Clarithromycin

Iupac Name：(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-12,13-dihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione

CAS No.: 81103-11-9

Molecular Weight：747.964

Modify Date.: 2023-02-26 17:33

Introduction: Clarithromycin is an acid stable macrolide antibiotic indicated for use in thetreatment of skin, urinary and respiratory tract infections. Compared to erythromycin,clarithromycin exhibits the same in vitro activity against conventional pathogens, butis better tolerated by generating less gastrointestinal problems. View more+

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1. Names and Identifiers

1.1 Name: Clarithromycin
1.2 Synonyms: (3R,4S,5R,6R,7R,9R,11R,12S,13S,14R)-6-{[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-14-ethyl-12,13-dihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetra hydro-2H-pyran-2-yl]oxy}-7-methoxy-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione (non-preferred name) (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-14-ethyl-12,13-dihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-7-methoxy-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-14-ethyl-12,13-dihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-7-methoxy-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione (non-preferred name) 6-(4-DIMETHYLAMINO-3-HYDROXY-6-METHYLTETRAHYDROPYRAN-2-YL-OXY)-14-ETHYL-12,13-DIHYDROXY-4-(5-HYDROXY) 6-O-Methylerythromycin 6-O-Methylerythromycin, A-56268, TE-031, Biaxin A-56268 Abbott 56268 BIAXIN chlarithromycin Clacee Clacid Claric Clarihexal Claris CLARITHROMYCIN(SUBJECTTOPATENTFREE) Clarosip Cyllind Erythromycin, 6-O-methyl- ERYTHROMYCIN,6-0-METHYL-6-0-METHYLERYTHROMYCIN /CLARITHROMYCIN Fromilid Infex Klacid Kladd Macladin Mavid Naxy Resclar te-03 TE-031 UNII-H1250JIK0A Veclam Vikrol Zeclar

1.3 CAS No.: 81103-11-9

1.4 CID: 84029

1.5 EINECS(EC#): 617-200-4

1.6 Molecular Formula: C38H69NO13 (isomer)

1.7 Inchi: InChI=1S/C38H69NO13/c1-15-26-38(10,45)31(42)21(4)28(40)19(2)17-37(9,47-14)33(52-35-29(41)25(39(11)12)16-20(3)48-35)22(5)30(23(6)34(44)50-26)51-27-18-36(8,46-13)32(43)24(7)49-27/h19-27,29-33,35,41-43,45H,15-18H2,1-14H3/t19-,20-,21+,22+,23-,24+,25+,26-,27+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1

1.8 InChkey: AGOYDEPGAOXOCK-KCBOHYOISA-N

1.9 Canonical Smiles: CCC1C(C(C(C(=O)C(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)N(C)C)O)(C)OC)C)C)O)(C)O

1.10 Isomers Smiles: CC[C@@H]1[C@@]([C@@H]([C@H](C(=O)[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)OC)C)C)O)(C)O

2. Properties

2.1 Density: 1.18 g/cm³

2.1 Melting point: 217-220℃

2.1 Boiling point: 805.5 °C at 760 mmHg

2.1 Refractive index: -92 ° (C=1, CHCl3)

2.1 Flash Point: 440.9 °C

2.1 Precise Quality: 747.47700

2.1 PSA: 182.91000

2.1 logP: 2.43970

2.1 Solubility: Soluble in DMSO

2.2 AnalyticLaboratory Methods: Analyte: Clarithromycin;; matrix: solutions; procedure: high performance liquid chromatography with ultraviolet detection at 210 nm

2.3 Appearance: Solid

2.4 Storage: Ambient temperatures.

2.5 Chemical Properties: Colourless Crystalline Needles

2.6 Color/Form: Colorless needles from chloroform; + diisopropyl ether; (1:2) ... Also reported as crystals from ethanol;

2.7 Decomposition: When heated to decomposition it emits toxic vapors of /oxides of nitrogen/.

2.8 Physical: Solid

2.9 pKa: pKa 8.99(H2O t=25.0 I=0.167) (Uncertain)

2.10 Water Solubility: 99.48mg/L(20 oC)

2.11 Stability: Store in Freezer

2.12 StorageTemp: -20°C

3. Use and Manufacturing

3.1 Definition: ChEBI: The 6-O-methyl ether of erythromycin A, clarithromycin is a macrolide antibiotic used in the treatment of respiratory-tract, skin and soft-tissue infections. It is also used to eradicate Helicobacter pylori in the treatment f peptic ulcer disease. It prevents bacteria from growing by interfering with their protein synthesis.

