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Details

Stereochemistry ABSOLUTE
Molecular Formula C89H99Cl2N9O33
Molecular Weight 1893.685
Optical Activity UNSPECIFIED
Defined Stereocenters 23 / 23
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TEICOPLANIN A2-5

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)CCCCCCCC(C)C)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=FHBQKTSCJKPYIO-RLDSMAAISA-N
InChI=1S/C89H99Cl2N9O33/c1-34(2)9-7-5-4-6-8-10-61(109)95-69-75(114)72(111)59(32-102)130-88(69)133-79-56-26-41-27-57(79)127-53-18-14-39(24-48(53)91)78(132-87-68(93-35(3)104)74(113)71(110)58(31-101)129-87)70-85(122)99-67(86(123)124)46-29-43(106)30-55(128-89-77(116)76(115)73(112)60(33-103)131-89)62(46)45-23-38(13-15-50(45)107)64(82(119)100-70)97-84(121)66(41)98-83(120)65-40-21-42(105)28-44(22-40)125-54-25-37(12-16-51(54)108)63(92)81(118)94-49(80(117)96-65)20-36-11-17-52(126-56)47(90)19-36/h11-19,21-30,34,49,58-60,63-78,87-89,101-103,105-108,110-116H,4-10,20,31-33,92H2,1-3H3,(H,93,104)(H,94,118)(H,95,109)(H,96,117)(H,97,121)(H,98,120)(H,99,122)(H,100,119)(H,123,124)/t49-,58-,59-,60-,63-,64-,65+,66-,67+,68-,69-,70+,71-,72-,73-,74-,75-,76+,77+,78-,87+,88+,89+/m1/s1

HIDE SMILES / InChI

Molecular Formula C89H99Cl2N9O33
Molecular Weight 1893.685
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 23 / 23
E/Z Centers 1
Optical Activity UNSPECIFIED

TEICOPLANIN A2-5 is a component of a teicoplanin complex antibiotic, which consist of six closely related glycopeptide subcomponents. TEICOPLANIN A2-5 being the most lipophilic in protein binding. Bacteria treated with the drug failed to incorporate GlcNAc, a peptidoglycan precursor, whereas they continued to synthesize DNA, RNA, and protein. The cell wall inhibition was accompanied by an accumulation of UDP-MurNAc-pentapeptide, thus indicating that the antibiotic interferes with the polymerization of the peptidoglycan but not with the synthesis of soluble precursors. Teicoplanin 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; complicated urinary tract infections; infective endocarditis; bacteraemia that occurs in association with any of the indications listed above. The following side-effects may occur: nausea, vomiting, diarrhea and stomach pain, skin rash and pruritus, bronchospasm, renal impairment. Teicoplanin should be administrated with caution in patients receiving concurrent nephrotoxic or ototoxic drugs, such as aminoglycosides, amphotericin B, cyclosporine and frusemide.

Originator

Curator's Comment: https://www.google.com/patents/US4239751

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Targocid

Approved Use

Targocid is indicated in adults and in children from birth for the parenteral treatment of the complicated skin and soft tissue infections.

Launch Date

5.5451517E11
Curative
Targocid

Approved Use

Targocid is indicated in adults and in children from birth for the parenteral treatment of the bone and joint infections.

Launch Date

5.5451517E11
Curative
Targocid

Approved Use

Targocid is indicated in adults and in children from birth for the parenteral treatment of the complicated urinary tract infections.

Launch Date

5.5451517E11
Curative
Teicoplanin

Approved Use

Targocid is indicated in adults and in children from birth for the parenteral treatment of the infective endocarditis.

Launch Date

5.5451517E11
Curative
Targocid

Approved Use

Targocid is indicated in adults and in children from birth for the parenteral treatment of the bacteraemia/septicemia.

Launch Date

5.5451517E11
PubMed

PubMed

TitleDatePubMed
Teichomycins, new antibiotics from Actinoplanes teichomyceticus nov. sp. IV. Separation and characterization of the components of teichomycin (teicoplanin).
1984 Jun
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Teicoplanin for clinical administration is a mixture of five teicoplanins (A2-1 to A2-5)
Urinary tract infections, skin and soft tissue infections. Loading dose: single injection of 400 mg on the first day; Maintenance dose: single injection of 200 mg/ml daily. Endocarditis, septicemia, joint and bone infections. Loading dose: for the first three doses – 400 mg every 12 hours; Maintenance dose: single injection of 400 mg daily. An intramuscular injection of Targocid should not exceed 3 ml (400 mg) at a single site.
Route of Administration: Other
In Vitro Use Guide
Minimal inhibitory concentration (MIC) was read as the lowest concentration, which showed no visible growth after 18-24 h incubation at 37° C. The obtained results are: Staphylococcus aureus – 0.2-0.8 ug/ml, Staphylococcus epidermidis – 0.2-0.8 ug/ml, Streptococcus pyogenes – 0.006-0.05 ug/ml, Streptococcus pneumoniae – 0.05-0.1 ug/ml, Streptococcus faecalis – 0.1-0.4 ug/ml, Streptococcus mitis – 0.025 ug/ml, Streptococcus solivarius – 0.05 ug/ml, Streptococcus sanguis – 0.05 ug/ml, Streptococcus bovis – 0.4 ug/ml, Streptococcus agalactiae – 0.1 ug/ml.
Substance Class Chemical
Created
by admin
on Thu Jul 06 02:42:34 UTC 2023
Edited
by admin
on Thu Jul 06 02:42:34 UTC 2023
Record UNII
55234TX04D
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TEICOPLANIN A2-5
MI  
Common Name English
TEICOPLANIN A2-5 [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-((9-METHYL-1-OXODECYL)AMINO)-.BETA.-D-GLUCOPYRANOSYL)-42-O-.ALPHA.-D-MANNOPYRANOSYL-
Common Name English
Code System Code Type Description
PUBCHEM
17748673
Created by admin on Thu Jul 06 02:42:34 UTC 2023 , Edited by admin on Thu Jul 06 02:42:34 UTC 2023
PRIMARY
CAS
91032-38-1
Created by admin on Thu Jul 06 02:42:34 UTC 2023 , Edited by admin on Thu Jul 06 02:42:34 UTC 2023
PRIMARY
CHEBI
34998
Created by admin on Thu Jul 06 02:42:34 UTC 2023 , Edited by admin on Thu Jul 06 02:42:34 UTC 2023
PRIMARY
ChEMBL
CHEMBL2103966
Created by admin on Thu Jul 06 02:42:34 UTC 2023 , Edited by admin on Thu Jul 06 02:42:34 UTC 2023
PRIMARY
FDA UNII
55234TX04D
Created by admin on Thu Jul 06 02:42:34 UTC 2023 , Edited by admin on Thu Jul 06 02:42:34 UTC 2023
PRIMARY
MERCK INDEX
M10525
Created by admin on Thu Jul 06 02:42:34 UTC 2023 , Edited by admin on Thu Jul 06 02:42:34 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID10872356
Created by admin on Thu Jul 06 02:42:34 UTC 2023 , Edited by admin on Thu Jul 06 02:42:34 UTC 2023
PRIMARY