AIC

(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

Created:	2001-02-17
Last modified:	2020-06-05

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8 entries where AIC is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	43
Chiral Atom Count	4
Bond Count	45
Aromatic Bond Count	6

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Chemical Component Summary
Name	(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
Synonyms	AMPICILLIN; D(-)-ALPHA-AMINOBENZYLPENICILLIN; 6-[D(-)-ALPHA-AMINOPHENYLLACETAMIDO]PENICILLANIC ACID
Systematic Name (OpenEye OEToolkits)	(2S,5R,6R)-6-[[(2R)-2-amino-2-phenyl-ethanoyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Formula	C₁₆ H₁₉ N₃ O₄ S
Molecular Weight	349.405
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=C(O)C2N3C(=O)C(NC(=O)C(c1ccccc1)N)C3SC2(C)C
SMILES	CACTVS	3.341	CC1(C)S[CH]2[CH](NC(=O)[CH](N)c3ccccc3)C(=O)N2[CH]1C(O)=O
SMILES	OpenEye OEToolkits	1.5.0	CC1(C(N2C(S1)C(C2=O)NC(=O)C(c3ccccc3)N)C(=O)O)C
Canonical SMILES	CACTVS	3.341	CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(O)=O
Canonical SMILES	OpenEye OEToolkits	1.5.0	CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](c3ccccc3)N)C(=O)O)C
InChI	InChI	1.03	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	InChI	1.03	AVKUERGKIZMTKX-NJBDSQKTSA-N

Drug Info: DrugBank

DrugBank ID	DB00415
Name	Ampicillin
Groups	approved vet_approved
Description	Ampicillin is a semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic.
Synonyms	D-(−)-6-(α-aminophenylacetamido)penicillanic acid Ampicillin sodium AP Ampicillin, anhydrous Ampicillin acid Ampicillinum Ampicillin Ampicilina Anhydrous ampicillin D-(−)-ampicillin Ampicillin (anhydrous) Ampicilline Ampicillin anhydrous Aminobenzylpenicillin Ampicillin trihydrate ABPC
Brand Names	Ampicin Inj 125mg/vial Apo Ampi Capsules 500mg Penbritin-1000 Pws 1000mg/vial Penbritin-250 Pws Im/iv 250mg/vial Unasyn Taro-ampicillin Cap 250mg AMPICILLIN and SULBACTAM Ampicillin for Injection, USP Sterile Ampicillin Sodium 250mg USP Jaa Amp Tab 125mg Novo-ampicillin Sus 250mg/5ml Penbritin-125 Pws 125mg/vial Ampicillin and Sulbactam Ampicillin Sodium and Sulbactam Sodium Ampicillin Sodium for Injection, USP Penbritin Cap 500mg Ampicillin Ampicin Inj 500mg Apo Ampi Liq 250mg/5ml Pro Biosan Kit Ampicillin Sodium Penbritin Pws 250mg/5ml Pro Ampi 500 Cap 500mg Penbritin Inj 2000mg Penbritin Inj 250mg Teva-ampicillin Ampicin Inj 1gm Penbritin Inj 500mg Pro Ampi 250 Cap 250mg Apo Ampi Capsules 250mg Nu-ampi Capsules 500mg Taro-ampicillin Cap 500mg Nu-ampi Capsules 250mg Ampicillin Trihydrate Penbritin Cap 250mg Apo Ampi Liq 125mg/5ml Ampicillin Sodium for Injection, BP Nu-ampi Sus 125mg/5ml Ampicillin sodium Ampicillin Sodium for Injection BP Ampicillin for Injection Ampicin Inj 2000mg Penbritin Inj 1000mg Nu-ampi Suspension 250mg/5ml Novo-ampicillin Sus 125mg/5ml Novo-ampicillin Pws 500mg/5ml Ampicin for Injection 250mg
Indication	For treatment of infection (Respiratory, GI, UTI and meningitis) due to E. coli, P. mirabilis, enterococci, Shigella, S. typhosa and other Salmonella, nonpenicillinase-producing N. gononhoeae, H. influenzae, staphylococci, streptococci including streptoc
Categories	Amides Aminopenicillins Anti-Bacterial Agents Anti-Infective Agents Antibacterials for Systemic Use Antiinfectives for Systemic Use Beta-Lactam Antibacterials beta-Lactams Drugs that are Mainly Renally Excreted Heterocyclic Compounds, Fused-Ring Lactams Ophthalmologicals Penicillin G Penicillins Penicillins With Extended Spectrum Sensory Organs Sulfur Compounds
ATC-Code	J01CR50 J01CA51 J01CA01 S01AA19
CAS number	69-53-4

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Penicillin-binding protein 2a	MKLDKLFEKFLSLFKKETSELEDSDSTILRRSRSDRKKLAQVGPIRKFWR...	unknown	inhibitor
Penicillin-binding protein 1b	MQNQLNELKRKMLEFFQQKQKNKKSARPGKKGSSTKKSKTLDKSAIFPAI...	unknown	inhibitor
Penicillin-binding protein 3	MKKIFLTLLTVSLLGGASTAVAQDFTIAAKHAIAVEANTGKILYEKDATQ...	unknown	inhibitor
Penicillin-binding protein 1A	MNKPTILRLIKYLSISFLSLVIAAIVLGGGVFFYYVSKAPSLSESKLVAT...	unknown	inhibitor
Penicillin-binding protein 2B	MRKFNSHSIPIRLNLLFSIVILLFMTIIGRLLYMQVLNKDFYEKKLASAS...	unknown	inhibitor
Solute carrier family 15 member 1	MGMSKSHSFFGYPLSIFFIVVNEFCERFSYYGMRAILILYFTNFISWDDN...	unknown
Solute carrier family 15 member 2	MNPFQKNESKETLFSPVSIEEVPPRPPSPPKKPSPTICGSNYPLSIAFIV...	unknown
Angiopoietin-1 receptor	MDSLASLVLCGVSLLLSGTVEGAMDLILINSLPLVSDAETSLTCIASGWR...	unknown
Serum albumin	MKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...	unknown	other/unknown
Solute carrier family 22 member 5	MRDYDEVTAFLGEWGPFQRLIFFLLSASIIPNGFTGLSSVFLIATPEHRC...	unknown	inhibitor
Solute carrier family 15 member 1	MGMSKSHSFFGYPLSIFFIVVNEFCERFSYYGMRAILILYFTNFISWDDN...	unknown	inhibitor
Solute carrier family 15 member 2	MNPFQKNESKETLFSPVSIEEVPPRPPSPPKKPSPTICGSNYPLSIAFIV...	unknown	inhibitor
Monocarboxylate transporter 1	MPPAVGGPVGYTPPDGGWGWAVVIGAFISIGFSYAFPKSITVFFKEIEGI...	unknown
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682