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Home> Encyclopedia >Antibiotic and antimicrobial agents>Pharmaceutical Intermediates>Pharmaceutical
Vancomycin hydrochloride structure
Vancomycin hydrochloride structure

Vancomycin hydrochloride

CAS No.: 1404-93-9
Molecular Weight:1485.723
Modify Date.: 2023-01-09 09:55
Introduction: The isolation of the glycopeptide antibiotic vancomycin(Vancocin, Vancoled) from Streptomyces orientalis (renamedA. orientalis) was described in 1956 by McCormick et al.232The organism originally was obtained from cultures of anIndonesian soil sample and subsequently has been obtainedfrom Indian soil. Vancomycin was introduced in 1958 as anantibiotic active against Gram-positive cocci, particularlystreptococci, staphylococci, and pneumococci. It is not activeagainst Gram-negative bacteria, with the exception ofNeisseria spp. Vancomycin is recommended for use wheninfections fail to respond to treatment with the more commonantibiotics or when the infection is known to be caused by aresistant organism. It is particularly effective for the treatmentof endocarditis caused by Gram-positive bacteria. Vancomycin hydrochloride is a free-flowing, tan tobrown powder that is relatively stable in the dry state. It isvery soluble in water and insoluble in organic solvents. Vancomycin inhibits cell wall synthesis by preventingthe synthesis of cell wall mucopeptide polymer. It does soby binding with the D-alanine-D-alanine terminus of theuridine diphosphate-N-acetylmuramyl peptides requiredfor mucopeptide polymerization.236 Details of the bindingwere elucidated by the elegant NMR studies of Williamson. View more+
1. Names and Identifiers
1.1 Name
Vancomycin hydrochloride
1.2 Synonyms

(1S,2R,18R,19R,22S,25R,28R,40S)-22-(2-Amino-2-oxoethyl)-48-{[(5Ξ)-2-O-(3-amino-2,3,6-trideoxy-3-methyl-α-L-lyxo-hexopyranosyl)-Β-D-xylo-hexopyranosyl]oxy}-5,15-dichloro-2,18,32,35,37-pentahydr oxy-19-[(N-methyl-D-leucyl)amino]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.2.2.1.1.0.0]pentaconta-3,5,8(48),9,11,14,16,29(45), 30,32,34,36,38,46,49-pentadecaene-40-carboxy (1S,2R,18R,19R,22S,25R,28R,40S)-22-(2-amino-2-oxoethyl)-48-{[2-O-(3-amino-2,3,6-trideoxy-3-methyl-α-L-lyxo-hexopyranosyl)-Β-D-glucopyranosyl]oxy}-5,15-dichloro-2,18,32,35,37-pentahydroxy-19-[(N-methyl-D-leucyl)amino]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.2.2.1.1.0.0]pentaconta-3,5,8(48),9,11,14,16,29(45),30,32,34,36,38,46,49-pentadecaene-40-carboxylic acid 6,38,46,49-pentadecaene-40-carboxylic acid LYPHOCIN Lyphocin (LyphoMed) VANCOCIN VANCOCIN HYDROCHLORIDE vancocinehydrochloride Vancomycin (hydrochloride) Vancomycin HCL Vancomycin Hydrochloride (4 vials, each vial contains 100,500 mcg of vancomycin activity) Vancomycin Hydrochloride (4 vials, each vial contains 99,300 mcg of vancomycin activity) VANCOMYCIN, HYDROCHLORIDE, STREPTOMYCES ORIENTALIS VANCOR

