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Clindamycin hydrochloride

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Name

Clindamycin hydrochloride

EINECS 244-398-6
CAS No. 21462-39-5 Density ==
PSA 127.56000 LogP 1.52030
Solubility water: 50 mg/mL, clear, colorless Melting Point 141 °C
Formula C18H33ClN2O5S.HCl Boiling Point 647 °C at 760 mmHg
Molecular Weight 461.45 Flash Point 345.1 °C
Transport Information N/A Appearance white crystalline powder
Safety 26-36-37/39 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 21462-39-5 (Clindamycin hydrochloride) Hazard Symbols IrritantXi
Synonyms

7(S)-Chloro-7-deoxylincomycin hyddrochloride;L-threo-a-D-galacto-Octopyranoside, methyl7-chloro-6,7,8-trideoxy-6-[[[(2S,4R)-1-methyl-4-propyl-2-pyrrolidinyl]carbonyl]amino]-1-thio-,hydrochloride (1:1);7-Chloro-7-deoxylincomycin hydrochloride;Antirobe vet.;

Article Data 3

Clindamycin hydrochloride Synthetic route

21462-39-5

clindamycin hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 60℃; for 1h; pH=1; pH-value; Temperature; Large scale;89.5%
21462-39-5

clindamycin hydrochloride

Clindamycin sulfoxide

Conditions
ConditionsYield
With dihydrogen peroxide In water at 10℃; for 2h;97.4%
693-38-9

vinyl palmitate

21462-39-5

clindamycin hydrochloride

clindamycin palmitate

Conditions
ConditionsYield
Stage #1: clindamycin hydrochloride With sodium hydroxide In water
Stage #2: vinyl palmitate In toluene at 20 - 40℃; for 12.5h; Reagent/catalyst; Solvent; Temperature; Enzymatic reaction; regioselective reaction;
90%
108-24-7

acetic anhydride

21462-39-5

clindamycin hydrochloride

2150-02-9

bis(2-mercaptoethyl)ether

1446499-11-1

C30H50N2O10S3

Conditions
ConditionsYield
Stage #1: clindamycin hydrochloride; bis(2-mercaptoethyl)ether With caesium carbonate In N,N-dimethyl-formamide at 50℃; for 12h;
Stage #2: acetic anhydride With pyridine; dmap
87%
7442-07-1

6-amino-2-mercaptobenzothiazole

21462-39-5

clindamycin hydrochloride

7(R)-7-(6-aminobenzo[d]thiazol-2-ylthio)-7-deoxylincomycin

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 16h;41%
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 16h;40%
21462-39-5

clindamycin hydrochloride

(2S,4R)-1-Methyl-4-propyl-pyrrolidine-2-carboxylic acid [(Z)-1-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propenyl]-amide

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 2.5h; Dehydrochlorination;36.28%
21462-39-5

clindamycin hydrochloride

clindamycin sulfoxide

Conditions
ConditionsYield
With sodium perborate pH=~ 8 - 9;
With (Dichloroiodo)benzene
21462-39-5

clindamycin hydrochloride

clindamycin sulfone

Conditions
ConditionsYield
With dihydrogen peroxide; sodium tungstate pH=< 1;
21462-39-5

clindamycin hydrochloride

24729-96-2

clindamycin phosphate

21462-39-5

clindamycin hydrochloride

1446499-23-5

C33H54N4O11S3

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: caesium carbonate / N,N-dimethyl-formamide / 12 h / 50 °C
2: caesium carbonate; tetra-(n-butyl)ammonium iodide / tetrahydrofuran / 16 h / 40 °C
View Scheme
Multi-step reaction with 3 steps
1: caesium carbonate / N,N-dimethyl-formamide / 12 h / 50 °C
2: sodium methylate; methanol / 3 h
3: caesium carbonate; tetra-(n-butyl)ammonium iodide / tetrahydrofuran / 16 h / 40 °C
View Scheme

Clindamycin hydrochloride Specification

The IUPAC name of Clindamycin HCl is (2S,4R)-N-[2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide hydrochloride. With the CAS registry number 21462-39-5, it is also named as 7-Chloro-7-deoxylincomycin hydrochloride. The product's categories are Antibiotic Explorer; Peptide Synthesis / Antibiotics. It is white crystalline powder with bitter taste which is easily soluble in water, soluble in methanol, pyridine, slightly soluble in ethanol, practically insoluble in acetone or chloroform. Additionally, this chemical should be stored at the temperature of 2-8 °C.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.83; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1; (4)ACD/LogD (pH 7.4): 1; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 20; (9)#H bond acceptors: 7; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 10; (12)Enthalpy of Vaporization: 109.28 kJ/mol; (13)Vapour Pressure: 1.79E-19 mmHg at 25°C; (14)Rotatable Bond Count: 7; (15)Tautomer Count: 2; (16)Exact Mass: 460.156548; (17)MonoIsotopic Mass: 460.156548; (18)Topological Polar Surface Area: 128; (19)Heavy Atom Count: 28; (20)Complexity: 502; (21)Defined Atom StereoCenter Count: 7; (22)Undefined Atom StereoCenter Count: 2.

Preparation and Uses of Clindamycin HCl: It is a derivative of lincomycin. And it is semi-synthetic antibiotics obtained from the replacement of lincomycin 7 hydroxyl by chlorine atom. The bactericidal activity to staphylococcus aureus and pneumococcal diseaseis is many times stronger than Lincomycin. So Clindamycin HCl is an antibiotic class medicine. The antimicrobial spectrum is similar to lincomycin.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.

People can use the following data to convert to the molecule structure.
1. SMILES:Cl.O[C@@H]1[C@@H](O)[C@@H](O)[C@H](O[C@@H]1SC)[C@H](NC(=O)[C@@H]2C[C@@H](CCC)CN2C)[C@H](C)Cl
2. InChI:InChI=1/C18H33ClN2O5S.ClH/c1-5-6-10-7-11(21(3)8-10)17(25)20-12(9(2)19)16-14(23)13(22)15(24)18(26-16)27-4;/h9-16,18,22-24H,5-8H2,1-4H3,(H,20,25);1H/t9-,10+,11-,12+,13-,14+,15+,16+,18+;/m0./s1

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intramuscular 1100mg/kg (1100mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA
Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 18, Pg. 354, 1971.
mouse LD50 intraperitoneal 361mg/kg (361mg/kg)   "Compounds Available for Fundamental Research, Volume II-6, Antibiotics, A Program of Upjohn Company Research Laboratory." Vol. 2(6), Pg. -, 1971.
mouse LD50 intravenous 245mg/kg (245mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Toxicology and Applied Pharmacology. Vol. 21, Pg. 516, 1972.
mouse LD50 oral 2539mg/kg (2539mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 18, Pg. 354, 1971.
mouse LD50 subcutaneous 1036mg/kg (1036mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 18, Pg. 354, 1971.
rat LD50 intramuscular 273mg/kg (273mg/kg)   Drugs in Japan Vol. -, Pg. 331, 1990.
rat LD50 intraperitoneal 745mg/kg (745mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 18, Pg. 354, 1971.
rat LD50 oral 2193mg/kg (2193mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 18, Pg. 354, 1971.
rat LD50 subcutaneous 2618mg/kg (2618mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Toxicology and Applied Pharmacology. Vol. 21, Pg. 516, 1972.

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