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Details

Stereochemistry ABSOLUTE
Molecular Formula C88H95Cl2N9O33
Molecular Weight 1877.642
Optical Activity UNSPECIFIED
Defined Stereocenters 23 / 23
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of TEICOPLANIN A2-1

SMILES

[H][C@@]%14(O[C@H]1[C@@H]2NC(=O)[C@]([H])(NC(=O)[C@]3([H])NC(=O)[C@@]4([H])NC(=O)[C@@H](CC5=CC=C(OC6=C(O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7NC(=O)CC\C=C/CCCCC)C(OC8=C(Cl)C=C1C=C8)=CC3=C6)C(Cl)=C5)NC(=O)[C@H](N)C9=CC(OC%10=CC4=CC(O)=C%10)=C(O)C=C9)C%11=CC(=C(O)C=C%11)C%12=C(C=C(O)C=C%12O[C@H]%13O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]%13O)[C@H](NC2=O)C(O)=O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]%14NC(C)=O

InChI

InChIKey=YMWQIYMUNZBOOV-CFYXQOLXSA-N
InChI=1S/C88H95Cl2N9O33/c1-3-4-5-6-7-8-9-10-60(108)94-68-74(113)71(110)58(32-101)129-87(68)132-78-55-26-40-27-56(78)126-52-18-14-38(24-47(52)90)77(131-86-67(92-34(2)103)73(112)70(109)57(31-100)128-86)69-84(121)98-66(85(122)123)45-29-42(105)30-54(127-88-76(115)75(114)72(111)59(33-102)130-88)61(45)44-23-37(13-15-49(44)106)63(81(118)99-69)96-83(120)65(40)97-82(119)64-39-21-41(104)28-43(22-39)124-53-25-36(12-16-50(53)107)62(91)80(117)93-48(79(116)95-64)20-35-11-17-51(125-55)46(89)19-35/h7-8,11-19,21-30,48,57-59,62-77,86-88,100-102,104-107,109-115H,3-6,9-10,20,31-33,91H2,1-2H3,(H,92,103)(H,93,117)(H,94,108)(H,95,116)(H,96,120)(H,97,119)(H,98,121)(H,99,118)(H,122,123)/b8-7-/t48-,57-,58-,59-,62-,63-,64+,65-,66+,67-,68-,69+,70-,71-,72-,73-,74-,75+,76+,77-,86+,87+,88+/m1/s1

HIDE SMILES / InChI

Molecular Formula C88H95Cl2N9O33
Molecular Weight 1877.642
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 23 / 23
E/Z Centers 2
Optical Activity UNSPECIFIED

Teicoplanin A2-1 is one of the main components of a lipoglycopeptide antibiotic, teicoplanin. Teicoplanin was first approved for marketing in Italy as Targocid, consisting of six closely related glycopeptide subcomponents (A2-1 to A2-5 and A3). Targocid is indicated in adults and in children from birth for the parenteral treatment of the following infections: complicated skin and soft tissue infections, bone and joint infections, hospital-acquired pneumonia, community acquired pneumonia, complicated urinary tract infections, infective endocarditis, peritonitis associated with continuous ambulatory peritoneal dialysis (CAPD), bacteraemia that occurs in association with any of the indications listed above. Targocid is also indicated as an alternative oral treatment for Clostridium difficile infection-associated diarrhea and colitis. Where appropriate, teicoplanin should be administered in combination with other antibacterial agents. Teicoplanin inhibits the growth of susceptible organisms by interfering with cell-wall biosynthesis at a site different from that affected by beta-lactams, by binding to the D-Ala-D-Ala C-terminus of peptidoglycan precursors.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: D-Ala-D-Ala C-terminus of peptidoglycan precursor
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Targocid

Approved Use

Targocid is indicated in adults and in children from birth for the parenteral treatment of the following infections: complicated skin and soft tissue infections, bone and joint infections, hospital acquired pneumonia, community acquired pneumonia, complicated urinary tract infections, infective endocarditis, peritonitis associated with continuous ambulatory peritoneal dialysis (CAPD), bacteraemia that occurs in association with any of the indications listed above. Targocid is also indicated as an alternative oral treatment for Clostridium difficile infection-associated diarrhoea and colitis. Where appropriate, teicoplanin should be administered in combination with other antibacterial agents. Consideration should be given to official guidance on the appropriate use of antibacterial agents.

Launch Date

5.5451517E11
Curative
Targocid

Approved Use

Targocid is indicated in adults and in children from birth for the parenteral treatment of the following infections: complicated skin and soft tissue infections, bone and joint infections, hospital acquired pneumonia, community acquired pneumonia, complicated urinary tract infections, infective endocarditis, peritonitis associated with continuous ambulatory peritoneal dialysis (CAPD), bacteraemia that occurs in association with any of the indications listed above. Targocid is also indicated as an alternative oral treatment for Clostridium difficile infection-associated diarrhoea and colitis. Where appropriate, teicoplanin should be administered in combination with other antibacterial agents. Consideration should be given to official guidance on the appropriate use of antibacterial agents.

Launch Date

5.5442879E11
Curative
Targocid

Approved Use

Targocid is indicated in adults and in children from birth for the parenteral treatment of the following infections: complicated skin and soft tissue infections, bone and joint infections, hospital acquired pneumonia, community acquired pneumonia, complicated urinary tract infections, infective endocarditis, peritonitis associated with continuous ambulatory peritoneal dialysis (CAPD), bacteraemia that occurs in association with any of the indications listed above. Targocid is also indicated as an alternative oral treatment for Clostridium difficile infection-associated diarrhoea and colitis. Where appropriate, teicoplanin should be administered in combination with other antibacterial agents. Consideration should be given to official guidance on the appropriate use of antibacterial agents.