1.3 CAS No.
1404-93-9
1.4 CID
24721356
1.5 EINECS(EC#)
604-193-8
1.6 Molecular Formula
C66H76Cl3N9O24 (isomer)
1.7 Inchi
InChI=1S/C66H75Cl2N9O24.ClH/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);1H/t24-,34+,35-,42?,44-,46+,47+,48-,49+,50-,51+,52+,53+,54-,56+,57+,65-,66-;/m0./s1
1.8 InChkey
LCTORFDMHNKUSG-DOUUZMDISA-N
1.9 Canonical Smiles
CC1C(C(CC(O1)OC2C(C(C(OC2OC3=C4C=C5C=C3OC6=C(C=C(C=C6)C(C(C(=O)NC(C(=O)NC5C(=O)NC7C8=CC(=C(C=C8)O)C9=C(C=C(C=C9O)O)C(NC(=O)C(C(C1=CC(=C(O4)C=C1)Cl)O)NC7=O)C(=O)O)CC(=O)N)NC(=O)C(CC(C)C)NC)O)Cl)CO)O)O)(C)N)O.Cl
1.10 Isomers Smiles
C[C@H]1[C@H]([C@@](C[C@@H](O1)O[C@@H]2[C@H]([C@@H](C(O[C@H]2OC3=C4C=C5C=C3OC6=C(C=C(C=C6)[C@H]([C@H](C(=O)N[C@H](C(=O)N[C@H]5C(=O)N[C@@H]7C8=CC(=C(C=C8)O)C9=C(C=C(C=C9O)O)[C@H](NC(=O)[C@H]([C@@H](C1=CC(=C(O4)C=C1)Cl)O)NC7=O)C(=O)O)CC(=O)N)NC(=O)[C@@H](CC(C)C)NC)O)Cl)CO)O)O)(C)N)O.Cl
2. Properties
2.1 Density
1.657
2.1 Melting point
>190°C (dec.)
2.1 Refractive index
1.735
2.1 Flash Point
87℃
2.1 Precise Quality
1483.41000
2.1 PSA
530.49000
2.1 logP
4.73460
2.1 Solubility
H2O: 50?mg/mL, clear, yellow
2.2 Appearance
off white powder
2.3 Storage
Store at -20°C.
2.4 Chemical Properties
off white powder
2.5 Color/Form
colorless to faint yellow or tan
2.6 PH
pH (50g/l, 25℃) : 2.5~4.5
2.7 Water Solubility
H2O: 50?mg/mL, clear, yellow | Soluble in water. Slightly soluble in methanol, ethanol and dimethylsulfoxide.
2.8 Stability
Stable at room temperature in closed containers under normal storage and handling conditions.
2.9 StorageTemp
2-8°C
3. Use and Manufacturing
3.1 General Description
The isolation of the glycopeptide antibiotic vancomycin(Vancocin, Vancoled) from Streptomyces orientalis (renamedA. orientalis) was described in 1956 by McCormick et al.232The organism originally was obtained from cultures of anIndonesian soil sample and subsequently has been obtainedfrom Indian soil. Vancomycin was introduced in 1958 as anantibiotic active against Gram-positive cocci, particularlystreptococci, staphylococci, and pneumococci. It is not activeagainst Gram-negative bacteria, with the exception ofNeisseria spp. Vancomycin is recommended for use wheninfections fail to respond to treatment with the more commonantibiotics or when the infection is known to be caused by aresistant organism. It is particularly effective for the treatmentof endocarditis caused by Gram-positive bacteria. Vancomycin hydrochloride is a free-flowing, tan tobrown powder that is relatively stable in the dry state. It isvery soluble in water and insoluble in organic solvents. Vancomycin inhibits cell wall synthesis by preventingthe synthesis of cell wall mucopeptide polymer. It does soby binding with the D-alanine-D-alanine terminus of theuridine diphosphate-N-acetylmuramyl peptides requiredfor mucopeptide polymerization.236 Details of the bindingwere elucidated by the elegant NMR studies of Williamson.
3.2 Usage
It has a narrow antimicrobial spectrum which is mainly against Gram-positive bacteria. It is a kind of narrow-spectrum antibiotics only effective in treating gram-positive bacteria, such as Streptococcus pneumoniae, Neisseria gonorrhoeae and enterococci; etc which are all sensitive to this drug. Staphylococcus aureus is particularly sensitive to this product. Its mechanism of action is inhibition of bacterial cell wall synthesis; it mainly binds to the bacterial cell wall and leaving some kinds of amino acids being unable to enter into the glycopeptides of the cell wall.
4. Safety and Handling
4.1 Symbol
GHS07
4.1 Hazard Codes
Xi
4.1 Signal Word
Warning
4.1 Risk Statements
R43
4.1 Safety Statements
S24/25
4.1 Exposure Standards and Regulations
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, including vancomycin hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Vancomycin hydrochloride/
4.2 Other Preventative Measures
Engineering controls such as exhaust ventilation are recommended. /Vancomycin hydrochloride/
As a general rule, when handling USP Reference Standards avoid all contact and inhalation of dust, mists, and/or vapors associated with the material. Wash thoroughly after handling. /Vancomycin hydrochloride/
SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
4.3 Hazard Declaration
H317
4.3 Cleanup Methods
Wear approved respiratory protection, chemically compatible gloves and protective clothing. Wipe spillage or collect spillage using a high efficiency vacuum cleaner. Avoid breathing dust. Place spillage in appropriately-labeled container for disposal. Wash spill site. /Vancomycin hydrochloride/
4.4 DisposalMethods
SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.
SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.
4.5 RIDADR
NONH for all modes of transport
4.5 Fire Fighting Procedures
As with all fires, evacuate personnel to a safe area. Firefighters should use self-contained breathing equipment and protective clothing. /Vancomycin hydrochloride/
Water spray, dry chemical, carbon dioxide or foam as appropriate for surrounding fire and materials. /Vancomycin hydrochloride/
4.6 FirePotential
This material is assumed to be combustible. /Vancomycin hydrochloride/
4.7 Caution Statement
P280
4.7 Formulations/Preparations
Vancomycin Hydrochloride Preparations Route of Administration Dosage Form Strength Brand or Generic Name (Manufacturer) Oral Capsules 125 mg (of vancomycin) Vancocin HCl Pulvules (ViroPharma) Oral Capsules 250 mg (of vancomycin) Vancocin HCl Pulvules (ViroPharma) Parenteral For injection 5 g (of vancomycin) pharmacy bulk package Vancomycin Hydrochloride for Injection (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Parenteral For injection 10 g (of vancomycin) pharmacy bulk package Vancomycin Hydrochloride for Injection (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Parenteral For injection, for IV infusion 500 mg (of vancomycin) Vancomycin Hydrochloride for Injection (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Parenteral For injection, for IV infusion 500 mg (of vancomycin) Vancomycin Hydrochloride Sterile ADD-Vantage (Hospira) Parenteral For injection, for IV infusion 1 g (of vancomycin) Vancomycin Hydrochloride for Injection (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Parenteral For injection, for IV infusion 1 g (of vancomycin) Vancomycin Hydrochloride for Injection ADD-Vantage (Hospira)
Grade: USP /Vancomycin hydrochloride/
Parenteral, Injection (frozen), for IV infusion 5 mg (of vancomycin) per mL (500 mg) in 5% Dextrose, Vancocin HCl in Iso-osmotic Dextrose Injection (Lilly)
4.8 WGK Germany
2
4.8 RTECS
YW4380000
4.8 Protective Equipment and Clothing
Gloves: Chemically compatible. Eye protection: Safety goggles or glasses. Protective clothing: Protect exposed skin. /Vancomycin hydrochloride/
Use a NIOSH approved respirator, if it is determined to be necessary by an industrial hygiene survey involving air monitoring. In the event that a respirator is not required, an approved dust mask should be used. /Vancomycin hydrochloride/
4.9 Skin, Eye, and Respiratory Irritations
Eye, skin, ... and/or respiratory tract irritation. /Vancomycin hydrochloride/
4.10 Safety

