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

Vancomycin

CAS No.: 1404-90-6
Molecular Weight:1449.265
Modify Date.: 2022-11-07 03:25
Introduction: Vancomycin is produced by fermentation of Amycol atopsis orientalis (formerly Nocardi a orientalis). It hasbeen available for approximately 40 years, but its popularity has increased significantly with the emergenceof MRSA in the early 1980s. Chemically, vancomycin has a glycosy lated hexapeptide chain that is rich inunusual amino acids, many of which contain aromatic rings cross-linked by aryl ether bonds into a rigidmolecular framework. View more+
1. Names and Identifiers
1.1 Name
Vancomycin
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 EINECS 215-772-6 MFCD05664587

1.3 CAS No.
1404-90-6
1.4 CID
14969
1.5 EINECS(EC#)
215-772-6
1.6 Molecular Formula
C66H75Cl2N9O24 (isomer)
1.7 Inchi
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
1.8 InChkey
MYPYJXKWCTUITO-LYRMYLQWSA-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
1.10 Isomers Smiles
C[C@H]1[C@H]([C@@](C[C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](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
2. Properties
2.1 Density
1.65
2.1 Boiling point
°Cat760mmHg
2.1 Refractive index
1.7350 (estimate)
2.1 Flash Point
°C
2.1 Precise Quality
1483.41000
2.1 PSA
530.49000
2.1 logP
4.73460
2.1 AnalyticLaboratory Methods
THIS REVERSE PHASE, HIGH PRESSURE LIQUID CHROMATOGRAPHIC METHOD APPLIES TO DETERMINATION OF THESE COMPOUNDS IN ANTIBIOTIC MIXTURES.
2.2 Appearance
Almost white powder
2.3 Decomposition
When heated to decomposition, it emits toxic fumes of /nitric oxide;/ and /chlorine;/.
2.4 Physical
Solid
2.5 pKa
pKa 2.18±0.08(H2Ot = 25.0±0.1I = 0.2 (NaCl)N2 atmosphere) (Uncertain);7.75±0.02(H2Ot = 25.0±0.1I = 0.2 (NaCl)N2 atmosphere) (Uncertain);8.89±0.01(H2Ot = 25.0±0.1I = 0.2 (NaCl)N2 atmosphere) (Uncertain)
2.6 Stability
When reconstituted with sterile water; for injection, <a class="pubchem-internal-link multiple-CIDs" href="https://pubchem.ncbi.nlm.nih.gov/compound/vancomycin%20hydrochloride">vancomycin hydrochloride</a> injection is stable for 2 weeks at room temperature; the manufacturers state that reconstituted injections may be stored for 96 hours at 2 - 8 deg C without substantial loss of potency. When reconstituted as directed in 0.9% sodium chloride; injection or 5% dextrose injection, solutions prepared from ADD-Vantage vials of the drug are stable for 24 hours at room temperature. Vancomycin; solutions containing 5 mg/mL in 0.9% sodium chloride; injection or 5% dextrose injection are reportedly stable for at least 17 days when stored at 24 deg C in glass or PVC containers and for at least 63 days when stored at 5 deg C or -10 deg C in glass containers. Following reconstitution with sterile water; for injection as directed, vancomycin; solutions that have been further diluted to a concentration of 5 mg/mL in 5 - 30% dextrose injection are stable when stored in plastic syringes for 24 hours at 4 eg C and then subsequently for 2 hours at room temperature.
3. Use and Manufacturing
3.1 Definition
ChEBI: A complex glycopeptide from Streptomyces orientalis. It inhibits a specific step in the synthesis of the peptidoglycan layer in the Gram-positive bacteria Staphylococcus aureus and Clostridium difficile.
3.2 Methods of Manufacturing
... Found in the culture broth of Streptomyces orientalis.
3.3 Usage
Vancomycin is used for serious bacterial infections caused by microorganisms sensitiveto this drug when penicillins and cephalosporins are ineffective for diseases such as sepsis,endocarditis, pneumonia, pulmonary abscess, osteomyelitis, meningitis, and enterocolitis,or when penicillins and cephalosporins cannot be tolerated by patients. Vancomycin is thedrug of choice for infections caused by methicillin-resistant forms of S. aureus, S. epidermidus, and other coagulase-negative staphylococci, as well as for endocarditis, diphtherioidinfections, and for patients very sick with colitis caused by C. difficile. A synonym of thisdrug is vancocin.
4. Safety and Handling
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 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 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 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 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
Moderately toxic by intraperitoneal and intravenous routes. Human systemic effects: agranulocytosis, allergic dermatitis, dermatitis, interstitial nephritis. When heated to decomposition it emits toxic fumes of NOx.
4.11 Specification

The Vancomycin, with the CAS registry number 1404-90-6, has the systematic name of (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-a mino-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).

