3D Mol Similar

Clindamycin phosphate

: Iupac Name：[6-[2-chloro-1-[[(2S,4R)-1-methyl-4-propylpyrrolidine-2-carbonyl]amino]propyl]-4,5-dihydroxy-2-methylsulfanyloxan-3-yl] dihydrogen phosphate; CAS No.: 24729-96-2; Molecular Weight：504.96; Modify Date.: 2022-11-25 02:28; Introduction: clindamycin phosphate is a water-soluble ester of the semisynthetic antibiotic produced by a 7 (S)-chloro-substitution of the 7 (R)-hydroxyl group of the parent antibiotic, lincomycin. It is a derivative of lincomycin(a lincosamide). It has primarily bacteriostatic action against Gram-positive aerobes and a wide range of anaerobicbacteria. Doses are expressed in terms of the base: Clindamycin 1g-1.2g clindamycin phosphate. View more+

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1. Names and Identifiers

: 1.1 Name; Clindamycin phosphate; 1.2 Synonyms; (2s-trans)- 2-(dihydrogenphosphate 7(S)-Chloro-7-deoxylincomycin 2-phosphate Cleocin phosphate Cleocin T Clinadac Clindac Clindagel Clindamycin 2-Dihydrogen Phosphate Clindamycin 2-phosphate Clindamycin phosphate BP98,USP25,EP97 CLINDAMYCIN PHOSPHATE/ 7-(S)-CHLORO-7-DEOXY-LINCOMYCIN-2-ORGANIC PHOSPHATE CLINDAMYCINPHOSPHATE,CRYSTAL,USP Clindaymcin Palmitate hydrochloride USP23 Clindesse Clindets Dalacin P Dalacin T L-threo-.alpha.-D-galacto-Octopyranoside, methyl 7-chloro-6,7,8-trideoxy-6-(2S,4R)-1-methyl-4-propyl-2-pyrrolidinylcarbonylamino-1-thio-, 2-(dihydrogen phosphate) L-threo-D-galacto-Octopyranoside, methyl 7-chloro-6,7,8-trideoxy-6-(1-methyl-4-propyl-L-2-pyrrolidinecarboxamido)-1-thio-, 2-(dihydrogen phosphate), trans- α- L-threo-α-D-galacto-Octopyranoside, methyl 7-chloro-6,7,8-trideoxy-6-[[(1-methyl-4-propyl-2-pyrrolidinyl)carbonyl]amino]-1-thio-, 2-(dihydrogen phosphate), (2S-trans)- L-threo-α-D-galacto-Octopyranoside, methyl 7-chloro-6,7,8-trideoxy-6-[[[(2S,4R)-1-methyl-4-propyl-2-pyrrolidinyl]carbonyl]amino]-1-thio-, 2-(dihydrogen phosphate) Methyl 7-chloro-6,7,8-trideoxy-6-trans-(1-methyl-4-propyl-L-2-pyrrolidinecarboxamido)-1-thio-L-threo-α-D-galacto-octopyranoside 2-(dihydrogen phosphate) NSC 618653 U 28508 U-28508E; View all

1.3 CAS No.: 24729-96-2

1.4 CID: 443385

1.5 EINECS(EC#): 246-433-0

1.6 Molecular Formula: C18H34ClN2O8PS (isomer)

1.7 Inchi: InChI=1S/C18H34ClN2O8PS/c1-5-6-10-7-11(21(3)8-10)17(24)20-12(9(2)19)15-13(22)14(23)16(18(28-15)31-4)29-30(25,26)27/h9-16,18,22-23H,5-8H2,1-4H3,(H,20,24)(H2,25,26,27)/t9-,10+,11-,12+,13+,14-,15+,16+,18+/m0/s1

1.8 InChIkey: UFUVLHLTWXBHGZ-MGZQPHGTSA-N

1.9 Canonical Smiles: CCCC1CC(N(C1)C)C(=O)NC(C2C(C(C(C(O2)SC)OP(=O)(O)O)O)O)C(C)Cl

1.10 Isomers Smiles: CCC[C@@H]1C[C@H](N(C1)C)C(=O)N[C@@H]([C@@H]2[C@@H]([C@@H]([C@H]([C@H](O2)SC)OP(=O)(O)O)O)O)[C@H](C)Cl

