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Vancomycin hydrochloride

Vancomycin hydrochloride

CAS: 1404-93-9

Molecular Formula: C66H76Cl3N9O24

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Vancomycin hydrochloride - Names and Identifiers

Name Vancomycin hydrochloride
Synonyms Vancor
VANCOR
VANCOCIN
LYPHOCIN
Vancomycin HCl
UNII-71WO621TJD
VANCOCIN HYDROCHLORIDE
vancocinehydrochloride
Vancocin hydrochloride
Vancocine hydrochloride
Vancomycin hydrochloride
Vancomycin monohydrochloride
VANCOMYCIN, HYDROCHLORIDE, STREPTOMYCES ORIENTALIS
Vancomycin Hydrochloride (4 vials, each vial contains 99,300 mcg of vancomycin activity)
Vancomycin Hydrochloride (4 vials, each vial contains 100,500 mcg of vancomycin activity)
(1S,2R,18R,19R,22S,25R,28R,40S)-48-{[(2S,3R,4S,5S,6R)-3-{[(2S,4S,5S,6S)-4-amino-5-hydroxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-22-(2-amino-2-oxoethyl)-5,15-dichloro-2,18,32,35,37-pentahydroxy-19-{[(2R)-4-methyl-2-(methylamino)pentanoyl]amino}-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.2~3,6~.2~14,17~.1~8,12~.1~29,33~.0~10,25~.0~34,39~]pentaconta-3,5,8(48),9,11,14,16,29(45),30,32,34,36,38,46,49-pentadecaene-40-carboxylic acid (non-preferred name)
CAS 1404-93-9
EINECS 604-193-8
InChI InChI=1/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

Vancomycin hydrochloride - Physico-chemical Properties

Molecular FormulaC66H76Cl3N9O24
Molar Mass1485.71
Melting Point>190°C (dec.)
Specific Rotation(α)[α]D20 -30~-40゜ (c=1, H2O)
Flash Point87℃
Water SolubilitySoluble in water. Slightly soluble in methanol, ethanol and dimethylsulfoxide.
Solubility Soluble in water.
Appearancewhite to brown powder
Colorcolorless to faint yellow or tan
Merck13,9995
BRN3704657
PHpH (50g/l, 25℃) : 2.5~4.5
Storage Condition2-8°C
StabilityHygroscopic
SensitiveHygroscopic
MDLMFCD03613611
UseNarrow antibacterial spectrum, mainly effective against gram-positive bacteria

Vancomycin hydrochloride - Risk and Safety

Hazard SymbolsXi - Irritant
Irritant
Risk CodesR43 - May cause sensitization by skin contact
R42 - May cause sensitization by inhalation
Safety DescriptionS36/37 - 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 Germany2
RTECSYW4380000
FLUKA BRAND F CODES8-10-21
HS Code29419090
ToxicityLD50 in mice (mg/kg): 489 i.v.; 1734 i.p.; 5000 s.c.; 5000 orally (Anderson)