Poison by intravenous route. Moderately toxic by intraperitoneal routes. Human systemic effects by intravenous route: cardiac arrythmias, blood pressure lowering, and allergic dermatitis. When heated to decomposition it emits toxic fumes of NOx and HCl.
Hazard Codes?of?Vancocin hydrochloride (CAS NO.1404-93-9):?IrritantXi
Risk Statements: 43?
R43: May cause sensitization by skin contact
Safety Statements: 36/37-24/25-22-36
S36/37: Wear suitable protective clothing and gloves
S24/25: Avoid contact with skin and eyes
S22: Do not breathe dust
S36: Wear suitable protective clothing
WGK Germany: 2
RTECS: YW4380000

4.11 Toxicity
Organic Compound; Organochloride; Amine; Ether; Drug; Anti-Bacterial Agent; Metabolite; Glycopeptide Antibacterial; Synthetic Compound
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin sensitization, Category 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H317 May cause an allergic skin reaction

Precautionary statement(s)
Prevention

P261 Avoid breathing dust/fume/gas/mist/vapours/spray.

P272 Contaminated work clothing should not be allowed out of the workplace.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

Response

P302+P352 IF ON SKIN: Wash with plenty of water/...

P333+P313 If skin irritation or rash occurs: Get medical advice/attention.

P321 Specific treatment (see ... on this label).

P362+P364 Take off contaminated clothing and wash it before reuse.