3.2 General Description: Some of the microbiological properties of clarithromycin appear to be superior to those of erythromycin. It exhibitsgreater potency against M. pneumoniae, Legionellaspp., Chlamydia pneumoniae, H. influenzae, and M. catarrhalisthan does erythromycin. Clarithromycin also hasactivity against unusual pathogens such as Borrelia burgdorferi(the cause of Lyme disease) and the Mycobacteriumavium complex (MAC). Clarithromycin is significantly moreactive than erythromycin against group A streptococci, S.pneumoniae, and the viridans group of streptococci in vivobecause of its superior oral bioavailability. Clarithromycin is,however, more expensive than erythromycin, which must beweighed against its potentially greater effectiveness.Adverse reactions to clarithromycin are rare. The mostcommon complaints relate to GI symptoms, but these seldomrequire discontinuance of therapy. Clarithromycin,like erythromycin, inhibits cytochrome P450 oxidases and,thus, can potentiate the actions of drugs metabolized bythese enzymes.Clarithromycin occurs as a white crystalline solid that ispractically insoluble in water, sparingly soluble in alcohol,and freely soluble in acetone. It is provided as 250- and 500-mg oral tablets and as granules for the preparation of aqueousoral suspensions containing 25 or 50 mg/mL.

3.3 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 150 companies from 9 notifications to the ECHA C&L Inventory.

H302 (99.33%): Harmful if swallowed [Warning Acute toxicity, oral]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P264, P270, P301+P312, P330, and P501

3.4 Methods of Manufacturing: Preparation: Y. Watanable, et al., EP 41355; eidem, US 4331803 (1981, 1982 both to Taisho)

3.5 Usage: A semi-synthetic macrolide antibiotic. A derivative of erythromycin

4. Safety and Handling

4.1 Symbol: GHS07

4.1 Hazard Codes: Xi; Xn

4.1 Signal Word: Warning

4.1 Risk Statements: R22

4.1 Safety Statements: 26-36

4.1 Hazard Declaration: H302

4.1 RIDADR: MAC

4.1 Caution Statement: P301 + P312 + P330

4.1 WGK Germany: 3

4.1 RTECS: KF4997000

4.1 Safety: A poison by intraperitoneal and intravenous routes. Moderately toxic by ingestion. Human systemic effects. When heated to decomposition it emits toxic vapors of NO_x.
Hazard Codes: Xn,Xi
Risk Statements: 22-36/37/38
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
RTECS: KF4997000

4.2 Specification: 6-o-Methoxyerythromycin , its cas register number 81103-11-9. It also can be called A-56268 ; Biaxin ; Klacid; TE-03 ; and Clarithromycin .
The first aid is as following. Such as: When on the skin: first, should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Secondly, get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While, it's inhaled: Remove from exposure and move to fresh air immediately. Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product : Wash mouth out with water, and get medical aid immediately. In addition, it should be stored only in original container, or keep its container tightly closed.

4.3 Toxicity: LD50 in male, female mice, male, female rats (mg/kg): 2740, 2700, 3470, 2700 orally, 1030, 850, 669, 753 i.p., >5000 all s.c. (Abe)

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. Synthesis Route

81103-11-9Total: 20 Synthesis Route

81103-09-5

81103-11-9 506 Suppliers

Literatures:
Heterocycles, , vol. 31, # 12 p. 2121 - 2124
Yield: null

930287-49-3

81103-11-9 506 Suppliers

Literatures:
Brunet, Ernesto; Munoz, Dulce Maria; Parra, Francisco; Mantecon, Susana; Juanes, Olga; Rodriguez-Ubis, Juan Carlos; Carmen Cruzado, Ma; Asensio, Ramon Tetrahedron Letters, 2007 , vol. 48, # 8 p. 1321 - 1324
Yield: ~97%