Launch Date

5.5442879E11
Curative
Targocid

Approved Use

Targocid is indicated in adults and in children from birth for the parenteral treatment of the following infections: complicated skin and soft tissue infections, bone and joint infections, hospital acquired pneumonia, community acquired pneumonia, complicated urinary tract infections, infective endocarditis, peritonitis associated with continuous ambulatory peritoneal dialysis (CAPD), bacteraemia that occurs in association with any of the indications listed above. Targocid is also indicated as an alternative oral treatment for Clostridium difficile infection-associated diarrhoea and colitis. Where appropriate, teicoplanin should be administered in combination with other antibacterial agents. Consideration should be given to official guidance on the appropriate use of antibacterial agents.

Launch Date

5.5442879E11
Curative
Targocid

Approved Use

Targocid is indicated in adults and in children from birth for the parenteral treatment of the following infections: complicated skin and soft tissue infections, bone and joint infections, hospital acquired pneumonia, community acquired pneumonia, complicated urinary tract infections, infective endocarditis, peritonitis associated with continuous ambulatory peritoneal dialysis (CAPD), bacteraemia that occurs in association with any of the indications listed above. Targocid is also indicated as an alternative oral treatment for Clostridium difficile infection-associated diarrhoea and colitis. Where appropriate, teicoplanin should be administered in combination with other antibacterial agents. Consideration should be given to official guidance on the appropriate use of antibacterial agents.

Launch Date

5.5442879E11
PubMed

PubMed

TitleDatePubMed
Teicoplanin, a new antibiotic from Actinoplanes teichomyceticus nov. sp.
1984 Dec
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: teicoplanin A2-1 is one of the main components of a lipoglycopeptide antibiotic, teicoplanin
Complicated skin and soft tissue infections; Pneumonia; Complicated urinary tract infections: loading dose regimen: 6 mg/kg body weight every 12 hours for 3 intravenous or intramuscular administrations. maintenance dose: 6 mg/kg body weight intravenous or intramuscular once a day. Bone and joint infections: loading dose regimen: 12 mg/kg body weight every 12 hours for 3 to 5 intravenous administrations. Maintenance dose: 12 mg/kg body weight intravenous or intramuscular once a day. Infective endocarditis: loading dose regimen: 12 mg/kg body weight every 12 hours for 3 to 5 intravenous administrations. Maintenance dose: 12 mg/kg body weight intravenous or intramuscular once a day.
Route of Administration: Other
In Vitro Use Guide
A cell-free system from Bacillus stearothermophilus, capable of synthesizing peptidoglycan, is 50% inhibited by teicoplanin (teicoplanin A2-1 is one of the main components teicoplanin) at 40 micrograms/ml and 100% inhibited at 100 micrograms/ml; suppression of peptidoglycan synthesis is accompanied by parallel accumulation of the lipid intermediate. Teicoplanin binds to cell walls and forms a complex with N,N'-diacetyl-L-lysyl-D-alanyl-D-alanine. The association constant of this complex is 2.56 X 10(6) liters mol-1, calculated by spectrophotometric titration.
Substance Class Chemical
Created
by admin
on Thu Jul 06 02:42:26 UTC 2023
Edited
by admin
on Thu Jul 06 02:42:26 UTC 2023
Record UNII
36DYU0VKRK
Record Status Validated (UNII)
Record Version
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Name Type Language
TEICOPLANIN A2-1
MI  
Common Name English
TEICOPLANIN A2-1 [MI]
Common Name English
RISTOMYCIN A AGLYCONE, 34-O-(2-(ACETYLAMINO)-2-DEOXY-.BETA.-D-GLUCOPYRANOSYL)-22,31-DICHLORO-7-DEMETHYL-64-O-DEMETHYL-19-DEOXY-56-O-(2-DEOXY-2-(((4Z)-1-OXO-4-DECENYL)AMINO)-.BETA.-D-GLUCOPYRANOSYL)-42-O-.ALPHA.-D-MANNOPYRANOSYL-
Common Name English
Code System Code Type Description
FDA UNII
36DYU0VKRK
Created by admin on Thu Jul 06 02:42:26 UTC 2023 , Edited by admin on Thu Jul 06 02:42:26 UTC 2023
PRIMARY
CAS
91032-34-7
Created by admin on Thu Jul 06 02:42:26 UTC 2023 , Edited by admin on Thu Jul 06 02:42:26 UTC 2023
PRIMARY
ChEMBL
CHEMBL1908353
Created by admin on Thu Jul 06 02:42:26 UTC 2023 , Edited by admin on Thu Jul 06 02:42:26 UTC 2023
PRIMARY
CHEBI
34995
Created by admin on Thu Jul 06 02:42:26 UTC 2023 , Edited by admin on Thu Jul 06 02:42:26 UTC 2023
PRIMARY
PUBCHEM
16135801
Created by admin on Thu Jul 06 02:42:26 UTC 2023 , Edited by admin on Thu Jul 06 02:42:26 UTC 2023
PRIMARY
EPA CompTox
DTXSID90872359
Created by admin on Thu Jul 06 02:42:26 UTC 2023 , Edited by admin on Thu Jul 06 02:42:26 UTC 2023
PRIMARY
MERCK INDEX
M10525
Created by admin on Thu Jul 06 02:42:26 UTC 2023 , Edited by admin on Thu Jul 06 02:42:26 UTC 2023
PRIMARY Merck Index