Storage

none

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

6. NMR Spectrum
7. Other Information
7.0 Usage
Inhibits bacterial mucopeptide synthesis.Vancomycin hydrochloride is used as an antiviral and anti bacterial. binds to bacterial cell wall. It exhibits potent activity against Gram positive bacteria and is highly effective against MRSA in vitro and in vivo.
7.1 Vancomycin
Vancomycin belongs to ploy-peptide antibiotics. It is a kind of glycopeptide antibiotics originate from the Streptomyces Orientalis or Amycolatopsis Orientalis. At the late 1950s, the drug had emerged due to its excellent efficacy in treating penicillin-resistant Staphylococcus and because a strong “trump card” antibiotics of anti-G + bacteria including Staphylococcus aureus, Streptococcus pyogenes, Streptococcus pneumoniae and so on. Subsequently, owing to the discovery of its relative high toxicity, together with the marketing of less-toxic anti-staphylococcal semi-synthetic penicillin and cephalosporin in 1960s and then not very sharp issue of drug resistance, its application was limited. In recent years, because of the increases in cases of infection of methicillin-resistant Staphylococcus aureus (MRSA) and methicillin-resistant Staphylococcus epidermidis as well as the demonstration of Clostridium difficile (CD) as the major reason causing antibiotic-associated pseudomembranous colitis, the application cases of vancomycin have been increasing which re-establish the special status of vancomycin in clinical practice. Since 1990s, vancomycin has been always regarded by international experts of antibiotics as "the last line of defense against human intractable drug-resistant strains".
From the results of some literature and the distribution of current clinical drug-resistant strains, vancomycin is the primary choice of drug for treating diseases caused by the infection of the MRSA and MRSE. The efficacy of vancomycin in treating CD-associated diarrhea or pseudomembranous colitis is also quite positive, especially for severely sick patients; in addition, for the severe infection caused by the rare penicillin-resistant pneumococcal infections G and penicillin-resistant Corynebacterium JK strain, vancomycin is also a top-grade drug for treating it.
Owing to the good efficacy of vancomycin in treating various kinds of diseases caused by drug-resistant bacteria, its marketing sales in nearly 10 years has kept increasing year by year. A few years ago, the increasing rate of international market of vancomycin was maintained at 3-4%, and has risen to 5-6% in the recent two years. According to the estimation of antibiotic expert, the global output in the middle of 1990 s of averaged 20-25 tons per year, and this value had risen to 30 tons in 1999.
7.2 Side effects
The main adverse reactions in clinical application of vancomycin hydrochloride as follows:
Ototoxicity: there may be a sense of fullness or tinnitus ear, hearing loss or absence, damage of auditory nerve. In large doses, long time application, the elderly or patients of renal insufficient, it is especially prone to get these symptoms.
Renal toxicity: The main damage is on renal tubules. At early stage, there may be proteinuria, urinary tube, followed by hematuria, oliguria, etc; in severe cases, there may be kidney failure. In high dose (plasma concentrations exceed 60~100mg/L), long time application, the elderly or patients of renal insufficient, it is especially prone to get these symptoms.
Allergy: upon fast, high-dose of intravenous administration, a small number of patients can get "red neck syndrome." Manifested as chills or fever, fainting, itching, nausea, vomiting, tachycardia, rash or facial flushing; redness or tingling(caused by the release of histamine) in root neck, upper body, back, arm, etc; there may be also occasionally low blood pressure and shock-like symptoms happening. The incidence is higher than norvancomycin and teicoplanin.
Local reactions: intramuscular injection or intravenous administration may cause severe pain at the injection site pain with causing thrombophlebitis in severe cases.
Gastrointestinal: Oral administration may cause nausea, vomiting, bad smell of mouth and so on.
7.3 Description
Vancomycin is a glycopeptide antibiotic identified for its utility in the treatment of gram-positive bacteria, including penicillin-resistant staphylococci. It acts by binding to bacterial cell wall protein precursors, interfering with continuing protein synthesis. Vancomycin resistance in staphylococcal species has recently emerged as a clinical issue.
7.4 Uses
Vancomycin Hydrochloride is an antibiotic used against gram-positive bacterial strains.