The physical properties of this chemical are as below: (1)# of Rule of 5 Violations: 3; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 1; (5)ACD/KOC (pH 7.4): 1; (6)#H bond acceptors: 33; (7)#H bond donors: 21; (8)#Freely Rotating Bonds: 23; (9)Polar Surface Area: 530.49; (10)Index of Refraction: 1.735; (11)Molar Refractivity: 350.837 cm3; (12)Molar Volume: 874.685 cm3; (13)Polarizability: 139.083×10-24 cm3; (14)Surface Tension: 105.146 dyne/cm; (15)Density: 1.657 g/cm3; (16)Exact Mass: 1447.4302; (17)MonoIsotopic Mass: 1447.4302; (18)Topological Polar Surface Area: 531; (19)Heavy Atom Count: 101; (20)Complexity: 2960.

In addition, you could convert the following datas into the molecular structure:
(1)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=C9C(NC(=O)C(C(C1=CC(=C(O4)C=C1)Cl)O)NC7=O)C(=O)O)O) O)CC(=O)N)NC(=O)C(CC(C)C)NC)O)Cl)CO)O)O)(C)N)O
(2)Isomeric SMILES: C[C@H]1[C@H]([C@@](C[C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](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=C9[C@H](NC(=O)[C@H]([C@@H](C1=CC(=C(O4)C=C1)Cl)O)NC7=O)(=O)O)O)O)CC(=O)N)NC(=O)[C@@H](CC(C)C)NC)O)Cl)CO)O)O)(C)N)O
(3)InChI: 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
(4)InChIKey: MYPYJXKWCTUITO-LYRMYLQWSA-N 

Below are the toxicity information of this chemical:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
infant TDLo intravenous 30mg/kg/20M-C (30mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

CARDIAC: OTHER CHANGES
Archives of Disease in Childhood. Vol. 73, Pg. F123, 1995.
infant TDLo intravenous 119mg/kg (119mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Journal of Toxicology, Clinical Toxicology. Vol. 34, Pg. 83, 1996.
 
infant TDLo intravenous 295mg/kg/3D-I (295mg/kg) KIDNEY, URETER, AND BLADDER: INTERSTITIAL NEPHRITIS Journal of Toxicology, Clinical Toxicology. Vol. 30, Pg. 285, 1992.
 
man TDLo intravenous 15mg/kg/2H-C (15mg/kg) VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Annals of Pharmacotherpy. Vol. 33, Pg. 1043, 1999.
 
mouse LD50 intraperitoneal 1734mg/kg (1734mg/kg)   "Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967Vol. -, Pg. 675, 1967.
mouse LD50 intravenous 430mg/kg (430mg/kg)   Journal of Antibiotics. Vol. 43, Pg. 913, 1990.
 
mouse LD50 subcutaneous 5gm/kg (5000mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 1, Pg. 315, 1980.
women TDLo intravenous 15mg/kg/90M-C (15mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE" New England Journal of Medicine. Vol. 313, Pg. 756, 1985.
 
women TDLo intravenous 170mg/kg/19D- (170mg/kg) BLOOD: AGRANULOCYTOSIS Canadian Medical Association Journal. Vol. 132, Pg. 39, 1985.
 
women TDLo multiple routes 30mg/kg/2D-I (30mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Annals of Internal Medicine. Vol. 115, Pg. 410, 1991.
 

4.12 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :
YW4375000
CHEMICAL NAME :
Vancomycin
CAS REGISTRY NUMBER :
1404-90-6
LAST UPDATED :
199612
DATA ITEMS CITED :
12
MOLECULAR FORMULA :
C66-H75-Cl2-N9-O24
MOLECULAR WEIGHT :
1449.40

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - infant
DOSE/DURATION :
119 mg/kg
TOXIC EFFECTS :
Cardiac - pulse rate increase, without fall in BP Vascular - BP lowering not characterized in autonomic section Lungs, Thorax, or Respiration - cyanosis
REFERENCE :
JTCTDW Journal of Toxicology, Clinical Toxicology. (Marcel Dekker, 270 Madison Ave., New York, NY 10016) V.19- 1982- Volume(issue)/page/year: 34,83,1996
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
15 mg/kg/90M-C
TOXIC EFFECTS :
Skin and Appendages - dermatitis, allergic (after systemic exposure)
REFERENCE :
NEJMAG New England Journal of Medicine. (Massachusetts Medical Soc., 10 Shattuck St., Boston, MA 02115) V.198- 1928- Volume(issue)/page/year: 313,756,1985
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
170 mg/kg/19D-I
TOXIC EFFECTS :
Blood - agranulocytosis
REFERENCE :
CMAJAX Canadian Medical Association Journal. (Canadian Medical Assoc., POB 8650, Ottawa, ON K1G 0G8, Canada) V.1- 1911- Volume(issue)/page/year: 132,39,1985
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - infant
DOSE/DURATION :
295 mg/kg/3D-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - interstitial nephritis
REFERENCE :
JTCTDW Journal of Toxicology, Clinical Toxicology. (Marcel Dekker, 270 Madison Ave., New York, NY 10016) V.19- 1982- Volume(issue)/page/year: 30,285,1992
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Multiple routes
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
30 mg/kg/2D-I
TOXIC EFFECTS :
Skin and Appendages - dermatitis, other (after systemic exposure)
REFERENCE :
AIMEAS Annals of Internal Medicine. (American College of Physicians, 4200 Pine St., Philadelphia, PA 19104) V.1- 1927- Volume(issue)/page/year: 115,410,1991
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1734 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
85FZAT "Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967 Volume(issue)/page/year: -,675,1967
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 1,315,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
430 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 43,913,1990 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
640 mg/kg/4D-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Kidney, Ureter, Bladder - other changes in urine composition
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 42,200,1995 *** REVIEWS *** TOXICOLOGY REVIEW DICPBB Drug Intelligence and Clinical Pharmacy. (POB 42435, Cincinnati, OH 45242) V.3- 1969- Volume(issue)/page/year: 8,520,1974 TOXICOLOGY REVIEW AJMEAZ American Journal of Medicine. (Technical Pub., 875 Third Ave., New York, NY 10022) V.1- 1946- Volume(issue)/page/year: 38,409,1965 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3663 No. of Facilities: 324 (estimated) No. of Industries: 1 No. of Occupations: 7 No. of Employees: 14913 (estimated) No. of Female Employees: 13290 (estimated)
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Respiratory sensitization, Category 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H334 May cause allergy or asthma symptoms or breathing difficulties if inhaled

