CAS No.81103-11-9,Clarithromycin Suppliers

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Basic Information

Molecular Structure:
CAS No.:	81103-11-9
Name:	Clarithromycin
Article Data:	13

Formula:	C₃₈H₆₉NO₁₃
Molecular Weight:	747.965
Synonyms:	Adel;Mabicrol;TE 031;Klaricid;Biaxin (TN);(3R,4S,5S,6R,7R,9R,11R,12R,13R,14R)-6-(4-dimethylamino-3-hydroxy-6-methyl-oxan-2-yl)oxy-14-ethyl-12,13-dihydroxy-4-(5-hydroxy-4-methoxy-4,6-dimethyl-oxan-2-yl)oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione;Clarithromycine [INN-French];Clacine;Trovafloxacin & Clarithromycin;6-o-Methoxyerythromycin;(3R,4S,6R,7R,9R,11R,12R,13R,14R)-6-[(2S,3R,4S,6R)-4-dimethylamino-3-hydroxy-6-methyl-oxan-2-yl]oxy-14-ethyl-12,13-dihydroxy-4-[(2S,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-oxan-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione;Abbott-56268;Clarith;Klacid;Claritromicina [INN-Spanish];Klaciped;6-O-Methylerythromycin A;Kofron;Heliclar;Klarin;TE-031;TE031;Maclar;Klaricid Pediatric;Biaxin;(3R,4S,5S,6R,7R,9R,11R,12R,13R,14R)-6-[(2S,3R,4S,6R)-4-dimethylamino-3-hydroxy-6-methyl-oxan-2-yl]oxy-14-ethyl-12,13-dihydroxy-4-[(2S,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-oxan-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione;Helas;Veclam;Klarid;Clathromycin;Zeclar;Clarithromycinum [INN-Latin];Claribid;Klax;Mavid;
EINECS:	1806241-263-5
Density:	1.184 g/cm³
Melting Point:	217-220 °C
Boiling Point:	805.478 °C at 760 mmHg
Flash Point:	440.937 °C
Solubility:	99.48mg/L(20 oC)
Appearance:	Colourless crystalline needles
Hazard Symbols:	Xn， Xi
Risk Codes:	22-36/37/38
Safety:	26-36
PSA:	182.91000
LogP:	2.43970

Synthetic route

: 118074-07-0
6-O-methylerythromycin A N-oxide

: 81103-11-9
clarithromycin

Conditions

Conditions	Yield
Stage #1: 6-O-methylerythromycin A N-oxide With tin(ll) chloride In isopropyl alcohol at 30 - 40℃; for 2h; Stage #2: With sodium hydrogencarbonate In water; isopropyl alcohol	96%
With bis(tri-n-butyltin) In tetrahydrofuran for 24h; Heating / reflux;	95%
With hydrogen; W4 Raney-nickel In ethanol at 40 - 50℃; for 3h;	92%
With potassium hydroxide; nickel-aluminum alloy In methanol; water at 35 - 40℃; for 3.5h;	92%
Stage #1: 6-O-methylerythromycin A N-oxide With tin(ll) chloride In dichloromethane at 20℃; for 1.5h; Stage #2: With sodium carbonate In dichloromethane; water	32%

: 930287-49-3
clarythromycin 9-O-(2-pyrimidyl)oxime

: 81103-11-9
clarithromycin

Conditions

Conditions	Yield
With sodium hydrogensulfite In ethanol; water at 80℃; for 6h;	95%

: 50-00-0
formaldehyd

: 118074-07-0
6-O-methylerythromycin A N-oxide

: 81103-11-9
clarithromycin

Conditions

Conditions	Yield
Stage #1: 6-O-methylerythromycin A N-oxide With sodium hydrogensulfite In ethanol; water at 20℃; for 1h; Stage #2: With sodium carbonate In ethanol; water Stage #3: formaldehyd With formic acid; sodium carbonate more than 3 stages;	92%
Stage #1: 6-O-methylerythromycin A N-oxide With sodium hydrogensulfite In ethanol; water at 20℃; for 1h; Stage #2: With sodium carbonate In ethanol; water Stage #3: formaldehyd With formic acid; ammonia more than 3 stages;	30%