Vancomycin hydrochloride - Reference

Reference
Show more
1. Wang Min. Analysis of the guiding significance of vancomycin blood concentration monitoring for clinical medication [J]. Clinical medical research and practice 2020 v.5(16):114-116.
2. Wu Qin, Xu Ziyang, Liu Liping, et al. Role of intestinal flora in stress-induced hypertension in rats [J]. Biotechnology Bulletin, 2020, v.36;No.331(02):88-95.
3. Zhe Hao, Xiaodong Lin, Jinjie Li, Yanliang Yin, Xia Gao, Shuo Wang, Yaqing Liu, Multifunctional nanoplatform for dual-mode sensitive detection of pathogenic bacteria and the real-time bacteria inactivation, Biosensors and Bioelectronics, Volume 173, 2021,
4. Wan, Mimi, et al. "in situ growth of mesoporous silica with drugs on titanium surface and its biomedical applications." ACS applied materials & interfaces 9.22 (2017): 18609-18618.https://doi.org/10.1021/acsami.7b05163
5. Yao, Ye, et al. "Berberine alleviates type 2 diabetic symptoms by altering gut microbiota and reducing aromatic amino acids." Biomedicine & Pharmacotherapy 131 (2020): 110669.https://doi.org/10.1016/j.biopha. 2020.110669
6. Rong, Qian, et al. "In vitro and in vivo bactericidal activity of Tinospora sagittata (Oliv.) Gagnep. var. craveniana (SY Hu) Lo and its main effective component, palmatine, against porcine Helicobacter pylori." BMC complementary and alternative medicine 1
7. [IF=5.458] Tong Li-Tao et al."Pea Protein Reduce Serum Cholesterol Levels in Hypercholesterolemia Hamsters by Modulating Compositions Of Gut Microbiota And Metabolites."iScience. 2021 Mar 12
8. [IF=6.475] Chunjun Li et al."Colon and gut microbiota greatly affect the absorption and utilization of astaxanthin derived from Haematococcus pluvialis."FOOD RESEARCH INTERNATIONAL. 2022 Jun;156:111324

Vancomycin hydrochloride - Standard

Authoritative Data Verified Data

The titer per 1 mg, calculated as anhydrous, shall not be less than 10.5 million units of natamycin.

Last Update:2024-01-02 23:10:35

Vancomycin hydrochloride - Trait

Authoritative Data Verified Data
  • This product is white or white powder; Easy to absorb moisture.
  • This product is soluble in water, very slightly soluble in methanol, and almost insoluble in ethanol or acetone.
Last Update:2022-01-01 14:20:17

Vancomycin hydrochloride - Introduction

The mechanism of action of this product is to bind alanyl-alanine at the end of the sensitive bacterial cell wall precursor peptide with high affinity to block the synthesis of polymer peptidoglycan that constitutes the bacterial cell wall, resulting in cell wall defects and killing bacteria. In addition, it may also alter bacterial cell membrane permeability and selectively inhibit RNA synthesis. The characteristic of this drug is that it has a strong bactericidal effect on gram-positive bacteria; oral administration has a good effect on the treatment of Clostridium difficile pseudomembranous colitis. This product has strong antibacterial activity against Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pyogenes, Streptococcus pneumoniae, etc.; against anaerobic Streptococcus, Clostridium difficile, Bacillus anthracis, Actinomycetes, Diphtheria bacillus, Neisseria gonorrhoeae, Streptococcus bovis, Streptococcus faecalis, etc. also have certain antibacterial effects. It is ineffective for most gram-negative bacteria, Mycobacterium, Rickettsia, Chlamydia or fungi.
Last Update:2022-10-16 17:13:51

Vancomycin hydrochloride - Differential diagnosis

Authoritative Data Verified Data
  1. take an appropriate amount of this product and vancomycin standard, add the mobile phase A under vancomycin B respectively to dissolve and dilute to make A solution containing 0.2mg per 1 ml, as the test solution and the standard solution, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the standard solution according to the chromatographic condition test under the vancomycin B check item.
  2. The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 1180).
  3. the aqueous solution of this product was chloride identification (1) of the reaction (General 0512).
Last Update:2022-01-01 14:20:18

Vancomycin hydrochloride - Exam

Authoritative Data Verified Data

acidity

take this product, add water to make a solution containing about 50mg per lml, according to the law (General 0631),pH value should be 2.5~4.5.


clarity and color of solution

take 5 parts of this product and add water respectively to make about 0.lg solution, the solution should be clear; If it is cloudy, it should not be more concentrated than the 1# turbidity standard solution (General 0902 first method); If it is colored, no deeper color shall be compared with the yellow or yellow-orange Standard Colorimetric solution No. 6 (General rule 0901, Method 1).


absorbance

take an appropriate amount of this product, add water to dissolve and quantitatively dilute to make about 0.lg of the solution, according to UV-visible spectrophotometry (General rule 0401), measured at a wavelength of 450nm, absorbance should not exceed 0.10.


