CLINDAMYCIN PHOSPHATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H34ClN2O8PS
Molecular Weight	504.963
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC[C@@H]1C[C@H](N(C)C1)C(=O)N[C@H]([C@H](C)Cl)[C@H]2O[C@H](SC)[C@H](OP(O)(O)=O)[C@@H](O)[C@H]2O

InChI

InChIKey=UFUVLHLTWXBHGZ-MGZQPHGTSA-N

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

HIDE SMILES / InChI

Molecular Formula	C18H34ClN2O8PS
Molecular Weight	504.963
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry
Defined Stereocenters	9 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Clindamycin phosphate is the prodrug of clindamycin with no antimicrobial activity in vitro but can be rapidly converted in vivo to the parent drug, clindamycin, by phosphatase ester hydrolysis. It is indicated in the treatment of serious infections caused by susceptible anaerobic bacteria: Lower respiratory tract infections including pneumonia, empyema, and lung abscess caused by anaerobes; Skin and skin structure infections; Gynecological infections including endometritis, nongonococcal tubo-ovarian abscess, pelvic cellulitis, and postsurgical vaginal cuff infection caused by susceptible anaerobes; Intra-abdominal infections; Septicemia; Bone and joint infections. Orally and parenterally administered clindamycin has been associated with severe colitis, which may end fatally. Abdominal pain, gastrointestinal disturbances, gram-negative folliculitis, eye pain and contact dermatitis have also been reported in association with the use of topical formulations of clindamycin. Clindamycin has been shown to have neuromuscular blocking properties that may enhance the action of other neuromuscular blocking agents

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial 70S ribosome 166	Inhibitor 7468	Skin Diseases, Bacterial
Bacterial 70S ribosome 166	Inhibitor 7468	Acne Vulgaris

Conditions

Condition	Modality	Targets	Highest Phase	Product
Reproductive Tract Infections 15	Primary	Bacterial 70S ribosome	Approved 7883	CLEOCIN HYDROCHLORIDE
Skin Diseases, Bacterial 59	Primary	Bacterial 70S ribosome	Approved 7883	CLEOCIN HYDROCHLORIDE
Pelvic Infection 14	Primary	Bacterial 70S ribosome	Approved 7883	CLEOCIN HYDROCHLORIDE
Respiratory Tract Infections 127	Primary	Bacterial 70S ribosome	Approved 7883	CLEOCIN HYDROCHLORIDE
Respiratory Tract Infections 127	Primary	Bacterial 70S ribosome	Approved 7883	CLEOCIN PHOSPHATE
Sepsis 39	Primary	Bacterial 70S ribosome	Approved 7883	CLEOCIN HYDROCHLORIDE
Bone Diseases, Infectious 26	Primary	Bacterial 70S ribosome	Approved 7883	CLEOCIN PHOSPHATE
Soft Tissue Infections 13	Primary	Bacterial 70S ribosome	Approved 7883	CLEOCIN HYDROCHLORIDE
Intraabdominal Infections 44	Primary	Bacterial 70S ribosome	Approved 7883	CLEOCIN HYDROCHLORIDE
Reproductive Tract Infections 15	Primary	Bacterial 70S ribosome	Approved 7883	CLEOCIN PHOSPHATE
Intraabdominal Infections 44	Primary	Bacterial 70S ribosome	Approved 7883	CLEOCIN PHOSPHATE
Acne Vulgaris 65	Primary	Bacterial 70S ribosome	Approved 7883	CLEOCIN T
Sepsis 39	Primary	Bacterial 70S ribosome	Approved 7883	CLEOCIN PHOSPHATE
Skin and Connective Tissue Diseases 6	Primary	Bacterial 70S ribosome	Approved 7883	CLEOCIN PHOSPHATE
Opportunistic infections of HIV infection 9			Approved (off-label) 8