118074-07-0 3 Suppliers

81103-11-9 506 Suppliers

Literatures:
Hanmi Pahrm. Co., Ltd. Patent: US6809188 B1, 2004 ; Location in patent: Page column 6; 7 ;
Yield: ~95%

View all

7. Precursor and Product

precursor:

13127-18-9

101666-32-4

101670-80-8

81103-09-5

127253-06-9

118074-07-0

119685-39-1

103450-87-9

930287-46-0

130034-54-7

643726-97-0

111321-02-9

791845-56-2

50-00-0

119699-81-9

930287-49-3

101666-16-4

930287-47-1

101666-67-5

View all

product :

144604-03-5

160145-83-5

101666-68-6

118058-75-6

191114-48-4

8. Other Information

8.0 Merck: 14,2339

8.1 Description: Clarithromycin is an acid stable macrolide antibiotic indicated for use in the treatment of skin, urinary and respiratory tract infections. Compared to erythromycin, clarithromycin exhibits the same in vitro activity against conventional pathogens, but is better tolerated by generating less gastrointestinal problems.

8.2 Description: Clarithromycin is a polyketide synthase-derived semisynthetic macrolide antibiotic. It is active against methicillin-susceptible, but not methicillin-resistant, S. aureus (MIC₅₀s = 0.06 and >128 μg/ml), S. pyogenes, L. monocytogenes, and B. pertussis (MIC₅₀ = 0.015, 0.25, and ≤0.008 μg/ml, respectively), among others. Clarithromycin (25 mg/kg) decreases the number of colony-forming units (CFUs) in the spleen in a mouse model of M. avium infection. Formulations containing clarithromycin have been used in the treatment of bacterial infections and, when used in combination with other antibiotics, in the treatment of H. pylori.

8.3 Chemical Properties: Colourless Crystalline Needles

8.4 Originator: Taisho (Japan)

8.5 Uses: A semi-synthetic macrolide antibiotic. A derivative of erythromycin

8.6 Uses: Macrolide antibacterial.

8.7 Uses: Clarithromycin is a semi-synthetic macrolide antibiotic. Clarithromycin is a derivative of Erythromycin (E650000).

8.8 Uses: Clarithromycin (6-methoxyerythromycin) is a macrolide antibiotic active against a broad range of Gram positive bacteria. Clarithromycin was designed to enhance acid stability and improve oral bioavailability compared with erythromycin which is highly unstable to acidic conditions, undergoing a series of internal ketalisations between the 9-keto moiety and alcohols at C6 and C11. Omura and colleagues found that protection of the labile 6-OH group by methylation provided a simple but elegant solution.

8.9 Uses: Labeled Clarithromycin, intended for use as an internal standard for the quantification of Clarithromycin by GC- or LC-mass spectrometry.

8.10 Uses: A macrolide antibiotic and protein synthesis inhibitor

8.11 Definition: ChEBI: The 6-O-methyl ether of erythromycin A, clarithromycin is a macrolide antibiotic used in the treatment of respiratory-tract, skin and soft-tissue infections. It is also used to eradicate Helicobacter pylori in the treatment f peptic ulcer disease. It prevents bacteria from growing by interfering with their protein synthesis.

