TEICOPLANIN A2-5

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 Search

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

Description
Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Report/2013/04/WC500142229.pdf | http://www.sanofi.com.au/products/aus_pi_targocid.pdf | https://www.cipla.co.za/wp-content/uploads/2014/05/cipla-teicoplanin-PI.pdf | https://www.ncbi.nlm.nih.gov/pubmed/6235204 | https://www.ncbi.nlm.nih.gov/pubmed/6240963

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
peptidoglycan-based cell wall biogenesis 2 Target ID: GO:0009273 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6240963	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Skin and soft tissue infections 33 Sources: https://www.cipla.co.za/wp-content/uploads/2014/05/cipla-teicoplanin-PI.pdf	Curative	Approved 8429	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
Bone and joint infections 27 Sources: https://www.cipla.co.za/wp-content/uploads/2014/05/cipla-teicoplanin-PI.pdf	Curative	Approved 8429	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
Urinary tract infections 205 Sources: https://www.cipla.co.za/wp-content/uploads/2014/05/cipla-teicoplanin-PI.pdf	Curative	Approved 8429	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
Endocarditis 16 Sources: https://www.cipla.co.za/wp-content/uploads/2014/05/cipla-teicoplanin-PI.pdf	Curative	Approved 8429	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
Sepsis 71 Sources: https://www.cipla.co.za/wp-content/uploads/2014/05/cipla-teicoplanin-PI.pdf	Curative	Approved 8429	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

Title	Date	PubMed
Teichomycins, new antibiotics from Actinoplanes teichomyceticus nov. sp. IV. Separation and characterization of the components of teichomycin (teicoplanin).	1984 Jun	6235204

Patents

Sample Use Guides

In Vivo Use Guide

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 `Fri Dec 15 19:39:13 UTC 2023` Edited by `admin` on `Fri Dec 15 19:39:13 UTC 2023`
Record UNII	55234TX04D
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TEICOPLANIN A2-5

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