Related substances

According to the method under vancomycin B, according to Formula 2, the single impurity should not exceed 4.0%, and the total amount of impurities should not exceed 7.0%.


residual solvent

take about 0.2g of this product, precision weigh it, place it in the top empty bottle, add 5ml of water to dissolve it, seal it, and use it as a test solution. Precision weigh an appropriate amount of anhydrous ethanol, A solution containing about 0.2mg per 1 ml was prepared by quantitative dilution with water, and 5ml was accurately weighed, placed in a headspace bottle, and sealed as a reference solution. According to the determination method of residual solvent (General rule 0861 first method), the capillary column with polyethylene glycol (PE020M)(or similar polarity) as stationary liquid is used as the column, and the column temperature is 50°C; the inlet temperature was 150°C; The detector temperature was 250°C; The headspace bottle equilibrium temperature was 80°C and the equilibrium time was 30 minutes. Measure the sample solution and the reference solution respectively by Headspace injection, record the chromatogram, and calculate the peak area according to the external standard method. The residual amount of ethanol should meet the requirements.


moisture

take this product, according to the determination of moisture (General 0832 first method 1), the water content shall not exceed 5.0%.


ignition residue

take l.Og of this product and check it according to law (General rule 0841). The residue left shall not exceed 0.5%.


Heavy metals

The residue left under the ignition residue item shall not contain more than 30 parts per million of heavy metal when examined by law (General rule 0821, Law II).


vancomycin B

  • measured by high performance liquid chromatography (General 0512).
  • chromatographic conditions and system suitability test using eighteen alkyl silane bonded silica gel as filler; Triethylamine buffer (take triethylamine 4ml, add water to 3.2 ML, adjust pH to with phosphoric acid)-Acetonitrile-tetrahydrofuran (92:7:1) as mobile phase A, with triethylamine buffer-acetonitrile-tetrahydrofuran (70:29:1) as mobile phase B; The flow rate was 1 per minute. Oml. The linear gradient elution was carried out according to the following table, and the detection wavelength was 280nm. Weigh about 10mg of this product accurately, put it in 5ml measuring flask, add mobile phase A to dissolve and dilute to scale, shake well, and use it as test solution (a ) ; Take 2ml accurately, place it in A 50ml measuring flask, dilute it to the scale with mobile phase A, shake it well, use it as the test solution (B), take 2.5 for precision measurement, and place it in A ml measuring flask, dilute to the scale with mobile phase A, shake, as A control solution; Take an appropriate amount of vancomycin standard, dissolve with water and make A solution containing 0.5mg per 1 ml, heat at 65°C for 24 hours, cool, as the system applicable solution, inject 20u1 into the liquid chromatograph, record the chromatogram, the separation degree between the two main peaks should be greater than 5.0; Another control solution 20u1 injection human liquid chromatograph, record the chromatogram, the signal-to-noise ratio of the main peak height should be greater than 5.0; Another 20ul of sample solution (B) was injected into the liquid chromatograph, and the chromatogram was recorded. The tailing factor of vancomycin peak B should be less than 1.60
  • .
  • measurement precision 20ul of the test solution (a), (B) and the control solution were respectively injected into the human liquid chromatograph, and the chromatograms were recorded.

bacterial endotoxin

take this product, check according to law (General rule 1143), the amount of endotoxin per 1 mg of vancomycin should be less than 0.25EU. (For injection)

Last Update:2022-01-01 14:20:19

Vancomycin hydrochloride - Content determination

Authoritative Data Verified Data

take the appropriate amount of this product, precision weighing, dissolving and quantitatively diluting with sterile water to make a solution containing about 10 million of the unit of the unit of the drug per 1 ml, determined according to microbiological assay for antibiotics (General rule 1201 first method).

Last Update:2022-01-01 14:20:20

Vancomycin hydrochloride - Category

Authoritative Data Verified Data

peptide antibiotics.