7.5 Brand name
Vancocin Hydrochloride (ViroPharma); Vancoled (Baxter Healthcare); Vancor (Pharmacia & Upjohn).
7.6 General Description
The isolation of the glycopeptide antibiotic vancomycin(Vancocin, Vancoled) from Streptomyces orientalis (renamedA. orientalis) was described in 1956 by McCormick et al.232The organism originally was obtained from cultures of anIndonesian soil sample and subsequently has been obtainedfrom Indian soil. Vancomycin was introduced in 1958 as anantibiotic active against Gram-positive cocci, particularlystreptococci, staphylococci, and pneumococci. It is not activeagainst Gram-negative bacteria, with the exception ofNeisseria spp. Vancomycin is recommended for use wheninfections fail to respond to treatment with the more commonantibiotics or when the infection is known to be caused by aresistant organism. It is particularly effective for the treatmentof endocarditis caused by Gram-positive bacteria.
Vancomycin hydrochloride is a free-flowing, tan tobrown powder that is relatively stable in the dry state. It isvery soluble in water and insoluble in organic solvents. Vancomycin inhibits cell wall synthesis by preventingthe synthesis of cell wall mucopeptide polymer. It does soby binding with the D-alanine-D-alanine terminus of theuridine diphosphate-N-acetylmuramyl peptides requiredfor mucopeptide polymerization.236 Details of the bindingwere elucidated by the elegant NMR studies of Williamson.
7.7 Biochem/physiol Actions
Vancomycin is a glycopeptide antibiotic that blocks bacterial cell wall biosynthesis at the level of peptidoglycan biosynthesis. It inhibits incorporation of terminal D-alanyl-D-alanine moieties of the NAM/NAG-peptides. It is effective against Gram-positive bacteria. Vancomycin also alters bacterial-cell-membrane permeability and RNA synthesis.
7.8 Veterinary Drugs and Treatments
Vancomycin should only be used to treat infections that are documented resistant to other antibiotics and susceptible to vancomycin, usually methicillin-resistant Staphylococcus spp. (MRSA) or multidrug-resistant Enterococcus spp. It potentially is useful for oral treatment of pseudomembranous colitis caused by Clostridia difficile.
7.9 Merck
13,9995
7.10 BRN
3704657
7.11 Glycopeptide antibiotics
Vancomycin hydrochloride is a glycopeptide antibiotic and is the hydrochloride salt of vancomycin. It is white or white-like crystalline powder at room temperature. Its mechanism of action is that it can bind with high affinity to the poly-terminus alanyl-alanine of the precursor peptide located on the cell wall the sensitive bacterial cells, blocking the biosynthesis of the peptide glycan polymer constituting the bacterial cell wall, and thus resulting in the defects of cell wall and further killing bacteria. In addition, it is also possible to change the permeability of the bacterial cell membrane, and selectively inhibit the synthesis of RNA. The characteristic of vancomycin hydrochloride is its strong bactericidal effect against Gram-positive bacteria such as Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pyogenes, and streptococcus pneumoniae. It also has certain anti-bacteria effects on Streptococci anaerobius, Clostridium difficile, Bacillus anthracis, Actinomycetes, Corynebacterium diphtheria, Neisseria gonorrhoeae, Streptococcus viridans, Streptococcus bovis, and Streptococcus faecalis. However, for most Gram-negative bacteria, Mycobacterium, Rickettsia genus, Chlamydia or fungi, it is invalid. It is clinically applicable to the treatment of infection caused by methicillin-resistant Staphylococcus aureus and other bacteria: sepsis, endocarditis, osteomyelitis, arthritis, burns injury, surgical trauma and other superficial secondary infection, pneumonia, lung abscess, empyema, peritonitis, meningitis, pseudomembranous colitis, and skin and soft tissue infections. It is the primary choice for patients who are allergic to penicillin and suffer from the enterococcal endocarditis and Corynebacterium (class diphtheria sp) endocarditis.
7.12 Pharmacokinetics
It is poor absorbed through oral administration. Intravenous administration can make it be widely distributed in most body tissues and fluids. Intravenous infusion of 500 mg and 1g yields a peak plasma concentration being 10-30mg/L and 25-50mg/L, respectively.
The volume of distribution of the drug is 0.43-1.25L/kg. Its effective antimicrobial concentrations can be achieved in the serum, pericardium, pleura, peritoneum, ascites, and synovial fluid but not in the bile. Vancomycin hydrochloride can penetrate through the placenta but not be able to quickly penetrate through the normal blood-brain barrier and can be introduced into cerebrospinal fluid to reach effective antimicrobial concentration only upon meninges inflammation.
