Product Name

  • Name

    Clindamycin hydrochloride

  • EINECS 244-398-6
  • CAS No. 21462-39-5
  • Article Data3
  • CAS DataBase
  • Density ==
  • 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
  • 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.;
  • PSA 127.56000
  • LogP 1.52030

Synthetic route

clindamycin hydrochloride
21462-39-5

clindamycin hydrochloride

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

clindamycin hydrochloride

Clindamycin sulfoxide

Clindamycin sulfoxide

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

vinyl palmitate

clindamycin hydrochloride
21462-39-5

clindamycin hydrochloride

clindamycin palmitate

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%
acetic anhydride
108-24-7

acetic anhydride

clindamycin hydrochloride
21462-39-5

clindamycin hydrochloride

bis(2-mercaptoethyl)ether
2150-02-9

bis(2-mercaptoethyl)ether

C30H50N2O10S3
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%
6-amino-2-mercaptobenzothiazole
7442-07-1

6-amino-2-mercaptobenzothiazole

clindamycin hydrochloride
21462-39-5

clindamycin hydrochloride

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

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%
clindamycin hydrochloride
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

(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%
clindamycin hydrochloride
21462-39-5

clindamycin hydrochloride

clindamycin sulfoxide

clindamycin sulfoxide

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

clindamycin hydrochloride

clindamycin sulfone

clindamycin sulfone

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

clindamycin hydrochloride

clindamycin phosphate
24729-96-2

clindamycin phosphate

clindamycin hydrochloride
21462-39-5

clindamycin hydrochloride

C33H54N4O11S3
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
21462-39-5

clindamycin hydrochloride

C37H62N4O12S5

C37H62N4O12S5

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: caesium carbonate / N,N-dimethyl-formamide / 12 h / 50 °C
2: methanol / 23 °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: methanol / 23 °C
View Scheme
clindamycin hydrochloride
21462-39-5

clindamycin hydrochloride

C22H42N2O6S3
1446499-12-2

C22H42N2O6S3

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: caesium carbonate / N,N-dimethyl-formamide / 12 h / 50 °C
2: sodium methylate; methanol / 3 h
View Scheme
clindamycin hydrochloride
21462-39-5

clindamycin hydrochloride

C44H82N4O12S6
1446499-13-3

C44H82N4O12S6

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: caesium carbonate / N,N-dimethyl-formamide / 12 h / 50 °C
2: sodium methylate / methanol; dichloromethane
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: sodium methylate / methanol; dichloromethane
View Scheme
clindamycin hydrochloride
21462-39-5

clindamycin hydrochloride

bis(2-mercaptoethyl)ether
2150-02-9

bis(2-mercaptoethyl)ether

C22H42N2O6S3
1446499-12-2

C22H42N2O6S3

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 50℃; for 12h;
clindamycin hydrochloride
21462-39-5

clindamycin hydrochloride

C32H55ClN2O6S

C32H55ClN2O6S

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: iodine / 20 °C / Inert atmosphere
2.1: dicyclohexyl-carbodiimide / dichloromethane / 0.25 h / 0 - 20 °C
2.2: 4 h / 0 °C
View Scheme
clindamycin hydrochloride
21462-39-5

clindamycin hydrochloride

clindamycin undecylenate

clindamycin undecylenate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: iodine / 20 °C / Inert atmosphere
2.1: dicyclohexyl-carbodiimide / dichloromethane / 0.25 h / 0 - 20 °C
2.2: 4 h / 0 °C
3.1: tetrafluoroboric acid; water / methanol / 1 h / 0 - 20 °C
View Scheme
clindamycin hydrochloride
21462-39-5

clindamycin hydrochloride

C30H43ClN2O8S

C30H43ClN2O8S

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: iodine / 20 °C / Inert atmosphere
2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 0 °C
2.2: 3 h / 0 °C
View Scheme
clindamycin hydrochloride
21462-39-5

clindamycin hydrochloride

C27H39ClN2O8S

C27H39ClN2O8S

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: iodine / 20 °C / Inert atmosphere
2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 0 °C
2.2: 3 h / 0 °C
3.1: tetrafluoroboric acid; water / methanol / 5 h / 0 °C
3.2: 72 h
View Scheme
clindamycin hydrochloride
21462-39-5

clindamycin hydrochloride

C51H86Cl2N4O12S2

C51H86Cl2N4O12S2

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: iodine / 20 °C / Inert atmosphere
2.1: dicyclohexyl-carbodiimide / dichloromethane / 0.25 h / 0 - 20 °C
2.2: 4 h / 0 °C
View Scheme
clindamycin hydrochloride
21462-39-5

clindamycin hydrochloride

Clindamycin Dimer of Azelaic Acid

Clindamycin Dimer of Azelaic Acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: iodine / 20 °C / Inert atmosphere
2.1: dicyclohexyl-carbodiimide / dichloromethane / 0.25 h / 0 - 20 °C
2.2: 4 h / 0 °C
3.1: tetrafluoroboric acid; water / methanol / 2 h / 0 °C
View Scheme
clindamycin hydrochloride
21462-39-5

clindamycin hydrochloride

C34H42Cl4N2O9S

C34H42Cl4N2O9S

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: iodine / 20 °C / Inert atmosphere
2.1: dmap / tetrahydrofuran / 1 h / 0 °C
2.2: 38 h / 0 - 35 °C
3.1: dicyclohexyl-carbodiimide / dichloromethane / 0.17 h / 0 °C
3.2: 3 h / 0 °C
4.1: tetrafluoroboric acid; water / methanol / 18 h / 0 °C
View Scheme
clindamycin hydrochloride
21462-39-5

clindamycin hydrochloride

C25H41ClN2O8S

C25H41ClN2O8S

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: iodine / 20 °C / Inert atmosphere
2.1: dmap / tetrahydrofuran / 1 h / 0 °C
2.2: 38 h / 0 - 35 °C
View Scheme
clindamycin hydrochloride
21462-39-5

clindamycin hydrochloride

C37H46Cl4N2O9S

C37H46Cl4N2O9S

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: iodine / 20 °C / Inert atmosphere
2.1: dmap / tetrahydrofuran / 1 h / 0 °C
2.2: 38 h / 0 - 35 °C
3.1: dicyclohexyl-carbodiimide / dichloromethane / 0.17 h / 0 °C
3.2: 3 h / 0 °C
View Scheme
acetone
67-64-1

acetone

clindamycin hydrochloride
21462-39-5

clindamycin hydrochloride

C21H37ClN2O5S

C21H37ClN2O5S

Conditions
ConditionsYield
With iodine at 20℃; Inert atmosphere;
calcium (R)-pantothenate
137-08-6

calcium (R)-pantothenate

clindamycin hydrochloride
21462-39-5

clindamycin hydrochloride

clindamycin mono-pantothenate

clindamycin mono-pantothenate

Conditions
ConditionsYield
In ethanol; water

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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