U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of CLINDAMYCIN PHOSPHATE

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

TargetsConditions
PubMed

PubMed

TitleDatePubMed
A simple, efficient and inexpensive program for preventing prematurity.
2001
Occurrence of metronidazole and imipenem resistance among Bacteroides fragilis group clinical isolates in Hungary.
2001
Efficacy of clindamycin vaginal ovule (3-day treatment) vs. clindamycin vaginal cream (7-day treatment) in bacterial vaginosis.
2001
Lemierre's syndrome with spondylitis and pulmonary and gluteal abscesses associated with Mycoplasma pneumoniae pneumonia.
2001 Apr
Clinical features of patients with invasive Eikenella corrodens infections and microbiological characteristics of the causative isolates.
2001 Apr
Chronic granulomatous disease: a case report.
2001 Apr
Thoracic spondylitis mimicking idiopathic scoliosis: a case report.
2001 Apr
Individualized pharmacokinetic monitoring results in less aminoglycoside-associated nephrotoxicity and fewer associated costs.
2001 Apr
Clindamycin suspension and endocarditis prophylaxis.
2001 Apr 28
Laparoscopic management of adnexal masses.
2001 Apr-Jun
Lipid analysis of follicular casts from cyanoacrylate strips as a new method for studying therapeutic effects of antiacne agents.
2001 Jul
A rare case of primary group A streptococcal peritonitis.
2001 Jul
Susceptibility of the Bacteroides fragilis group to newer quinolones and other standard anti-anaerobic agents.
2001 Jul
Elution characteristics of vancomycin, teicoplanin, gentamicin and clindamycin from calcium sulphate beads.
2001 Jul
Cutaneous botryomycosis of the cervicofacial region.
2001 Jul
Comparison of in-vitro activities of SCH27899 and other antibiotics against Mycoplasma pneumoniae.
2001 Jun
The emergence of erythromycin-resistant Streptococcus pyogenes in Seoul, Korea.
2001 Jun
Eikenella corrodens: an unusual cause of severe parapneumonic infection and empyema in immunocompetent patients.
2001 Jun
[Chronic osteomyelitis of the ilium after autologous bone harvesting in Albers-Schonberg osteopetrosis. A case report].
2001 Jun
Bilateral peritonsillar abscess: case report and presentation of its clinical appearance.
2001 Jun
Transfusion-transmitted babesiosis in Ontario: first reported case in Canada.
2001 Jun 12
Infection of hamsters with epidemiologically important strains of Clostridium difficile.
2001 Jun 15
A meta-analysis of salvage therapy for Pneumocystis carinii pneumonia.
2001 Jun 25
[Antibiotic prophylaxis in oncologic pharyngolaryngeal surgery: ceftriaxone versus clindamycin and gentamycin].
2001 Mar
Antibiotic susceptibility of Clostridium difficile isolates from adult patients at two Jamaican hospitals. Clinical and epidemiological implications.
2001 Mar
[Ocular parasitoses and mycoses: cases diagnosed in the Central University Hospital of Sfax between 1996 and 1999].
2001 Mar
Prevalence and phenotypes of erythromycin-resistant Streptococcus pneumoniae in Shanghai, China.
2001 Mar
A 2-step non-surgical procedure and systemic antibiotics in the treatment of rapidly progressive periodontitis.
2001 Mar
Persistence of Plasmodium falciparum in the placenta after apparently effective quinidine/clindamycin therapy.
2001 Mar
[The therapeutic approach to necrotizing fasciitis].
2001 Mar
[Cellulitis and necrotizing fasciitis: microbiology and pathogenesis].
2001 Mar
Antimicrobial resistance in viridans group streptococci among patients with and without the diagnosis of cancer in the USA, Canada and Latin America.
2001 Mar
In vitro activity and pharmacodynamics of azithromycin and clarithromycin against Streptococcus pneumoniae based on serum and intrapulmonary pharmacokinetics.
2001 Mar
Antimicrobial susceptibilities of Erysipelothrix rhusiopathiae isolated from pigs with swine erysipelas in Japan, 1988-1998.
2001 Mar
Dose-escalation, phase I/II study of azithromycin and pyrimethamine for the treatment of toxoplasmic encephalitis in AIDS.
2001 Mar 30
[Dermo-hypodermitis and necrotizing fasciitis].
2001 Mar 31