: 103450-87-9, 127253-05-8, 127253-06-9
clarithromycin 9-oxime

: 81103-11-9
clarithromycin

Conditions

Conditions	Yield
With sodium disulfide In ethanol Heating;	68%

: 130034-54-7
9-deoxo-9-imino-6-O-methylerythromycin A

: 81103-11-9
clarithromycin

Conditions

Conditions	Yield
With water In methanol at 23℃; pH 12.4 or pH 7;
With hydrogenchloride; water In ethanol pH=5 - 6;

: 2',4''-[O-bis(trimethylsilyl)]clarithromycin 9-[O-(dimethylthexylsilyl)oxime]

: 81103-11-9
clarithromycin

Conditions

Conditions	Yield
With sodium metabisulfite; formic acid In ethanol for 0.5h; Hydrolysis; Heating;	4.32 g

: 930287-46-0
6-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-14-ethyl-7,12,13-trihydroxy-4-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione 10-(O-pyrimidin-2-yl-oxime)

: 81103-11-9
clarithromycin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 90 percent / trimethylsilyl-imidazole / CH2Cl2 / 2 h / 0 °C 2: 83 percent / KOH / dimethylsulfoxide 3: 97 percent / HCO2H / ethanol; H2O 4: 95 percent / sodium hydrogen sulfite / ethanol; H2O / 6 h / 80 °C View Scheme

: 930287-48-2
C48H88N4O13Si2

: 81103-11-9
clarithromycin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 97 percent / HCO2H / ethanol; H2O 2: 95 percent / sodium hydrogen sulfite / ethanol; H2O / 6 h / 80 °C View Scheme

: 930287-47-1
2',4''-O-bistrimethylsilyl erythromycin A 9-O-(2-pyrimydyl)oxime

: 81103-11-9
clarithromycin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 83 percent / KOH / dimethylsulfoxide 2: 97 percent / HCO2H / ethanol; H2O 3: 95 percent / sodium hydrogen sulfite / ethanol; H2O / 6 h / 80 °C View Scheme

: erythromycin A (9E)-oxime hydrochloride

: 81103-11-9
clarithromycin

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 93 percent / t-BuOK / 2 h / 80 °C 2: 90 percent / trimethylsilyl-imidazole / CH2Cl2 / 2 h / 0 °C 3: 83 percent / KOH / dimethylsulfoxide 4: 97 percent / HCO2H / ethanol; H2O 5: 95 percent / sodium hydrogen sulfite / ethanol; H2O / 6 h / 80 °C View Scheme

Raw Materials

13127-18-9

50-00-0

119699-81-9

111321-02-9

74-88-4

Downstream Products

160145-83-5

191114-48-4

Total:306 Page 1 of 9 1 2 3 4 5 6 …9 Next>>

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Specification

1. Introduction of Clarithromycin
Clarithromycin is one kind of white or almost white crystalline powder or colourless crystalline needles. The Systematic (IUPAC) name of this chemical is (3R,4S,5S,6R,7R,9R,11S,12R,13S,14S)-6-{[(2S,3R,4S,6R) -4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy} -14-ethyl-12,13-dihydroxy-4-{[(2R,4S,5S,6S)-5-hydroxy -4-methoxy-4,6-dimethyloxan-2-yl]oxy}-7 -methoxy-3,5,7,9,11,13-hexamethyl -1-oxacyclotetradecane-2,10-dione. The Classification Code of it is Anti-Bacterial Agents; Anti-Infective Agents; Antibacterial; Drug / Therapeutic Agent; Enzyme Inhibitors; Human Data; Protein synthesis inhibitors.

Clarithromycin belongs to Antibiotics;APIs;Antibiotics for Research and Experimental Use;Biochemistry;Macrolides (Antibiotics for Research and Experimental Use);Intermediates & Fine Chemicals;Pharmaceuticals;API's;1694 Pharmaceuticals&Personal Care Products;A - KAntibiotics;Antibacterial;Antibiotics A to;Antibiotics A-FAntibiotics;Chemical Structure Class;MacrolidesEPA;Neats;Spectrum of Activity. Besides, it should stored in -20°C Freezer.