2. Properties

2.1 Density: 1.41 g/cm³

2.1 Melting point: 114 °C

2.1 Boiling point: 159°C

2.1 Refractive index: 122 ° (C=1, H2O)

2.1 Precise Quality: 504.14600

2.1 PSA: 183.90000

2.1 logP: 0.83530

2.1 Solubility: DMSO: soluble224mg/mL at 25°C

2.2 Appearance: White solid

2.3 Storage: 2-8℃

2.4 Chemical Properties: solid

2.5 Contact Allergens: This lincosanide antibiotic is used in topical form for acne,or systemically has been responsible for exanthematousrashes and acute generalized exanthematous pustulosis.

2.6 pKa: pKa 0.964±0.06(H2O t=21) (Uncertain);6.06 ±0.06 (I=0.008)(H2O t=21) (Uncertain)

2.7 Water Solubility: Freely soluble in water;DMSO: soluble 224mg/mL at 25°C

2.8 Stability: Stable, but store cool. Incompatible with strong oxidizing agents, calcium gluconate, barbiturates, magnesium sulfate, phenytoin, B group sodium vitamins.

2.9 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 General Description: Clindamycin phosphate (Cleocin Phosphate) is the 2-phosphateester of clindamycin. It exists as a zwitterionic structurethat is very soluble in water. It is intended for parenteral(intravenous or intramuscular) administration for the treatmentof serious infections and instances when oral administrationis not feasible. Solutions of clindamycin phosphateare stable at room temperature for 16 days and for up to 32days when refrigerated.

3.2 Usage: Clindamycin phosphate is used topically alone or in conjunction with benzoyl peroxide in the treatment of inflammatory acne vulgaris. In weighing the potential benefits of topical clindamycin therapy, the possibility of serious adverse GI effects associated with the drug should be considered. Therapy of acne vulgaris must be individualized and frequently modified depending on the types of acne lesions which predominate and the response to therapy. Topical anti-infectives, including clindamycin, generally are effective in the treatment of mild to moderate inflammatory acne. However, use of topical anti-infectives as monotherapy may lead to bacterial resistance; this resistance is associated with decreased clinical efficacy.Topical clindamycin is particularly useful when used with benzoyl peroxide or topical retinoids. Results of clinical studies indicate that combination therapy results in a reduction in total lesion counts of 50-70%.

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: R22

4.1 Safety Statements: 36-26

4.1 Hazard Declaration: H302

4.1 RIDADR: NONH for all modes of transport

4.1 Caution Statement: P301 + P312 + P330

4.1 Incompatibilities: Clindamycin phosphate is incompatible with natural rubber closures. Aminophylline, ampicillin, calcium gluconate, ceftriaxone, ciprofloxacin,doxapram, drotrecogin alfa (activated), fluconazole, magnesium sulfate,phenytoin sodium, ranitidine, tramadol.

4.2 WGK Germany: 3

4.2 RTECS: GF2625000

4.2 Safety: Safety Information of?Clindamycin-2-phosphate (CAS NO.24729-96-2):?
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: 36-26?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36: Wear suitable protective clothing.
WGK Germany: 3
RTECS: GF2625000
Poison by intravenous route. Moderately toxic by ingestion, intramuscular, and subcutaneous routes. Human systemic effects by intravenous route: pulse rate increase, blood pressure lowering. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of Cl^?, PO_x, SO_x, and NO_x.; View all