Last Update:2022-01-01 14:20:20

Vancomycin hydrochloride - Storage

Authoritative Data Verified Data

sealed and stored at 2-8°C.

Last Update:2022-01-01 14:20:20

Vancomycin hydrochloride - Vancorin (Vancomycin Hydrochloride for Injection)

Authoritative Data Verified Data

This product is a sterile freeze-dried product made of vancomycin hydrochloride and suitable excipients. The titer per lmg calculated as anhydrous substance shall not be less than 10 million units. Based on the average loading, the vancomycin content shall be between 90.0% and 115.0% of the labeled amount.


trait

This product is white or off-white powder or loose lumps.


identification

take this product, according to the item of vancomycin hydrochloride under the identification of (1), (3) test, showed the same results.


examination

  • acidity of this product, according to the label amount of water to make 50,000 units per lml of solution, according to the law (General 0631),pH value should be 2.5~4.5.
  • the clarity and color of the solution take 5 bottles of this product, and add water to make a solution containing 100,000 units per 1 ml according to the marked amount. The solution should be clear; If it is turbid, no one shall be more concentrated than the turbidity standard liquid No. 1 (General rule 0902 method 1); If the color is colored, it shall not be deeper than the yellow or orange 4 standard colorimetric liquid (General rule 0901 method 1).
  • absorbance: Take appropriate amount of this product, add water to be dissolved and quantitatively diluted to prepare a solution containing 100,000 units per 1 ml, and perform UV-Vis spectrophotometry (General rule 0401 ), measured at a wavelength of 450nm, the absorbance should not exceed 0.10.
  • insoluble particles take 3 bottles of this product and add 10ml of sodium fumarate injection respectively to dissolve. After the solution is clarified, check according to law (General rule 0903), and make blank test correction at the same time. No more than 6000 particles of 10um and more than 10m in each sample container, and no more than 600 particles of 25um and more than 25um.
  • sterile take this product, dissolve and dilute with appropriate solvent, after the membrane filtration method, inspection according to law (General rule 1101), should comply with the provisions.
  • the related substances, moisture, vancomycin B and bacterial endotoxin shall be checked according to the method under vancomycin hydrochloride, and shall comply with the regulations.
  • others should comply with the relevant provisions under injection (General 0102).

Content determination

The content under the item of loading amount difference was obtained by measuring according to the method under the item of vancomycin hydrochloride.


category

Same as vancomycin hydrochloride.


specification

0.5g (500,000 units) (as per C66H75C12N9024).


storage

sealed and stored at 30°C or less.