PubMed

Title	Date	PubMed
A simple, efficient and inexpensive program for preventing prematurity.	2001	11447924
Occurrence of metronidazole and imipenem resistance among Bacteroides fragilis group clinical isolates in Hungary.	2001	11426861
Efficacy of clindamycin vaginal ovule (3-day treatment) vs. clindamycin vaginal cream (7-day treatment) in bacterial vaginosis.	2001	11368263
Lemierre's syndrome with spondylitis and pulmonary and gluteal abscesses associated with Mycoplasma pneumoniae pneumonia.	2001 Apr	11399017
Clinical features of patients with invasive Eikenella corrodens infections and microbiological characteristics of the causative isolates.	2001 Apr	11399011
Chronic granulomatous disease: a case report.	2001 Apr	11393130
Thoracic spondylitis mimicking idiopathic scoliosis: a case report.	2001 Apr	11360774
Individualized pharmacokinetic monitoring results in less aminoglycoside-associated nephrotoxicity and fewer associated costs.	2001 Apr	11310518
Clindamycin suspension and endocarditis prophylaxis.	2001 Apr 28	11352383
Laparoscopic management of adnexal masses.	2001 Apr-Jun	11394427
Lipid analysis of follicular casts from cyanoacrylate strips as a new method for studying therapeutic effects of antiacne agents.	2001 Jul	11453902
A rare case of primary group A streptococcal peritonitis.	2001 Jul	11450776
Susceptibility of the Bacteroides fragilis group to newer quinolones and other standard anti-anaerobic agents.	2001 Jul	11418523
Elution characteristics of vancomycin, teicoplanin, gentamicin and clindamycin from calcium sulphate beads.	2001 Jul	11418521
Cutaneous botryomycosis of the cervicofacial region.	2001 Jul	11400249
Comparison of in-vitro activities of SCH27899 and other antibiotics against Mycoplasma pneumoniae.	2001 Jun	11455504
The emergence of erythromycin-resistant Streptococcus pyogenes in Seoul, Korea.	2001 Jun	11455497
Eikenella corrodens: an unusual cause of severe parapneumonic infection and empyema in immunocompetent patients.	2001 Jun	11446395
[Chronic osteomyelitis of the ilium after autologous bone harvesting in Albers-Schonberg osteopetrosis. A case report].	2001 Jun	11446071
Bilateral peritonsillar abscess: case report and presentation of its clinical appearance.	2001 Jun	11433841
Transfusion-transmitted babesiosis in Ontario: first reported case in Canada.	2001 Jun 12	11450217
Infection of hamsters with epidemiologically important strains of Clostridium difficile.	2001 Jun 15	11372028
A meta-analysis of salvage therapy for Pneumocystis carinii pneumonia.	2001 Jun 25	11427101
[Antibiotic prophylaxis in oncologic pharyngolaryngeal surgery: ceftriaxone versus clindamycin and gentamycin].	2001 Mar	11428270
Antibiotic susceptibility of Clostridium difficile isolates from adult patients at two Jamaican hospitals. Clinical and epidemiological implications.	2001 Mar	11398289
[Ocular parasitoses and mycoses: cases diagnosed in the Central University Hospital of Sfax between 1996 and 1999].	2001 Mar	11346972
Prevalence and phenotypes of erythromycin-resistant Streptococcus pneumoniae in Shanghai, China.	2001 Mar	11337187
A 2-step non-surgical procedure and systemic antibiotics in the treatment of rapidly progressive periodontitis.	2001 Mar	11327054
Persistence of Plasmodium falciparum in the placenta after apparently effective quinidine/clindamycin therapy.	2001 Mar	11324359
[The therapeutic approach to necrotizing fasciitis].	2001 Mar	11319371
[Cellulitis and necrotizing fasciitis: microbiology and pathogenesis].	2001 Mar	11319369
Antimicrobial resistance in viridans group streptococci among patients with and without the diagnosis of cancer in the USA, Canada and Latin America.	2001 Mar	11318814
In vitro activity and pharmacodynamics of azithromycin and clarithromycin against Streptococcus pneumoniae based on serum and intrapulmonary pharmacokinetics.	2001 Mar	11318076
Antimicrobial susceptibilities of Erysipelothrix rhusiopathiae isolated from pigs with swine erysipelas in Japan, 1988-1998.	2001 Mar	11315521
Dose-escalation, phase I/II study of azithromycin and pyrimethamine for the treatment of toxoplasmic encephalitis in AIDS.	2001 Mar 30	11316995
[Dermo-hypodermitis and necrotizing fasciitis].	2001 Mar 31	11345864
Serotyping and antimicrobial susceptibility of group B Streptococcus over an eight-year period in southern Taiwan.	2001 May	11453594
Effect of clindamycin therapy on phagocytic and oxidative activity profiles of spleen mononuclear cells in Babesia rodhaini-infected mice.	2001 May	11411505
Clinical inquiries. What are the most effective treatments for bacterial vaginosis in nonpregnant women?	2001 May	11350701
Antibiotic resistance patterns of group B streptococci in late third-trimester rectovaginal cultures.	2001 May	11349176
Vaginal clindamycin in preventing preterm birth and peripartal infections in asymptomatic women with bacterial vaginosis: a randomized, controlled trial.	2001 May	11339909
High prevalence of carriage of antibiotic-resistant Streptococcus pneumoniae in children in Kampala Uganda.	2001 May	11337227
When to suspect and how to monitor babesiosis.	2001 May 15	11388711
Worldwide prevalence of antimicrobial resistance in Streptococcus pneumoniae, Haemophilus influenzae, and Moraxella catarrhalis in the SENTRY Antimicrobial Surveillance Program, 1997-1999.	2001 May 15	11320449
Sensitive and specific determination of clindamycin in human serum and bone tissue applying liquid chromatography-atmospheric pressure chemical ionization-mass spectrometry.	2001 May 5	11393698
Multi-laboratory assessment of the linezolid spectrum of activity using the Kirby-Bauer disk diffusion method: Report of the Zyvox Antimicrobial Potency Study (ZAPS) in the United States.	2001 May-Jun	11448565
Intravitreal clindamycin and dexamethasone for toxoplasmic retinochoroiditis.	2001 May-Jun	11371084
Prevalence of serotypes and molecular epidemiology of Streptococcus pneumoniae strains isolated from children in Beijing, China: identification of two novel multiply-resistant clones.	2001 Spring	11310804
In vitro activity of 19 antimicrobial agents against enterococci from healthy subjects and hospitalized patients and use of an ace gene probe from Enterococcus faecalis for species identification.	2001 Spring	11310802
Erythromycin and amoxicillin?	2001 Winter	11324196