The protein binding rate of this drug is about 55%. Its elimination half-life in adults is 6 hours (4-11 hours) in average and can extend to 7.5 day in patients with severe renal insufficiency; for children, it is about 2-3 hours. The drug is metabolized through the liver with about 80%-90% being excreted through renal within 24 hours in its prototype and a small amount being excreted through milk and bile. Hemodialysis or peritoneal dialysis is not able to effectively remove the drug; however, it has been reported that blood perfusion or blood filtration can improve the clearance rate.
7.13 Side effects
The main adverse reactions in clinical application of vancomycin hydrochloride as follows:
Ototoxicity: there may be a sense of fullness or tinnitus ear, hearing loss or absence, damage of auditory nerve. In large doses, long time application, the elderly or patients of renal insufficient, it is especially prone to get these symptoms.
Renal toxicity: The main damage is on renal tubules. At early stage, there may be proteinuria, urinary tube, followed by hematuria, oliguria, etc; in severe cases, there may be kidney failure. In high dose (plasma concentrations exceed 60~100mg/L), long time application, the elderly or patients of renal insufficient, it is especially prone to get these symptoms.
Allergy: upon fast, high-dose of intravenous administration, a small number of patients can get "red neck syndrome." Manifested as chills or fever, fainting, itching, nausea, vomiting, tachycardia, rash or facial flushing; redness or tingling(caused by the release of histamine) in root neck, upper body, back, arm, etc; there may be also occasionally low blood pressure and shock-like symptoms happening. The incidence is higher than norvancomycin and teicoplanin.
Local reactions: intramuscular injection or intravenous administration may cause severe pain at the injection site pain with causing thrombophlebitis in severe cases.
Gastrointestinal: Oral administration may cause nausea, vomiting, bad smell of mouth and so on.
7.14 Uses
It has a narrow antimicrobial spectrum which is mainly against Gram-positive bacteria.
It is a kind of narrow-spectrum antibiotics only effective in treating gram-positive bacteria, such as Streptococcus pneumoniae, Neisseria gonorrhoeae and enterococci; etc which are all sensitive to this drug. Staphylococcus aureus is particularly sensitive to this product. Its mechanism of action is inhibition of bacterial cell wall synthesis; it mainly binds to the bacterial cell wall and leaving some kinds of amino acids being unable to enter into the glycopeptides of the cell wall.
7.15 Chemical Properties
off white powder
7.16 Uses
Amphoteric glycopeptide antibiotic produced by Streptomyces orientalis discovered in soil. Inhibits bacterial cell wall synthesis by binding to peptidoglycan. Antibacterial.
7.17 Uses
Vancomycin hydrochloride is the salt of a glycopeptide antibiotic isolated from Amycolatopsis orientalis in 1956. Vancomycin exhibits potent activity against Gram positive bacteria and is highly effective against MRSA in vitro and in vivo. Vancomycin interferes with cell wall synthesis by binding to D-alanine-D-alanine residues.
7.18 Brand name
Vancocin Hydrochloride (ViroPharma); Vancoled (Baxter Healthcare); Vancor (Pharmacia & Upjohn).
7.19 Description
Vancomycin is a glycopeptide antibiotic identified for its utility in the treatment of gram-positive bacteria, including penicillin-resistant staphylococci. It acts by binding to bacterial cell wall protein precursors, interfering with continuing protein synthesis. Vancomycin resistance in staphylococcal species has recently emerged as a clinical issue.
8. Computational chemical data
  • Molecular Weight: 1485.723g/mol
  • Molecular Formula: C66H76Cl3N9O24
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 1483.406877
  • Monoisotopic Mass: 1483.406877
  • Complexity: 2960
  • Rotatable Bond Count: 13
  • Hydrogen Bond Donor Count: 20
  • Hydrogen Bond Acceptor Count: 26
  • Topological Polar Surface Area: 531
  • Heavy Atom Count: 102
  • Defined Atom Stereocenter Count: 17
  • Undefined Atom Stereocenter Count: 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 2
  • CACTVS Substructure Key Fingerprint: AAADcfB//gAGAAAAAAAAAAAAAAAAAAAAAAA0aMGDAAAAAAABVAAAHgIQCAAADb7xmCcyDoLABgCIAiHSGACCCAAgJUAIiIGOj4gfdz+H9zu2eCrn9hWfuAf9/P/OoAADKAAYSABAAAZQADCQAAAAAAAAAA==
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