8.12 Manufacturing Process: In a mixture of 50 ml of dry dimethylsulfoxide and 100 ml of dry tetrahydrofuran were dissolved 30 g of O,N-dibenzyloxycarbonyl-des-Nmethylerythromycin A and 18 ml of methyl iodide. The solution was stirred
under cooling at -12-10°C in a nitrogen stream and 2.4 g of 55-65% sodium hydride oily dispersion were added thereto in small portions. The mixture was stirred for a further one hour. After completion of the reaction, 50 ml of triethylamine were poured into the reaction mixture with stirring under icecooling, and the precipitates were filtered off. The obtained solid product was washed thoroughly with ethyl acetate, and the washings and the mother liquor were combined. The combined liquor was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo and the crude product was applied onto a silica gel dry column (E. Merck Darmstadt; silica gel 60 for column chromatography, 70-230 mesh). The mixture was eluted with of ethyl acetate/n-hexane (1:1).
15 ml each of fraction was collected and analyzed by silica gel thin layer chromatography, developing in a mixture of ethyl acetate and n-hexane (1:1). The fractions having Rf value 0.16 were combined (c.f., Rf value of starting compound 0.07) and the solvent was evaporated in vacuo, affording 12.2 g of
a colorless froth. In a mixture of 1.32 g of sodium acetate, 0.8 ml of sodium acetate, 40 ml of water and 200 ml of ethanol were dissolved 10 g of the colorless froth obtained, and 1.0 g of palladium black was added to the above solution. Catalytic reduction was performed for 5 hours at room temperature under atmospheric pressure in a gentle hydrogen stream. 32 ml of 37% aqueous formaldehyde solution were poured into the reaction mixture and the catalytic reduction was continued for a further 7 hours. After completion of the reaction, the catalyst was filtered off and the filtrate was concentrated under reduced pressure approximately to a quarter volume. To the concentrate were added 100 ml of water, and the mixture was adjusted to about pH 10 with an aqueous sodium carbonate solution. The mixture was extracted thoroughly with chloroform and the extract was washed with water and dried. After evaporation of the solvent in vacuo, the residue was recrystallized from a mixture of chloroform and diethyl ether, giving 6 g of crystals. The crystals were stirred for 5 hours in 500 ml of diethyl ether and filtered off. The filtrate was concentrated to dryness and the residual substance was recrystallized from a mixture of chloroform and diethyl ether, giving 4.5 g of 6-O-methylerythromycin A (Clarithromycin) in the form of colorless needles; m.p. 217-220°C (with decomposition).

8.13 Brand name: Biaxin (Abbott);Klacid.

8.14 Therapeutic Function: Antibiotic

8.15 Antimicrobial activity: Activity against susceptible common pathogens is two to four times greater than that of erythromycin A . Most respiratory pathogens, with the exception of H. influenzae, are inhibited at a concentration of ≤0.25 mg/L. It inhibits Mycoplasma pneumoniae at 0.004 mg/L and Mor. catarrhalis at 0.06 mg/L. It is eight times more active than erythromycin A against Legionella spp., C. trachomatis and Ch. pneumoniae. Against anaerobic species, activity is similar to that of erythromycin A. Against H. influenzae the 14-hydroxy metabolite is twice as active as the parent compound.

8.16 General Description: Some of the microbiological properties of clarithromycin appear to be superior to those of erythromycin. It exhibitsgreater potency against M. pneumoniae, Legionellaspp., Chlamydia pneumoniae, H. influenzae, and M. catarrhalisthan does erythromycin. Clarithromycin also hasactivity against unusual pathogens such as Borrelia burgdorferi(the cause of Lyme disease) and the Mycobacteriumavium complex (MAC). Clarithromycin is significantly moreactive than erythromycin against group A streptococci, S.pneumoniae, and the viridans group of streptococci in vivobecause of its superior oral bioavailability. Clarithromycin is,however, more expensive than erythromycin, which must beweighed against its potentially greater effectiveness.
Adverse reactions to clarithromycin are rare. The mostcommon complaints relate to GI symptoms, but these seldomrequire discontinuance of therapy. Clarithromycin,like erythromycin, inhibits cytochrome P450 oxidases and,thus, can potentiate the actions of drugs metabolized bythese enzymes.
Clarithromycin occurs as a white crystalline solid that ispractically insoluble in water, sparingly soluble in alcohol,and freely soluble in acetone. It is provided as 250- and 500-mg oral tablets and as granules for the preparation of aqueousoral suspensions containing 25 or 50 mg/mL.

8.17 Hazard: Moderately toxic by ingestion. Human sys-temic effects.

8.18 Pharmaceutical Applications: A semisynthetic erythromycin A derivative (6-O- methyl erythromycin A) formulated for oral and intravenous use.

