PRD_000204

Vancomycin

Created:	2012-02-01
Last modified:	2022-01-06

PRD_000204 is described in the Biologically Interesting Molecule Reference Dictionary (BIRD).

The representative PDB ID is 1AA5.

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12 entries where PRD_000204 is present

Chemical Details
Formal Charge	0
Atom Count	176
Chiral Atom Count	18
Bond Count	185
Aromatic Bond Count	30

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Chemical Component Summary
Name	Vancomycin
Systematic Name (OpenEye OEToolkits)	n/a
Formula	C₆₆ H₇₅ Cl₂ N₉ O₂₄
Molecular Weight	1,449.254
Type	PEPTIDE-LIKE

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	O=C(O)C1NC(=O)C2NC(=O)C(NC(=O)C3NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)c4ccc(Oc5cc3cc(Oc3ccc(cc3Cl)C2O)c5OC2OC(CO)C(O)C(O)C2OC2CC(C)(N)C(O)C(C)O2)c(Cl)c4)c2ccc(O)c(c2)c2c(O)cc(O)cc21
SMILES	CACTVS	3.385	CN[CH](CC(C)C)C(=O)N[CH]1[CH](O)c2ccc(Oc3cc4cc(Oc5ccc(cc5Cl)[CH](O)[CH]6NC(=O)[CH](NC(=O)[CH]4NC(=O)[CH](CC(N)=O)NC1=O)c7ccc(O)c(c7)c8c(O)cc(O)cc8[CH](NC6=O)C(O)=O)c3O[CH]9O[CH](CO)[CH](O)[CH](O)[CH]9O[CH]%10C[C](C)(N)[CH](O)[CH](C)O%10)c(Cl)c2
SMILES	OpenEye OEToolkits	2.0.7	CC1C(C(CC(O1)OC2C(C(C(OC2Oc3c4cc5cc3Oc6ccc(cc6Cl)C(C(C(=O)NC(C(=O)NC5C(=O)NC7c8ccc(c(c8)-c9c(cc(cc9O)O)C(NC(=O)C(C(c1ccc(c(c1)Cl)O4)O)NC7=O)C(=O)O)O)CC(=O)N)NC(=O)C(CC(C)C)NC)O)CO)O)O)(C)N)O
Canonical SMILES	CACTVS	3.385	CN[C@H](CC(C)C)C(=O)N[C@@H]1[C@H](O)c2ccc(Oc3cc4cc(Oc5ccc(cc5Cl)[C@@H](O)[C@@H]6NC(=O)[C@H](NC(=O)[C@@H]4NC(=O)[C@H](CC(N)=O)NC1=O)c7ccc(O)c(c7)c8c(O)cc(O)cc8[C@H](NC6=O)C(O)=O)c3O[C@@H]9O[C@H](CO)[C@@H](O)[C@H](O)[C@H]9O[C@H]%10C[C@](C)(N)[C@H](O)[C@H](C)O%10)c(Cl)c2
Canonical SMILES	OpenEye OEToolkits	2.0.7	C[C@H]1[C@H]([C@@](C[C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2Oc3c4cc5cc3Oc6ccc(cc6Cl)[C@H]([C@H](C(=O)N[C@H](C(=O)N[C@H]5C(=O)N[C@@H]7c8ccc(c(c8)-c9c(cc(cc9O)O)[C@H](NC(=O)[C@H]([C@@H](c1ccc(c(c1)Cl)O4)O)NC7=O)C(=O)O)O)CC(=O)N)NC(=O)[C@@H](CC(C)C)NC)O)CO)O)O)(C)N)O
InChI	InChI	1.03	InChI=1S/C66H75Cl2N9O24/c1-23(2)12-34(71-5)58(88)76-49-51(83)26-7-10-38(32(67)14-26)97-40-16-28-17-41(55(40)101-65-56(54(86)53(85)42(22-78)99-65)100-44-21-66(4,70)57(87)24(3)96-44)98-39-11-8-27(15-33(39)68)52(84)50-63(93)75-48(64(94)95)31-18-29(79)19-37(81)45(31)30-13-25(6-9-36(30)80)46(60(90)77-50)74-61(91)47(28)73-59(89)35(20-43(69)82)72-62(49)92/h6-11,13-19,23-24,34-35,42,44,46-54,56-57,65,71,78-81,83-87H,12,20-22,70H2,1-5H3,(H2,69,82)(H,72,92)(H,73,89)(H,74,91)(H,75,93)(H,76,88)(H,77,90)(H,94,95)/t24-,34+,35-,42+,44-,46+,47+,48-,49+,50-,51+,52+,53+,54-,56+,57+,65-,66-/m0/s1
InChIKey	InChI	1.03	MYPYJXKWCTUITO-LYRMYLQWSA-N

