UTC 2023
Code System Code Type Description
EVMPD
SUB05487MIG
Created by admin on Fri Dec 15 15:11:14 UTC 2023 , Edited by admin on Fri Dec 15 15:11:14 UTC 2023
PRIMARY
NCI_THESAURUS
C239
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
PRIMARY
WIKIPEDIA
AMPICILLIN
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
AMPICILLIN
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
PRIMARY Description: A white or almost white, crystalline powder; odourless or almost odourless. Solubility: Slightly soluble in water; practically insoluble in ethanol (~750 g/l) TS and ether R. Category: Antibiotic. Storage: Ampicillin should be kept in a tightly closed container, protected from light. Labelling: The designation on the container of Ampicillin should state whether the substance is in the anhydrous form or is the trihydrate. Additional information: Even in the absence of light, Ampicillin is gradually degraded on exposure to a humid atmosphere, the decomposition being faster at higher temperatures. Definition: Ampicillin contains not less than 95.0% and not more than 102.0% of C16H19N3O4S, calculated with reference to the anhydrous substance.
LACTMED
Ampicillin
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
PRIMARY
CHEBI
31209
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
PRIMARY
RXCUI
221058
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
PRIMARY
DRUG BANK
DB00415
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
PRIMARY
DRUG CENTRAL
198
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
PRIMARY
EVMPD
SUB11710MIG
Created by admin on Fri Dec 15 15:11:14 UTC 2023 , Edited by admin on Fri Dec 15 15:11:14 UTC 2023
PRIMARY
EPA CompTox
DTXSID4022602
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
PRIMARY
RS_ITEM_NUM
1033000
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
PRIMARY
MESH
D000667
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
PRIMARY
DAILYMED
7C782967RD
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
PRIMARY
LACTMED
Ampicillin and Sulbactam
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
PRIMARY
RXCUI
733
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
ALTERNATIVE
PUBCHEM
6249
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
PRIMARY
SMS_ID
100000092323
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-709-7
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
PRIMARY
FDA UNII
7C782967RD
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
PRIMARY
CHEBI
28971
Created by admin on Fri Dec 15 15:11:14 UTC 2023 , Edited by admin on Fri Dec 15 15:11:14 UTC 2023
PRIMARY
NSC
528986
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
PRIMARY
MERCK INDEX
m1853
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
PRIMARY Merck Index
ChEMBL
CHEMBL174
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
PRIMARY
HSDB
3009
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
PRIMARY
INN
1339
Created by admin on Fri Dec 15 15:11:15 UTC 2023 , Edited by admin on Fri Dec 15 15:11:15 UTC 2023
PRIMARY
CAS
69-53-4
Created by admin on Fri Dec 15 15:11:14 UTC 2023 , Edited by admin on Fri Dec 15 15:11:14 UTC 2023
PRIMARY
Related Record Type Details
Structure of AMPICILLIN HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Structure of AMPICILLIN HEMISULFATE
SALT/SOLVATE -> PARENT
Structure of AMPICILLIN SODIUM
SALT/SOLVATE -> PARENT
PEPT-1
TRANSPORTER -> SUBSTRATE
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
Structure of AMPICILLIN
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
EP
Structure of AMPICILLIN BENZATHINE
SALT/SOLVATE -> PARENT
Structure of AMPICILLIN
BASIS OF STRENGTH->SUBSTANCE
Ampicillin is anhydrous or contains three molecules of water of hydration
ASSAY (HPLC)
USP
Structure of AMPICILLIN POTASSIUM
SALT/SOLVATE -> PARENT
OXA-48 (Beta-lactamase)
ENZYME->SUBSTRATE
Leads to resistance to the antibiotic.
Structure of METAMPICILLIN SODIUM
PARENT -> DEGRADENT
Structure of AMPICILLIN TRIHYDRATE
SOLVATE->ANHYDROUS
Structure of AMPICILLIN TRIHYDRATE
SALT/SOLVATE -> PARENT
For the trihydrate use about 0.1 g of the substance; the water content is not less than 120 mg/g and not more than 150 mg/g.
Related Record Type Details
Structure of HETACILLIN
PRODRUG -> METABOLITE ACTIVE
Structure of SARPICILLIN
PRODRUG -> METABOLITE ACTIVE
Structure of BACAMPICILLIN
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
Structure of AMPICILLIN OLIGOMER 1 (DIMER)
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 3,6-DIPHENYLPIPERAZINE-2,5-DIONE, (3R,6R)-
IMPURITY -> PARENT
Structure of DIKETOPIPERAZINES OF AMPICILLIN
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of PHENYLGLYCINE, D-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 2-((2,2-DIMETHYLPROPANOYL)AMINO)-2-PHENYLACETIC ACID, (2R)-
IMPURITY -> PARENT
Structure of 6-AMINOPENICILLANIC ACID
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of AMPICILLINYL-D-PHENYLGLYCINE
IMPURITY -> PARENT
Structure of AMPICILLIN THIAZEPINE ANALOG
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of PIPERACILLIN SODIUM
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of PHENYLGLYCYLAMPICILLIN, D-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of AMPICILLIN, L-
IMPURITY -> PARENT
Structure of PENILLOIC ACIDS OF AMPICILLIN
PARENT -> IMPURITY
Structure of AMPICILLIN OLIGOMER 1 (TRIMER)
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of AMPICILLIN OLIGOMER 2
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of (2S,5R,6R)-6-((2,2-DIMETHYLPROPANOYL)AMINO)-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID
IMPURITY -> PARENT
Structure of AMPICILLOIC ACID
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 3-Phenyl-2(1H)-pyrazinone
IMPURITY -> PARENT
Structure of SULTAMICILLIN
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of AMPICILLIN
ACTIVE MOIETY
For the anhydrous form use about 0.8 g of the substance; the water content is not more than 15 mg/g.
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
NIH
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