8.19 Biochem/physiol Actions: Macrolides, such as clarithromycin, prevent protein synthesis in bacteria, by binding to 50S ribosomal subunit. It also binds to other ribosomal proteins, and prevents the translocation of pepti-dyl-tRNA. In patients with refractory asthma, it is capable of regulating the levels of interleukin-8 (IL-8), and neutrophil accumulation and activation in lungs. Thus, it might be used as an additional therapy in asthma to reduce noneosinophilic airway inflammation.

8.20 Pharmacokinetics: Oral absorption： 55%
Cmax 50 mg oral： 0.75 mg/L after 1.7 h
500 mg oral： 1.65 mg/L after 2 h
Terminal half-life： 2.7–3.5 h
Volume of distribution ：250 L
Plasma protein binding 80%
absorption and distribution
It is more stable to gastric acid than erythromycin, but internal ketalization between the 9-keto group and the C-12 hydroxyl group has been described resulting in an inactive product: pseudo clarithromycin. It is rapidly absorbed orally and absorption is not affected by food. Concentrations in tonsil and lung tissues exceed the simultaneous plasma level by a factor of two and four, respectively.
Metabolism and excretion
The primary metabolic pathway is N-demethylation of the d-desosamine and stereospecific hydroxylation at the 14- position of the erythronolide A ring. Metabolism to the 14-hydroxy derivative is saturable above 800 mg. Around 20&ndash：40% of the administered dose is eliminated in urine. The apparent elimination half-life of the 14-hydroxy metabolite is around 7 h. The parent compound and its principal metabolite are retained in renal impairment, resulting in long apparent elimination half-lives, exceeding 30 and 45 h, respectively, in patients whose creatinine clearance is less than 30 mL/min.

8.21 Side effects: Clarithromycin is well tolerated, producing little gastrointestinal disturbance and only transient changes in some liver function tests.

8.22 Chemical Synthesis: Clarithromycin, (2R,3S,4S, 5R,6R,8R,10R,11R,12S,13R)-3-(2,6-dideoxy- 3-C-3-O-dimethyl-α-L-ribo-hexopyranosyloxy)-6-methoxy-9-oxo-11,12-dihydroxy- 2,4,6,8,10,12-hexamethyl-5-(3,4,6-trideoxy-3-dimethylamino-β-D-xylo-hexopyranosyloxy) cyclopentadecan-13-olide (32.2.2), is a semisynthetic analog of erythromycin A, in which the hydroxyl group at C6 is replaced with a methoxyl group.

8.23 Veterinary Drugs and Treatments: In small animal medicine, clarithromycin is primarily of interest in treating atypical mycobacterial infections or treatment of Helicobacter spp. infections in cats and ferrets. In equine medicine, clarithromycin may be useful in treating Rhodococcus equi infections in foals.

8.24 Usage: A macrolide antibiotic that inhibits bacterial growth by targeting the 50S ribosomal subunit

9. Computational chemical data

Molecular Weight: 747.964g/mol
Molecular Formula: C₃₈H₆₉NO₁₃
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 747.47689126
Monoisotopic Mass: 747.47689126
Complexity: 1190
Rotatable Bond Count: 8
Hydrogen Bond Donor Count: 4
Hydrogen Bond Acceptor Count: 14
Topological Polar Surface Area: 183
Heavy Atom Count: 52
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+PAAAAAAAAAAAAAAAAAAAAAAAAAAkSAAAAAAAAAAAAAAAHgAACAAADXzxgAcCCAMABgAIAICQCAAAAAAAAAAAAAEIAAATEBYAgAAmQAAHIAAXAAHK7PzOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

10. Question & Answer

Are there any interactions between carvidelol and clarithromycin? Jan 08 2022
Interactions happen when multiple medicines are taken together at one time. You should follow the instructions which your doctor has told you to follow. Yes, both clarithromycin and carvidelol do interact with each other. My advice is do not take them together as you experience side effects related...

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Clarithromycin CAS 81103-11-9