Drug Info: DrugBank

DrugBank ID	DB00512
Name	Vancomycin
Groups	approved
Description	Antibacterial obtained from Streptomyces orientalis. It is a glycopeptide related to ristocetin that inhibits bacterial cell wall assembly and is toxic to kidneys and the inner ear. As of January 29 2018, CutisPharma's Firvanq is the only FDA approved vancomycin oral liquid treatment option available for the the treatment of _Clostridium difficile_ associated diarrhea and enterocolitis caused by _Staphylococcus aureus_, including methicillin-resistant strains [LP1196]. Such an oral liquid formulation is expected to make _Clostridium difficile_ associated diarrhea therapy more accessible in comparison to previously available specialty compounding products [LP1196].
Synonyms	Vancomicina Vancomycin Vancomycinum Vancomycin hydrochloride Vancomycine
Brand Names	Vancocin Cp Add-vantage Inj 500mg/vial Vancomycin Hydrocloride Vancomycin Injection USP In 5% Dextrose Vancomycin hydrochloride Vancomycin Hydrochloride for Oral Solution Sterile Vancomycin HCl USP 500mg/vial Sterile Vancomycin Hydrochloride, USP Vancomycin HCl Sterile Vancomycin HCl 5.0gm/vial PMS-vancomycin Sterile Vancomycin Hydrochloride Pmsc-vancomycin Vancomycin Hydrochloride for Injection USP Vancomycin Hydrochloride Vancocin Inj 1gm/vial Advantage Vancomycin Hydrochloride for Injection, USP Vancomycin PMS-vancomycin 1 G PMS-vancomycin 500 mg Jamp-vancomycin Vancomycin Injection USP In 0.9% Sodium Chloride Jamp Vancomycin Firvanq Vancocin Vancomycin Hydrochloride for Injection Sterile Vancomycin HCl USP 1.0gm/vial Vancomycin Hydrochloride Capsules, USP
Indication	Administered intravenously, vancomycin is indicated in adult and pediatric patients for the treatment of septicemia, infective endocarditis, skin and skin structure infections, bone infections, and lower respiratory tract infections.[L41529] Administered orally, vancomycin is indicated in adult and pediatric patients for the treatment of _Clostridium difficile_-associated diarrhea and for enterocolitis caused by _Staphylococcus aureus_ (including methicillin-resistant strains).[L41534]
Categories	Agents that produce neuromuscular block (indirect) Alimentary Tract and Metabolism Amino Acids, Peptides, and Proteins Anti-Bacterial Agents Anti-Infective Agents Antibacterials for Systemic Use Antidiarrheals, Intestinal Antiinflammatory/antiinfective Agents Antiinfectives for Systemic Use Carbohydrates Drugs that are Mainly Renally Excreted Drugs that are Mainly Renally Excreted with a Narrow Therapeutic Index Glycoconjugates Glycopeptide Antibacterials Glycopeptides Intestinal Antiinfectives Narrow Therapeutic Index Drugs Nephrotoxic agents Ophthalmologicals Peptides Sensory Organs
ATC-Code	J01XA01 A07AA09 S01AA28
CAS number	1404-90-6

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
D-Ala-D-Ala moiety of NAM/NAG peptide subunits of peptidoglycan	-	unknown	ligand
Serum albumin	MKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...	unknown	substrate
alpha1-acid glycoprotein	MALSWVLTVLSLLPLLEAQIPLCANLVPVPITNATLDQITGKWFYIASAF...	unknown	substrate
Histamine H1 receptor	MSLPNTSSASEDKMCEGNRTAMASPQLLPLVVVLSSISLVTVGLNLLVLY...	unknown	substrate

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