Patents

Sample Use Guides

In Vivo Use Guide

150 to 300 mg every 6 hours (Serious infections), 300 to 450 mg every 6 hours (More severe infections), 8 to 16 mg/kg/day divided into three or four equal doses (Serious infections in pediatric patients), 16 to 20 mg/kg/day divided into three or four equal doses (More severe infections in pediatric patients).

Route of Administration: Topical; Vaginal; Intramuscular; Intravenous

In Vitro Use Guide

MIC=0.03-0.12 ug/ml (Aerobic Pathogens), MIC=0.06-0.25 ug/ml (Anaerobes).

Substance Class	Chemical Created by `admin` on `Tue Oct 22 00:37:02 UTC 2019` Edited by `admin` on `Tue Oct 22 00:37:02 UTC 2019`
Record UNII	EH6D7113I8
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CLINDAMYCIN PHOSPHATE

Official Name

English

DUAC COMPONENT CLINDAMYCIN PHOSPHATE

Common Name

English

CLINDETS

Brand Name

English

ACANYA COMPONENT CLINDAMYCIN PHOSPHATE

Common Name

English

BENZACLIN COMPONENT CLINDAMYCIN PHOSPHATE

Common Name

English

CLINDA-DERM

Brand Name

English

CLINDAMYCIN PHOSPHATE [USP-RS]

Common Name

English

CLINDAC

Brand Name

English

CLINDAMYCIN PHOSPHATE [USP]

Common Name

English

CLINDAMYCIN PHOSPHATE [WHO-IP]

Common Name

English

CLINDESSE

Brand Name

English

CLINDAMYCIN PHOSPHATE [WHO-DD]

Common Name

English

L-THREO-.ALPHA.-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)-

Common Name

English

CLEOCIN PHOSPHATE

Brand Name

English

CLINDAMYCINI PHOSPHAS [WHO-IP LATIN]

Common Name

English

NSC-618653

Code

English

CLINDAMYCIN PHOSPHATE [MART.]

Common Name

English

CLINDAGEL

Brand Name

English

DALACIN T

Brand Name

English

U-28,508

Code

English

CLINDAMYCIN PHOSPHATE [USAN]

Common Name

English

U-28508

Code

English

CLINDAMYCIN PHOSPHATE [VANDF]

Common Name

English

ZIANA COMPONENT CLINDAMYCIN PHOSPHATE

Common Name

English

VELTIN COMPONENT CLINDAMYCIN PHOSPHATE

Brand Name

English

CLINDAMYCIN PHOSPHATE COMPONENT OF VELTIN

Brand Name

English

CLINDAMYCIN PHOSPHATE [ORANGE BOOK]

Common Name

English

CLINDAMYCIN PHOSPHATE [JAN]

Common Name

English

CLINDAMYCIN (AS PHOSPHATE)

Common Name

English

CLINDAMYCIN 2-DIHYDROGEN PHOSPHATE

Common Name

English

CLINDAMYCIN PHOSPHATE COMPONENT OF ZIANA

Common Name

English

EVOCLIN

Brand Name

English

CLINDAMYCIN PHOSPHATE COMPONENT OF BENZACLIN

Common Name

English

7(S)-CHLORO-7-DEOXYLINCOMYCIN 2-PHOSPHATE

Common Name

English

METHYL 7-CHLORO-6,7,8-TRIDEOXY-6-(1-METHYL-TRANS-4-PROPYL-L-2-PYRROLIDINECARBOXAMIDO)-1-THIO-L-THREO-.ALPHA.-D-GALACTO-OCTOPYRANOSIDE 2-(DIHYDROGEN PHOSPHATE)

Common Name

English

L-THREO-.ALPHA.-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)

Common Name

English

CLINDAMYCIN PHOSPHATE COMPONENT OF ACANYA

Common Name

English

CLINADAC

Brand Name

English

CLEOCIN

Brand Name

English

CLINDAMYCIN 2-PHOSPHATE

Common Name

English

CLINDAMYCIN PHOSPHATE COMPONENT OF DUAC

Common Name

English

CLINDAMYCIN 2-DIHYDROGEN PHOSPHATE [MI]

Common Name

English

CLINDAMYCIN PHOSPHATE [EP]

Common Name

English

CLEOCIN T

Brand Name

English

CLINDAMYCIN PHOSPHATE HYDRATE

Official Name

English

U 28508

Code

English

DALACIN P

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C82922