Last Update:2022-01-01 14:20:21

Vancomycin hydrochloride - Reference Information

glycopeptide antibiotics vancomycin hydrochloride is a glycopeptide antibiotic, which is the hydrochloride salt of vancomycin and is white or white-like crystalline powder at room temperature. Its mechanism of action is alanyl alanine that binds to the terminal of the precursor peptide of the cell wall of sensitive bacteria with high affinity, blocking the synthesis of the polymer peptidoglycan that constitutes the bacterial cell wall, resulting in cell wall defects and killing bacteria. In addition, it may also alter bacterial cell membrane permeability and selectively inhibit RNA synthesis. Vancomycin hydrochloride is characterized by a strong bactericidal effect on gram-positive bacteria, and a strong antibacterial activity against Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pyogenes, Streptococcus pneumoniae, etc.; Anaerobic Streptococcus, Clostridium difficile, Bacillus anthracis, Actinomycetes, Diphtheria, Neisseria, Streptococcus viridans, Streptococcus bovis, Streptococcus faecalis, etc. also have certain antibacterial effects. It is ineffective for most gram-negative bacteria, Mycobacterium, Rickettsia, Chlamydia or fungi. Clinically suitable for the treatment of infections caused by methicillin-resistant Staphylococcus aureus and other bacteria: sepsis, infective endocarditis, osteomyelitis, arthritis, burns, surgical trauma and other superficial secondary infections, Pneumonia, lung abscess, empyema, peritonitis, meningitis, pseudomembranous enteritis, skin and soft tissue infections, etc. The first choice for the treatment of enterococcal endocarditis and corynebacterium (diphtheria-like bacilli) endocarditis in penicillin-allergic patients.
Andy edited and sorted out the above information.
vancomycin vancomycin is a polypeptide antibiotic. Glycopeptide antibiotics from Streptomyces orientalis (Orientalis of Streptomyces) or Agromycetes (Orientalis of Amycolatopsis). In the late 1950s, the drug came out with its good effect on penicillin-resistant Staphylococcus, and became a powerful "trump card" antibiotic against G bacteria, such as Staphylococcus aureus, Streptococcus pyogenes, and Streptococcus pneumoniae. Later, due to the discovery of its greater toxicity, coupled with the less toxic anti-staphylococcal semi-synthetic penicillin and cephalosporins successively on the market in the 1960s, and the drug resistance problem at that time was not very acute, which restricted its application. In recent years, due to methicillin-resistant Staphylococcus aureus (MRSA), methicillin-resistant Staphylococcus epidermidis (MRSE) infections have increased, and it has been found that Clostridium difficile (CD) is the main cause of antibiotic-related pseudomembranous enteritis. The application of vancomycin has been increasing day by day, and the special status of vancomycin has been re-established in clinical practice. Since the 1990s, it has been praised by international antibiotic experts as "the last line of defense for humans to deal with refractory drug-resistant strains".
according to the results of some literatures and the distribution of clinical drug-resistant strains at present, vancomycin is the first choice for diseases caused by MRSA and MRSE infection. vancomycin treatment for related diarrhea or pseudomembranous enteritis caused by CD is also quite certain, especially for critically ill patients. In addition, vancomycin is also the top grade for rare penicillin-G-resistant pneumococcal infection and severe infection caused by penicillin-resistant corynebacterium JK strain.
because vancomycin has good curative effect on diseases caused by multiple drug-resistant bacteria, its market sales have increased year by year in the past 10 years. In the past few years, the annual growth rate of vancomycin in the international market has been maintained at 3-4%, and has risen to 5-6% in the past two years. According to antibiotic experts, the global total output of vancomycin in the mid-1990s averaged 20-25 tons per year, and in 1999 it has risen to 30 tons.
pharmacokinetics oral malabsorption, intravenous administration can be widely distributed in most tissues and body fluids throughout the body. The peak blood concentrations of 500mg and 1g were 10-30mg/L and 25-50mg/L, respectively.
the distribution volume of this drug is 0.43-1.25L/kg. Its effective antibacterial concentration can be reached in serum, pericardium, pleura, peritoneum, ascites and synovial fluid, but not in bile. Vancomycin hydrochloride can penetrate the placenta, but cannot quickly penetrate the normal blood-cerebrospinal fluid barrier. When the meninges are inflamed, it can penetrate into the cerebrospinal fluid and reach an effective antibacterial concentration.
The protein binding rate of this drug is about 55%. The elimination half-life is 6 hours (4-11 hours) in adults, and can be extended to 7.5 days in patients with severe renal insufficiency; about 2-3 hours in children. The drug is metabolized by the liver, and about 80%-90% is excreted through the kidney in its original form within 24 hours, and a small amount is excreted with bile and milk. Hemodialysis or peritoneal dialysis cannot effectively remove this drug; however, there are reports that blood perfusion or blood filtration can improve clearance.
instructions for administration (1). this drug is strongly irritating to tissues and should not be injected intramuscularly or intravenously. Leakage of liquid medicine should be avoided as far as possible during intravenous drip.
(2), in order to reduce the incidence of adverse reactions (such as "red neck syndrome", thrombophlebitis), the speed of intravenous drip should not be too fast, and the time of each drip should be at least 1 hour.
(3), when treating staphylococcal endocarditis, the course of treatment should be not less than 28 days.
(4), vancomycin hydrochloride is incompatibility with chloramphenicol, heparin, aminophylline, sodium bicarbonate, steroid hormone, methicillin, heavy metal drugs, alkaline solution, etc.
(5), treatment of overdose: excessive use of vancomycin hydrochloride can cause oliguria and renal failure. Treatment includes:(1) symptomatic and supportive treatment. (2) Conventional hemodialysis and peritoneal dialysis are not effective for drug removal; however, hemoperfusion or hemofiltration can improve drug clearance.
(6) preparation of solution:(1) preparation of oral liquid: vancomycin containing 500mg per bottle is diluted with distilled water to prepare a solution of 500mg/6ml for oral administration. the oral liquid can be stored for 14 days in a refrigerator at 4 ℃. (2) Preparation of intravenous drip solution: ① During intermittent infusion, the solution is prepared with 500mg of medicine and 10ml of water, then added to 5% glucose injection or 0.9% sodium chloride injection, diluted to less than 5 mg/ml, and then injected. 500mg dose infusion time at least 60 minutes or 1000mg infusion time at least 100 minutes. For patients who need to limit the amount of fluid, the maximum concentration can reach 10mg/ml. ② For continuous intravenous drip, 1~2g dose should be added to 5% glucose injection or 0.9% sodium chloride injection.
(7), the maintenance amount of patients with renal dysfunction is calculated by the following formula: maintenance dose (md/d)= 150 +(15 × creatinine clearance rate ml/min).
(8), blood drug concentration must be monitored during treatment, peak concentration should not exceed 25~40 μg/ml, valley concentration should not exceed 5~10 μg/ml. Above 60 μg/ml is the poisoning range. If the blood concentration cannot be monitored, adjust the dose according to the creatinine clearance rate.
adverse reactions the main adverse reactions of vancomycin hydrochloride clinically are as follows: ototoxicity: tinnitus or ear fullness, hearing loss or even loss, auditory nerve damage, etc. It is especially easy to occur when applied in large doses, for a long time, in the elderly or in people with renal insufficiency. Nephrotoxicity: Mainly damages renal tubules. Early may have proteinuria, tubular urine, followed by hematuria, oliguria, etc.; severe cases can cause renal failure. It is especially easy to occur in large doses (blood concentration exceeds 60~100mg/L), long-term, elderly or renal insufficiency. Allergy: "Red neck syndrome" may occur in a small number of patients with rapid and high-dose intravenous administration ". Manifested as chills or fever, syncope, itching, nausea, vomiting, tachycardia, rash or facial flushing; redness or tingling of the neck root, upper body, back, arms, etc. (caused by histamine release), occasionally hypotension and shock-like symptoms. Its incidence was higher than that of norvancomycin and teicoplanin. Local reaction: severe pain at the injection site may occur during intramuscular injection or intravenous administration, and thrombophlebitis may occur in severe cases. Gastrointestinal tract: oral administration may have nausea, vomiting, oral odor and other symptoms.
use narrow antibacterial spectrum, mainly effective against gram-positive bacteria
narrow antibacterial spectrum, mainly effective against gram-positive bacteria.
it is a narrow-spectrum antibiotic, which is only effective for gram-positive bacteria, such as hemolytic streptococcus, pneumococcus, gonococcus and enterococcus, which are sensitive to drug-resistant Staphylococcus aureus. Its mechanism of action is to inhibit the synthesis of the bacterial cell wall. It mainly binds to the bacterial cell wall, and some amino acids cannot enter the glycopeptides in the cell wall.
Last Update:2024-04-09 19:05:03
Vancomycin hydrochloride
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View History
Vancomycin hydrochloride
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4-(6-ETHYL-THIENO[2,3-D]PYRIMIDIN-4-YLAMINO)-BUTYRIC ACID
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2-HYDROXYETHYL N-METHYLCARBAMATE
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DICHLOROMETHANE,[14C]
3-(4-溴-2-氟苯基)丙烯酸甲酯
(R)-(-)-1-(1-萘基)异氰酸乙酯
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