2. Properties of Clarithromycin
Physical properties about Clarithromycin are:
(1)Index of Refraction: 1.526; (2)Molar Refractivity: 194 cm³; (3)Molar Volume: 631.9 cm³; (4)Density: 1.18 g/cm³; (5)Solubility: Insoluble; (6)Flash Point: 440.9 °C; (7)Melting Point: 217-220 °C; (8)Surface Tension: 48.7 dyne/cm; (9)Enthalpy of Vaporization: 133.36 kJ/mol; (10)Vapour Pressure: 5.06E-30 mmHg at 25 °C; (11)Boiling Point of 6-o-Methoxyerythromycin: 805.5 °C at 760 mmHg.

3. Structure Descriptors of Clarithromycin
(1)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
(2)Isomeric 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
(3)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
(4)InChIKey: AGOYDEPGAOXOCK-KCBOHYOISA-N

4. Toxicity of Clarithromycin

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LD	oral	> 5gm/kg (5000mg/kg)	GASTROINTESTINAL: NAUSEA OR VOMITING BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BLOOD: HEMORRHAGE	Kiso to Rinsho. Clinical Report. Vol. 22, Pg. 1453, 1988.
mouse	LD50	intraperitoneal	850mg/kg (850mg/kg)	LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE	Chemotherapy Vol. 36(Suppl,
mouse	LD50	intravenous	173mg/kg (173mg/kg)		Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 22, Pg. 769, 1991.
mouse	LD50	oral	1230mg/kg (1230mg/kg)	BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)	Kiso to Rinsho. Clinical Report. Vol. 22, Pg. 1433, 1988.
mouse	LD50	subcutaneous	> 5gm/kg (5000mg/kg)	SKIN AND APPENDAGES (SKIN): CORROSIVE: AFTER TOPICAL EXPOSURE	Chemotherapy Vol. 36(Suppl,
rat	LD50	intraperitoneal	669mg/kg (669mg/kg)	LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE	Chemotherapy Vol. 36(Suppl,
rat	LD50	oral	1270mg/kg (1270mg/kg)	BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)	Kiso to Rinsho. Clinical Report. Vol. 22, Pg. 1433, 1988.
rat	LD50	subcutaneous	> 5gm/kg (5000mg/kg)	SKIN AND APPENDAGES (SKIN): CORROSIVE: AFTER TOPICAL EXPOSURE	Chemotherapy Vol. 36(Suppl,
women	TDLo	oral	30mg/kg/3D-I (30mg/kg)	CARDIAC: CHANGE IN RATE CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP	Annals of Emergency Medicine. Vol. 30, Pg. 542, 1997.

5. Physical Properties of Clarithromycin

Physical Property	Value	Units	Temp (deg C)	Source
Melting Point	220 dec	deg C		EXP
pKa Dissociation Constant	8.99	(none)	25	EXP
log P (octanol-water)	3.16	(none)		EXP
Water Solubility	0.342	mg/L	25	EST
Vapor Pressure	8.60E-27	mm Hg	25	EST
Henry's Law Constant	1.73E-29	atm-m3/mole	25	EST
Atmospheric OH Rate Constant	4.78E-10	cm3/molecule-sec	25	EST

6. Safety information of Clarithromycin
A poison by intraperitoneal and intravenous routes. Moderately toxic by ingestion. Human systemic effects. When heated to decomposition it emits toxic vapors of NOx.
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

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.

7. Uses of Clarithromycin
The usage of Clarithromycin (CAS NO.81103-11-9) is a semi-synthetic macrolide antibiotic, a derivative of erythromycin. And it is a macrolide antibiotic used to treat upper and lower respiratory tract infections, skin and soft tissue infections. Clarithromycin is a macrolide antibiotic used to treat pharyngitis, tonsillitis, acute maxillary sinusitis, acute bacterial exacerbation of chronic bronchitis, pneumonia, skin and skin structure infections. In addition, it is sometimes used to treat legionellosis, Helicobacter pylori, and lyme disease.

8. Production of Clarithromycin
(1)Use Erythromycin as the raw material and get the methyl off amino by using hydrolysis.
(2)Then get it reaction with Benzyl chloroformate and protect 5-tetrahydropyran ring side-chain hydroxyl and amino.
(3)In the methyl iodide reaction of dimethyl sulfoxide and tetrahydrofuran, carry out six on the methylation of hydroxyl and deprotected by catalytic hydrogenolysis,then reaction with the amino-formaldehyde.
(4)Finally,it is reduced to methyl, named clarithromycin.

The detailed steps are as follows:

Production of Clarithromycin