4.3 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intramuscular	1100mg/kg (1100mg/kg)	?	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 14, Pg. 484, 1983.
mouse	LD50	intraperitoneal	784mg/kg (784mg/kg)	?	Drugs under Experimental and Clinical Research. Vol. 3, Pg. 79, 1977.
mouse	LD50	intravenous	820mg/kg (820mg/kg)	?	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 14, Pg. 484, 1983.
mouse	LD50	oral	2539mg/kg (2539mg/kg)	?	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 14, Pg. 484, 1983.
mouse	LD50	subcutaneous	1036mg/kg (1036mg/kg)	?	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 14, Pg. 484, 1983.
rat	LD50	intramuscular	> 3500mg/kg (3500mg/kg)	?	Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 25, Pg. 691, 1983.
rat	LD50	intraperitoneal	745mg/kg (745mg/kg)	?	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 14, Pg. 484, 1983.
rat	LD50	intravenous	321mg/kg (321mg/kg)	?	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 14, Pg. 484, 1983.
rat	LD50	oral	1832mg/kg (1832mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Toxicology and Applied Pharmacology. Vol. 27, Pg. 308, 1974.
rat	LD50	subcutaneous	3861mg/kg (3861mg/kg)	?	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 14, Pg. 484, 1983.
women	TDLo	intravenous	12mg/kg (12mg/kg)	CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP CARDIAC: OTHER CHANGES VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION	Southern Medical Journal. Vol. 75, Pg. 768, 1982.

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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. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

7. Synthesis Route

24729-96-2Total: 1 Synthesis Route

21462-39-5 335 Suppliers

24729-96-2 371 Suppliers

Literatures:
US4849515 A1, ;
Yield: null

8. Precursor and Product

precursor:

21462-39-5

9. Other Information

9.0 Usage: Antibiotic U-28508E, effective against Gram-positive bacteria

9.1 Mesh: Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

9.2 Mesh Entry Terms: Cleocin phosphate

9.3 Use Classification: Human Drugs -> EU pediatric investigation plans|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

10. Computational chemical data

Molecular Weight: 504.96g/mol
Molecular Formula: C₁₈H₃₄ClN₂O₈PS
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 504.1462019
Monoisotopic Mass: 504.1462019
Complexity: 658
Rotatable Bond Count: 9
Hydrogen Bond Donor Count: 5
Hydrogen Bond Acceptor Count: 10
Topological Polar Surface Area: 174
Heavy Atom Count: 31
Defined Atom Stereocenter Count: 9
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: AAADcfB7PAJEAAAAAAAAAAAAAAAAAWAAAAAkAAAAAAAAAAAAAAAAHgYQCCAADT/lwEaCAAPABxgIQAEQEIAAAAAAABAAAIGIAgADUBIhgCBXQAAHFgCTAAH42aOOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

11. Question & Answer

Is 2% Clindamycin Phosphate Vaginal Gel Effective for Treating Bacterial Vaginosis? Sep 24 2024
2% Clindamycin Phosphate Vaginal Gel is a thermosetting bioadhesive formulation that contains 2% clindamycin phosphate and is used to treat bacterial vaginosis (BV). Studies have shown that this vagin..
Why is Clindamycin Phosphate Used in Medicine? Jun 04 2024
Clindamycin phosphate is a derivative of lincomycin synthesized by Magerlein et al. in 1966, belonging to the lincosamide class of antibiotics. It is an antibiotic drug that has no antibacterial activ..
Why is Clindamycin Phosphate the Preferred Form of Clindamycin Injection? Mar 28 2023
Clindamycin, a derivative of lincomycin synthesized by Magerlein et al. in 1966, belongs to the lincosamide class of antibiotics. It has a broad spectrum of antibacterial activity, high oral absorptio..
What is Clindamycin phosphate and can it be used as an antibiotic? Mar 01 2023
Clindamycin phosphate, a lesser-known antibacterial agent, has excellent antimicrobial activity. Upon entering the body, it rapidly hydrolyzes into clindamycin and exhibits unique pharmacological effe..

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13. Realated Product Infomation

28708-34-1 Clindamycin 3-Phosphate

54887-31-9 Clindamycin B 2-Phosphate

620181-05-7 7-Epi Clindamycin 2-Phosphate

1309349-64-1 3'-6'-Dehydro Clindamycin 2-Phosphate

18323-44-9 Clindamycin

25507-13-5 Clindamycin

21462-39-5 Clindamycin hydrochloride

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