Precautionary statement(s)
Prevention

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

P284 [In case of inadequate ventilation] wear respiratory protection.

Response

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P342+P311 If experiencing respiratory symptoms: Call a POISON CENTER/doctor/...

Storage

none

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

7. Precursor and Product
8. Other Information
8.0 Indication and Administration
Vancomycin is active against most strains of Clostridia, resistant strains), coagulase-negative Staphylococci, and Viridans group Staphylococci and Enterococci. Vancomycin is not effective against Gram-negative bacteria[12]. Vancomycin is one of the antibiotics of last resort, used only after treatment with other antibiotics has failed in the treatment of life-threatening infections by Gram-positive bacteria. Even though vancomycin has great potential in treating infections in animals, the use of vancomycin in veterinary medicine is limited because it is expensive and requires continuous intravenous infusion[13]. Powdered vancomycin is reconstituted in sterile water, which results in a dark-colored solution, and it is further diluted in 5% dextrose or saline when it is administered. The reconstituted solution is stable for 14 days either at room temperature or in a refrigerator. Additionally, 125 mg and 250 mg vancomycin tablets are available for oral administration[14]
8.1 Brand Name(s) in US
Vancocin, Vancoled
8.2 Mode of action
The mechanism of action of this antimicrobial agent is via the inhibition of bacterial cell wall biosynthesis or, more specifically, the inhibition of peptidoglycan biosynthesis. It is, therefore, bactericidal for reproductive bacteria[1]. The bacterial cell wall contains peptidoglycan that encircles the whole bacteria. In Gram-positive bacteria this substance is more significantly present, and it forms large and insoluble layers on the outer part of the cell membrane, totaling up to 40 layers which consist of multiple skeletons of amino sugars: N-acetylglucosamine and N-acetylmuramic[24]. The latter contains lateral short peptide residues with cross-links, which form a high-level resistant polymeric chain. The drug inhibits this polymerization or the transglycosylase reaction once it binds with high affinity to the C-terminal D-alanyl D-alanine residues of lipid-linked cell wall precursors and blocks the linkage to the glycopeptide polymer1. As a result, it hinders the cross-links of peptides from binding to tetrapeptide side chains; namely, it prevents its linkage to the growing tip of the peptidoglycan[24].
8.3 Uses
Antibacterial.
8.4 Definition
ChEBI: A complex glycopeptide from Streptomyces orientalis. It inhibits a specific step in the synthesis of the peptidoglycan layer in the Gram-positive bacteria Staphylococcus aureus and Clostridium difficile.
8.5 Brand name
Vancocin Hydrochloride (ViroPharma); Vancoled (Baxter Healthcare); Vancor (Pharmacia & Upjohn).
9. Computational chemical data
  • Molecular Weight: 1449.265g/mol
  • Molecular Formula: C66H75Cl2N9O24
  • Compound Is Canonicalized: True
  • XLogP3-AA: -2.6
  • Exact Mass: 1447.4301997
  • Monoisotopic Mass: 1447.4301997
  • Complexity: 2960
  • Rotatable Bond Count: 13
  • Hydrogen Bond Donor Count: 19
  • Hydrogen Bond Acceptor Count: 26
  • Topological Polar Surface Area: 531
  • Heavy Atom Count: 101
  • Defined Atom Stereocenter Count: 18
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADcfB//gAGAAAAAAAAAAAAAAAAAAAAAAA0aMGDAAAAAAABVAAAHgIQCAAADb7xmCcyDoLABgCIAiHSGACCCAAgJUAIiIGOj4gfdz+H9zu2eCrn9hWfuAf9/P/OoAADKAAYSABAAAZQADCQAAAAAAAAAA==
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