Serotyping and antimicrobial susceptibility of group B Streptococcus over an eight-year period in southern Taiwan.
2001 May
Effect of clindamycin therapy on phagocytic and oxidative activity profiles of spleen mononuclear cells in Babesia rodhaini-infected mice.
2001 May
Clinical inquiries. What are the most effective treatments for bacterial vaginosis in nonpregnant women?
2001 May
Antibiotic resistance patterns of group B streptococci in late third-trimester rectovaginal cultures.
2001 May
Vaginal clindamycin in preventing preterm birth and peripartal infections in asymptomatic women with bacterial vaginosis: a randomized, controlled trial.
2001 May
High prevalence of carriage of antibiotic-resistant Streptococcus pneumoniae in children in Kampala Uganda.
2001 May
When to suspect and how to monitor babesiosis.
2001 May 15
Worldwide prevalence of antimicrobial resistance in Streptococcus pneumoniae, Haemophilus influenzae, and Moraxella catarrhalis in the SENTRY Antimicrobial Surveillance Program, 1997-1999.
2001 May 15
Sensitive and specific determination of clindamycin in human serum and bone tissue applying liquid chromatography-atmospheric pressure chemical ionization-mass spectrometry.
2001 May 5
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
Intravitreal clindamycin and dexamethasone for toxoplasmic retinochoroiditis.
2001 May-Jun
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
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
Erythromycin and amoxicillin?
2001 Winter
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
  • Download
Name Type Language
CLINDAMYCIN PHOSPHATE
EP   MART.   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
USAN  
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
MI  
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
JAN  
Official Name English
U 28508
Code English
DALACIN P
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C82922
Created by admin on Tue Oct 22 00:37:02 UTC 2019 , Edited by admin on Tue Oct 22 00:37:02 UTC 2019
Code System Code Type Description
RXCUI
797272
Created by admin on Tue Oct 22 00:37:02 UTC 2019 , Edited by admin on Tue Oct 22 00:37:02 UTC 2019
PRIMARY RxNorm
EPA CompTox
24729-96-2
Created by admin on Tue Oct 22 00:37:02 UTC 2019 , Edited by admin on Tue Oct 22 00:37:02 UTC 2019
PRIMARY
ECHA (EC/EINECS)
246-433-0
Created by admin on Tue Oct 22 00:37:02 UTC 2019 , Edited by admin on Tue Oct 22 00:37:02 UTC 2019
PRIMARY
PUBCHEM
443385
Created by admin on Tue Oct 22 00:37:02 UTC 2019 , Edited by admin on Tue Oct 22 00:37:02 UTC 2019
PRIMARY
JAPANESE REVIEW
DUAC
Created by admin on Tue Oct 22 00:37:02 UTC 2019 , Edited by admin on Tue Oct 22 00:37:02 UTC 2019
PRIMARY APPROVED MARCH 2015
ChEMBL
CHEMBL3184512
Created by admin on Tue Oct 22 00:37:02 UTC 2019 , Edited by admin on Tue Oct 22 00:37:02 UTC 2019
PRIMARY
CAS
24729-96-2
Created by admin on Tue Oct 22 00:37:02 UTC 2019 , Edited by admin on Tue Oct 22 00:37:02 UTC 2019
PRIMARY
EVMPD
SUB01344MIG
Created by admin on Tue Oct 22 00:37:02 UTC 2019 , Edited by admin on Tue Oct 22 00:37:02 UTC 2019
PRIMARY
NCI_THESAURUS
C47978
Created by admin on Tue Oct 22 00:37:02 UTC 2019 , Edited by admin on Tue Oct 22 00:37:02 UTC 2019
PRIMARY
MERCK INDEX
M3624
Created by admin on Tue Oct 22 00:37:02 UTC 2019 , Edited by admin on Tue Oct 22 00:37:02 UTC 2019
PRIMARY Merck Index
WHO INTERNATIONAL PHARMACOPEIA
CLINDAMYCIN PHOSPHATE
Created by admin on Tue Oct 22 00:37:02 UTC 2019 , Edited by admin on Tue Oct 22 00:37:02 UTC 2019
PRIMARY Description: A white or almost white, crystalline powder.Solubility: Freely soluble in water; very slightly soluble in ethanol (~750 g/l) TS and acetone R.Category: Antibacterial drug.Storage: Clindamycin phosphate should be kept in a tightly closed container.Labelling: The designation Clindamycin phosphate for parenteral use indicates that the substance complies with the additionalrequirements and may be used for parenteral administration. Expiry date.Additional information: Clindamycin phosphate is slightly hygroscopic.
Related Record Type Details
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY